MiMeDB: Showing metabocard for PG(15:0cyclo/12:0(3-OH)) (MMDBc0031450)

Microbial

Human

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-18 00:49:37 UTC

Update Date

2023-02-07 23:25:06 UTC

Metabolite ID

MMDBc0031450

Metabolite Identification

Common Name

PG(15:0cyclo/12:0(3-OH))

Description

PG(12:0(3-OH)/15:0cyclo) is a phosphatidylglycerol. Phosphatidylglycerols consist of a glycerol 3-phosphate backbone esterified to either saturated or unsaturated fatty acids on carbons 1 and 2. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PG(12:0(3-OH)/15:0cyclo), in particular, consists of one 3-hydroxydodecanoyl chain to the C-1 atom, and one cis-9,10-Methylenetetradecanoic acid to the C-2 atom. In E. coli glycerophospholipid metabolism, phosphatidylglycerol is formed from phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by a sequence of enzymatic reactions that proceeds via two intermediates, cytidine diphosphate diacylglycerol (CDP-diacylglycerol) and phosphatidylglycerophosphate (PGP, a phosphorylated phosphatidylglycerol). Phosphatidylglycerols, along with CDP-diacylglycerol, also serve as precursor molecules for the synthesis of cardiolipin, a phospholipid found in membranes.

Structure

MOL SDF PDB SMILES InChI

m24
  Mrv1572012091514062D          

 47 47  0  0  1  0            999 V2000
   14.0374  -24.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3624  -24.5493    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.6871  -24.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7126  -24.5493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0120  -24.5493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8354  -25.3289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3878  -24.1595    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.9979  -23.4844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7775  -24.8347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0628  -23.7697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7379  -24.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4131  -23.7697    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.0883  -24.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9501  -25.3586    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.7261  -23.7330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9894  -23.0847    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.8011  -23.0847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1210  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1210  -26.5128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4069  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6928  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6928  -26.5128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9786  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2645  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5504  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8362  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1221  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4079  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6938  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9796  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2655  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2975  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2975  -23.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5834  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8693  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1551  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4410  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7268  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0127  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2985  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5844  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8703  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1561  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4420  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7279  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0137  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2996  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  2  6  1  0  0  0  0
  2 14  1  1  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  5 32  1  0  0  0  0
  7  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 12 16  1  6  0  0  0
 12 17  1  0  0  0  0
 13 12  1  0  0  0  0
 13 15  1  0  0  0  0
 18  6  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
M  END

m24
  Mrv1572012091514062D          

 47 47  0  0  1  0            999 V2000
   14.0374  -24.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3624  -24.5493    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.6871  -24.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7126  -24.5493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0120  -24.5493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8354  -25.3289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3878  -24.1595    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.9979  -23.4844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7775  -24.8347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0628  -23.7697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7379  -24.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4131  -23.7697    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.0883  -24.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9501  -25.3586    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.7261  -23.7330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9894  -23.0847    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.8011  -23.0847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1210  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1210  -26.5128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4069  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6928  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6928  -26.5128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9786  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2645  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5504  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8362  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1221  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4079  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6938  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9796  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2655  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2975  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2975  -23.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5834  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8693  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1551  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4410  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7268  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0127  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2985  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5844  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8703  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1561  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4420  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7279  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0137  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2996  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  2  6  1  0  0  0  0
  2 14  1  1  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  5 32  1  0  0  0  0
  7  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 12 16  1  6  0  0  0
 12 17  1  0  0  0  0
 13 12  1  0  0  0  0
 13 15  1  0  0  0  0
 18  6  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031450

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCC)OC(=O)CC(O)CCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C33H63O11P/c1-3-5-7-8-9-12-15-19-29(35)22-33(38)44-31(26-43-45(39,40)42-24-30(36)23-34)25-41-32(37)20-16-13-10-11-14-18-28-21-27(28)17-6-4-2/h27-31,34-36H,3-26H2,1-2H3,(H,39,40)/t27?,28?,29?,30-,31+/m0/s1

> <INCHI_KEY>
RKRSSXLZASRFAF-AIMSBCCHSA-N

> <FORMULA>
C33H63O11P

> <MOLECULAR_WEIGHT>
666.83

> <EXACT_MASS>
666.410799847

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
108

> <JCHEM_AVERAGE_POLARIZABILITY>
75.91327960163842

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxydodecanoyl)oxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid

> <ALOGPS_LOGP>
4.97

> <JCHEM_LOGP>
6.704572087333334

> <ALOGPS_LOGS>
-5.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.622641796894055

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8907737767519066

> <JCHEM_PKA_STRONGEST_BASIC>
-2.798759057602271

> <JCHEM_POLAR_SURFACE_AREA>
169.05

> <JCHEM_REFRACTIVITY>
171.91240000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
33

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.14e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxydodecanoyl)oxy]propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-DEC-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: m24                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-DEC-15         0                                  
HETATM    1  C   UNK     0      26.203 -45.098   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.943 -45.825   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.683 -45.098   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      27.464 -45.825   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      22.422 -45.825   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      23.959 -47.281   0.000  0.00  0.00           O+0
HETATM    7  P   UNK     0      28.724 -45.098   0.000  0.00  0.00           P+0
HETATM    8  O   UNK     0      27.996 -43.837   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      29.451 -46.358   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      29.984 -44.370   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      31.244 -45.098   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      32.504 -44.370   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      33.765 -45.098   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0      26.040 -47.336   0.000  0.00  0.00           H+0
HETATM   15  O   UNK     0      34.955 -44.302   0.000  0.00  0.00           O+0
HETATM   16  H   UNK     0      33.580 -43.091   0.000  0.00  0.00           H+0
HETATM   17  O   UNK     0      31.362 -43.091   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      22.626 -48.051   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      22.626 -49.491   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      21.293 -47.279   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      19.960 -48.051   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      19.960 -49.491   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      18.627 -47.279   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.294 -48.051   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.961 -47.279   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.628 -48.051   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.295 -47.279   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.961 -48.051   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.628 -47.279   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.295 -48.051   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.962 -47.279   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      21.089 -45.055   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      21.089 -43.615   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      19.756 -45.827   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      18.423 -45.055   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      17.090 -45.827   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      15.756 -45.055   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      14.423 -45.827   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      13.090 -45.055   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      11.757 -45.827   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      10.424 -45.055   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       9.091 -45.827   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       7.758 -45.055   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       6.425 -45.827   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       5.092 -45.055   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       3.759 -45.827   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       2.426 -45.055   0.000  0.00  0.00           C+0
CONECT    1    2    4                                                       
CONECT    2    1    6   14    3                                             
CONECT    3    2    5                                                       
CONECT    4    1    7                                                       
CONECT    5    3   32                                                       
CONECT    6    2   18                                                       
CONECT    7    4    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   16   17   13                                             
CONECT   13   12   15                                                       
CONECT   14    2                                                            
CONECT   15   13                                                            
CONECT   16   12                                                            
CONECT   17   12                                                            
CONECT   18    6   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32    5   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41   43                                                       
CONECT   43   41   42   44                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46                                                            
MASTER        0    0    0    0    0    0    0    0   47    0   94    0
END

Synonyms

Not Available

Molecular Formula

C₃₃H₆₃O₁₁P

Average Mass

666.83

Monoisotopic Mass

666.410799847

IUPAC Name

[(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxydodecanoyl)oxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid

Traditional Name

(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxydodecanoyl)oxy]propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCC)OC(=O)CC(O)CCCCCCCCC

InChI Identifier

InChI=1S/C33H63O11P/c1-3-5-7-8-9-12-15-19-29(35)22-33(38)44-31(26-43-45(39,40)42-24-30(36)23-34)25-41-32(37)20-16-13-10-11-14-18-28-21-27(28)17-6-4-2/h27-31,34-36H,3-26H2,1-2H3,(H,39,40)/t27?,28?,29?,30-,31+/m0/s1

InChI Key

RKRSSXLZASRFAF-AIMSBCCHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphatidylglycerols. These are glycerophosphoglycerols in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoglycerols

Direct Parent

Phosphatidylglycerols

Alternative Parents

Substituents

1,2-diacylglycerophosphoglycerol
Beta-hydroxy acid
Dialkyl phosphate
Fatty acid ester
Fatty acyl
Alkyl phosphate
Dicarboxylic acid or derivatives
Phosphoric acid ester
Organic phosphoric acid derivative
Hydroxy acid
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Alcohol
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00071 g/L	ALOGPS
logP	4.97	ALOGPS
logP	6.7	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	1.89	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	169.05 Å²	ChemAxon
Rotatable Bond Count	33	ChemAxon
Refractivity	171.91 m³·mol⁻¹	ChemAxon
Polarizability	75.91 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-3650709000-ed26c16bfc2b1855af70	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0032-5940513000-973ef2fa134edc4cfe6f	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052b-9840201000-50419d0de3033078c060	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01bj-0390313000-1c79facaea2e5f4d2a5c	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00g0-5591110000-7baa60aaf0b068bc269b	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9120000000-b2cdaab4fe68e53343ef	2019-02-23	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	260.9
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	87.9
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	849.8
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	975.2
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	1052.7
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	177.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (retained)	2025-10-23	3891.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	245.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	270.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	687.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	138.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	180.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	270.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	62.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-23	212.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	745.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	547.9
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	2111.6
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1793.4

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_1	CCCCCCCCCC(O)CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(O)OC[C@H](CO)O[Si](C)(C)C	standard non polar	2025-10-24	1288.15
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_2	CCCCCCCCCC(O)CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(O)OC[C@@H](O)CO[Si](C)(C)C	standard non polar	2025-10-24	2416.49
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_3	CCCCCCCCCC(CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(O)OC[C@@H](O)CO)O[Si](C)(C)C	standard non polar	2025-10-24	1418.23
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_4	CCCCCCCCCC(O)CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(OC[C@@H](O)CO)O[Si](C)(C)C	standard non polar	2025-10-24	2153.65
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_5	CCCCCCCCCC(CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(O)OC[C@H](CO)O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	1842.52
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_6	CCCCCCCCCC(O)CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(O)OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	1341.1
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_7	CCCCCCCCCC(O)CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(OC[C@H](CO)O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	1087.84
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_8	CCCCCCCCCC(CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(O)OC[C@@H](O)CO[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	2959.22
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_9	CCCCCCCCCC(O)CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(OC[C@@H](O)CO[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	1019.82
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_10	CCCCCCCCCC(CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(OC[C@@H](O)CO)O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	1658.68
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_11	CCCCCCCCCC(CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(O)OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	1862.16
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_12	CCCCCCCCCC(CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(OC[C@H](CO)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	2292.39
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_13	CCCCCCCCCC(O)CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	2432.61
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_14	CCCCCCCCCC(CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(OC[C@@H](O)CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	2850.66
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_1	CCCCCCCCCC(O)CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(O)OC[C@H](CO)O[Si](C)(C)C	standard polar	2025-10-24	2213.18
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_2	CCCCCCCCCC(O)CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(O)OC[C@@H](O)CO[Si](C)(C)C	standard polar	2025-10-24	1595.18
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_3	CCCCCCCCCC(CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(O)OC[C@@H](O)CO)O[Si](C)(C)C	standard polar	2025-10-24	1476.4
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_4	CCCCCCCCCC(O)CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(OC[C@@H](O)CO)O[Si](C)(C)C	standard polar	2025-10-24	1564.49
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_5	CCCCCCCCCC(CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(O)OC[C@H](CO)O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2059.11
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_6	CCCCCCCCCC(O)CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(O)OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2163.17
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_7	CCCCCCCCCC(O)CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(OC[C@H](CO)O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2085.41
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_8	CCCCCCCCCC(CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(O)OC[C@@H](O)CO[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2106.26
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_9	CCCCCCCCCC(O)CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(OC[C@@H](O)CO[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2367.22
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_10	CCCCCCCCCC(CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(OC[C@@H](O)CO)O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2161.53
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_11	CCCCCCCCCC(CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(O)OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	1952.47
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_12	CCCCCCCCCC(CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(OC[C@H](CO)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2501.21
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_13	CCCCCCCCCC(O)CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2729.08
Gas Chromatography	PG(15:0cyclo/12:0(3-OH))_TMS_14	CCCCCCCCCC(CC(=O)O[C@H](COC(=O)CCCCCCCC1CC1CCCC)COP(=O)(OC[C@@H](O)CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2743.18

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Name	SMPDB/PathBank	Species
Phospholipid Biosynthesis CL(15:0cyclo/12:0(3-OH)/15:0cyclo/12:0(3-OH))		Escherichia coli Pseudomonas aeruginosa Escherichia coli SMS-3-5 Escherichia coli UTI89 Escherichia coli 55989 Escherichia coli SE11 Mycobacterium marinum M Pseudomonas aeruginosa PA7 Acinetobacter sp. ADP1 Actinobacillus succinogenes 130Z Escherichia coli CFT073 Myxococcus xanthus DK 1622 Ochrobactrum anthropi Bacillus subtilis Pseudomonas stutzeri Mycobacterium tuberculosis Klebsiella pneumoniae Bacillus cereus Pseudomonas fluorescens Pf-5 Streptomyces griseus subsp. griseus NBRC 13350 Mycobacterium tuberculosis CDC1551 Bacillus amyloliquefaciens Streptococcus pneumoniae Roseburia intestinalis L1-82 Clostridium saccharoperbutylacetonicum N1-4(HMT) Salmonella enterica Clostridium acetobutylicum ATCC 824 Helicobacter pylori Staphylococcus aureus Haemophilus influenzae Haemophilus influenzae Rd KW20 Clostridium perfringens Clostridium sporogenes Rhodospirillum rubrum ATCC 11170 Lactobacillus fermentum IFO 3956 Streptococcus pneumoniae TIGR4 Aromatoleum aromaticum EbN1 Saccharopolyspora erythraea NRRL 2338 Streptomyces avermitilis MA-4680 Shewanella denitrificans OS217 Acinetobacter baumannii Akkermansia muciniphila ATCC BAA-835 Anaerococcus prevotii DSM 20548 Anaerostipes caccae Anaerostipes hadrus Arcobacter butzleri RM4018 Bacillus cereus AH187 (F4810/72) Bacillus halodurans C-125 Alkalihalobacillus pseudofirmus OF4 Bacillus timonensis 10403023 Bacteroides caccae Bacteroides cellulosilyticus Bacteroides eggerthii Bacteroides fragilis Bacteroides fragilis 638R Bacteroides fragilis YCH46 Bacteroides ovatus Bacteroides stercoris Bacteroides stercoris ATCC 43183 Bacteroides thetaiotaomicron Bacteroides thetaiotaomicron VPI-5482 Bacteroides xylanisolvens XB1A Blautia hansenii DSM 20583 Blautia obeum A2-162 Blautia obeum ATCC 29174 Brevibacillus brevis NBRC 100599 Campylobacter fetus subsp. fetus 82-40 Campylobacter hominis ATCC BAA-381 Clostridium beijerinckii NCIMB 8052 Clostridium botulinum Clostridium perfringens ATCC 13124 Clostridium saccharolyticum Clostridium sticklandii Dorea formicigenerans ATCC 27755 Dysgonomonas gadei ATCC BAA-286 Eubacterium eligens ATCC 27750 Eubacterium rectale ATCC 33656 Fusobacterium nucleatum subsp. nucleatum ATCC 25586 Geobacter metallireducens Haemophilus parainfluenzae T3T1 Limosilactobacillus fermentum Lactobacillus reuteri Methylobacterium nodulans Ochrobactrum anthropi ATCC 49188 Ochrobactrum intermedium LMG 3301 Prevotella intermedia Roseburia hominis A2-183 Ruminococcus bicirculans Ruminococcus champanellensis 18P13 = JCM 17042 Ruminococcus torques L2-14 Streptococcus salivarius lactobacillus crispatus lactobacillus vaginalis Pelobacter carbinolicus Spirochaeta thermophila Campylobacter concisus Campylobacter curvus Campylobacter lari Campylobacter rectus Campylobacter showae Comamonas testosteroni Burkholderia cepacia Pseudomonas fluorescens Pseudomonas mendocina Pseudomonas putida Pseudomonas syringae Xanthomonas campestris Bradyrhizobium japonicum Mesorhizobium loti Sinorhizobium meliloti Methylococcus capsulatus Moraxella catarrhalis Neisseria flavescens Neisseria gonorrhoeae Neisseria mucosa Acidiphilium cryptum Chromobacterium violaceum Citrobacter koseri Proteus mirabilis Shigella boydii Shigella dysenteriae Shigella flexneri Shigella sonnei Aeromonas hydrophila Vibrio vulnificus Bacteroides uniformis Campylobacter gracilis Fusobacterium gonidiaformans Fusobacterium periodonticum Fusobacterium ulcerans Desulfovibrio salexigens Desulfovibrio piger Acidithiobacillus ferrooxidans Chlorobium phaeobacteroides Ruminococcus albus Streptococcus gordonii Streptococcus oralis Streptococcus sanguinis Bacillus licheniformis Priestia megaterium Bacillus mycoides Bacillus thuringiensis Clostridium butyricum Moorella thermoacetica Clostridium kluyveri Clostridium novyi Weissella confusa Lactobacillus delbrueckii Lactobacillus helveticus Lactobacillus gasseri Lactobacillus sakei Lactobacillus coryniformis Listeria monocytogenes Actinomyces viscosus Mycobacterium avium Mycoplasma capricolum Mycoplasma gallisepticum Mycoplasma pulmonis Mycoplasma arthritidis Mycoplasma mobile Desulfobacterium autotrophicum Thermotoga neapolitana Xylella fastidiosa Roseobacter denitrificans Acidothermus cellulolyticus Campylobacter upsaliensis Neisseria subflava Staphylococcus saprophyticus Pelobacter propionicus Lactobacillus johnsonii Eubacterium brachy Helicobacter pullorum Thiobacillus denitrificans Helicobacter bilis Enterococcus casseliflavus Eubacterium eligens Eubacterium ramulus Eubacterium ventriosum Sulfurimonas denitrificans Stenotrophomonas maltophilia Leptotrichia buccalis Actinosynnema mirum Streptococcus cristatus Blautia hydrogenotrophica Desulfotomaculum reducens Burkholderia vietnamiensis Sodalis glossinidius Enterobacter cancerogenus Streptococcus constellatus Bacillus clausii Bacillus pseudofirmus Clostridium methylpentosum Bacillus selenitireducens Achromobacter xylosoxidans Burkholderia multivorans Dorea longicatena Peptacetobacter hiranonis Burkholderia cenocepacia Methylibium petroleiphilum Pelotomaculum thermopropionicum Syntrophobacter fumaroxidans Citrobacter youngae Ureaplasma parvum Collinsella stercoris Burkholderia ambifaria Prevotella copri Ilyobacter polytropus Marvinbryantia formatexigens Alicycliphilus denitrificans Desulfovibrio magneticus Shewanella denitrificans Methylocella silvestris Escherichia albertii Geobacter bemidjiensis Lactobacillus antri Lactobacillus ultunensis Streptococcus pseudopneumoniae Bacteroides nordii Phocaeicola coprocola Bacteroides pyogenes Geobacter lovleyi Syntrophus aciditrophicus Bacteroides intestinalis Bacteroides salanitronis Coprococcus comes Actinomyces oris Bacteroides fluxus Bacteroides oleiciplenus Bacteroides faecis Agrobacterium tumefaciens Alistipes shahii Bacteroides helcogenes Bacteroides xylanisolvens Blautia hansenii Blautia obeum Campylobacter coli Campylobacter hominis Campylobacter jejuni Clostridium beijerinckii Dorea formicigenerans Dysgonomonas gadei Fusobacterium nucleatum Gemella sanguinis Haemophilus parainfluenzae Klebsiella variicola Lactobacillus ruminis Leuconostoc citreum Streptococcus mitis Streptococcus parasanguinis Gemella haemolysans Rothia mucilaginosa Actinomyces graevenitzii Achromobacter xylosoxidans A8 Acinetobacter baumannii SDF Acinetobacter baumannii ACICU Acinetobacter baumannii AB0057 Acinetobacter baumannii AB307-0294 Actinobacillus pleuropneumoniae serovar 5b str. L20 Actinobacillus pleuropneumoniae serovar 3 str. JL03 Actinobacillus pleuropneumoniae serovar 7 str. AP76 Aeromonas hydrophila subsp. hydrophila ATCC 7966 Bacillus cereus ATCC 10987 Bacillus megaterium QM B1551 Bacillus thuringiensis serovar konkukian str. 97-27 Bacillus licheniformis ATCC 14580 Bacillus clausii KSM-K16 Bacillus amyloliquefaciens FZB42 Bacillus cereus B4264 Bacillus cereus AH820 Bacillus cereus G9842 Bacillus cereus Q1 Priestia megaterium DSM 319 Bacillus subtilis subsp. spizizenii str. W23 Bacillus amyloliquefaciens DSM 7 Bartonella quintana str. Toulouse Bradyrhizobium japonicum USDA 110 Campylobacter jejuni subsp. jejuni 81-176 Campylobacter jejuni subsp. doylei 269.97 Campylobacter curvus 525.92 Campylobacter concisus 13826 Campylobacter lari RM2100 Chlamydia trachomatis D/UW-3/CX Chlamydia trachomatis A/HAR-13 Chlamydia trachomatis L2b/UCH-1/proctitis Citrobacter koseri ATCC BAA-895 Clostridium perfringens str. 13 Clostridium botulinum A str. Hall Clostridium botulinum B1 str. Okra Clostridium botulinum A2 str. Kyoto Clostridium botulinum Ba4 str. 657 Clostridium sticklandii DSM 519 Clostridium sp. SY8519 Clostridium perfringens SM101 Corynebacterium aurimucosum ATCC 700975 Cronobacter sakazakii ATCC BAA-894 Delftia acidovorans SPH-1 Enterobacter cloacae subsp. cloacae ATCC 13047 Escherichia coli APEC O1 Escherichia coli E24377A Escherichia coli O127:H6 str. E2348/69 Escherichia coli UMN026 Escherichia fergusonii ATCC 35469 Escherichia coli ED1a Escherichia coli IAI39 Finegoldia magna ATCC 29328 Haemophilus influenzae 86-028NP Haemophilus influenzae PittGG Helicobacter pylori J99 Helicobacter pylori G27 Helicobacter pylori P12 Klebsiella pneumoniae subsp. pneumoniae MGH 78578 Kocuria rhizophila DC2201 Kytococcus sedentarius DSM 20547 Lactobacillus johnsonii NCC 533 Lactobacillus brevis ATCC 367 Lactobacillus reuteri DSM 20016 Lactobacillus reuteri SD2112 Laribacter hongkongensis HLHK9 Leptotrichia buccalis C-1013-b Lysinibacillus sphaericus C3-41 Mesorhizobium loti MAFF303099 Methylobacterium radiotolerans JCM 2831 Methylobacterium populi BJ001 Mobiluncus curtisii ATCC 43063 Mycobacterium avium subsp. paratuberculosis K-10 Mycobacterium avium 104 Neisseria gonorrhoeae FA 1090 Neisseria meningitidis MC58 Neisseria meningitidis Z2491 Neisseria meningitidis FAM18 Neisseria gonorrhoeae NCCP11945 Tropheryma whipplei str. Twist Escherichia coli 042 Acinetobacter calcoaceticus PHEA-2 Edwardsiella tarda FL6-60 Filifactor alocis ATCC 35896 Pediococcus pentosaceus ATCC 25745 Propionibacterium freudenreichii subsp. shermanii CIRM-BIA1 Proteus mirabilis HI4320 Pseudomonas putida KT2440 Pseudomonas fluorescens Pf0-1 Pseudomonas stutzeri A1501 Pseudomonas fluorescens SBW25 Pseudomonas putida GB-1 Rhizobium leguminosarum bv. viciae 3841 Rhizobium leguminosarum bv. trifolii WSM2304 Rhodococcus erythropolis PR4 Rothia mucilaginosa DY-18 Rothia dentocariosa ATCC 17931 Ruminococcus albus 7 Salmonella enterica subsp. enterica serovar Typhimurium str. LT2 Salmonella enterica subsp. enterica serovar Newport str. SL254 Salmonella enterica subsp. enterica serovar Heidelberg str. SL476 Salmonella enterica subsp. enterica serovar Agona str. SL483 Salmonella enterica subsp. enterica serovar Dublin str. CT02021853 Shigella sonnei Ss046 Shigella dysenteriae Sd197 Shigella flexneri 5 str. 8401 Spirosoma linguale DSM 74 Staphylococcus aureus subsp. aureus Mu50 Staphylococcus aureus subsp. aureus COL Staphylococcus aureus subsp. aureus MRSA252 Staphylococcus saprophyticus subsp. saprophyticus ATCC 15305 Staphylococcus aureus subsp. aureus NCTC 8325 Stenotrophomonas maltophilia K279a Stenotrophomonas maltophilia R551-3 Streptococcus pneumoniae D39 Streptococcus sanguinis SK36 Streptococcus gordonii str. Challis substr. CH1 Streptococcus pneumoniae Hungary19A-6 Streptococcus pneumoniae JJA Vibrio parahaemolyticus RIMD 2210633 Wolinella succinogenes DSM 1740 Yersinia enterocolitica subsp. enterocolitica 8081 Yersinia pseudotuberculosis IP 31758 Aquifex aeolicus Bacteroides cellulosilyticus DSM 14838 Bacteroides eggerthii 1_2_48FAA Bacteroides fluxus YIT 12057 Bacteroides graminisolvens Bacteroides graminisolvens DSM 19988 = JCM 15093 Bacteroides intestinalis DSM 17393 Bacteroides nordii CL02T12C05 Bacteroides oleiciplenus YIT 12058 Bacteroides ovatus ATCC 8483 Bacteroides pyogenes DSM 20611 = JCM 6294 Bacteroides uniformis ATCC 8492 Bacteroides xylanisolvens SD CC 1b Bacteroides sp. 1_1_14 Bacteroides sp. 1_1_30 Bacteroides sp. 2_1_22 Bacteroides sp. 2_2_4 Bacteroides sp. D2 Bacteroides sp. D20 Bacteroides sp. D22 Paraprevotella clara YIT 11840 Paraprevotella xylaniphila YIT 11841 Prevotella buccae ATCC 33574 Prevotella denticola Prevotella oralis ATCC 33269 Prevotella pallens ATCC 700821 Prevotella timonensis CRIS 5C-B1 Parabacteroides johnsonii DSM 18315 Spirosoma linguale Chlorobium limicola Cetobacterium somerae ATCC BAA-474 Fusobacterium gonidiaformans 3-1-5R Fusobacterium nucleatum subsp. animalis 4_8 Fusobacterium nucleatum subsp. animalis 7_1 Fusobacterium nucleatum subsp. animalis D11 Fusobacterium nucleatum subsp. vincentii 4_1_13 Fusobacterium periodonticum 1_1_41FAA Thermodesulfovibrio yellowstonii Bartonella quintana Beijerinckia indica Bradyrhizobium elkanii Methylobacterium mesophilicum Methylobacterium mesophilicum SR1.6/6 Rhizobium etli Azorhizobium caulinodans Xanthobacter autotrophicus Ehrlichia chaffeensis Rickettsia rickettsii Alcaligenes faecalis Burkholderia cepacia GG4 Lautropia mirabilis Lautropia mirabilis ATCC 51599 Parasutterella excrementihominis YIT 11859 Sutterella parvirubra Sutterella parvirubra YIT 11816 Laribacter hongkongensis Eikenella corrodens Eikenella corrodens ATCC 23834 Kingella oralis Kingella oralis ATCC 51147 Neisseria cinerea ATCC 14685 Neisseria elongata Neisseria elongata subsp. glycolytica ATCC 29315 Neisseria macacae Neisseria macacae ATCC 33926 Neisseria meningitidis Neisseria mucosa ATCC 25996 Neisseria subflava NJ9703 Nitrosospira multiformis Methyloversatilis universalis Methyloversatilis universalis FAM5 Desulfococcus oleovorans Bilophila wadsworthia 3_1_6 Desulfovibrio piger ATCC 29098 Arcobacter butzleri Campylobacter gracilis RM3268 Campylobacter hyointestinalis Campylobacter rectus RM3267 Campylobacter showae CSUNSWCD Campylobacter upsaliensis JV21 Helicobacter bilis ATCC 43879 Helicobacter pullorum MIT 98-5489 Aeromonas caviae Aeromonas media Aeromonas veronii Succinatimonas hippei Succinatimonas hippei YIT 12066 Succinivibrio dextrinosolvens Allochromatium vinosum Cedecea davisae Cedecea davisae DSM 4568 Citrobacter amalonaticus Citrobacter amalonaticus Y19 Citrobacter freundii Citrobacter youngae ATCC 29220 Enterobacter hormaechei Escherichia albertii TW07627 Klebsiella aerogenes Salmonella Salmonella enterica subsp. enterica serovar Typhimurium Trabulsiella guamensis Trabulsiella guamensis ATCC 49490 Tatumella ptyseos Tatumella ptyseos ATCC 33301 Edwardsiella tarda Edwardsiella tarda ATCC 23685 Hafnia alvei Hafnia alvei ATCC 51873 Morganella morganii Morganella morganii subsp. morganii KT Providencia rustigianii DSM 4541 Providencia stuartii ATCC 25827 Serratia marcescens subsp. marcescens Db11 Yersinia enterocolitica Yersinia pestis Yersinia pseudotuberculosis Plesiomonas shigelloides 302-73 Legionella pneumophila Actinobacillus pleuropneumoniae Aggregatibacter aphrophilus Haemophilus haemolyticus Haemophilus sputorum Acinetobacter pittii Acinetobacter haemolyticus Acinetobacter johnsonii Acinetobacter johnsonii SH046 Acinetobacter junii SH205 Francisella tularensis Grimontia hollisae CIP 101886 Vibrio fluvialis Vibrio fluvialis PG41 Vibrio parahaemolyticus Vibrio mimicus Chlamydia trachomatis Leptospira interrogans Acetomicrobium hydrogeniformans Actinomyces graevenitzii C83 Actinomyces naeslundii Actinomyces naeslundii str. Howell 279 Actinomyces urogenitalis DSM 15434 Actinomyces viscosus C505 Mobiluncus curtisii Corynebacterium aurimucosum Corynebacterium durum Corynebacterium durum F0235 Gordonia terrae C-6 Rhodococcus erythropolis Brevibacterium casei S18 Brevibacterium linens Microbacterium oleivorans Kocuria palustris PEL Rothia aeria F0474 Tropheryma whipplei Propionibacterium Streptomyces avermitilis Thermomonospora curvata Collinsella stercoris DSM 13279 Slackia piriformis YIT 12062 Bacillus altitudinis Bacillus infantis NRRL B-14911 Bacillus firmus DS1 Lysinibacillus sphaericus Listeria grayi Listeria grayi DSM 20601 Listeria monocytogenes 10403S Aneurinibacillus aneurinilyticus Aneurinibacillus aneurinilyticus ATCC 12856 Paenibacillus lactis 154 Gemella haemolysans ATCC 10379 Exiguobacterium aurantiacum Abiotrophia defectiva Abiotrophia defectiva ATCC 49176 Enterococcus caccae ATCC BAA-1240 Enterococcus casseliflavus ATCC 12755 Lactobacillus ultunensis DSM 16047 Lactobacillus ruminis ATCC 25644 Lactobacillus antri DSM 16041 Lactobacillus vaginalis DSM 5837 = ATCC 49540 Lactobacillus reuteri CF48-3A Lactobacillus reuteri MM4-1A Pediococcus pentosaceus Lactococcus garvieae Streptococcus constellatus subsp. pharyngis SK1060 = CCUG 46377 Streptococcus australis ATCC 700641 Streptococcus infantis ATCC 700779 Butyricicoccus pullicaecorum Butyricicoccus pullicaecorum 1.2 Clostridium butyricum E4 str. BoNT E BL5262 Clostridium celatum DSM 1785 Clostridium sartagoforme AAU1 Eubacterium ramulus ATCC 29099 Eubacterium ventriosum ATCC 27560 [Eubacterium] cellulosolvens 6 Pseudoramibacter alactolyticus ATCC 23263 Anaerostipes caccae DSM 14662 Blautia hydrogenotrophica DSM 10507 Blautia wexlerae Coprococcus comes ATCC 27758 Dorea longicatena DSM 13814 Clostridium asparagiforme DSM 15981 [Clostridium] bolteae ATCC BAA-613 Clostridium citroniae WAL-17108 [Clostridium] hylemonae DSM 15053 [Clostridium] symbiosum WAL-14163 Lachnospira multipara [Ruminococcus] gnavus ATCC 29149 [Ruminococcus] lactaris ATCC 29176 [Ruminococcus] torques ATCC 27756 Oribacterium sinus F0268 Roseburia inulinivorans DSM 16841 Pseudoflavonifractor capillosus ATCC 29799 Ruminococcus champanellensis [Bacteroides] pectinophilus ATCC 43243 Mogibacterium timidum Mogibacterium timidum ATCC 33093 Eubacterium brachy ATCC 33089 Eubacterium saphenum ATCC 49989 Eggerthia catenaformis OT 569 = DSM 20559 [Clostridium] innocuum 2959 Clostridium spiroforme [Clostridium] spiroforme DSM 1552 Kandleria vitulina Kandleria vitulina DSM 20405 Solobacterium moorei F0204 Parvimonas micra ATCC 33270 Streptomyces coelicolor A3(2) Bordetella pertussis Tohama I Bordetella parapertussis 12822 Ralstonia eutropha H16 Xanthomonas campestris pv. campestris str. ATCC 33913 Xanthomonas campestris pv. campestris str. B100 Xanthomonas campestris pv. campestris str. 8004 Vibrio cholerae M66-2 Vibrio cholerae O1 biovar El Tor str. N16961 Shewanella frigidimarina NCIMB 400 Bacillus cytotoxicus NVH 391-98 Lachnoclostridium phytofermentans ISDg Lactobacillus ruminis ATCC 27782 Leuconostoc citreum KM20 Streptococcus mitis B6 Streptococcus parasanguinis ATCC 15912 Streptococcus parasanguinis FW213 Acidothermus cellulolyticus 11B Alicyclobacillus acidocaldarius subsp. acidocaldarius DSM 446 Alkaliphilus metalliredigens QYMF Alkaliphilus oremlandii OhILAs Amycolatopsis mediterranei U32 Anoxybacillus flavithermus WK1 Arthrobacter aurescens TC1 Bacillus selenitireducens MLS10 Beutenbergia cavernae DSM 12333 Butyrivibrio proteoclasticus B316 Onion yellows phytoplasma OY-M Catenulispora acidiphila DSM 44928 Clavibacter michiganensis subsp. michiganensis NCPPB 382 Clostridium tetani E88 Clostridium novyi NT Clostridium kluyveri DSM 555 Clostridium kluyveri NBRC 12016 Clostridium cellulolyticum H10 Corynebacterium jeikeium K411 Corynebacterium urealyticum DSM 7109 Corynebacterium resistens DSM 45100 Desulfotomaculum reducens MI-1 Exiguobacterium sibiricum 255-15 Exiguobacterium sp. AT1b Frankia alni ACN14a Frankia sp. EuI1c Geobacillus kaustophilus HTA426 Geobacillus thermodenitrificans NG80-2 Gordonia bronchialis DSM 43247 Intrasporangium calvum DSM 43043 Kineococcus radiotolerans SRS30216 Lactobacillus crispatus ST1 Listeria innocua Clip11262 Macrococcus caseolyticus JCSC5402 Mycobacterium leprae TN Mycobacterium bovis AF2122/97 Mycobacterium ulcerans Agy99 Mycobacterium vanbaalenii PYR-1 Mycobacterium bovis BCG str. Pasteur 1173P2 Mycobacterium tuberculosis H37Ra Mycobacterium abscessus ATCC 19977 Mycobacterium leprae Br4923 Mycobacterium sp. Spyr1 Mycobacterium sp. JDM601 Mycobacterium canettii CIPT 140010059 Nakamurella multipartita DSM 44233 Nocardia farcinica IFM 10152 Nocardioides sp. JS614 Oceanobacillus iheyensis HTE831 Aster yellows witches'-broom phytoplasma AYWB Ureaplasma urealyticum serovar 10 str. ATCC 33699 Dictyoglomus turgidum DSM 6724 Bacillus tusciae DSM 2912 Mycoplasma leachii PG50 Pelotomaculum thermopropionicum SI Pseudonocardia dioxanivorans CB1190 Rhodococcus opacus B4 Rhodococcus jostii RHA1 Rhodococcus equi 103S Salinispora tropica CNB-440 Sanguibacter keddieii DSM 10542 Slackia heliotrinireducens DSM 20476 Stackebrandtia nassauensis DSM 44728 Staphylococcus carnosus subsp. carnosus TM300 Streptosporangium roseum DSM 43021 Thermoanaerobacter sp. X514 Thermoanaerobacter pseudethanolicus ATCC 33223 Thermoanaerobacter italicus Ab9 Thermoanaerobacterium thermosaccharolyticum DSM 571 Thermobispora bispora DSM 43833 Thermomonospora curvata DSM 43183 Tsukamurella paurometabola DSM 20162 Ureaplasma parvum serovar 3 str. ATCC 700970 Ureaplasma parvum serovar 3 str. ATCC 27815 Aspergillus nomiae NRRL 13137 Aspergillus novofumigatus Aspergillus novofumigatus IBT 16806 Aspergillus parasiticus SU-1 Aspergillus phoenicis Aspergillus ruber Aspergillus sclerotioniger Aspergillus glaucus Aspergillus aculeatus ATCC 16872 Aspergillus leporis Aspergillus niger ATCC 1015 Aspergillus oryzae RIB40 Aspergillus terreus NIH2624 Aspergillus wentii Aspergillus clavatus NRRL 1 Aspergillus fischeri NRRL 181 Aspergillus fumigatus A1163 Aspergillus fumigatus Af293 Aspergillus calidoustus Aspergillus nidulans FGSC A4 Aspergillus taichungensis Aspergillus tamarii Aspergillus thermomutatus Aspergillus tubingensis Aspergillus violaceofuscus Aspergillus viridinutans Penicillium brasilianum Penicillium brevicompactum Penicillium canescens Penicillium chermesinum Penicillium citrinum Penicillium concentricum Penicillium daleae Penicillium decumbens Penicillium griseofulvum Penicillium hordei Penicillium italicum Penicillium nalgiovense Penicillium oxalicum Penicillium polonicum Penicillium roqueforti FM164 Penicillium solitum Penicillium steckii Penicillium thymicola Penicillium vulpinum Verticillium alfalfae VaMs.102 Trichoderma arundinaceum Trichoderma asperellum Trichoderma atroviride IMI 206040 Trichoderma citrinoviride Trichoderma harzianum Trichoderma longibrachiatum Trichoderma parareesei Trichoderma reesei QM6a Trichoderma virens Trichoderma virens Gv29-8 Fusarium acutatum Fusarium fujikuroi IMI 58289 Fusarium mangiferae Fusarium nygamai Fusarium proliferatum ET1 Fusarium subglutinans Fusarium verticillioides 7600 Fusarium heterosporum Fusarium equiseti Fusarium oxysporum Fo5176 Fusarium oxysporum f. sp. lycopersici 4287 Fusarium austroamericanum Fusarium graminearum PH-1 Fusarium poae Fusarium pseudograminearum CS3096 Fusarium sporotrichioides Fusarium vanettenii Fusarium vanettenii 77-13-4 Fusarium tricinctum Paraburkholderia graminis C4D1M Schaalia cardiffensis F0333 Schaalia odontolytica ATCC 17982 Schaalia turicensis ACS-279-V-Col4 Mycolicibacterium fortuitum subsp. fortuitum DSM 46621 = ATCC 6841 Rhodococcus hoagii ATCC 33707 Acidipropionibacterium acidipropionici ATCC 4875 Anaerobutyricum hallii DSM 3353 Bacteroides helcogenes P 36-108 Bacteroides salanitronis DSM 18170 Klebsiella aerogenes KCTC 2190 Halanaerobium hydrogeniformans Acidiphilium cryptum JF-5 Acidiphilium multivorum AIU301 Acidithiobacillus ferrooxidans ATCC 23270 Acidobacterium capsulatum ATCC 51196 Acidovorax citrulli AAC00-1 Acidovorax sp. JS42 Acidovorax ebreus TPSY Aeromonas salmonicida subsp. salmonicida A449 Agrobacterium vitis S4 Agrobacterium radiobacter K84 Rhodoferax ferrireducens T118 Alcanivorax borkumensis SK2 Alicycliphilus denitrificans K601 Vibrio fischeri MJ11 Aliivibrio salmonicida LFI1238 Alkalilimnicola ehrlichii MLHE-1 Anabaena variabilis ATCC 29413 Anaeromyxobacter dehalogenans 2CP-C Anaeromyxobacter sp. Fw109-5 Anaeromyxobacter sp. K Anaeromyxobacter dehalogenans 2CP-1 Anaplasma phagocytophilum HZ Anaplasma marginale str. Florida Aquifex aeolicus VF5 Arcobacter nitrofigilis DSM 7299 Azorhizobium caulinodans ORS 571 Azotobacter vinelandii DJ Bartonella bacilliformis KC583

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0037527	PG(15:0cyclo/12:0(3-OH))	8‐(2‐Butylcyclopropyl)octanoic acid	Unknown Protein		RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Taylor SS, Heath EC: The incorporation of beta-hydroxy fatty acids into a phospholipid of Escherichia coli B. J Biol Chem. 1969 Dec 25;244(24):6605-16. [PubMed:4902888 ]
Kanehisa M, Goto S, Sato Y, Furumichi M, Tanabe M: KEGG for integration and interpretation of large-scale molecular data sets. Nucleic Acids Res. 2012 Jan;40(Database issue):D109-14. doi: 10.1093/nar/gkr988. Epub 2011 Nov 10. [PubMed:22080510 ]

Showing metabocard for PG(15:0cyclo/12:0(3-OH)) (MMDBc0031450)

MOL for #<Metabolite:0x00007f2e2c887398>

3D MOL for #<Metabolite:0x00007f2e2c887398>

3D SDF for #<Metabolite:0x00007f2e2c887398>

3D-SDF for #<Metabolite:0x00007f2e2c887398>

PDB for #<Metabolite:0x00007f2e2c887398>

3D PDB for #<Metabolite:0x00007f2e2c887398>

SMILES for #<Metabolite:0x00007f2e2c887398>

INCHI for #<Metabolite:0x00007f2e2c887398>

Structure for #<Metabolite:0x00007f2e2c887398>

3D Structure for #<Metabolite:0x00007f2e2c887398>