MiMeDB: Showing metabocard for PG(12:0(3-OH)/16:0) (MMDBc0031488)

Microbial

Human

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-18 00:51:06 UTC

Update Date

2023-02-07 23:19:57 UTC

Metabolite ID

MMDBc0031488

Metabolite Identification

Common Name

PG(12:0(3-OH)/16:0)

Description

PG(16:0/12:0(3-OH)) 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(16:0/12:0(3-OH)), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one 3-hydroxydodecanoyl 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

m74
  Mrv1572012091514072D          

 48 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
    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
    3.5514  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8373  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1231  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4090  -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
    9.8693  -23.3654    0.0000 O   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  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 35  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
 22 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
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  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
 47 48  1  0  0  0  0
M  END

m74
  Mrv1572012091514072D          

 48 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
    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
    3.5514  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8373  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1231  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4090  -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
    9.8693  -23.3654    0.0000 O   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  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 35  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
 22 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
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  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
 47 48  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031488

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C34H67O11P/c1-3-5-7-9-11-12-13-14-15-16-18-20-22-24-33(38)45-32(29-44-46(40,41)43-27-31(37)26-35)28-42-34(39)25-30(36)23-21-19-17-10-8-6-4-2/h30-32,35-37H,3-29H2,1-2H3,(H,40,41)/t30?,31-,32+/m0/s1

> <INCHI_KEY>
XPVZBRWLBUHJQB-XXWVNBFBSA-N

> <FORMULA>
C34H67O11P

> <MOLECULAR_WEIGHT>
682.873

> <EXACT_MASS>
682.442099975

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
113

> <JCHEM_AVERAGE_POLARIZABILITY>
80.05256434463476

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S)-2,3-dihydroxypropoxy][(2R)-2-(hexadecanoyloxy)-3-[(3-hydroxydodecanoyl)oxy]propoxy]phosphinic acid

> <ALOGPS_LOGP>
5.79

> <JCHEM_LOGP>
7.9279657923333335

> <ALOGPS_LOGS>
-6.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.622642515611275

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8907737771575963

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7987515577175683

> <JCHEM_POLAR_SURFACE_AREA>
169.05

> <JCHEM_REFRACTIVITY>
178.4204

> <JCHEM_ROTATABLE_BOND_COUNT>
36

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.76e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2,3-dihydroxypropoxy((2R)-2-(hexadecanoyloxy)-3-[(3-hydroxydodecanoyl)oxy]propoxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-DEC-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: m74                                               
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  C   UNK     0      18.627 -47.279   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.294 -48.051   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.961 -47.279   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.628 -48.051   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.295 -47.279   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.961 -48.051   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.628 -47.279   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.295 -48.051   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.962 -47.279   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.629 -48.051   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.296 -47.279   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.963 -48.051   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.630 -47.279   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      21.089 -45.055   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      21.089 -43.615   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      19.756 -45.827   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      18.423 -45.055   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      18.423 -43.615   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      17.090 -45.827   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      15.756 -45.055   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      14.423 -45.827   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      13.090 -45.055   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      11.757 -45.827   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      10.424 -45.055   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       9.091 -45.827   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       7.758 -45.055   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       6.425 -45.827   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   35                                                       
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                                                       
CONECT   22   21   23                                                       
CONECT   23   22   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   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35    5   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47                                                            
MASTER        0    0    0    0    0    0    0    0   48    0   94    0
END

Synonyms

Not Available

Molecular Formula

C₃₄H₆₇O₁₁P

Average Mass

682.873

Monoisotopic Mass

682.442099975

IUPAC Name

[(2S)-2,3-dihydroxypropoxy][(2R)-2-(hexadecanoyloxy)-3-[(3-hydroxydodecanoyl)oxy]propoxy]phosphinic acid

Traditional Name

(2S)-2,3-dihydroxypropoxy((2R)-2-(hexadecanoyloxy)-3-[(3-hydroxydodecanoyl)oxy]propoxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C34H67O11P/c1-3-5-7-9-11-12-13-14-15-16-18-20-22-24-33(38)45-32(29-44-46(40,41)43-27-31(37)26-35)28-42-34(39)25-30(36)23-21-19-17-10-8-6-4-2/h30-32,35-37H,3-29H2,1-2H3,(H,40,41)/t30?,31-,32+/m0/s1

InChI Key

XPVZBRWLBUHJQB-XXWVNBFBSA-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 acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00058 g/L	ALOGPS
logP	5.79	ALOGPS
logP	7.93	ChemAxon
logS	-6.1	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	36	ChemAxon
Refractivity	178.42 m³·mol⁻¹	ChemAxon
Polarizability	80.05 Å³	ChemAxon
Number of Rings	0	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_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-016s-3560719000-fa8d22561a44fb8dc8ae	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00p1-6980534000-fa5fccd26a69168e3f19	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bt9-9660131000-9cf73fc7057d67413ade	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05nb-1980515000-274542bc1c7aec18f731	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00vj-5950101000-74abfa8bb1d6edd79207	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9120000000-27bfddae7eef74fb711d	2019-02-23	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 (void)	2025-10-23	244.4
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	88.1
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	898.1
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	1027.2
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	1149.7
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	185.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	4203.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	296.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	259.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	742.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	191.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	179.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	282.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	28.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-23	244.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	769.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	573.0
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	2257.9
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	2031.1

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_1	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(O)OC[C@H](CO)O[Si](C)(C)C	standard non polar	2025-10-24	2194.32
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_2	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(O)OC[C@@H](O)CO[Si](C)(C)C	standard non polar	2025-10-24	483.206
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_3	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(CCCCCCCCC)O[Si](C)(C)C)COP(=O)(O)OC[C@@H](O)CO	standard non polar	2025-10-24	2372.82
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_4	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(OC[C@@H](O)CO)O[Si](C)(C)C	standard non polar	2025-10-24	1742.08
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_5	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(CCCCCCCCC)O[Si](C)(C)C)COP(=O)(O)OC[C@H](CO)O[Si](C)(C)C	standard non polar	2025-10-24	2464.57
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_6	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(O)OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	1474.08
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_7	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(OC[C@H](CO)O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	786.706
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_8	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(CCCCCCCCC)O[Si](C)(C)C)COP(=O)(O)OC[C@@H](O)CO[Si](C)(C)C	standard non polar	2025-10-24	2602.65
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_9	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(OC[C@@H](O)CO[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	2461.41
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_10	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(CCCCCCCCC)O[Si](C)(C)C)COP(=O)(OC[C@@H](O)CO)O[Si](C)(C)C	standard non polar	2025-10-24	2383.54
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_11	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(CCCCCCCCC)O[Si](C)(C)C)COP(=O)(O)OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	2608.57
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_12	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(CCCCCCCCC)O[Si](C)(C)C)COP(=O)(OC[C@H](CO)O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	1696.0
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_13	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)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	1711.95
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_14	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(CCCCCCCCC)O[Si](C)(C)C)COP(=O)(OC[C@@H](O)CO[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	852.826
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_1	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(O)OC[C@H](CO)O[Si](C)(C)C	standard polar	2025-10-24	2470.06
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_2	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(O)OC[C@@H](O)CO[Si](C)(C)C	standard polar	2025-10-24	2553.09
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_3	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(CCCCCCCCC)O[Si](C)(C)C)COP(=O)(O)OC[C@@H](O)CO	standard polar	2025-10-24	1953.07
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_4	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(OC[C@@H](O)CO)O[Si](C)(C)C	standard polar	2025-10-24	1898.73
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_5	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(CCCCCCCCC)O[Si](C)(C)C)COP(=O)(O)OC[C@H](CO)O[Si](C)(C)C	standard polar	2025-10-24	1162.18
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_6	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(O)OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	579.109
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_7	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(OC[C@H](CO)O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	1041.25
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_8	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(CCCCCCCCC)O[Si](C)(C)C)COP(=O)(O)OC[C@@H](O)CO[Si](C)(C)C	standard polar	2025-10-24	2193.34
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_9	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(OC[C@@H](O)CO[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	1427.31
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_10	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(CCCCCCCCC)O[Si](C)(C)C)COP(=O)(OC[C@@H](O)CO)O[Si](C)(C)C	standard polar	2025-10-24	1710.27
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_11	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(CCCCCCCCC)O[Si](C)(C)C)COP(=O)(O)OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2803.15
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_12	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(CCCCCCCCC)O[Si](C)(C)C)COP(=O)(OC[C@H](CO)O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	1911.49
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_13	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)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	1204.05
Gas Chromatography	PG(12:0(3-OH)/16:0)_TMS_14	CCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CC(CCCCCCCCC)O[Si](C)(C)C)COP(=O)(OC[C@@H](O)CO[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	363.131

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

Not Available

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
MMDBr0021264	PGP(16:0/12:0(3-OH))	PG(12:0(3-OH)/16:0)	Phosphatidylglycerophosphatase B	Dephosphorylation	PathBank	31602464
MMDBr0021265	PE(16:0/12:0(3-OH))	Ethanolamine	Cardiolipin synthase C	Synthesis	PathBank	31602464
MMDBr0021267	PG(12:0(3-OH)/16:0)	Glycerol	Cardiolipin synthase A	Synthesis	PathBank	31602464
MMDBr0037775	PG(12:0(3-OH)/16:0)	3-Hydroxydodecanoic 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

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for PG(12:0(3-OH)/16:0) (MMDBc0031488)

MOL for #<Metabolite:0x00005643239d2dc8>

3D MOL for #<Metabolite:0x00005643239d2dc8>

3D SDF for #<Metabolite:0x00005643239d2dc8>

3D-SDF for #<Metabolite:0x00005643239d2dc8>

PDB for #<Metabolite:0x00005643239d2dc8>

3D PDB for #<Metabolite:0x00005643239d2dc8>

SMILES for #<Metabolite:0x00005643239d2dc8>

INCHI for #<Metabolite:0x00005643239d2dc8>

Structure for #<Metabolite:0x00005643239d2dc8>

3D Structure for #<Metabolite:0x00005643239d2dc8>