MiMeDB: Showing metabocard for PE(12:0(3-OH)/17:0cycw7c) (MMDBc0031261)

Microbial

Human

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 00:42:05 UTC

Update Date

2022-08-31 18:08:31 UTC

Metabolite ID

MMDBc0031261

Metabolite Identification

Common Name

PE(12:0(3-OH)/17:0cycw7c)

Description

PE(12:0(3-OH)/17:0cycw7c) is a phosphatidylethanolamine. It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 atoms. PE(12:0(3-OH)/17:0cycw7c), in particular, consists of one 3-hydroxydodecanoyl chain to the C-1 atom, and one heptadec-9-10-cyclo-anoyl to the C-2 atom. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS.

Structure

MOL SDF PDB SMILES InChI

PE(12:0(3-OH)/17:0cycw7)
  Mrv1652308101903232D          

 46 46  0  0  1  0            999 V2000
   19.3839   -5.5239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7088   -5.9135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.0337   -5.5239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0590   -5.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3586   -5.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1819   -6.6932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7340   -5.5239    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.3443   -4.8487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1238   -6.1990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4092   -5.1341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0843   -5.5239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7594   -5.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4345   -5.5239    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2965   -6.7228    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.6440   -5.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6440   -4.7296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9299   -5.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2157   -5.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2157   -4.7296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5016   -5.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7875   -5.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0734   -5.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3593   -5.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6452   -5.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9311   -5.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2170   -5.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5028   -5.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7887   -5.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4675   -7.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4675   -7.8771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7534   -6.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0392   -7.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3251   -6.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6110   -7.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8969   -6.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1828   -7.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4686   -6.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7545   -7.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0404   -6.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3263   -7.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6122   -6.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8981   -7.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1840   -6.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4698   -7.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7557   -6.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0416   -7.1057    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 15  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
 13 12  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  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
 29  6  1  0  0  0  0
 29 30  2  0  0  0  0
 29 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
 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
 38 40  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
 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
M  END

PE(12:0(3-OH)/17:0cycw7)
  Mrv1652308101903232D          

 46 46  0  0  1  0            999 V2000
   19.3839   -5.5239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7088   -5.9135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.0337   -5.5239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0590   -5.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3586   -5.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1819   -6.6932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7340   -5.5239    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.3443   -4.8487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1238   -6.1990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4092   -5.1341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0843   -5.5239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7594   -5.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4345   -5.5239    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2965   -6.7228    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.6440   -5.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6440   -4.7296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9299   -5.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2157   -5.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2157   -4.7296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5016   -5.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7875   -5.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0734   -5.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3593   -5.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6452   -5.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9311   -5.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2170   -5.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5028   -5.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7887   -5.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4675   -7.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4675   -7.8771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7534   -6.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0392   -7.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3251   -6.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6110   -7.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8969   -6.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1828   -7.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4686   -6.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7545   -7.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0404   -6.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3263   -7.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6122   -6.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8981   -7.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1840   -6.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4698   -7.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7557   -6.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0416   -7.1057    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 15  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
 13 12  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  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
 29  6  1  0  0  0  0
 29 30  2  0  0  0  0
 29 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
 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
 38 40  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
 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
M  END
> <DATABASE_ID>
MMDBc0031261

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](COC(=O)CC(O)CCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCC1CC1CCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C34H66NO9P/c1-3-5-7-9-10-13-17-21-31(36)26-34(38)41-27-32(28-43-45(39,40)42-24-23-35)44-33(37)22-18-14-11-12-16-20-30-25-29(30)19-15-8-6-4-2/h29-32,36H,3-28,35H2,1-2H3,(H,39,40)/t29?,30?,31?,32-/m1/s1

> <INCHI_KEY>
CKPSPCARDZUMFL-KIHBOBKYSA-N

> <FORMULA>
C34H66NO9P

> <MOLECULAR_WEIGHT>
663.874

> <EXACT_MASS>
663.447519707

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
111

> <JCHEM_AVERAGE_POLARIZABILITY>
78.33768309015787

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-aminoethoxy)[(2R)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-3-[(3-hydroxydodecanoyl)oxy]propoxy]phosphinic acid

> <ALOGPS_LOGP>
6.08

> <JCHEM_LOGP>
7.107573256702926

> <ALOGPS_LOGS>
-6.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.00011509166211

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8688003136232716

> <JCHEM_PKA_STRONGEST_BASIC>
9.999924995252952

> <JCHEM_POLAR_SURFACE_AREA>
154.60999999999999

> <JCHEM_REFRACTIVITY>
176.8094

> <JCHEM_ROTATABLE_BOND_COUNT>
34

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.67e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-aminoethoxy((2R)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-3-[(3-hydroxydodecanoyl)oxy]propoxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-AUG-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PE(12:0(3-OH)/17:0cycw7)                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-AUG-19         0                                  
HETATM    1  C   UNK     0      36.183 -10.311   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      34.923 -11.039   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      33.663 -10.311   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      37.443 -11.039   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      32.403 -11.039   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      33.940 -12.494   0.000  0.00  0.00           O+0
HETATM    7  P   UNK     0      38.703 -10.311   0.000  0.00  0.00           P+0
HETATM    8  O   UNK     0      37.976  -9.051   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      39.431 -11.571   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      39.964  -9.584   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      41.224 -10.311   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      42.484  -9.584   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      43.744 -10.311   0.000  0.00  0.00           N+0
HETATM   14  H   UNK     0      36.020 -12.549   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0      31.069 -10.269   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      31.069  -8.829   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      29.736 -11.040   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.403 -10.269   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      28.403  -8.829   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      27.070 -11.040   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.737 -10.269   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      24.404 -11.040   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      23.071 -10.269   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      21.738 -11.040   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.405 -10.269   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      19.072 -11.040   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.739 -10.269   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.406 -11.040   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      32.606 -13.264   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      32.606 -14.704   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      31.273 -12.493   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      29.940 -13.264   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      28.607 -12.493   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      27.274 -13.264   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      25.941 -12.493   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      24.608 -13.264   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      23.275 -12.493   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      21.942 -13.264   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      20.609 -12.493   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      19.276 -13.264   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      17.943 -12.493   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      16.610 -13.264   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      15.277 -12.493   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      13.944 -13.264   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      12.611 -12.493   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      11.278 -13.264   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   15                                                       
CONECT    6    2   29                                                       
CONECT    7    4    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14    2                                                            
CONECT   15    5   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   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                                                            
CONECT   29    6   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38   40                                                       
CONECT   40   38   39   41                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45                                                            
MASTER        0    0    0    0    0    0    0    0   46    0   92    0
END

Synonyms

Not Available

Molecular Formula

C₃₄H₆₆NO₉P

Average Mass

663.874

Monoisotopic Mass

663.447519707

IUPAC Name

(2-aminoethoxy)[(2R)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-3-[(3-hydroxydodecanoyl)oxy]propoxy]phosphinic acid

Traditional Name

2-aminoethoxy((2R)-2-{[8-(2-hexylcyclopropyl)octanoyl]oxy}-3-[(3-hydroxydodecanoyl)oxy]propoxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](COC(=O)CC(O)CCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCC1CC1CCCCCC

InChI Identifier

InChI=1S/C34H66NO9P/c1-3-5-7-9-10-13-17-21-31(36)26-34(38)41-27-32(28-43-45(39,40)42-24-23-35)44-33(37)22-18-14-11-12-16-20-30-25-29(30)19-15-8-6-4-2/h29-32,36H,3-28,35H2,1-2H3,(H,39,40)/t29?,30?,31?,32-/m1/s1

InChI Key

CKPSPCARDZUMFL-KIHBOBKYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphatidylethanolamines. These are glycerophosphoetahnolamines in which two fatty acids are bonded to the glycerol moiety through ester linkages.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoethanolamines

Direct Parent

Phosphatidylethanolamines

Alternative Parents

Substituents

Diacylglycero-3-phosphoethanolamine
Phosphoethanolamine
Dialkyl phosphate
Fatty acid ester
Beta-hydroxy acid
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Hydroxy acid
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Alcohol
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	0.00027 g/L	ALOGPS
logP	6.08	ALOGPS
logP	7.11	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	10	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	154.61 Å²	ChemAxon
Rotatable Bond Count	34	ChemAxon
Refractivity	176.81 m³·mol⁻¹	ChemAxon
Polarizability	78.34 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_3) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0007-9221102000-c652fe48e30bbb84e94f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9320011000-0b6819a9fa07ccf28f21	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9340000000-39164d0b10c81771eee7	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-02td-1972106000-71d98f22744ff13007eb	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00mn-4940101000-f62d760a817b21824b9c	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9310000000-0ab2a3434e695abb79a0	2015-09-15	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	310.9
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	91.9
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	840.8
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	918.0
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	1088.6
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	181.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	3582.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	547.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	250.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	742.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	134.9
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	283.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	40.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-23	234.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	767.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	550.3
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	2029.4
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1915.9

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	PE(12:0(3-OH)/17:0cycw7c)_TMS_1	CCCCCCCCCC(CC(=O)OC[C@H](COP(=O)(O)OCCN)OC(=O)CCCCCCCC1CC1CCCCCC)O[Si](C)(C)C	standard non polar	2025-10-24	905.408
Gas Chromatography	PE(12:0(3-OH)/17:0cycw7c)_TMS_2	CCCCCCCCCC(O)CC(=O)OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C)OC(=O)CCCCCCCC1CC1CCCCCC	standard non polar	2025-10-24	376.526
Gas Chromatography	PE(12:0(3-OH)/17:0cycw7c)_TMS_3	CCCCCCCCCC(O)CC(=O)OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C)OC(=O)CCCCCCCC1CC1CCCCCC	standard non polar	2025-10-24	2204.08
Gas Chromatography	PE(12:0(3-OH)/17:0cycw7c)_TMS_4	CCCCCCCCCC(CC(=O)OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C)OC(=O)CCCCCCCC1CC1CCCCCC)O[Si](C)(C)C	standard non polar	2025-10-24	1462.64
Gas Chromatography	PE(12:0(3-OH)/17:0cycw7c)_TMS_5	CCCCCCCCCC(CC(=O)OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C)OC(=O)CCCCCCCC1CC1CCCCCC)O[Si](C)(C)C	standard non polar	2025-10-24	1714.53
Gas Chromatography	PE(12:0(3-OH)/17:0cycw7c)_TMS_6	CCCCCCCCCC(O)CC(=O)OC[C@H](COP(=O)(OCCN[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCC1CC1CCCCCC	standard non polar	2025-10-24	2712.21
Gas Chromatography	PE(12:0(3-OH)/17:0cycw7c)_TMS_7	CCCCCCCCCC(O)CC(=O)OC[C@H](COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C)OC(=O)CCCCCCCC1CC1CCCCCC	standard non polar	2025-10-24	741.716
Gas Chromatography	PE(12:0(3-OH)/17:0cycw7c)_TMS_8	CCCCCCCCCC(CC(=O)OC[C@H](COP(=O)(OCCN[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCC1CC1CCCCCC)O[Si](C)(C)C	standard non polar	2025-10-24	2652.83
Gas Chromatography	PE(12:0(3-OH)/17:0cycw7c)_TMS_9	CCCCCCCCCC(CC(=O)OC[C@H](COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C)OC(=O)CCCCCCCC1CC1CCCCCC)O[Si](C)(C)C	standard non polar	2025-10-24	1102.78
Gas Chromatography	PE(12:0(3-OH)/17:0cycw7c)_TMS_10	CCCCCCCCCC(O)CC(=O)OC[C@H](COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCC1CC1CCCCCC	standard non polar	2025-10-24	2086.31
Gas Chromatography	PE(12:0(3-OH)/17:0cycw7c)_TMS_1	CCCCCCCCCC(CC(=O)OC[C@H](COP(=O)(O)OCCN)OC(=O)CCCCCCCC1CC1CCCCCC)O[Si](C)(C)C	standard polar	2025-10-24	2820.11
Gas Chromatography	PE(12:0(3-OH)/17:0cycw7c)_TMS_2	CCCCCCCCCC(O)CC(=O)OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C)OC(=O)CCCCCCCC1CC1CCCCCC	standard polar	2025-10-24	1641.96
Gas Chromatography	PE(12:0(3-OH)/17:0cycw7c)_TMS_3	CCCCCCCCCC(O)CC(=O)OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C)OC(=O)CCCCCCCC1CC1CCCCCC	standard polar	2025-10-24	2424.71
Gas Chromatography	PE(12:0(3-OH)/17:0cycw7c)_TMS_4	CCCCCCCCCC(CC(=O)OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C)OC(=O)CCCCCCCC1CC1CCCCCC)O[Si](C)(C)C	standard polar	2025-10-24	1468.24
Gas Chromatography	PE(12:0(3-OH)/17:0cycw7c)_TMS_5	CCCCCCCCCC(CC(=O)OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C)OC(=O)CCCCCCCC1CC1CCCCCC)O[Si](C)(C)C	standard polar	2025-10-24	3294.47
Gas Chromatography	PE(12:0(3-OH)/17:0cycw7c)_TMS_6	CCCCCCCCCC(O)CC(=O)OC[C@H](COP(=O)(OCCN[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCC1CC1CCCCCC	standard polar	2025-10-24	1757.38
Gas Chromatography	PE(12:0(3-OH)/17:0cycw7c)_TMS_7	CCCCCCCCCC(O)CC(=O)OC[C@H](COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C)OC(=O)CCCCCCCC1CC1CCCCCC	standard polar	2025-10-24	1855.37
Gas Chromatography	PE(12:0(3-OH)/17:0cycw7c)_TMS_8	CCCCCCCCCC(CC(=O)OC[C@H](COP(=O)(OCCN[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCC1CC1CCCCCC)O[Si](C)(C)C	standard polar	2025-10-24	3674.29
Gas Chromatography	PE(12:0(3-OH)/17:0cycw7c)_TMS_9	CCCCCCCCCC(CC(=O)OC[C@H](COP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C)OC(=O)CCCCCCCC1CC1CCCCCC)O[Si](C)(C)C	standard polar	2025-10-24	1907.22
Gas Chromatography	PE(12:0(3-OH)/17:0cycw7c)_TMS_10	CCCCCCCCCC(O)CC(=O)OC[C@H](COP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCC1CC1CCCCCC	standard polar	2025-10-24	2643.38

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
MMDBr0018957	PS(12:0(3-OH)/17:0cycw7c)	PE(12:0(3-OH)/17:0cycw7c)	Phosphatidylserine decarboxylase proenzyme	Carboxylation	PathBank	31602464
MMDBr0018958	PG(12:0/12:0)	Ethanolamine	Cardiolipin synthase C	Synthesis	PathBank	31602464
MMDBr0021861	PE(12:0(3-OH)/17:0cycw7c)	Ethanolamine	Cardiolipin synthase C	Synthesis	PathBank	31602464
MMDBr0038410	PE(12:0(3-OH)/17:0cycw7c)	8‐(2‐Hexylcyclopropyl)octanoic acid	Lipid droplet phospholipase 1	Hydrolysis	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 PE(12:0(3-OH)/17:0cycw7c) (MMDBc0031261)

MOL for #<Metabolite:0x00007f9ad180eee0>

3D MOL for #<Metabolite:0x00007f9ad180eee0>

3D SDF for #<Metabolite:0x00007f9ad180eee0>

3D-SDF for #<Metabolite:0x00007f9ad180eee0>

PDB for #<Metabolite:0x00007f9ad180eee0>

3D PDB for #<Metabolite:0x00007f9ad180eee0>

SMILES for #<Metabolite:0x00007f9ad180eee0>

INCHI for #<Metabolite:0x00007f9ad180eee0>

Structure for #<Metabolite:0x00007f9ad180eee0>

3D Structure for #<Metabolite:0x00007f9ad180eee0>