MiMeDB: Showing metabocard for PS(12:0(3-OH)/18:1(9Z)) (MMDBc0031358)

Microbial

Human

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 00:45:44 UTC

Update Date

2022-08-31 18:09:36 UTC

Metabolite ID

MMDBc0031358

Metabolite Identification

Common Name

PS(12:0(3-OH)/18:1(9Z))

Description

PS(12:0(3-OH)/18:1(9Z)) is a phosphatidylserine. It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 atoms.. PS(12:0(3-OH)/18:1(9Z)), in particular, consists of one 3-hydroxydodecanoyl chain to the C-1 atom, and one 9Z-octadecenoyl to the C-2 atom. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine. 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. Phosphatidylserines typically carry a net charge of -1 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. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE.

Structure

MOL SDF PDB SMILES InChI

PS(12:0(3-OH)/18:1(9Z))
  Mrv1652308101903212D          

 51 50  0  0  1  0            999 V2000
   21.1276   -3.1272    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.2288   -4.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5536   -4.5894    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.8784   -4.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9038   -4.5894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2032   -4.5894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0267   -5.3690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5790   -4.1996    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   19.1892   -3.5244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9688   -4.8747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2541   -3.8098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9292   -4.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6043   -3.8098    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.1413   -5.3987    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.3005   -3.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0978   -3.6582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3005   -2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1079   -4.4925    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4888   -4.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4888   -3.4055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7747   -4.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0605   -4.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0605   -3.4055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3464   -4.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6322   -4.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9181   -4.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2039   -4.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4898   -4.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7757   -4.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0615   -4.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3474   -4.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6333   -4.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3122   -5.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3122   -6.5530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5981   -5.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8839   -5.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1698   -5.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4556   -5.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7415   -5.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0273   -5.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3132   -5.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5991   -5.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7741   -5.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0600   -5.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3458   -5.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6317   -5.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9175   -5.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2034   -5.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4892   -5.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7751   -5.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0610   -5.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  3  7  1  0  0  0  0
  3 14  1  1  0  0  0
  4  3  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  6 19  1  0  0  0  0
  8  5  1  0  0  0  0
  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
 11  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 13 15  1  0  0  0  0
 13 18  1  0  0  0  0
 13  1  1  6  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 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
 33  7  1  0  0  0  0
 33 34  2  0  0  0  0
 33 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
 42 43  2  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
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
M  END

PS(12:0(3-OH)/18:1(9Z))
  Mrv1652308101903212D          

 51 50  0  0  1  0            999 V2000
   21.1276   -3.1272    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.2288   -4.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5536   -4.5894    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.8784   -4.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9038   -4.5894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2032   -4.5894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0267   -5.3690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5790   -4.1996    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   19.1892   -3.5244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9688   -4.8747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2541   -3.8098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9292   -4.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6043   -3.8098    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.1413   -5.3987    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.3005   -3.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0978   -3.6582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3005   -2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1079   -4.4925    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4888   -4.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4888   -3.4055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7747   -4.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0605   -4.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0605   -3.4055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3464   -4.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6322   -4.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9181   -4.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2039   -4.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4898   -4.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7757   -4.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0615   -4.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3474   -4.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6333   -4.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3122   -5.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3122   -6.5530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5981   -5.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8839   -5.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1698   -5.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4556   -5.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7415   -5.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0273   -5.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3132   -5.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5991   -5.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7741   -5.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0600   -5.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3458   -5.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6317   -5.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9175   -5.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2034   -5.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4892   -5.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7751   -5.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0610   -5.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  3  7  1  0  0  0  0
  3 14  1  1  0  0  0
  4  3  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  6 19  1  0  0  0  0
  8  5  1  0  0  0  0
  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
 11  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 13 15  1  0  0  0  0
 13 18  1  0  0  0  0
 13  1  1  6  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 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
 33  7  1  0  0  0  0
 33 34  2  0  0  0  0
 33 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
 42 43  2  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
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031358

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](COC(=O)CC(O)CCCCCCCCC)(COP(O)(=O)OC[C@]([H])(N)C(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C36H68NO11P/c1-3-5-7-9-11-12-13-14-15-16-17-18-20-22-24-26-34(39)48-32(29-46-49(43,44)47-30-33(37)36(41)42)28-45-35(40)27-31(38)25-23-21-19-10-8-6-4-2/h14-15,31-33,38H,3-13,16-30,37H2,1-2H3,(H,41,42)(H,43,44)/b15-14-/t31?,32-,33+/m1/s1

> <INCHI_KEY>
PEMVHLPHPDHBKB-JWIXMMIBSA-N

> <FORMULA>
C36H68NO11P

> <MOLECULAR_WEIGHT>
721.91

> <EXACT_MASS>
721.452999012

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
117

> <JCHEM_AVERAGE_POLARIZABILITY>
83.23271350332774

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-({hydroxy[(2R)-3-[(3-hydroxydodecanoyl)oxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphoryl}oxy)propanoic acid

> <ALOGPS_LOGP>
3.18

> <JCHEM_LOGP>
7.011636711924548

> <ALOGPS_LOGS>
-6.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
2.178396015638225

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4680339991090863

> <JCHEM_PKA_STRONGEST_BASIC>
9.376603434428583

> <JCHEM_POLAR_SURFACE_AREA>
191.91

> <JCHEM_REFRACTIVITY>
190.2639

> <JCHEM_ROTATABLE_BOND_COUNT>
37

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.52e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-3-{[hydroxy((2R)-3-[(3-hydroxydodecanoyl)oxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy)phosphoryl]oxy}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-AUG-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PS(12:0(3-OH)/18:1(9Z))                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-AUG-19         0                                  
HETATM    1  H   UNK     0      39.438  -5.837   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      34.027  -7.839   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      32.767  -8.567   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      31.506  -7.839   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      35.287  -8.567   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      30.246  -8.567   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      31.783 -10.022   0.000  0.00  0.00           O+0
HETATM    8  P   UNK     0      36.547  -7.839   0.000  0.00  0.00           P+0
HETATM    9  O   UNK     0      35.820  -6.579   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      37.275  -9.100   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      37.808  -7.112   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      39.068  -7.839   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      40.328  -7.112   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0      33.864 -10.078   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0      41.628  -5.967   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      43.116  -6.829   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      41.628  -4.390   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      41.268  -8.386   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      28.912  -7.797   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      28.912  -6.357   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      27.579  -8.568   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.246  -7.797   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      26.246  -6.357   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      24.913  -8.568   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      23.580  -7.797   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.247  -8.568   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.914  -7.797   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      19.581  -8.568   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      18.248  -7.797   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.915  -8.568   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.582  -7.797   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.249  -8.568   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      30.449 -10.792   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      30.449 -12.232   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      29.116 -10.021   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      27.783 -10.792   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      26.450 -10.021   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      25.117 -10.792   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      23.784 -10.021   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      22.451 -10.792   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      21.118 -10.021   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      19.785 -10.792   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      18.245 -10.792   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      16.912 -10.021   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      15.579 -10.792   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      14.246 -10.021   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      12.913 -10.792   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      11.580 -10.021   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      10.247 -10.792   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       8.914 -10.021   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       7.580 -10.792   0.000  0.00  0.00           C+0
CONECT    1   13                                                            
CONECT    2    3    5                                                       
CONECT    3    2    7   14    4                                             
CONECT    4    3    6                                                       
CONECT    5    2    8                                                       
CONECT    6    4   19                                                       
CONECT    7    3   33                                                       
CONECT    8    5    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   15   18    1                                             
CONECT   14    3                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13                                                            
CONECT   19    6   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   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                                                            
CONECT   33    7   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   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                                                       
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   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  100    0
END

Synonyms

Not Available

Molecular Formula

C₃₆H₆₈NO₁₁P

Average Mass

721.91

Monoisotopic Mass

721.452999012

IUPAC Name

(2S)-2-amino-3-({hydroxy[(2R)-3-[(3-hydroxydodecanoyl)oxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphoryl}oxy)propanoic acid

Traditional Name

(2S)-2-amino-3-{[hydroxy((2R)-3-[(3-hydroxydodecanoyl)oxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy)phosphoryl]oxy}propanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](COC(=O)CC(O)CCCCCCCCC)(COP(O)(=O)OC[C@]([H])(N)C(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC

InChI Identifier

InChI=1S/C36H68NO11P/c1-3-5-7-9-11-12-13-14-15-16-17-18-20-22-24-26-34(39)48-32(29-46-49(43,44)47-30-33(37)36(41)42)28-45-35(40)27-31(38)25-23-21-19-10-8-6-4-2/h14-15,31-33,38H,3-13,16-30,37H2,1-2H3,(H,41,42)(H,43,44)/b15-14-/t31?,32-,33+/m1/s1

InChI Key

PEMVHLPHPDHBKB-JWIXMMIBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphatidylserines. These are glycerophosphoserines 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

Glycerophosphoserines

Direct Parent

Phosphatidylserines

Alternative Parents

Substituents

Diacyl-glycerol-3-phosphoserine
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Tricarboxylic acid or derivatives
Phosphoethanolamine
Fatty acid ester
Beta-hydroxy acid
Dialkyl phosphate
Hydroxy acid
Phosphoric acid ester
Alkyl phosphate
Organic phosphoric acid derivative
Fatty acyl
Secondary alcohol
Carboxylic acid ester
Amino acid
Amino acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Organooxygen compound
Primary amine
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Amine
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Primary aliphatic amine
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	0.00025 g/L	ALOGPS
logP	3.18	ALOGPS
logP	7.01	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Acidic)	1.47	ChemAxon
pKa (Strongest Basic)	9.38	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	191.91 Å²	ChemAxon
Rotatable Bond Count	37	ChemAxon
Refractivity	190.26 m³·mol⁻¹	ChemAxon
Polarizability	83.23 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_5) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	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 (retained)	2025-10-23	400.5
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	106.4
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	898.3
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	853.2
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	1081.7
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	176.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	3862.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	628.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	274.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	698.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	125.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	185.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	277.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	15.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-23	273.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	761.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	573.6
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	2047.6
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	2064.6

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	PS(12:0(3-OH)/18:1(9Z))_TMS_1	CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CC(CCCCCCCCC)O[Si](C)(C)C)COP(=O)(O)OC[C@H](N)C(=O)O	standard non polar	2025-10-24	3186.8
Gas Chromatography	PS(12:0(3-OH)/18:1(9Z))_TMS_2	CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(O)OC[C@H](N)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1715.63
Gas Chromatography	PS(12:0(3-OH)/18:1(9Z))_TMS_3	CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(OC[C@H](N)C(=O)O)O[Si](C)(C)C	standard non polar	2025-10-24	2318.22
Gas Chromatography	PS(12:0(3-OH)/18:1(9Z))_TMS_4	CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(O)OC[C@H](N[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	1164.73
Gas Chromatography	PS(12:0(3-OH)/18:1(9Z))_TMS_5	CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CC(CCCCCCCCC)O[Si](C)(C)C)COP(=O)(O)OC[C@H](N)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1347.34
Gas Chromatography	PS(12:0(3-OH)/18:1(9Z))_TMS_6	CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CC(CCCCCCCCC)O[Si](C)(C)C)COP(=O)(OC[C@H](N)C(=O)O)O[Si](C)(C)C	standard non polar	2025-10-24	1527.84
Gas Chromatography	PS(12:0(3-OH)/18:1(9Z))_TMS_7	CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CC(CCCCCCCCC)O[Si](C)(C)C)COP(=O)(O)OC[C@H](N[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	2018.04
Gas Chromatography	PS(12:0(3-OH)/18:1(9Z))_TMS_8	CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(OC[C@H](N)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	3553.98
Gas Chromatography	PS(12:0(3-OH)/18:1(9Z))_TMS_9	CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(O)OC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	481.207
Gas Chromatography	PS(12:0(3-OH)/18:1(9Z))_TMS_10	CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(OC[C@H](N[Si](C)(C)C)C(=O)O)O[Si](C)(C)C	standard non polar	2025-10-24	1270.01
Gas Chromatography	PS(12:0(3-OH)/18:1(9Z))_TMS_11	CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(O)OC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2821.89
Gas Chromatography	PS(12:0(3-OH)/18:1(9Z))_TMS_1	CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CC(CCCCCCCCC)O[Si](C)(C)C)COP(=O)(O)OC[C@H](N)C(=O)O	standard polar	2025-10-24	2777.98
Gas Chromatography	PS(12:0(3-OH)/18:1(9Z))_TMS_2	CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(O)OC[C@H](N)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	3281.24
Gas Chromatography	PS(12:0(3-OH)/18:1(9Z))_TMS_3	CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(OC[C@H](N)C(=O)O)O[Si](C)(C)C	standard polar	2025-10-24	2187.8
Gas Chromatography	PS(12:0(3-OH)/18:1(9Z))_TMS_4	CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(O)OC[C@H](N[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	2884.4
Gas Chromatography	PS(12:0(3-OH)/18:1(9Z))_TMS_5	CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CC(CCCCCCCCC)O[Si](C)(C)C)COP(=O)(O)OC[C@H](N)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2354.46
Gas Chromatography	PS(12:0(3-OH)/18:1(9Z))_TMS_6	CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CC(CCCCCCCCC)O[Si](C)(C)C)COP(=O)(OC[C@H](N)C(=O)O)O[Si](C)(C)C	standard polar	2025-10-24	2977.93
Gas Chromatography	PS(12:0(3-OH)/18:1(9Z))_TMS_7	CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CC(CCCCCCCCC)O[Si](C)(C)C)COP(=O)(O)OC[C@H](N[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	2176.66
Gas Chromatography	PS(12:0(3-OH)/18:1(9Z))_TMS_8	CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(OC[C@H](N)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	1661.59
Gas Chromatography	PS(12:0(3-OH)/18:1(9Z))_TMS_9	CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(O)OC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2500.13
Gas Chromatography	PS(12:0(3-OH)/18:1(9Z))_TMS_10	CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(OC[C@H](N[Si](C)(C)C)C(=O)O)O[Si](C)(C)C	standard polar	2025-10-24	2852.64
Gas Chromatography	PS(12:0(3-OH)/18:1(9Z))_TMS_11	CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CC(O)CCCCCCCCC)COP(=O)(O)OC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2556.73

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

This table shows at most 5 pathways. For the full list of associated pathways:

See All Associated Bacterial Pathways

Name	SMPDB/PathBank	Species
Cardiolipin Biosynthesis CL(12:0(3-OH)/18:1(9Z)/12:0(3-OH)/18:1(9Z))
Cardiolipin Biosynthesis CL(14:0/14:0/14:0/14:0)
Cardiolipin Biosynthesis CL(14:0/14:0/14:0/15:0)
Cardiolipin Biosynthesis CL(14:0/14:0/14:0/16:0)
Cardiolipin Biosynthesis CL(14:0/14:0/14:0/16:1(9Z))

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
MMDBr0018802	PS(12:0(3-OH)/18:1(9Z))	PE(12:0(3-OH)/18:1(9Z))	Phosphatidylserine decarboxylase proenzyme	Carboxylation	PathBank	31602464
MMDBr0021865	L-Serine	Cytidine monophosphate	CDP-diacylglycerol--serine O-phosphatidyltransferase	Transfer of CDP-diacylglycerol--serine O-phosphatidyl group	PathBank	31602464

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 PS(12:0(3-OH)/18:1(9Z)) (MMDBc0031358)

MOL for #<Metabolite:0x00007f2e029cd240>

3D MOL for #<Metabolite:0x00007f2e029cd240>

3D SDF for #<Metabolite:0x00007f2e029cd240>

3D-SDF for #<Metabolite:0x00007f2e029cd240>

PDB for #<Metabolite:0x00007f2e029cd240>

3D PDB for #<Metabolite:0x00007f2e029cd240>

SMILES for #<Metabolite:0x00007f2e029cd240>

INCHI for #<Metabolite:0x00007f2e029cd240>

Structure for #<Metabolite:0x00007f2e029cd240>

3D Structure for #<Metabolite:0x00007f2e029cd240>