MiMeDB: Showing metabocard for PS(14:0(3-OH)/19:iso) (MMDBc0031378)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 00:46:30 UTC

Update Date

2022-08-31 18:09:49 UTC

Metabolite ID

MMDBc0031378

Metabolite Identification

Common Name

PS(14:0(3-OH)/19:iso)

Description

PS(14:0(3-OH)/19:iso) 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(14:0(3-OH)/19:iso), in particular, consists of one 3-hydroxytetradecanoyl chain to the C-1 atom, and one 17-methylocatdecanoyl 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


  Mrv0541 10241215392D          

 52 51  0  0  1  0            999 V2000
   30.5171    9.3690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5171    8.5440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8026    8.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0881    8.5440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0881    9.3690    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   28.2631    9.3690    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   29.9131    9.3690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0881   10.1940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8026   10.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8026   11.4315    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   29.0881   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3737   11.4315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6592   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6592   12.6690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9447   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2302   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2302   12.6690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5158   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8013   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0868   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3724   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6579   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9434   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2289   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5145   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8000   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0855   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3711   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5171   11.8440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2315   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2315   10.6065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9460   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6605   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3749   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0894   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8039   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5184   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2328   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9473   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6618   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3762   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0907   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8052   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5197   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2341   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9486   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6631   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3775   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6631   10.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2315    8.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2315    7.3065    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   31.9460    8.5440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 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
 10 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 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
 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
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  1  0  0  0  0
  2 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  2  0  0  0  0
M  CHG  2   6  -1  51  -1
M  END


  Mrv0541 10241215392D          

 52 51  0  0  1  0            999 V2000
   30.5171    9.3690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5171    8.5440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8026    8.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0881    8.5440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0881    9.3690    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   28.2631    9.3690    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   29.9131    9.3690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0881   10.1940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8026   10.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8026   11.4315    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   29.0881   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3737   11.4315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6592   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6592   12.6690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9447   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2302   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2302   12.6690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5158   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8013   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0868   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3724   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6579   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9434   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2289   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5145   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8000   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0855   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3711   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5171   11.8440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2315   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2315   10.6065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9460   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6605   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3749   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0894   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8039   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5184   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2328   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9473   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6618   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3762   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0907   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8052   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5197   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2341   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9486   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6631   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3775   11.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6631   10.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2315    8.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2315    7.3065    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   31.9460    8.5440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 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
 10 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 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
 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
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  1  0  0  0  0
  2 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  2  0  0  0  0
M  CHG  2   6  -1  51  -1
M  END
> <DATABASE_ID>
MMDBc0031378

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCCCCC(O)CC(=O)OC[C@H](COP([O-])(=O)OCC(N)C([O-])=O)OC(=O)CCCCCCCCCCCCCCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C39H76NO11P/c1-4-5-6-7-8-14-18-21-24-27-34(41)29-38(43)48-30-35(31-49-52(46,47)50-32-36(40)39(44)45)51-37(42)28-25-22-19-16-13-11-9-10-12-15-17-20-23-26-33(2)3/h33-36,41H,4-32,40H2,1-3H3,(H,44,45)(H,46,47)/p-2/t34?,35-,36?/m1/s1

> <INCHI_KEY>
JEGOABAWJMQMLJ-OXKMBYBQSA-L

> <FORMULA>
C39H74NO11P

> <MOLECULAR_WEIGHT>
763.9787

> <EXACT_MASS>
763.499948727

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
89.59412267210377

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-{[(2R)-3-[(3-hydroxytetradecanoyl)oxy]-2-[(17-methyloctadecanoyl)oxy]propyl phosphonato]oxy}propanoate

> <ALOGPS_LOGP>
6.89

> <JCHEM_LOGP>
8.549714794924547

> <ALOGPS_LOGS>
-6.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
2.1783960156382274

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4680339991090845

> <JCHEM_PKA_STRONGEST_BASIC>
9.376603434428583

> <JCHEM_POLAR_SURFACE_AREA>
197.56999999999996

> <JCHEM_REFRACTIVITY>
212.61330000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
40

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.51e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-3-{[(2R)-3-[(3-hydroxytetradecanoyl)oxy]-2-[(17-methyloctadecanoyl)oxy]propyl phosphonato]oxy}propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-OCT-12         0                                  
HETATM    1  N   UNK     0      56.965  17.489   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      56.965  15.949   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      55.632  15.179   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      54.298  15.949   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0      54.298  17.489   0.000  0.00  0.00           P+0
HETATM    6  O   UNK     0      52.758  17.489   0.000  0.00  0.00           O-1
HETATM    7  O   UNK     0      55.838  17.489   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      54.298  19.029   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      55.632  19.799   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      55.632  21.339   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      54.298  22.109   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      52.964  21.339   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      51.631  22.109   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      51.631  23.649   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      50.297  21.339   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      48.963  22.109   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      48.963  23.649   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      47.629  21.339   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      46.296  22.109   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      44.962  21.339   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      43.628  22.109   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      42.295  21.339   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      40.961  22.109   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      39.627  21.339   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      38.294  22.109   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      36.960  21.339   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      35.626  22.109   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      34.293  21.339   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      56.965  22.109   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      58.299  21.339   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      58.299  19.799   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      59.633  22.109   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      60.966  21.339   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      62.300  22.109   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      63.634  21.339   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      64.967  22.109   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      66.301  21.339   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      67.635  22.109   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      68.968  21.339   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      70.302  22.109   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      71.636  21.339   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      72.969  22.109   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      74.303  21.339   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      75.637  22.109   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      76.970  21.339   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      78.304  22.109   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      79.638  21.339   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      80.971  22.109   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      79.638  19.799   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      58.299  15.179   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      58.299  13.639   0.000  0.00  0.00           O-1
HETATM   52  O   UNK     0      59.633  15.949   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   50                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   29                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   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   10   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   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                                                       
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   49                                                  
CONECT   48   47                                                            
CONECT   49   47                                                            
CONECT   50    2   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  102    0
END

Synonyms

Not Available

Molecular Formula

C₃₉H₇₄NO₁₁P

Average Mass

763.9787

Monoisotopic Mass

763.499948727

IUPAC Name

2-amino-3-{[(2R)-3-[(3-hydroxytetradecanoyl)oxy]-2-[(17-methyloctadecanoyl)oxy]propyl phosphonato]oxy}propanoate

Traditional Name

2-amino-3-{[(2R)-3-[(3-hydroxytetradecanoyl)oxy]-2-[(17-methyloctadecanoyl)oxy]propyl phosphonato]oxy}propanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCC(O)CC(=O)OC[C@H](COP([O-])(=O)OCC(N)C([O-])=O)OC(=O)CCCCCCCCCCCCCCCC(C)C

InChI Identifier

InChI=1S/C39H76NO11P/c1-4-5-6-7-8-14-18-21-24-27-34(41)29-38(43)48-30-35(31-49-52(46,47)50-32-36(40)39(44)45)51-37(42)28-25-22-19-16-13-11-9-10-12-15-17-20-23-26-33(2)3/h33-36,41H,4-32,40H2,1-3H3,(H,44,45)(H,46,47)/p-2/t34?,35-,36?/m1/s1

InChI Key

JEGOABAWJMQMLJ-OXKMBYBQSA-L

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. 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 positions.

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 or derivatives
Alpha-amino acid
Tricarboxylic acid or derivatives
Phosphoethanolamine
Dialkyl phosphate
Fatty acid ester
Beta-hydroxy acid
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Hydroxy acid
Amino acid
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
Carboxylic acid
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
Organic anion
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	0.00015 g/L	ALOGPS
logP	6.89	ALOGPS
logP	8.55	ChemAxon
logS	-6.7	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	2	ChemAxon
Polar Surface Area	197.57 Å²	ChemAxon
Rotatable Bond Count	40	ChemAxon
Refractivity	212.61 m³·mol⁻¹	ChemAxon
Polarizability	89.59 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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-6240000900-0d772ce34f051dcb5f34	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052u-9440000500-16e013ba53175c256bbf	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9430000000-a6ffad534f93f62ce2cc	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-6240000900-0d772ce34f051dcb5f34	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052u-9440000500-16e013ba53175c256bbf	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9430000000-a6ffad534f93f62ce2cc	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03dm-3190000500-ed457e504ef01c9c7793	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002g-1290000100-30a14806c289453e2175	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002e-4390000000-a95139b340229d8502cb	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

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

Metabolic Reactions

Not Available

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	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	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

References

Synthesis Reference

Not Available

General References

Casadei MA, Manas P, Niven G, Needs E, Mackey BM: Role of membrane fluidity in pressure resistance of Escherichia coli NCTC 8164. Appl Environ Microbiol. 2002 Dec;68(12):5965-72. doi: 10.1128/AEM.68.12.5965-5972.2002. [PubMed:12450817 ]
Kanehisa M, Goto S, Sato Y, Furumichi M, Tanabe M: KEGG for integration and interpretation of large-scale molecular data sets. Nucleic Acids Res. 2012 Jan;40(Database issue):D109-14. doi: 10.1093/nar/gkr988. Epub 2011 Nov 10. [PubMed:22080510 ]
Yuan Y, Leeds JA, Meredith TC: Pseudomonas aeruginosa directly shunts beta-oxidation degradation intermediates into de novo fatty acid biosynthesis. J Bacteriol. 2012 Oct;194(19):5185-96. doi: 10.1128/JB.00860-12. Epub 2012 Jun 29. [PubMed:22753057 ]

Showing metabocard for PS(14:0(3-OH)/19:iso) (MMDBc0031378)

MOL for #<Metabolite:0x00007fece1fc1f90>

3D MOL for #<Metabolite:0x00007fece1fc1f90>

3D SDF for #<Metabolite:0x00007fece1fc1f90>

3D-SDF for #<Metabolite:0x00007fece1fc1f90>

PDB for #<Metabolite:0x00007fece1fc1f90>

3D PDB for #<Metabolite:0x00007fece1fc1f90>

SMILES for #<Metabolite:0x00007fece1fc1f90>

INCHI for #<Metabolite:0x00007fece1fc1f90>

Structure for #<Metabolite:0x00007fece1fc1f90>

3D Structure for #<Metabolite:0x00007fece1fc1f90>