MiMeDB: Showing metabocard for PS(19:iso/15:0) (MMDBc0031417)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 00:48:09 UTC

Update Date

2022-08-31 18:10:28 UTC

Metabolite ID

MMDBc0031417

Metabolite Identification

Common Name

PS(19:iso/15:0)

Description

PS(19:iso/15:0) 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(19:iso/15:0), in particular, consists of one 17-methylocatdecanoyl chain to the C-1 atom, and one pentadecanoyl 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 10241215422D          

 52 51  0  0  1  0            999 V2000
   33.8980   14.6210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.8980   15.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6124   15.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3269   15.4460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3269   14.6210    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   36.1519   14.6210    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   34.5019   14.6210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3269   13.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.6124   13.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6124   12.5585    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   33.8980   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1835   12.5585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4690   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4690   11.3210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7546   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0401   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3256   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6112   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8967   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1822   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4677   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7533   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0388   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3243   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6099   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8954   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1809   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4664   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7520   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0375   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3230   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0375   11.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3269   12.1460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.0414   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0414   13.3835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.7559   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4703   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1848   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8993   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6137   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3282   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0427   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7572   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4716   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1861   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.9006   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.6150   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.3295   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.0440   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1835   15.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1835   16.6835    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   32.4690   15.4460    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
 17 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
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 10 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 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
 48 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 10241215422D          

 52 51  0  0  1  0            999 V2000
   33.8980   14.6210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.8980   15.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6124   15.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3269   15.4460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3269   14.6210    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   36.1519   14.6210    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   34.5019   14.6210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3269   13.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.6124   13.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6124   12.5585    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   33.8980   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1835   12.5585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4690   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4690   11.3210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7546   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0401   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3256   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6112   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8967   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1822   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4677   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7533   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0388   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3243   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6099   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8954   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1809   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4664   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7520   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0375   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3230   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0375   11.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3269   12.1460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.0414   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0414   13.3835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.7559   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4703   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1848   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8993   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6137   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3282   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0427   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7572   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4716   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1861   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.9006   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.6150   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.3295   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.0440   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1835   15.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1835   16.6835    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   32.4690   15.4460    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
 17 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
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 10 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 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
 48 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>
MMDBc0031417

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCC(C)C)COP([O-])(=O)OCC(N)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C40H78NO10P/c1-4-5-6-7-8-9-10-15-19-22-25-28-31-39(43)51-36(33-49-52(46,47)50-34-37(41)40(44)45)32-48-38(42)30-27-24-21-18-16-13-11-12-14-17-20-23-26-29-35(2)3/h35-37H,4-34,41H2,1-3H3,(H,44,45)(H,46,47)/p-2/t36-,37?/m1/s1

> <INCHI_KEY>
JWIQDPGAOBKMHO-RKROREJRSA-L

> <FORMULA>
C40H76NO10P

> <MOLECULAR_WEIGHT>
762.0059

> <EXACT_MASS>
761.520684169

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
90.64571322830905

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
7.73

> <JCHEM_LOGP>
10.225094526899271

> <ALOGPS_LOGS>
-6.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
2.17839601565545

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4680339991787514

> <JCHEM_PKA_STRONGEST_BASIC>
9.376604467850063

> <JCHEM_POLAR_SURFACE_AREA>
177.34

> <JCHEM_REFRACTIVITY>
215.69880000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
41

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.50e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-3-{[(2R)-3-[(17-methyloctadecanoyl)oxy]-2-(pentadecanoyloxy)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      63.276  27.293   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      63.276  28.833   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      64.610  29.603   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      65.944  28.833   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0      65.944  27.293   0.000  0.00  0.00           P+0
HETATM    6  O   UNK     0      67.484  27.293   0.000  0.00  0.00           O-1
HETATM    7  O   UNK     0      64.404  27.293   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      65.944  25.753   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      64.610  24.983   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      64.610  23.443   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      63.276  22.673   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      61.943  23.443   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      60.609  22.673   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      60.609  21.133   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      59.275  23.443   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      57.942  22.673   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      56.608  23.443   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      55.274  22.673   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      53.941  23.443   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      52.607  22.673   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      51.273  23.443   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      49.939  22.673   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      48.606  23.443   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      47.272  22.673   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      45.938  23.443   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      44.605  22.673   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      43.271  23.443   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      41.937  22.673   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      40.604  23.443   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      39.270  22.673   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      37.936  23.443   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      39.270  21.133   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      65.944  22.673   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      67.277  23.443   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      67.277  24.983   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      68.611  22.673   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      69.945  23.443   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      71.278  22.673   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      72.612  23.443   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      73.946  22.673   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      75.279  23.443   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      76.613  22.673   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      77.947  23.443   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      79.280  22.673   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      80.614  23.443   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      81.948  22.673   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      83.281  23.443   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      84.615  22.673   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      85.949  23.443   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      61.943  29.603   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      61.943  31.143   0.000  0.00  0.00           O-1
HETATM   52  O   UNK     0      60.609  28.833   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   33                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   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   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   10   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   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                                                            
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

C₄₀H₇₆NO₁₀P

Average Mass

762.0059

Monoisotopic Mass

761.520684169

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCC(C)C)COP([O-])(=O)OCC(N)C([O-])=O

InChI Identifier

InChI=1S/C40H78NO10P/c1-4-5-6-7-8-9-10-15-19-22-25-28-31-39(43)51-36(33-49-52(46,47)50-34-37(41)40(44)45)32-48-38(42)30-27-24-21-18-16-13-11-12-14-17-20-23-26-29-35(2)3/h35-37H,4-34,41H2,1-3H3,(H,44,45)(H,46,47)/p-2/t36-,37?/m1/s1

InChI Key

JWIQDPGAOBKMHO-RKROREJRSA-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
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Amino acid
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
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	8.5e-05 g/L	ALOGPS
logP	7.73	ALOGPS
logP	10.23	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Acidic)	1.47	ChemAxon
pKa (Strongest Basic)	9.38	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	177.34 Å²	ChemAxon
Rotatable Bond Count	41	ChemAxon
Refractivity	215.7 m³·mol⁻¹	ChemAxon
Polarizability	90.65 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	splash10-03dl-6250000900-b9375364f67179385726	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000l-9440000300-7d7dcf54555727bcf773	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9530000000-3cb982ee7cb15a54b981	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01ow-3090000500-0ef211f81760eb833df1	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-1090000100-16ed87da81d3399798de	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002e-4190000000-fff7e2df1e29ce270673	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	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 ]

Showing metabocard for PS(19:iso/15:0) (MMDBc0031417)

MOL for #<Metabolite:0x00007fed149e8f78>

3D MOL for #<Metabolite:0x00007fed149e8f78>

3D SDF for #<Metabolite:0x00007fed149e8f78>

3D-SDF for #<Metabolite:0x00007fed149e8f78>

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Structure for #<Metabolite:0x00007fed149e8f78>

3D Structure for #<Metabolite:0x00007fed149e8f78>