MiMeDB: Showing metabocard for PS(19:iso/19:iso) (MMDBc0031424)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 00:48:28 UTC

Update Date

2022-08-31 18:10:33 UTC

Metabolite ID

MMDBc0031424

Metabolite Identification

Common Name

PS(19:iso/19:iso)

Description

PS(19:iso/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 positions. PS(19:iso/19:iso), in particular, consists of two 17-methylocatdecanoyl chains at positions C-1 and C-2. 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          

 56 55  0  0  1  0            999 V2000
   35.8499   10.7980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.8499    9.9730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1355    9.5605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4210    9.9730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.4210   10.7980    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   33.5960   10.7980    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   35.2460   10.7980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.4210   11.6230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.1355   12.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1355   12.8605    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   34.4210   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7065   12.8605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.9921   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9921   14.0980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.2776   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5631   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8487   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1342   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4197   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7052   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9908   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2763   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5618   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8474   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1329   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4184   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7039   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9895   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2750   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5605   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8461   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5605   14.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8499   13.2730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.5644   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5644   12.0355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.2789   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9934   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7078   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4223   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1368   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8512   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5657   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2802   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9947   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7091   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.4236   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.1381   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.8525   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.5670   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.2815   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.9960   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.7104   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.9960   12.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5644    9.5605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5644    8.7355    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   37.2789    9.9730    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  1  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
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
  2 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  2  0  0  0  0
M  CHG  2   6  -1  55  -1
M  END


  Mrv0541 10241215422D          

 56 55  0  0  1  0            999 V2000
   35.8499   10.7980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.8499    9.9730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1355    9.5605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4210    9.9730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.4210   10.7980    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   33.5960   10.7980    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   35.2460   10.7980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.4210   11.6230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.1355   12.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1355   12.8605    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   34.4210   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7065   12.8605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.9921   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9921   14.0980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.2776   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5631   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8487   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1342   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4197   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7052   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9908   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2763   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5618   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8474   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1329   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4184   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7039   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9895   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2750   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5605   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8461   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5605   14.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8499   13.2730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.5644   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5644   12.0355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.2789   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9934   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7078   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4223   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1368   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8512   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5657   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2802   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9947   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7091   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.4236   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.1381   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.8525   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.5670   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.2815   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.9960   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.7104   13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.9960   12.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5644    9.5605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5644    8.7355    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   37.2789    9.9730    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  1  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
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
  2 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  2  0  0  0  0
M  CHG  2   6  -1  55  -1
M  END
> <DATABASE_ID>
MMDBc0031424

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C44H86NO10P/c1-38(2)31-27-23-19-15-11-7-5-9-13-17-21-25-29-33-42(46)52-35-40(36-53-56(50,51)54-37-41(45)44(48)49)55-43(47)34-30-26-22-18-14-10-6-8-12-16-20-24-28-32-39(3)4/h38-41H,5-37,45H2,1-4H3,(H,48,49)(H,50,51)/p-2/t40-,41?/m1/s1

> <INCHI_KEY>
UTCODXKLFXERFJ-AXHXVYJZSA-L

> <FORMULA>
C44H84NO10P

> <MOLECULAR_WEIGHT>
818.1122

> <EXACT_MASS>
817.583284425

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
98.88922618725128

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
8.06

> <JCHEM_LOGP>
11.845819618232607

> <ALOGPS_LOGS>
-7.28

> <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>
234.05040000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
44

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.49e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-3-{[(2R)-2,3-bis[(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      66.920  20.156   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      66.920  18.616   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      65.586  17.846   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      64.253  18.616   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0      64.253  20.156   0.000  0.00  0.00           P+0
HETATM    6  O   UNK     0      62.713  20.156   0.000  0.00  0.00           O-1
HETATM    7  O   UNK     0      65.793  20.156   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      64.253  21.696   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      65.586  22.466   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      65.586  24.006   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      64.253  24.776   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      62.919  24.006   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      61.585  24.776   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      61.585  26.316   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      60.252  24.006   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      58.918  24.776   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      57.584  24.006   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      56.251  24.776   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      54.917  24.006   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      53.583  24.776   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      52.249  24.006   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      50.916  24.776   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      49.582  24.006   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      48.248  24.776   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      46.915  24.006   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      45.581  24.776   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      44.247  24.006   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      42.914  24.776   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      41.580  24.006   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      40.246  24.776   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      38.913  24.006   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      40.246  26.316   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      66.920  24.776   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      68.254  24.006   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      68.254  22.466   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      69.587  24.776   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      70.921  24.006   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      72.255  24.776   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      73.588  24.006   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      74.922  24.776   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      76.256  24.006   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      77.589  24.776   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      78.923  24.006   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      80.257  24.776   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      81.590  24.006   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      82.924  24.776   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      84.258  24.006   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      85.591  24.776   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      86.925  24.006   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      88.259  24.776   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      89.593  24.006   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      90.926  24.776   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      89.593  22.466   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      68.254  17.846   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      68.254  16.306   0.000  0.00  0.00           O-1
HETATM   56  O   UNK     0      69.587  18.616   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   54                                                  
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   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51                                                            
CONECT   54    2   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  110    0
END

Synonyms

Not Available

Molecular Formula

C₄₄H₈₄NO₁₀P

Average Mass

818.1122

Monoisotopic Mass

817.583284425

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C44H86NO10P/c1-38(2)31-27-23-19-15-11-7-5-9-13-17-21-25-29-33-42(46)52-35-40(36-53-56(50,51)54-37-41(45)44(48)49)55-43(47)34-30-26-22-18-14-10-6-8-12-16-20-24-28-32-39(3)4/h38-41H,5-37,45H2,1-4H3,(H,48,49)(H,50,51)/p-2/t40-,41?/m1/s1

InChI Key

UTCODXKLFXERFJ-AXHXVYJZSA-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	4.5e-05 g/L	ALOGPS
logP	8.06	ALOGPS
logP	11.85	ChemAxon
logS	-7.3	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	44	ChemAxon
Refractivity	234.05 m³·mol⁻¹	ChemAxon
Polarizability	98.89 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	splash10-014i-5020000090-b2e042065d5db96adc38	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000l-9130000220-eb94c55b4e53beda5f9e	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4u-9241000000-8b1947cf3073033d9fdd	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014j-5090000080-f3aae4cd2ece3fdfb2cc	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-1090000010-bd3175e3243311a96bf4	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002b-5090000000-d9c506f2c09dff13a3d8	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

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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

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(19:iso/19:iso) (MMDBc0031424)

MOL for #<Metabolite:0x00007fecf0d06350>

3D MOL for #<Metabolite:0x00007fecf0d06350>

3D SDF for #<Metabolite:0x00007fecf0d06350>

3D-SDF for #<Metabolite:0x00007fecf0d06350>

PDB for #<Metabolite:0x00007fecf0d06350>

3D PDB for #<Metabolite:0x00007fecf0d06350>

SMILES for #<Metabolite:0x00007fecf0d06350>

INCHI for #<Metabolite:0x00007fecf0d06350>

Structure for #<Metabolite:0x00007fecf0d06350>

3D Structure for #<Metabolite:0x00007fecf0d06350>