MiMeDB: Showing metabocard for PS(19:iso/18:1(9Z)) (MMDBc0031422)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 00:48:23 UTC

Update Date

2022-08-31 18:10:31 UTC

Metabolite ID

MMDBc0031422

Metabolite Identification

Common Name

PS(19:iso/18:1(9Z))

Description

PS(19:iso/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(19:iso/18:1(9Z)), in particular, consists of one 17-methylocatdecanoyl 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


  Mrv0541 10241215422D          

 55 54  0  0  1  0            999 V2000
   28.7565  -14.9526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4710  -14.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4710  -13.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1855  -13.3026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1855  -12.4776    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   29.3605  -12.4776    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   31.0105  -12.4776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1855  -11.6526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.8999  -11.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8999  -10.4151    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   30.1855  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4710  -10.4151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7565  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7565   -9.1776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0421  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3276  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6131  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8987  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1842  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4697  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7552  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0408  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3263  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6118  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8974  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1829  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4684  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7539  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0395  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3250  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6105  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3250   -9.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6144  -10.0026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3289  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3289  -11.2401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.0434  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7578  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4723  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1868  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9012  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6157  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3302  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0447  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7591  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7591   -9.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4736   -8.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1881   -9.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9025   -8.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6170   -9.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3315   -8.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0460   -9.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7604   -8.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1855  -14.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8999  -14.5401    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   30.1855  -15.7776    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  2  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
  2 53  1  0  0  0  0
 53 54  1  0  0  0  0
 53 55  2  0  0  0  0
M  CHG  2   6  -1  54  -1
M  END


  Mrv0541 10241215422D          

 55 54  0  0  1  0            999 V2000
   28.7565  -14.9526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4710  -14.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4710  -13.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1855  -13.3026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1855  -12.4776    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   29.3605  -12.4776    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   31.0105  -12.4776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1855  -11.6526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.8999  -11.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8999  -10.4151    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   30.1855  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4710  -10.4151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7565  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7565   -9.1776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0421  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3276  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6131  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8987  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1842  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4697  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7552  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0408  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3263  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6118  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8974  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1829  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4684  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7539  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0395  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3250  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6105  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3250   -9.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6144  -10.0026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3289  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3289  -11.2401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.0434  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7578  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4723  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1868  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9012  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6157  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3302  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0447  -10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7591  -10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7591   -9.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4736   -8.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1881   -9.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9025   -8.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6170   -9.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3315   -8.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0460   -9.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7604   -8.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1855  -14.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8999  -14.5401    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   30.1855  -15.7776    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  2  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
  2 53  1  0  0  0  0
 53 54  1  0  0  0  0
 53 55  2  0  0  0  0
M  CHG  2   6  -1  54  -1
M  END
> <DATABASE_ID>
MMDBc0031422

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C43H82NO10P/c1-4-5-6-7-8-9-10-11-12-15-19-22-25-28-31-34-42(46)54-39(36-52-55(49,50)53-37-40(44)43(47)48)35-51-41(45)33-30-27-24-21-18-16-13-14-17-20-23-26-29-32-38(2)3/h11-12,38-40H,4-10,13-37,44H2,1-3H3,(H,47,48)(H,49,50)/p-2/b12-11-/t39-,40?/m1/s1

> <INCHI_KEY>
VKZSRAUQABMPLV-AWQHUTMPSA-L

> <FORMULA>
C43H80NO10P

> <MOLECULAR_WEIGHT>
802.0698

> <EXACT_MASS>
801.551984297

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
95.64331810958596

> <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-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}propanoate

> <ALOGPS_LOGP>
8.13

> <JCHEM_LOGP>
11.196878865232605

> <ALOGPS_LOGS>
-7.19

> <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>
230.61840000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
43

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.46e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-3-{[(2R)-3-[(17-methyloctadecanoyl)oxy]-2-[(9Z)-octadec-9-enoyloxy]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      53.679 -27.912   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      55.013 -27.142   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      55.013 -25.602   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      56.346 -24.832   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0      56.346 -23.292   0.000  0.00  0.00           P+0
HETATM    6  O   UNK     0      54.806 -23.292   0.000  0.00  0.00           O-1
HETATM    7  O   UNK     0      57.886 -23.292   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      56.346 -21.752   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      57.680 -20.982   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      57.680 -19.442   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      56.346 -18.672   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      55.013 -19.442   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      53.679 -18.672   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      53.679 -17.132   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      52.345 -19.442   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      51.012 -18.672   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      49.678 -19.442   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      48.344 -18.672   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      47.011 -19.442   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      45.677 -18.672   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      44.343 -19.442   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      43.009 -18.672   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      41.676 -19.442   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      40.342 -18.672   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      39.008 -19.442   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      37.675 -18.672   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      36.341 -19.442   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      35.007 -18.672   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      33.674 -19.442   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      32.340 -18.672   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      31.006 -19.442   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      32.340 -17.132   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      59.014 -18.672   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      60.347 -19.442   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      60.347 -20.982   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      61.681 -18.672   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      63.015 -19.442   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      64.348 -18.672   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      65.682 -19.442   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      67.016 -18.672   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      68.349 -19.442   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      69.683 -18.672   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      71.017 -19.442   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      72.350 -18.672   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      72.350 -17.132   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      73.684 -16.362   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      75.018 -17.132   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      76.351 -16.362   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      77.685 -17.132   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      79.019 -16.362   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      80.353 -17.132   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      81.686 -16.362   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      56.346 -27.912   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      57.680 -27.142   0.000  0.00  0.00           O-1
HETATM   55  O   UNK     0      56.346 -29.452   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   53                                                  
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                                                       
CONECT   52   51                                                            
CONECT   53    2   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  108    0
END

Synonyms

Not Available

Molecular Formula

C₄₃H₈₀NO₁₀P

Average Mass

802.0698

Monoisotopic Mass

801.551984297

IUPAC Name

2-amino-3-{[(2R)-3-[(17-methyloctadecanoyl)oxy]-2-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}propanoate

Traditional Name

2-amino-3-{[(2R)-3-[(17-methyloctadecanoyl)oxy]-2-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}propanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCC\C=C/CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCC(C)C)COP([O-])(=O)OCC(N)C([O-])=O

InChI Identifier

InChI=1S/C43H82NO10P/c1-4-5-6-7-8-9-10-11-12-15-19-22-25-28-31-34-42(46)54-39(36-52-55(49,50)53-37-40(44)43(47)48)35-51-41(45)33-30-27-24-21-18-16-13-14-17-20-23-26-29-32-38(2)3/h11-12,38-40H,4-10,13-37,44H2,1-3H3,(H,47,48)(H,49,50)/p-2/b12-11-/t39-,40?/m1/s1

InChI Key

VKZSRAUQABMPLV-AWQHUTMPSA-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	5.5e-05 g/L	ALOGPS
logP	8.13	ALOGPS
logP	11.2	ChemAxon
logS	-7.2	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	43	ChemAxon
Refractivity	230.62 m³·mol⁻¹	ChemAxon
Polarizability	95.64 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	splash10-0udi-7130000190-3c54f979efdd37360b12	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f7c-9130000200-a8a2b793dd03aec68d09	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4u-9230000000-0a19fcdc26c0e606657c	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-7130000190-3c54f979efdd37360b12	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f7c-9130000200-a8a2b793dd03aec68d09	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4u-9230000000-0a19fcdc26c0e606657c	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udj-5090000170-97a2b9bab71700a26862	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-1090000000-41084a8b22b67cd7bdaf	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0032-4090000000-4642c5ee33b393ecbf8d	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/18:1(9Z)) (MMDBc0031422)

MOL for #<Metabolite:0x00007fecd28079f8>

3D MOL for #<Metabolite:0x00007fecd28079f8>

3D SDF for #<Metabolite:0x00007fecd28079f8>

3D-SDF for #<Metabolite:0x00007fecd28079f8>

PDB for #<Metabolite:0x00007fecd28079f8>

3D PDB for #<Metabolite:0x00007fecd28079f8>

SMILES for #<Metabolite:0x00007fecd28079f8>

INCHI for #<Metabolite:0x00007fecd28079f8>

Structure for #<Metabolite:0x00007fecd28079f8>

3D Structure for #<Metabolite:0x00007fecd28079f8>