MiMeDB: Showing metabocard for PS(18:1(9Z)/19:iso) (MMDBc0031406)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 00:47:39 UTC

Update Date

2022-08-31 18:10:12 UTC

Metabolite ID

MMDBc0031406

Metabolite Identification

Common Name

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

Description

PS(18:1(9Z)/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(18:1(9Z)/19:iso), in particular, consists of one 9Z-octadecenoyl 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 10241215412D          

 55 54  0  0  1  0            999 V2000
   22.3263    5.4651    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0408    5.8776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0408    6.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7552    7.1151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7552    7.9401    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   22.9302    7.9401    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   24.5802    7.9401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7552    8.7651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4697    9.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4697   10.0026    0.0000 C   0  0  1  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 O   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
   22.3263   11.2401    0.0000 O   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
   15.8961   10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8961    9.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1816    8.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1816    7.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4671    7.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4671    6.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7526    6.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7526    5.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0382    5.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1842   10.4151    0.0000 O   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
   25.8987    9.1776    0.0000 O   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
   27.3276   10.0026    0.0000 C   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
   28.7565   10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4710   10.4151    0.0000 C   0  0  0  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
   30.8999   10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6144   10.0026    0.0000 C   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
   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
   37.3302    9.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7552    5.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4697    5.8776    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   23.7552    4.6401    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  2  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
 10 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  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
 50 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 10241215412D          

 55 54  0  0  1  0            999 V2000
   22.3263    5.4651    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0408    5.8776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0408    6.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7552    7.1151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7552    7.9401    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   22.9302    7.9401    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   24.5802    7.9401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7552    8.7651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4697    9.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4697   10.0026    0.0000 C   0  0  1  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 O   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
   22.3263   11.2401    0.0000 O   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
   15.8961   10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8961    9.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1816    8.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1816    7.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4671    7.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4671    6.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7526    6.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7526    5.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0382    5.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1842   10.4151    0.0000 O   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
   25.8987    9.1776    0.0000 O   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
   27.3276   10.0026    0.0000 C   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
   28.7565   10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4710   10.4151    0.0000 C   0  0  0  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
   30.8999   10.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6144   10.0026    0.0000 C   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
   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
   37.3302    9.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7552    5.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4697    5.8776    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   23.7552    4.6401    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  2  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
 10 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  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
 50 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>
MMDBc0031406

> <DATABASE_NAME>
MIME

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

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

> <FORMULA>
C43H80NO10P

> <MOLECULAR_WEIGHT>
802.0698

> <EXACT_MASS>
801.551984297

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
95.68079111083384

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
8.13

> <JCHEM_LOGP>
11.196878865232605

> <ALOGPS_LOGS>
-7.20

> <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>
230.61840000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
43

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.29e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-3-{[(2R)-2-[(17-methyloctadecanoyl)oxy]-3-[(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      41.676  10.202   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      43.009  10.972   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      43.009  12.512   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      44.343  13.282   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0      44.343  14.822   0.000  0.00  0.00           P+0
HETATM    6  O   UNK     0      42.803  14.822   0.000  0.00  0.00           O-1
HETATM    7  O   UNK     0      45.883  14.822   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      44.343  16.362   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      45.677  17.132   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      45.677  18.672   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      44.343  19.442   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      43.009  18.672   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      41.676  19.442   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      41.676  20.982   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      40.342  18.672   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      39.008  19.442   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      37.675  18.672   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      36.341  19.442   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      35.007  18.672   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      33.674  19.442   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      32.340  18.672   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      31.006  19.442   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      29.673  18.672   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      29.673  17.132   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      28.339  16.362   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      28.339  14.822   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      27.005  14.052   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      27.005  12.512   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      25.672  11.742   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      25.672  10.202   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      24.338   9.432   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      47.011  19.442   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      48.344  18.672   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      48.344  17.132   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      49.678  19.442   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      51.012  18.672   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      52.345  19.442   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      53.679  18.672   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      55.013  19.442   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      56.346  18.672   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      57.680  19.442   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      59.014  18.672   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      60.347  19.442   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      61.681  18.672   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      63.015  19.442   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      64.348  18.672   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      65.682  19.442   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      67.016  18.672   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      68.349  19.442   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      69.683  18.672   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      71.017  19.442   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      69.683  17.132   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      44.343  10.202   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      45.677  10.972   0.000  0.00  0.00           O-1
HETATM   55  O   UNK     0      44.343   8.662   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   32                                                  
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                                                       
CONECT   31   30                                                            
CONECT   32   10   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50                                                            
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)-2-[(17-methyloctadecanoyl)oxy]-3-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}propanoate

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

QXULAZJRRRBYEV-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	5.3e-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	95.68 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-7140000190-635eef39cd2db0ba52b8	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f7c-9140000200-e2260336cca7b5a6fb78	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4u-9330000000-80b0db34f24eb10ecec8	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udj-6060000290-411d89769af9d20d011f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udj-3090000140-25f65c9c567151f75c5e	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0032-5090000000-0a3ea0701de90ca17875	2015-09-15	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(18:1(9Z)/19:iso) (MMDBc0031406)

MOL for #<Metabolite:0x00007f46ca2179e8>

3D MOL for #<Metabolite:0x00007f46ca2179e8>

3D SDF for #<Metabolite:0x00007f46ca2179e8>

3D-SDF for #<Metabolite:0x00007f46ca2179e8>

PDB for #<Metabolite:0x00007f46ca2179e8>

3D PDB for #<Metabolite:0x00007f46ca2179e8>

SMILES for #<Metabolite:0x00007f46ca2179e8>

INCHI for #<Metabolite:0x00007f46ca2179e8>

Structure for #<Metabolite:0x00007f46ca2179e8>

3D Structure for #<Metabolite:0x00007f46ca2179e8>