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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (10) Show 10 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:48 UTC

Update Date

2022-03-07 02:51:34 UTC

HMDB ID

HMDB0014291

Secondary Accession Numbers

HMDB14291

Metabolite Identification

Common Name

Phosphatidylserine

Description

Phosphatidylserine (PS) is a phospholipid nutrient found in fish, green leafy vegetables, soybeans and rice, and is essential for the normal functioning of neuronal cell membranes and activates Protein kinase C (PKC) which has been shown to be involved in memory function. In apoptosis, phosphatidylserine is transferred to the outer leaflet of the plasma membrane. This is part of the process by which the cell is targeted for phagocytosis. PS has been shown to slow cognitive decline in animal models. PS has been investigated in a small number of double-blind placebo trials and has been shown to increase memory performance in the elderly. Because of the potentail cognitive benefits of phosphatidylserine, the substance is sold as a dietary supplement to people who believe they can benefit from an increased intake. The dietary supplement was originally processed from bovine sources however Prion disease scares in the 1990s outlawed this process, and a soy-based alternative was adopted.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652304032018292D          

 27 26  0  0  1  0            999 V2000
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8375    3.5724    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1875   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    4.2868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0750    4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0750    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020    1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4730    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    2.1434    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2500    2.8579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  4  1  0  0  0  0
 12  5  1  0  0  0  0
 13 10  1  0  0  0  0
 10 14  1  1  0  0  0
 15 11  2  0  0  0  0
 16 12  2  0  0  0  0
 17 13  2  0  0  0  0
 18 13  1  0  0  0  0
 21  6  1  0  0  0  0
 21 11  1  0  0  0  0
 22  7  1  0  0  0  0
 23  8  1  0  0  0  0
  9 24  1  6  0  0  0
 24 12  1  0  0  0  0
 25 19  1  0  0  0  0
 25 20  2  0  0  0  0
 25 22  1  0  0  0  0
 25 23  1  0  0  0  0
  9 26  1  6  0  0  0
 10 27  1  1  0  0  0
M  END

HMDB0014291
     RDKit          3D
Phosphatidylserine
 49 48  0  0  0  0  0  0  0  0999 V2000
   -4.1715   -4.1632    0.9309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9571   -3.2210    0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0552   -2.5291   -0.9546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0314   -1.7520   -0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0444   -1.7549    1.0248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0700   -1.0299   -0.9271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1132   -0.3042   -0.2077 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0550    1.1528   -0.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2495    1.8414   -0.4970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9314    2.0611    0.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4415    1.5973    1.7306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2138    2.8153    0.7498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8528    4.2211    1.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2839   -0.8578   -0.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2315   -0.1333    0.2301 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7519   -0.7951   -0.1292 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.2965   -1.3269    1.2004 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6142   -2.0491   -1.2537 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7750    0.3591   -0.7759 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9652    0.4579   -0.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8849    1.5018   -0.6329 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2453    1.2024   -2.0014 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0824    1.5893    0.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9421    1.8298    1.4558 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3285    1.3932   -0.3448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4900   -5.2095    0.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3261   -3.8964    1.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0947   -4.0539    0.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7616   -3.7965   -0.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4860   -2.4976    0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6800   -1.8234   -1.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5901   -3.2884   -1.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2596   -0.4067    0.8834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7820    1.1490   -1.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1974    1.5985   -0.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6674    2.9477   -0.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9038    2.3314    1.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8994    4.5082    0.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6547    4.9503    1.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6472    4.1414    2.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3796   -1.9141   -0.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4357   -0.7132   -1.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0101   -1.8246   -2.1166 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4276   -0.5457   -0.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7351    0.7671    0.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3200    2.4608   -0.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6799    0.4319   -2.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3574    2.0269   -2.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8802    0.5506   -0.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
  7 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 23 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  7 33  1  1
  8 34  1  0
  8 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 18 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  6
 22 47  1  0
 22 48  1  0
 25 49  1  0
M  END


  Mrv1652304032018292D          

 27 26  0  0  1  0            999 V2000
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8375    3.5724    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1875   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    4.2868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0750    4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0750    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020    1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4730    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    2.1434    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2500    2.8579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  4  1  0  0  0  0
 12  5  1  0  0  0  0
 13 10  1  0  0  0  0
 10 14  1  1  0  0  0
 15 11  2  0  0  0  0
 16 12  2  0  0  0  0
 17 13  2  0  0  0  0
 18 13  1  0  0  0  0
 21  6  1  0  0  0  0
 21 11  1  0  0  0  0
 22  7  1  0  0  0  0
 23  8  1  0  0  0  0
  9 24  1  6  0  0  0
 24 12  1  0  0  0  0
 25 19  1  0  0  0  0
 25 20  2  0  0  0  0
 25 22  1  0  0  0  0
 25 23  1  0  0  0  0
  9 26  1  6  0  0  0
 10 27  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0014291

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CC)OC(=O)CCC)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H24NO10P/c1-3-5-12(16)24-9(6-21-11(15)4-2)7-22-25(19,20)23-8-10(14)13(17)18/h9-10H,3-8,14H2,1-2H3,(H,17,18)(H,19,20)/t9-,10+/m1/s1

> <INCHI_KEY>
UNJJBGNPUUVVFQ-ZJUUUORDSA-N

> <FORMULA>
C13H24NO10P

> <MOLECULAR_WEIGHT>
385.3041

> <EXACT_MASS>
385.113782505

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
35.59029554631411

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-({[(2R)-2-(butanoyloxy)-3-(propanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid

> <ALOGPS_LOGP>
-1.02

> <JCHEM_LOGP>
-1.6207098594369584

> <ALOGPS_LOGS>
-2.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
2.17839601565745

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4680339991867495

> <JCHEM_PKA_STRONGEST_BASIC>
9.376604467850063

> <JCHEM_POLAR_SURFACE_AREA>
171.67999999999998

> <JCHEM_REFRACTIVITY>
81.8088

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phosphatidylserine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014291
     RDKit          3D
Phosphatidylserine
 49 48  0  0  0  0  0  0  0  0999 V2000
   -4.1715   -4.1632    0.9309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9571   -3.2210    0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0552   -2.5291   -0.9546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0314   -1.7520   -0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0444   -1.7549    1.0248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0700   -1.0299   -0.9271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1132   -0.3042   -0.2077 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0550    1.1528   -0.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2495    1.8414   -0.4970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9314    2.0611    0.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4415    1.5973    1.7306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2138    2.8153    0.7498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8528    4.2211    1.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2839   -0.8578   -0.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2315   -0.1333    0.2301 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7519   -0.7951   -0.1292 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.2965   -1.3269    1.2004 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6142   -2.0491   -1.2537 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7750    0.3591   -0.7759 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9652    0.4579   -0.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8849    1.5018   -0.6329 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2453    1.2024   -2.0014 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0824    1.5893    0.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9421    1.8298    1.4558 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3285    1.3932   -0.3448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4900   -5.2095    0.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3261   -3.8964    1.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0947   -4.0539    0.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7616   -3.7965   -0.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4860   -2.4976    0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6800   -1.8234   -1.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5901   -3.2884   -1.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2596   -0.4067    0.8834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7820    1.1490   -1.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1974    1.5985   -0.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6674    2.9477   -0.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9038    2.3314    1.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8994    4.5082    0.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6547    4.9503    1.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6472    4.1414    2.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3796   -1.9141   -0.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4357   -0.7132   -1.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0101   -1.8246   -2.1166 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4276   -0.5457   -0.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7351    0.7671    0.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3200    2.4608   -0.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6799    0.4319   -2.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3574    2.0269   -2.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8802    0.5506   -0.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
  7 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 23 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  7 33  1  1
  8 34  1  0
  8 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 18 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  6
 22 47  1  0
 22 48  1  0
 25 49  1  0
M  END

HEADER    PROTEIN                                 03-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-APR-20         0                                  
HETATM    1  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.860  -2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.090  -1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.620   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.240   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.240   2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.860   5.335   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.470   1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.630   6.668   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.550  -1.334   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.160   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.170   6.668   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      13.860   8.002   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      10.780  -2.667   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       6.930  -1.334   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      16.940   8.002   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      16.940   5.335   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      12.884   3.231   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      10.216   4.771   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      10.780   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.780   2.667   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      12.320   5.335   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.930   1.334   0.000  0.00  0.00           O+0
HETATM   25  P   UNK     0      11.550   4.001   0.000  0.00  0.00           P+0
HETATM   26  H   UNK     0      10.010   1.334   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      15.400   5.335   0.000  0.00  0.00           H+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2   11                                                       
CONECT    5    3   12                                                       
CONECT    6    9   21                                                       
CONECT    7    9   22                                                       
CONECT    8   10   23                                                       
CONECT    9    6    7   24   26                                             
CONECT   10    8   13   14   27                                             
CONECT   11    4   15   21                                                  
CONECT   12    5   16   24                                                  
CONECT   13   10   17   18                                                  
CONECT   14   10                                                            
CONECT   15   11                                                            
CONECT   16   12                                                            
CONECT   17   13                                                            
CONECT   18   13                                                            
CONECT   19   25                                                            
CONECT   20   25                                                            
CONECT   21    6   11                                                       
CONECT   22    7   25                                                       
CONECT   23    8   25                                                       
CONECT   24    9   12                                                       
CONECT   25   19   20   22   23                                             
CONECT   26    9                                                            
CONECT   27   10                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   52    0
END

COMPND    HMDB0014291
HETATM    1  C1  UNL     1      -4.171  -4.163   0.931  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.957  -3.221   0.049  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.055  -2.529  -0.955  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.031  -1.752  -0.227  1.00  0.00           C  
HETATM    5  O1  UNL     1      -3.044  -1.755   1.025  1.00  0.00           O  
HETATM    6  O2  UNL     1      -2.070  -1.030  -0.927  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.113  -0.304  -0.208  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.055   1.153  -0.654  1.00  0.00           C  
HETATM    9  O3  UNL     1      -2.249   1.841  -0.497  1.00  0.00           O  
HETATM   10  C7  UNL     1      -2.931   2.061   0.669  1.00  0.00           C  
HETATM   11  O4  UNL     1      -2.442   1.597   1.731  1.00  0.00           O  
HETATM   12  C8  UNL     1      -4.214   2.815   0.750  1.00  0.00           C  
HETATM   13  C9  UNL     1      -3.853   4.221   1.229  1.00  0.00           C  
HETATM   14  C10 UNL     1       0.284  -0.858  -0.489  1.00  0.00           C  
HETATM   15  O5  UNL     1       1.232  -0.133   0.230  1.00  0.00           O  
HETATM   16  P1  UNL     1       2.752  -0.795  -0.129  1.00  0.00           P  
HETATM   17  O6  UNL     1       3.296  -1.327   1.200  1.00  0.00           O  
HETATM   18  O7  UNL     1       2.614  -2.049  -1.254  1.00  0.00           O  
HETATM   19  O8  UNL     1       3.775   0.359  -0.776  1.00  0.00           O  
HETATM   20  C11 UNL     1       4.965   0.458  -0.051  1.00  0.00           C  
HETATM   21  C12 UNL     1       5.885   1.502  -0.633  1.00  0.00           C  
HETATM   22  N1  UNL     1       6.245   1.202  -2.001  1.00  0.00           N  
HETATM   23  C13 UNL     1       7.082   1.589   0.245  1.00  0.00           C  
HETATM   24  O9  UNL     1       6.942   1.830   1.456  1.00  0.00           O  
HETATM   25  O10 UNL     1       8.328   1.393  -0.345  1.00  0.00           O  
HETATM   26  H1  UNL     1      -4.490  -5.209   0.730  1.00  0.00           H  
HETATM   27  H2  UNL     1      -4.326  -3.896   1.983  1.00  0.00           H  
HETATM   28  H3  UNL     1      -3.095  -4.054   0.646  1.00  0.00           H  
HETATM   29  H4  UNL     1      -5.762  -3.796  -0.467  1.00  0.00           H  
HETATM   30  H5  UNL     1      -5.486  -2.498   0.694  1.00  0.00           H  
HETATM   31  H6  UNL     1      -4.680  -1.823  -1.555  1.00  0.00           H  
HETATM   32  H7  UNL     1      -3.590  -3.288  -1.618  1.00  0.00           H  
HETATM   33  H8  UNL     1      -1.260  -0.407   0.883  1.00  0.00           H  
HETATM   34  H9  UNL     1      -0.782   1.149  -1.729  1.00  0.00           H  
HETATM   35  H10 UNL     1      -0.197   1.599  -0.113  1.00  0.00           H  
HETATM   36  H11 UNL     1      -4.667   2.948  -0.252  1.00  0.00           H  
HETATM   37  H12 UNL     1      -4.904   2.331   1.476  1.00  0.00           H  
HETATM   38  H13 UNL     1      -2.899   4.508   0.725  1.00  0.00           H  
HETATM   39  H14 UNL     1      -4.655   4.950   1.012  1.00  0.00           H  
HETATM   40  H15 UNL     1      -3.647   4.141   2.315  1.00  0.00           H  
HETATM   41  H16 UNL     1       0.380  -1.914  -0.234  1.00  0.00           H  
HETATM   42  H17 UNL     1       0.436  -0.713  -1.593  1.00  0.00           H  
HETATM   43  H18 UNL     1       3.010  -1.825  -2.117  1.00  0.00           H  
HETATM   44  H19 UNL     1       5.428  -0.546  -0.056  1.00  0.00           H  
HETATM   45  H20 UNL     1       4.735   0.767   0.991  1.00  0.00           H  
HETATM   46  H21 UNL     1       5.320   2.461  -0.619  1.00  0.00           H  
HETATM   47  H22 UNL     1       5.680   0.432  -2.408  1.00  0.00           H  
HETATM   48  H23 UNL     1       6.357   2.027  -2.598  1.00  0.00           H  
HETATM   49  H24 UNL     1       8.880   0.551  -0.173  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4   31   32
CONECT    4    5    5    6
CONECT    6    7
CONECT    7    8   14   33
CONECT    8    9   34   35
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   36   37
CONECT   13   38   39   40
CONECT   14   15   41   42
CONECT   15   16
CONECT   16   17   17   18   19
CONECT   18   43
CONECT   19   20
CONECT   20   21   44   45
CONECT   21   22   23   46
CONECT   22   47   48
CONECT   23   24   24   25
CONECT   25   49
END

HMDB0014291
     RDKit          3D
Phosphatidylserine
 49 48  0  0  0  0  0  0  0  0999 V2000
   -4.1715   -4.1632    0.9309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9571   -3.2210    0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0552   -2.5291   -0.9546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0314   -1.7520   -0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0444   -1.7549    1.0248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0700   -1.0299   -0.9271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1132   -0.3042   -0.2077 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0550    1.1528   -0.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2495    1.8414   -0.4970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9314    2.0611    0.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4415    1.5973    1.7306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2138    2.8153    0.7498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8528    4.2211    1.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2839   -0.8578   -0.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2315   -0.1333    0.2301 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7519   -0.7951   -0.1292 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.2965   -1.3269    1.2004 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6142   -2.0491   -1.2537 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7750    0.3591   -0.7759 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9652    0.4579   -0.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8849    1.5018   -0.6329 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2453    1.2024   -2.0014 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0824    1.5893    0.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9421    1.8298    1.4558 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3285    1.3932   -0.3448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4900   -5.2095    0.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3261   -3.8964    1.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0947   -4.0539    0.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7616   -3.7965   -0.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4860   -2.4976    0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6800   -1.8234   -1.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5901   -3.2884   -1.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2596   -0.4067    0.8834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7820    1.1490   -1.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1974    1.5985   -0.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6674    2.9477   -0.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9038    2.3314    1.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8994    4.5082    0.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6547    4.9503    1.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6472    4.1414    2.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3796   -1.9141   -0.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4357   -0.7132   -1.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0101   -1.8246   -2.1166 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4276   -0.5457   -0.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7351    0.7671    0.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3200    2.4608   -0.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6799    0.4319   -2.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3574    2.0269   -2.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8802    0.5506   -0.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
  7 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 23 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  7 33  1  1
  8 34  1  0
  8 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 18 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  6
 22 47  1  0
 22 48  1  0
 25 49  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-O-sn-Phosphatidyl-L-serine	HMDB
O3-Phosphatidyl-L-serine	HMDB
Phosphatidyl-L-serine	HMDB
(2S)-2-Amino-3-({[(2R)-2-(butanoyloxy)-3-(propanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoate	Generator
2-Acetamido-2-deoxy-D-glucose	ChEBI, HMDB
D-GlcNAc	ChEBI, HMDB
N-Acetyl-D-glucosamine	ChEBI, HMDB
N-Acetylchitosamine	ChEBI, HMDB
N Acetyl D glucosamine	HMDB
2 Acetamido 2 deoxy D glucose	HMDB
2 Acetamido 2 deoxyglucose	HMDB
2-Acetamido-2-deoxyglucose	HMDB
Acetylglucosamine	HMDB

Chemical Formula

C₁₃H₂₄NO₁₀P

Average Molecular Weight

385.3041

Monoisotopic Molecular Weight

385.113782505

IUPAC Name

(2S)-2-amino-3-({[(2R)-2-(butanoyloxy)-3-(propanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid

Traditional Name

phosphatidylserine

CAS Registry Number

8002-43-5

SMILES

[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CC)OC(=O)CCC)C(O)=O

InChI Identifier

InChI=1S/C13H24NO10P/c1-3-5-12(16)24-9(6-21-11(15)4-2)7-22-25(19,20)23-8-10(14)13(17)18/h9-10H,3-8,14H2,1-2H3,(H,17,18)(H,19,20)/t9-,10+/m1/s1

InChI Key

UNJJBGNPUUVVFQ-ZJUUUORDSA-N

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
Alpha-amino acid or derivatives
L-alpha-amino acid
Tricarboxylic acid or derivatives
Phosphoethanolamine
Fatty acid ester
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Amino acid
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Carbonyl group
Organic oxide
Primary amine
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3.7 g/L	Not Available
LogP	-3.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.7 g/L	ALOGPS
logP	-1	ALOGPS
logP	-1.6	ChemAxon
logS	-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	3	ChemAxon
Polar Surface Area	171.68 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	81.81 m³·mol⁻¹	ChemAxon
Polarizability	35.59 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	190.426	31661259
DarkChem	[M-H]-	183.428	31661259
DeepCCS	[M+H]+	170.724	30932474
DeepCCS	[M-H]-	168.329	30932474
DeepCCS	[M-2H]-	202.107	30932474
DeepCCS	[M+Na]+	176.879	30932474
AllCCS	[M+H]+	187.9	32859911
AllCCS	[M+H-H2O]+	185.6	32859911
AllCCS	[M+NH4]+	189.9	32859911
AllCCS	[M+Na]+	190.5	32859911
AllCCS	[M-H]-	181.4	32859911
AllCCS	[M+Na-2H]-	182.2	32859911
AllCCS	[M+HCOO]-	183.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.15 minutes	32390414
Predicted by Siyang on May 30, 2022	11.1535 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.91 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	385.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	703.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	203.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	74.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	60.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	316.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	326.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	762.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	674.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	199.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	872.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	217.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	222.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	473.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	290.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	563.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phosphatidylserine	[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CC)OC(=O)CCC)C(O)=O	3561.3	Standard polar	33892256
Phosphatidylserine	[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CC)OC(=O)CCC)C(O)=O	2523.9	Standard non polar	33892256
Phosphatidylserine	[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CC)OC(=O)CCC)C(O)=O	2789.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phosphatidylserine,1TMS,isomer #1	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@H](N)C(=O)O[Si](C)(C)C	2550.0	Semi standard non polar	33892256
Phosphatidylserine,1TMS,isomer #2	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N)C(=O)O)O[Si](C)(C)C	2597.0	Semi standard non polar	33892256
Phosphatidylserine,1TMS,isomer #3	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@H](N[Si](C)(C)C)C(=O)O	2666.9	Semi standard non polar	33892256
Phosphatidylserine,2TMS,isomer #1	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	2566.1	Semi standard non polar	33892256
Phosphatidylserine,2TMS,isomer #1	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	2524.7	Standard non polar	33892256
Phosphatidylserine,2TMS,isomer #1	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	4421.3	Standard polar	33892256
Phosphatidylserine,2TMS,isomer #2	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	2626.6	Semi standard non polar	33892256
Phosphatidylserine,2TMS,isomer #2	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	2653.5	Standard non polar	33892256
Phosphatidylserine,2TMS,isomer #2	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	4273.0	Standard polar	33892256
Phosphatidylserine,2TMS,isomer #3	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N[Si](C)(C)C)C(=O)O)O[Si](C)(C)C	2667.9	Semi standard non polar	33892256
Phosphatidylserine,2TMS,isomer #3	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N[Si](C)(C)C)C(=O)O)O[Si](C)(C)C	2627.8	Standard non polar	33892256
Phosphatidylserine,2TMS,isomer #3	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N[Si](C)(C)C)C(=O)O)O[Si](C)(C)C	3837.4	Standard polar	33892256
Phosphatidylserine,2TMS,isomer #4	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2812.0	Semi standard non polar	33892256
Phosphatidylserine,2TMS,isomer #4	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2697.9	Standard non polar	33892256
Phosphatidylserine,2TMS,isomer #4	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	4374.1	Standard polar	33892256
Phosphatidylserine,3TMS,isomer #1	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	2651.0	Semi standard non polar	33892256
Phosphatidylserine,3TMS,isomer #1	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	2678.7	Standard non polar	33892256
Phosphatidylserine,3TMS,isomer #1	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	3413.6	Standard polar	33892256
Phosphatidylserine,3TMS,isomer #2	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2820.9	Semi standard non polar	33892256
Phosphatidylserine,3TMS,isomer #2	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2731.7	Standard non polar	33892256
Phosphatidylserine,3TMS,isomer #2	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3897.2	Standard polar	33892256
Phosphatidylserine,3TMS,isomer #3	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2819.4	Semi standard non polar	33892256
Phosphatidylserine,3TMS,isomer #3	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2729.2	Standard non polar	33892256
Phosphatidylserine,3TMS,isomer #3	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	3550.1	Standard polar	33892256
Phosphatidylserine,4TMS,isomer #1	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2840.2	Semi standard non polar	33892256
Phosphatidylserine,4TMS,isomer #1	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2749.9	Standard non polar	33892256
Phosphatidylserine,4TMS,isomer #1	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	3247.7	Standard polar	33892256
Phosphatidylserine,1TBDMS,isomer #1	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C	2797.0	Semi standard non polar	33892256
Phosphatidylserine,1TBDMS,isomer #2	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N)C(=O)O)O[Si](C)(C)C(C)(C)C	2820.9	Semi standard non polar	33892256
Phosphatidylserine,1TBDMS,isomer #3	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O	2866.9	Semi standard non polar	33892256
Phosphatidylserine,2TBDMS,isomer #1	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3033.7	Semi standard non polar	33892256
Phosphatidylserine,2TBDMS,isomer #1	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2826.7	Standard non polar	33892256
Phosphatidylserine,2TBDMS,isomer #1	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4383.0	Standard polar	33892256
Phosphatidylserine,2TBDMS,isomer #2	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3084.9	Semi standard non polar	33892256
Phosphatidylserine,2TBDMS,isomer #2	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2957.1	Standard non polar	33892256
Phosphatidylserine,2TBDMS,isomer #2	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	4246.7	Standard polar	33892256
Phosphatidylserine,2TBDMS,isomer #3	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)O[Si](C)(C)C(C)(C)C	3115.3	Semi standard non polar	33892256
Phosphatidylserine,2TBDMS,isomer #3	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)O[Si](C)(C)C(C)(C)C	2929.5	Standard non polar	33892256
Phosphatidylserine,2TBDMS,isomer #3	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)O[Si](C)(C)C(C)(C)C	3901.9	Standard polar	33892256
Phosphatidylserine,2TBDMS,isomer #4	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3244.6	Semi standard non polar	33892256
Phosphatidylserine,2TBDMS,isomer #4	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2993.8	Standard non polar	33892256
Phosphatidylserine,2TBDMS,isomer #4	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4300.5	Standard polar	33892256
Phosphatidylserine,3TBDMS,isomer #1	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3327.0	Semi standard non polar	33892256
Phosphatidylserine,3TBDMS,isomer #1	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3091.5	Standard non polar	33892256
Phosphatidylserine,3TBDMS,isomer #1	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3637.2	Standard polar	33892256
Phosphatidylserine,3TBDMS,isomer #2	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3474.1	Semi standard non polar	33892256
Phosphatidylserine,3TBDMS,isomer #2	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3163.2	Standard non polar	33892256
Phosphatidylserine,3TBDMS,isomer #2	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3961.2	Standard polar	33892256
Phosphatidylserine,3TBDMS,isomer #3	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3497.0	Semi standard non polar	33892256
Phosphatidylserine,3TBDMS,isomer #3	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3127.3	Standard non polar	33892256
Phosphatidylserine,3TBDMS,isomer #3	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3697.7	Standard polar	33892256
Phosphatidylserine,4TBDMS,isomer #1	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3713.2	Semi standard non polar	33892256
Phosphatidylserine,4TBDMS,isomer #1	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3284.7	Standard non polar	33892256
Phosphatidylserine,4TBDMS,isomer #1	CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3535.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phosphatidylserine GC-MS (Non-derivatized) - 70eV, Positive	splash10-06xx-9331000000-5397fe5806bdc09af389	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phosphatidylserine GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9125000000-a42f2f526549a4b9fc5c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phosphatidylserine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphatidylserine 10V, Positive-QTOF	splash10-000l-9013000000-a48d79654fdd42e7b832	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphatidylserine 20V, Positive-QTOF	splash10-000f-9010000000-3e5d23a16d25de896747	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphatidylserine 40V, Positive-QTOF	splash10-000f-9200000000-a15a472f35148d4c5da0	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphatidylserine 10V, Negative-QTOF	splash10-05fr-9123000000-667f29964b87dbc7f6bc	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphatidylserine 20V, Negative-QTOF	splash10-05i0-9110000000-798e4cca9186bc74d867	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphatidylserine 40V, Negative-QTOF	splash10-004i-9000000000-a8525ea4757be1346489	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphatidylserine 10V, Positive-QTOF	splash10-14i6-0049000000-3f7053b983ba7bcf4ea7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphatidylserine 20V, Positive-QTOF	splash10-0k96-0449000000-907abccf1ab74e57402a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphatidylserine 40V, Positive-QTOF	splash10-0k96-0449000000-907abccf1ab74e57402a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphatidylserine 10V, Negative-QTOF	splash10-001i-0009000000-cec6e0edd55251e4e184	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphatidylserine 20V, Negative-QTOF	splash10-001i-0019000000-8bafada2a22438e2959f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphatidylserine 40V, Negative-QTOF	splash10-05gs-4092000000-a16c91e5323676b08b10	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphatidylserine 10V, Positive-QTOF	splash10-0ab9-0016900000-3028e5441df826078ff9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphatidylserine 20V, Positive-QTOF	splash10-0a4i-0002900000-b6e85ac16efffc16be00	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphatidylserine 40V, Positive-QTOF	splash10-0a4i-0092100000-a487704ac6b4572cc472	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphatidylserine 10V, Positive-QTOF	splash10-000i-0019000000-eec474a40e6a95ff2065	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphatidylserine 20V, Positive-QTOF	splash10-0uds-0297000000-c05ccb25e22017ff2bf6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphatidylserine 40V, Positive-QTOF	splash10-0udj-0294000000-1c85e78190b31b5c1a7f	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00144	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00144	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00144

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

13628254

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phosphatidylserine

METLIN ID

Not Available

PubChem Compound

6323481

PDB ID

Not Available

ChEBI ID

18303

Food Biomarker Ontology

Not Available

VMH ID

PS_HS

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
van Engeland M, Nieland LJ, Ramaekers FC, Schutte B, Reutelingsperger CP: Annexin V-affinity assay: a review on an apoptosis detection system based on phosphatidylserine exposure. Cytometry. 1998 Jan 1;31(1):1-9. [PubMed:9450519 ]
Vance JE, Tasseva G: Formation and function of phosphatidylserine and phosphatidylethanolamine in mammalian cells. Biochim Biophys Acta. 2013 Mar;1831(3):543-54. doi: 10.1016/j.bbalip.2012.08.016. Epub 2012 Aug 29. [PubMed:22960354 ]
Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
Jean E. Vance (2008). Thematic Review Series: Glycerolipids. Phosphatidylserine and phosphatidylethanolamine in mammalian cells: two metabolically related aminophospholipids. The Journal of Lipid Research, 49, 1377-1387..

Enzymes

Enzyme Details

1. Diacylglycerol kinase gamma

General function:: Involved in diacylglycerol kinase activity
Specific function:: Reverses the normal flow of glycerolipid biosynthesis by phosphorylating diacylglycerol back to phosphatidic acid
Gene Name:: DGKG
Uniprot ID:: P49619
Molecular weight:: 89095.3

References

Yamaguchi Y, Shirai Y, Matsubara T, Sanse K, Kuriyama M, Oshiro N, Yoshino K, Yonezawa K, Ono Y, Saito N: Phosphorylation and up-regulation of diacylglycerol kinase gamma via its interaction with protein kinase C gamma. J Biol Chem. 2006 Oct 20;281(42):31627-37. Epub 2006 Aug 11. [PubMed:16905533 ]

Enzyme Details

2. Diacylglycerol kinase delta

General function:: Involved in diacylglycerol kinase activity
Specific function:: Isoform 2 may be involved in cell growth and tumorigenesis. Involved in clathrin-dependent endocytosis
Gene Name:: DGKD
Uniprot ID:: Q16760
Molecular weight:: 134524.2

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Bregoli L, Baldassare JJ, Raben DM: Nuclear diacylglycerol kinase-theta is activated in response to alpha-thrombin. J Biol Chem. 2001 Jun 29;276(26):23288-95. Epub 2001 Apr 17. [PubMed:11309392 ]
Sakane F, Imai S, Kai M, Wada I, Kanoh H: Molecular cloning of a novel diacylglycerol kinase isozyme with a pleckstrin homology domain and a C-terminal tail similar to those of the EPH family of protein-tyrosine kinases. J Biol Chem. 1996 Apr 5;271(14):8394-401. [PubMed:8626538 ]

Enzyme Details

3. Protein kinase C alpha type

General function:: Involved in protein serine/threonine kinase activity
Specific function:: PKC is activated by diacylglycerol which in turn phosphorylates a range of cellular proteins. PKC also serves as the receptor for phorbol esters, a class of tumor promoters
Gene Name:: PRKCA
Uniprot ID:: P17252
Molecular weight:: 76763.5

References

Yu D, Kazanietz MG, Harvey RG, Penning TM: Polycyclic aromatic hydrocarbon o-quinones inhibit the activity of the catalytic fragment of protein kinase C. Biochemistry. 2002 Oct 1;41(39):11888-94. [PubMed:12269833 ]
Rodriguez-Alfaro JA, Gomez-Fernandez JC, Corbalan-Garcia S: Role of the lysine-rich cluster of the C2 domain in the phosphatidylserine-dependent activation of PKCalpha. J Mol Biol. 2004 Jan 23;335(4):1117-29. [PubMed:14698304 ]
Lopez-Andreo MJ, Torrecillas A, Conesa-Zamora P, Corbalan-Garcia S, Gomez-Fernandez JC: Retinoic acid as a modulator of the activity of protein kinase Calpha. Biochemistry. 2005 Aug 30;44(34):11353-60. [PubMed:16114872 ]
Corbin JA, Evans JH, Landgraf KE, Falke JJ: Mechanism of specific membrane targeting by C2 domains: localized pools of target lipids enhance Ca2+ affinity. Biochemistry. 2007 Apr 10;46(14):4322-36. Epub 2007 Mar 17. [PubMed:17367165 ]

Enzyme Details

4. Probable phospholipid-transporting ATPase IA

General function:: Involved in ATP binding
Specific function:: May play a role in the transport of aminophospholipids from the outer to the inner leaflet of various membranes and the maintenance of asymmetric distribution of phospholipids, mainly in secretory vesicles
Gene Name:: ATP8A1
Uniprot ID:: Q9Y2Q0
Molecular weight:: 131368.2

References

Bettache N, Baisamy L, Baghdiguian S, Payrastre B, Mangeat P, Bienvenue A: Mechanical constraint imposed on plasma membrane through transverse phospholipid imbalance induces reversible actin polymerization via phosphoinositide 3-kinase activation. J Cell Sci. 2003 Jun 1;116(Pt 11):2277-84. Epub 2003 Apr 15. [PubMed:12697835 ]
Wolfs JL, Comfurius P, Rasmussen JT, Keuren JF, Lindhout T, Zwaal RF, Bevers EM: Activated scramblase and inhibited aminophospholipid translocase cause phosphatidylserine exposure in a distinct platelet fraction. Cell Mol Life Sci. 2005 Jul;62(13):1514-25. [PubMed:15971000 ]
Mandal D, Mazumder A, Das P, Kundu M, Basu J: Fas-, caspase 8-, and caspase 3-dependent signaling regulates the activity of the aminophospholipid translocase and phosphatidylserine externalization in human erythrocytes. J Biol Chem. 2005 Nov 25;280(47):39460-7. Epub 2005 Sep 22. [PubMed:16179347 ]
Paterson JK, Renkema K, Burden L, Halleck MS, Schlegel RA, Williamson P, Daleke DL: Lipid specific activation of the murine P4-ATPase Atp8a1 (ATPase II). Biochemistry. 2006 Apr 25;45(16):5367-76. [PubMed:16618126 ]

Enzyme Details

5. Phosphatidylserine synthase 1

General function:: Involved in phosphatidylserine biosynthetic process
Specific function:: Catalyzes a base-exchange reaction in which the polar head group of phosphatidylethanolamine (PE) or phosphatidylcholine (PC) is replaced by L-serine. In membranes, PTDSS1 catalyzes mainly the conversion of phosphatidylcholine. Also converts, in vitro and to a lesser extent, phosphatidylethanolamine.
Gene Name:: PTDSS1
Uniprot ID:: P48651
Molecular weight:: 55527.18

References

Kuge O, Nishijima M: Biosynthetic regulation and intracellular transport of phosphatidylserine in mammalian cells. J Biochem. 2003 Apr;133(4):397-403. [PubMed:12761285 ]
Kuge O, Hasegawa K, Ohsawa T, Saito K, Nishijima M: Purification and characterization of Chinese hamster phosphatidylserine synthase 2. J Biol Chem. 2003 Oct 24;278(43):42692-8. Epub 2003 Aug 11. [PubMed:12912985 ]
Ohsawa T, Nishijima M, Kuge O: Functional analysis of Chinese hamster phosphatidylserine synthase 1 through systematic alanine mutagenesis. Biochem J. 2004 Aug 1;381(Pt 3):853-9. [PubMed:15130088 ]
Steenbergen R, Nanowski TS, Nelson R, Young SG, Vance JE: Phospholipid homeostasis in phosphatidylserine synthase-2-deficient mice. Biochim Biophys Acta. 2006 Mar;1761(3):313-23. Epub 2006 Mar 31. [PubMed:16627002 ]

Enzyme Details

6. Scavenger receptor class B member 1

General function:: Involved in cell adhesion
Specific function:: Receptor for different ligands such as phospholipids, cholesterol ester, lipoproteins, phosphatidylserine and apoptotic cells. Probable receptor for HDL, located in particular region of the plasma membrane, called caveolae. Facilitates the flux of free and esterified cholesterol between the cell surface and extracellular donors and acceptors, such as HDL and to a lesser extent, apoB-containing lipoproteins and modified lipoproteins. Probably involved in the phagocytosis of apoptotic cells, via its phosphatidylserine binding activity. Receptor for hepatitis C virus glycoprotein E2. Binding between SCARB1 and E2 was found to be independent of the genotype of the viral isolate. Plays an important role in the uptake of HDL cholesteryl ester
Gene Name:: SCARB1
Uniprot ID:: Q8WTV0
Molecular weight:: 60877.4

References

Yan X, Poelstra K, Scherphof GL, Kamps JA: A role for scavenger receptor B-I in selective transfer of rhodamine-PE from liposomes to cells. Biochem Biophys Res Commun. 2004 Dec 17;325(3):908-14. [PubMed:15541376 ]
Yancey PG, Kawashiri MA, Moore R, Glick JM, Williams DL, Connelly MA, Rader DJ, Rothblat GH: In vivo modulation of HDL phospholipid has opposing effects on SR-BI- and ABCA1-mediated cholesterol efflux. J Lipid Res. 2004 Feb;45(2):337-46. Epub 2003 Nov 1. [PubMed:14594995 ]
Nakagawa A, Shiratsuchi A, Tsuda K, Nakanishi Y: In vivo analysis of phagocytosis of apoptotic cells by testicular Sertoli cells. Mol Reprod Dev. 2005 Jun;71(2):166-77. [PubMed:15791597 ]
Zhang J, Fujii S, Wu Z, Hashioka S, Tanaka Y, Shiratsuchi A, Nakanishi Y, Nakanishi H: Involvement of COX-1 and up-regulated prostaglandin E synthases in phosphatidylserine liposome-induced prostaglandin E2 production by microglia. J Neuroimmunol. 2006 Mar;172(1-2):112-20. Epub 2005 Dec 20. [PubMed:16371234 ]
Osada Y, Shiratsuchi A, Nakanishi Y: Involvement of mitogen-activated protein kinases in class B scavenger receptor type I-induced phagocytosis of apoptotic cells. Exp Cell Res. 2006 Jun 10;312(10):1820-30. Epub 2006 Mar 10. [PubMed:16530182 ]

Enzyme Details

7. Phosphatidylserine decarboxylase proenzyme

General function:: Involved in phosphatidylserine decarboxylase activity
Specific function:: Not Available
Gene Name:: PISD
Uniprot ID:: Q9UG56
Molecular weight:: 43046.33

References

Wu WI, Voelker DR: Reconstitution of phosphatidylserine transport from chemically defined donor membranes to phosphatidylserine decarboxylase 2 implicates specific lipid domains in the process. J Biol Chem. 2004 Feb 20;279(8):6635-42. Epub 2003 Dec 4. [PubMed:14660568 ]
Burgermeister M, Birner-Grunberger R, Heyn M, Daum G: Contribution of different biosynthetic pathways to species selectivity of aminoglycerophospholipids assembled into mitochondrial membranes of the yeast Saccharomyces cerevisiae. Biochim Biophys Acta. 2004 Nov 8;1686(1-2):148-60. [PubMed:15522831 ]
Burgermeister M, Birner-Grunberger R, Nebauer R, Daum G: Contribution of different pathways to the supply of phosphatidylethanolamine and phosphatidylcholine to mitochondrial membranes of the yeast Saccharomyces cerevisiae. Biochim Biophys Acta. 2004 Nov 8;1686(1-2):161-8. [PubMed:15522832 ]
Roggero R, Zufferey R, Minca M, Richier E, Calas M, Vial H, Ben Mamoun C: Unraveling the mode of action of the antimalarial choline analog G25 in Plasmodium falciparum and Saccharomyces cerevisiae. Antimicrob Agents Chemother. 2004 Aug;48(8):2816-24. [PubMed:15273086 ]
Voelker DR: Protein and lipid motifs regulate phosphatidylserine traffic in yeast. Biochem Soc Trans. 2005 Nov;33(Pt 5):1141-5. [PubMed:16246067 ]

Enzyme Details

8. Phosphatidylserine synthase 2

General function:: Involved in phosphatidylserine biosynthetic process
Specific function:: Catalyzes a base-exchange reaction in which the polar head group of phosphatidylethanolamine (PE) or phosphatidylcholine (PC) is replaced by L-serine. PTDSS2 is specific for phosphatatidylethanolamine and does not act on phosphatidylcholine.
Gene Name:: PTDSS2
Uniprot ID:: Q9BVG9
Molecular weight:: 56252.55

References

Bergo MO, Gavino BJ, Steenbergen R, Sturbois B, Parlow AF, Sanan DA, Skarnes WC, Vance JE, Young SG: Defining the importance of phosphatidylserine synthase 2 in mice. J Biol Chem. 2002 Dec 6;277(49):47701-8. Epub 2002 Oct 1. [PubMed:12361952 ]
Vance JE, Vance DE: Phospholipid biosynthesis in mammalian cells. Biochem Cell Biol. 2004 Feb;82(1):113-28. [PubMed:15052332 ]
Dygas A, Baranska J, Santella L: Ca2+-dependent phosphatidylserine synthesis in immature and mature starfish oocytes. Acta Biochim Pol. 2003;50(2):377-87. [PubMed:12833164 ]
Grandmaison PA, Nanowski TS, Vance JE: Externalization of phosphatidylserine during apoptosis does not specifically require either isoform of phosphatidylserine synthase. Biochim Biophys Acta. 2004 Feb 27;1636(1):1-11. [PubMed:14984733 ]
Wen Z, Kim HY: Inhibition of phosphatidylserine biosynthesis in developing rat brain by maternal exposure to ethanol. J Neurosci Res. 2007 May 15;85(7):1568-78. [PubMed:17387686 ]

Enzyme Details

9. Sphingomyelin phosphodiesterase 3

General function:: Involved in metal ion binding
Specific function:: Catalyzes the hydrolysis of sphingomyelin to form ceramide and phosphocholine. Ceramide mediates numerous cellular functions, such as apoptosis and growth arrest, and is capable of regulating these 2 cellular events independently. Also hydrolyzes sphingosylphosphocholine. Regulates the cell cycle by acting as a growth suppressor in confluent cells. Probably acts as a regulator of postnatal development and participates in bone and dentin mineralization.
Gene Name:: SMPD3
Uniprot ID:: Q9NY59
Molecular weight:: 71080.1

References

Krut O, Wiegmann K, Kashkar H, Yazdanpanah B, Kronke M: Novel tumor necrosis factor-responsive mammalian neutral sphingomyelinase-3 is a C-tail-anchored protein. J Biol Chem. 2006 May 12;281(19):13784-93. Epub 2006 Mar 3. [PubMed:16517606 ]
Marchesini N, Luberto C, Hannun YA: Biochemical properties of mammalian neutral sphingomyelinase 2 and its role in sphingolipid metabolism. J Biol Chem. 2003 Apr 18;278(16):13775-83. Epub 2003 Feb 3. [PubMed:12566438 ]

Enzyme Details

10. Sphingomyelin phosphodiesterase 4

General function:: Involved in metal ion binding
Specific function:: Catalyzes the hydrolysis of membrane sphingomyelin to form phosphorylcholine and ceramide.
Gene Name:: SMPD4
Uniprot ID:: Q9NXE4
Molecular weight:: 86192.575

References

Krut O, Wiegmann K, Kashkar H, Yazdanpanah B, Kronke M: Novel tumor necrosis factor-responsive mammalian neutral sphingomyelinase-3 is a C-tail-anchored protein. J Biol Chem. 2006 May 12;281(19):13784-93. Epub 2006 Mar 3. [PubMed:16517606 ]

Showing metabocard for Phosphatidylserine (HMDB0014291)

MOL for HMDB0014291 (Phosphatidylserine)

3D MOL for HMDB0014291 (Phosphatidylserine)

3D SDF for HMDB0014291 (Phosphatidylserine)

3D-SDF for HMDB0014291 (Phosphatidylserine)

PDB for HMDB0014291 (Phosphatidylserine)

3D PDB for HMDB0014291 (Phosphatidylserine)

SMILES for HMDB0014291 (Phosphatidylserine)

INCHI for HMDB0014291 (Phosphatidylserine)

Structure for HMDB0014291 (Phosphatidylserine)

3D Structure for HMDB0014291 (Phosphatidylserine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

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