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Showing metabocard for Phosphatidylserine (HMDB0014291)

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enzymes (10) Show 10 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:48 UTC
Update Date2022-03-07 02:51:34 UTC
HMDB IDHMDB0014291
Secondary Accession Numbers
  • HMDB14291
Metabolite Identification
Common NamePhosphatidylserine
DescriptionPhosphatidylserine (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
Data?1582753164
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0014291 (Phosphatidylserine)


  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
Download

3D MOL for HMDB0014291 (Phosphatidylserine)

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
Download

3D SDF for HMDB0014291 (Phosphatidylserine)


  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

$$$$
Download

3D-SDF for HMDB0014291 (Phosphatidylserine)

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
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PDB for HMDB0014291 (Phosphatidylserine)

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
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3D PDB for HMDB0014291 (Phosphatidylserine)

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
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SMILES for HMDB0014291 (Phosphatidylserine)

[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CC)OC(=O)CCC)C(O)=O
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INCHI for HMDB0014291 (Phosphatidylserine)

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
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
3-O-sn-Phosphatidyl-L-serineHMDB
O3-Phosphatidyl-L-serineHMDB
Phosphatidyl-L-serineHMDB
(2S)-2-Amino-3-({[(2R)-2-(butanoyloxy)-3-(propanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoateGenerator
2-Acetamido-2-deoxy-D-glucoseChEBI, HMDB
D-GlcNAcChEBI, HMDB
N-Acetyl-D-glucosamineChEBI, HMDB
N-AcetylchitosamineChEBI, HMDB
N Acetyl D glucosamineHMDB
2 Acetamido 2 deoxy D glucoseHMDB
2 Acetamido 2 deoxyglucoseHMDB
2-Acetamido-2-deoxyglucoseHMDB
AcetylglucosamineHMDB
Chemical FormulaC13H24NO10P
Average Molecular Weight385.3041
Monoisotopic Molecular Weight385.113782505
IUPAC Name(2S)-2-amino-3-({[(2R)-2-(butanoyloxy)-3-(propanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid
Traditional Namephosphatidylserine
CAS Registry Number8002-43-5
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 KeyUNJJBGNPUUVVFQ-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoserines
Direct ParentPhosphatidylserines
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 FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.7 g/LNot Available
LogP-3.5Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.7 g/LALOGPS
logP-1ALOGPS
logP-1.6ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.47ChemAxon
pKa (Strongest Basic)9.38ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area171.68 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity81.81 m³·mol⁻¹ChemAxon
Polarizability35.59 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+190.42631661259
DarkChem[M-H]-183.42831661259
DeepCCS[M+H]+170.72430932474
DeepCCS[M-H]-168.32930932474
DeepCCS[M-2H]-202.10730932474
DeepCCS[M+Na]+176.87930932474
AllCCS[M+H]+187.932859911
AllCCS[M+H-H2O]+185.632859911
AllCCS[M+NH4]+189.932859911
AllCCS[M+Na]+190.532859911
AllCCS[M-H]-181.432859911
AllCCS[M+Na-2H]-182.232859911
AllCCS[M+HCOO]-183.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Phosphatidylserine[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CC)OC(=O)CCC)C(O)=O3561.3Standard polar33892256
Phosphatidylserine[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CC)OC(=O)CCC)C(O)=O2523.9Standard non polar33892256
Phosphatidylserine[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CC)OC(=O)CCC)C(O)=O2789.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phosphatidylserine,1TMS,isomer #1CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@H](N)C(=O)O[Si](C)(C)C2550.0Semi standard non polar33892256
Phosphatidylserine,1TMS,isomer #2CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N)C(=O)O)O[Si](C)(C)C2597.0Semi standard non polar33892256
Phosphatidylserine,1TMS,isomer #3CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@H](N[Si](C)(C)C)C(=O)O2666.9Semi standard non polar33892256
Phosphatidylserine,2TMS,isomer #1CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N)C(=O)O[Si](C)(C)C)O[Si](C)(C)C2566.1Semi standard non polar33892256
Phosphatidylserine,2TMS,isomer #1CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N)C(=O)O[Si](C)(C)C)O[Si](C)(C)C2524.7Standard non polar33892256
Phosphatidylserine,2TMS,isomer #1CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N)C(=O)O[Si](C)(C)C)O[Si](C)(C)C4421.3Standard polar33892256
Phosphatidylserine,2TMS,isomer #2CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C2626.6Semi standard non polar33892256
Phosphatidylserine,2TMS,isomer #2CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C2653.5Standard non polar33892256
Phosphatidylserine,2TMS,isomer #2CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C4273.0Standard polar33892256
Phosphatidylserine,2TMS,isomer #3CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N[Si](C)(C)C)C(=O)O)O[Si](C)(C)C2667.9Semi standard non polar33892256
Phosphatidylserine,2TMS,isomer #3CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N[Si](C)(C)C)C(=O)O)O[Si](C)(C)C2627.8Standard non polar33892256
Phosphatidylserine,2TMS,isomer #3CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N[Si](C)(C)C)C(=O)O)O[Si](C)(C)C3837.4Standard polar33892256
Phosphatidylserine,2TMS,isomer #4CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2812.0Semi standard non polar33892256
Phosphatidylserine,2TMS,isomer #4CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2697.9Standard non polar33892256
Phosphatidylserine,2TMS,isomer #4CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C4374.1Standard polar33892256
Phosphatidylserine,3TMS,isomer #1CCCC(=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)C2651.0Semi standard non polar33892256
Phosphatidylserine,3TMS,isomer #1CCCC(=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)C2678.7Standard non polar33892256
Phosphatidylserine,3TMS,isomer #1CCCC(=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)C3413.6Standard polar33892256
Phosphatidylserine,3TMS,isomer #2CCCC(=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)C2820.9Semi standard non polar33892256
Phosphatidylserine,3TMS,isomer #2CCCC(=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)C2731.7Standard non polar33892256
Phosphatidylserine,3TMS,isomer #2CCCC(=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)C3897.2Standard polar33892256
Phosphatidylserine,3TMS,isomer #3CCCC(=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)C2819.4Semi standard non polar33892256
Phosphatidylserine,3TMS,isomer #3CCCC(=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)C2729.2Standard non polar33892256
Phosphatidylserine,3TMS,isomer #3CCCC(=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)C3550.1Standard polar33892256
Phosphatidylserine,4TMS,isomer #1CCCC(=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)C2840.2Semi standard non polar33892256
Phosphatidylserine,4TMS,isomer #1CCCC(=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)C2749.9Standard non polar33892256
Phosphatidylserine,4TMS,isomer #1CCCC(=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)C3247.7Standard polar33892256
Phosphatidylserine,1TBDMS,isomer #1CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C2797.0Semi standard non polar33892256
Phosphatidylserine,1TBDMS,isomer #2CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(OC[C@H](N)C(=O)O)O[Si](C)(C)C(C)(C)C2820.9Semi standard non polar33892256
Phosphatidylserine,1TBDMS,isomer #3CCCC(=O)O[C@H](COC(=O)CC)COP(=O)(O)OC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O2866.9Semi standard non polar33892256
Phosphatidylserine,2TBDMS,isomer #1CCCC(=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)C3033.7Semi standard non polar33892256
Phosphatidylserine,2TBDMS,isomer #1CCCC(=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)C2826.7Standard non polar33892256
Phosphatidylserine,2TBDMS,isomer #1CCCC(=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)C4383.0Standard polar33892256
Phosphatidylserine,2TBDMS,isomer #2CCCC(=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)C3084.9Semi standard non polar33892256
Phosphatidylserine,2TBDMS,isomer #2CCCC(=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)C2957.1Standard non polar33892256
Phosphatidylserine,2TBDMS,isomer #2CCCC(=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)C4246.7Standard polar33892256
Phosphatidylserine,2TBDMS,isomer #3CCCC(=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)C3115.3Semi standard non polar33892256
Phosphatidylserine,2TBDMS,isomer #3CCCC(=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)C2929.5Standard non polar33892256
Phosphatidylserine,2TBDMS,isomer #3CCCC(=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)C3901.9Standard polar33892256
Phosphatidylserine,2TBDMS,isomer #4CCCC(=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)C3244.6Semi standard non polar33892256
Phosphatidylserine,2TBDMS,isomer #4CCCC(=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)C2993.8Standard non polar33892256
Phosphatidylserine,2TBDMS,isomer #4CCCC(=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)C4300.5Standard polar33892256
Phosphatidylserine,3TBDMS,isomer #1CCCC(=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)C3327.0Semi standard non polar33892256
Phosphatidylserine,3TBDMS,isomer #1CCCC(=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)C3091.5Standard non polar33892256
Phosphatidylserine,3TBDMS,isomer #1CCCC(=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)C3637.2Standard polar33892256
Phosphatidylserine,3TBDMS,isomer #2CCCC(=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)C3474.1Semi standard non polar33892256
Phosphatidylserine,3TBDMS,isomer #2CCCC(=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)C3163.2Standard non polar33892256
Phosphatidylserine,3TBDMS,isomer #2CCCC(=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)C3961.2Standard polar33892256
Phosphatidylserine,3TBDMS,isomer #3CCCC(=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)C3497.0Semi standard non polar33892256
Phosphatidylserine,3TBDMS,isomer #3CCCC(=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)C3127.3Standard non polar33892256
Phosphatidylserine,3TBDMS,isomer #3CCCC(=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)C3697.7Standard polar33892256
Phosphatidylserine,4TBDMS,isomer #1CCCC(=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)C3713.2Semi standard non polar33892256
Phosphatidylserine,4TBDMS,isomer #1CCCC(=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)C3284.7Standard non polar33892256
Phosphatidylserine,4TBDMS,isomer #1CCCC(=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)C3535.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Phosphatidylserine GC-MS (Non-derivatized) - 70eV, Positivesplash10-06xx-9331000000-5397fe5806bdc09af3892017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phosphatidylserine GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9125000000-a42f2f526549a4b9fc5c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phosphatidylserine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylserine 10V, Positive-QTOFsplash10-000l-9013000000-a48d79654fdd42e7b8322017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylserine 20V, Positive-QTOFsplash10-000f-9010000000-3e5d23a16d25de8967472017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylserine 40V, Positive-QTOFsplash10-000f-9200000000-a15a472f35148d4c5da02017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylserine 10V, Negative-QTOFsplash10-05fr-9123000000-667f29964b87dbc7f6bc2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylserine 20V, Negative-QTOFsplash10-05i0-9110000000-798e4cca9186bc74d8672017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylserine 40V, Negative-QTOFsplash10-004i-9000000000-a8525ea4757be13464892017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylserine 10V, Positive-QTOFsplash10-14i6-0049000000-3f7053b983ba7bcf4ea72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylserine 20V, Positive-QTOFsplash10-0k96-0449000000-907abccf1ab74e57402a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylserine 40V, Positive-QTOFsplash10-0k96-0449000000-907abccf1ab74e57402a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylserine 10V, Negative-QTOFsplash10-001i-0009000000-cec6e0edd55251e4e1842021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylserine 20V, Negative-QTOFsplash10-001i-0019000000-8bafada2a22438e2959f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylserine 40V, Negative-QTOFsplash10-05gs-4092000000-a16c91e5323676b08b102021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylserine 10V, Positive-QTOFsplash10-0ab9-0016900000-3028e5441df826078ff92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylserine 20V, Positive-QTOFsplash10-0a4i-0002900000-b6e85ac16efffc16be002021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylserine 40V, Positive-QTOFsplash10-0a4i-0092100000-a487704ac6b4572cc4722021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylserine 10V, Positive-QTOFsplash10-000i-0019000000-eec474a40e6a95ff20652021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylserine 20V, Positive-QTOFsplash10-0uds-0297000000-c05ccb25e22017ff2bf62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphatidylserine 40V, Positive-QTOFsplash10-0udj-0294000000-1c85e78190b31b5c1a7f2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00144 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00144 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00144
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID13628254
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhosphatidylserine
METLIN IDNot Available
PubChem Compound6323481
PDB IDNot Available
ChEBI ID18303
Food Biomarker OntologyNot Available
VMH IDPS_HS
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  6. 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 ]
  7. 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 ]
  8. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  10. 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
  1. 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
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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
  1. Kuge O, Nishijima M: Biosynthetic regulation and intracellular transport of phosphatidylserine in mammalian cells. J Biochem. 2003 Apr;133(4):397-403. [PubMed:12761285 ]
  2. 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 ]
  3. 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 ]
  4. 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
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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
  1. 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 ]
  2. Vance JE, Vance DE: Phospholipid biosynthesis in mammalian cells. Biochem Cell Biol. 2004 Feb;82(1):113-28. [PubMed:15052332 ]
  3. 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 ]
  4. 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 ]
  5. 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
  1. 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 ]
  2. 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
  1. 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 ]