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Showing NP-Card for Phosphatidylserine (NP0334557)

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Record Information
Version2.0
Created at2024-09-10 18:53:33 UTC
Updated at2024-09-10 18:53:33 UTC
NP-MRD IDNP0334557
Secondary Accession NumbersNone
Natural Product Identification
Common NamePhosphatidylserine
DescriptionPhosphatidylserine 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. PS has been investigated in a small number of double-blind placebo trials and has been shown to increase memory performance in the elderly. There are no reports of overdosage. 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. Phosphatidylserine is a very strong basic compound (based on its pKa). In humans, phosphatidylserine is involved in phosphatidylethanolamine biosynthesis. PS has been shown to slow cognitive decline in animal models.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334557 (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 NP0334557 (Phosphatidylserine)

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3D SDF for NP0334557 (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>
NP0334557

> <DATABASE_NAME>
NP-MRD

> <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 NP0334557 (Phosphatidylserine)
Download
PDB for NP0334557 (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

Download
3D PDB for NP0334557 (Phosphatidylserine)
Download
SMILES for NP0334557 (Phosphatidylserine)
[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CC)OC(=O)CCC)C(O)=O
Download
INCHI for NP0334557 (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 JSmol
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 Mass385.3041 Da
Monoisotopic Mass385.11378 Da
IUPAC Name(2S)-2-amino-3-({[(2R)-2-(butanoyloxy)-3-(propanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid
Traditional Namephosphatidylserine
CAS Registry NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0014291  
DrugBank IDDB00144  
Phenol Explorer Compound IDNot Available
FoodDB 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  
Good Scents IDNot Available
References
General References