Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001540
Identification
Name: 1-Octadecanoyl-sn-glycerol 3-phosphate
Description:1-octadecanoyl-sn-glycerol 3-phosphate belongs to the class of Lysophosphatidic Acids. These are glycerophosphates where the glycerol is esterified with one saturated fatty acid. (inferred from compound structure)
Structure
Thumb
Synonyms:
  • 1-Octadecanoyl-sn-glycerol 3-phosphoric acid
  • 1-Stearoylglycerol 3-phosphate
  • 1-Stearoylglycerol 3-phosphoric acid
Chemical Formula: C21H41O7P
Average Molecular Weight: 436.5198
Monoisotopic Molecular Weight: 436.258990178
InChI Key: LAYXSTYJRSVXIH-HXUWFJFHSA-L
InChI:InChI=1S/C21H43O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h20,22H,2-19H2,1H3,(H2,24,25,26)/p-2/t20-/m1/s1
CAS number: Not Available
IUPAC Name:(2R)-2-hydroxy-3-(phosphonatooxy)propyl octadecanoate
Traditional IUPAC Name: (2R)-2-hydroxy-3-(phosphonatooxy)propyl octadecanoate
SMILES:[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCC)COP([O-])([O-])=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Glycerophospholipids
Sub ClassGlycerophosphates
Direct Parent 1-acylglycerol-3-phosphates
Alternative Parents
Substituents
  • 1-acylglycerol-3-phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Secondary alcohol
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Organic anion
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00155 mg/mLALOGPS
logP5.7ALOGPS
logP5.85ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)1.51ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area118.95 Å2ChemAxon
Rotatable Bond Count22ChemAxon
Refractivity111.94 m3·mol-1ChemAxon
Polarizability50.36 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0121900000-96d3a6e7107944798dc9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-4585900000-a948ca4102435e3f95adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar0-9551000000-dde025bb4e363d734be6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0019-0090800000-1765a6e7e1e9db037c53View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090100000-5391737f7370e55fd411View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00m0-4190000000-1239a3907229b7365c5eView in MoNA
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID74565
HMDB IDNot Available
Pubchem Compound ID49859619
Kegg IDNot Available
ChemSpider ID29368344
Wikipedia IDNot Available
BioCyc IDCPD0-2113
EcoCyc IDCPD0-2113

Enzymes

General function:
Involved in transferase activity, transferring acyl groups
Specific function:
Catalyzes the transfer of an acyl group from acyl-ACP to glycerol-3-phosphate (G3P) to form lysophosphatidic acid (LPA). This enzyme can utilize either acyl-CoA or acyl-ACP as the fatty acyl donor
Gene Name:
plsB
Locus Tag:
PA3673
Molecular weight:
94.8 kDa
Reactions
Acyl-CoA + sn-glycerol 3-phosphate = CoA + 1-acyl-sn-glycerol 3-phosphate.
General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes only long chain acyl thioesters (C12-C18). Specificity similar to chymotrypsin
Gene Name:
tesA
Locus Tag:
PA2856
Molecular weight:
21 kDa
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.
General function:
Involved in fatty acid biosynthetic process
Specific function:
Carrier of the growing fatty acid chain in fatty acid biosynthesis
Gene Name:
acpP
Locus Tag:
PA2966
Molecular weight:
8.7 kDa