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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-09-12 01:12:53 UTC
Update Date2020-02-26 21:27:00 UTC
HMDB IDHMDB0007003
Secondary Accession Numbers
  • HMDB07003
Metabolite Identification
Common NameCPA(16:0/0:0)
DescriptioncPA(16:0/0:0) is a cyclic phosphatidic acid or cyclic lysophosphatidic acid. It is a glycerophospholipid in which a cyclic phosphate moiety occupies two glycerol substitution sites. Lysophosphatidic acids can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1). Fatty acids containing 16 and 18 carbons are the most common. Cyclic phosphatidic acids have been detected in a wide range of organisms including humans, especially in the brain but also in serum (at a concentration of 10-7M). cPA's have a cyclic phosphate at the sn-2 and sn-3 positions of the glycerol carbons, and this structure is absolutely necessary for their activities. In particular, it is found in tissues subject to injury, and while it may have some similar signalling functions to lysophosphatidic acid per se, it also has some quite distinct biological activities. For example, cyclic phosphatidic acid is known to be a specific inhibitor of DNA polymerase alpha. It has an appreciable effect on the inhibition of cancer cell invasion and metastasis.
Structure
Data?1582752420
Synonyms
ValueSource
1-Hexadecanoyl-cyclophosphatidic acidHMDB
1-Palmitoyl-glycero-3-cyclophosphateHMDB
CPA(16:0)HMDB
Cyclic phosphatidic acid(16:0)HMDB
Cyclic phosphatidic acid(16:0/0:0)HMDB
(2-Hydroxy-2-oxo-1,3,2λ⁵-dioxaphospholan-4-yl)methyl hexadecanoic acidGenerator
Chemical FormulaC19H37O6P
Average Molecular Weight392.4672
Monoisotopic Molecular Weight392.232775428
IUPAC Name(2-hydroxy-2-oxo-1,3,2λ⁵-dioxaphospholan-4-yl)methyl hexadecanoate
Traditional Name(2-hydroxy-2-oxo-1,3,2λ⁵-dioxaphospholan-4-yl)methyl hexadecanoate
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(=O)OCC1COP(O)(=O)O1
InChI Identifier
InChI=1S/C19H37O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(20)23-16-18-17-24-26(21,22)25-18/h18H,2-17H2,1H3,(H,21,22)
InChI KeyWLYRJURLXSFXRK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-acyl-sn-glycerol-2,3-cyclic-phosphates. These are monoacylglycerophosphates consisting of a sn-glycerol 2,3-cyclic phosphate that carries an acyl group at the 1-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct Parent1-acyl-sn-glycerol-2,3-cyclic-phosphates
Alternative Parents
Substituents
  • 1-acyl-sn-glycerol-2,3-cyclic-phosphate
  • Fatty acid ester
  • Organic phosphoric acid derivative
  • Fatty acyl
  • 1,3_dioxaphospholane
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.003 g/LALOGPS
logP5.12ALOGPS
logP5.86ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)1.84ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area82.06 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity101.2 m³·mol⁻¹ChemAxon
Polarizability45.41 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-2941000000-a7754b3d4d0b019ecd15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000f-5859000000-3e458c8ea3e85d9bbe45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-7961000000-376022ff01155f430544Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000m-6920000000-77c63fe8998476b2c35bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4u-0195000000-72b269827d76881aa8f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-2391000000-870f830b62d92cff6547Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9020000000-63a5c62523e8cc061b89Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue Locations
  • All Tissues
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024197
KNApSAcK IDNot Available
Chemspider ID7977702
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9801940
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available