CPA(16:0/0:0) (CHEM036353)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:25:04 UTC
Update Date2016-11-09 01:21:29 UTC
Accession NumberCHEM036353
Identification
Common NameCPA(16:0/0:0)
ClassSmall Molecule
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.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass392.467 g/mol
Monoisotopic Mass392.233 g/mol
CAS Registry NumberNot Available
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
SMILESCCCCCCCCCCCCCCCC(=O)OCC1COP(O)(=O)O1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-2941000000-a7754b3d4d0b019ecd15Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-0619000000-1210e56060ec93566a5dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-4590000000-d96abd5e1fa5ad56efb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9520000000-d31380c77196dfd340b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-3709000000-85e4fffd82d840924cb5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-5901000000-3ff44f491b8a9d6e8a74Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9300000000-00f6f81aa8aba1e3fef5Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0007003
FooDB IDFDB024197
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID7977702
ChEBI ID170100
PubChem Compound ID9801940
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available