CPA(18:0/0:0) (CHEM036354)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:25:06 UTC
Update Date2016-11-09 01:21:29 UTC
Accession NumberCHEM036354
Identification
Common NameCPA(18:0/0:0)
ClassSmall Molecule
DescriptioncPA(18:0/0:0) 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-Octadecanoyl-cyclophosphatidic acidHMDB
1-Stearoyl-glycero-3-cyclophosphateHMDB
CPA(18:0)HMDB
Cyclic phosphatidic acid(18:0)HMDB
Cyclic phosphatidic acid(18:0/0:0)HMDB
(2-Hydroxy-2-oxo-1,3,2λ⁵-dioxaphospholan-4-yl)methyl octadecanoic acidGenerator
Chemical FormulaC21H41O6P
Average Molecular Mass420.520 g/mol
Monoisotopic Mass420.264 g/mol
CAS Registry NumberNot Available
IUPAC Name(2-hydroxy-2-oxo-1,3,2λ⁵-dioxaphospholan-4-yl)methyl octadecanoate
Traditional Name(2-hydroxy-2-oxo-1,3,2λ⁵-dioxaphospholan-4-yl)methyl octadecanoate
SMILESCCCCCCCCCCCCCCCCCC(=O)OCC1COP(O)(=O)O1
InChI IdentifierInChI=1S/C21H41O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(22)25-18-20-19-26-28(23,24)27-20/h20H,2-19H2,1H3,(H,23,24)
InChI KeyBAAJXXGEGGUMMX-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 Solubility0.0013 g/LALOGPS
logP5.87ALOGPS
logP6.74ChemAxon
logS-5.5ALOGPS
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 Count19ChemAxon
Refractivity110.4 m³·mol⁻¹ChemAxon
Polarizability49.53 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-2962000000-080c27238137c4fd88e7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00y3-6860900000-aead5a658b6b9df3a229Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-7981200000-125f7a030ba3d6ccb11bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-8980000000-eae1a15d5077995f96c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0159-0190500000-768b8bee8dbec5a31a71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00lr-2390000000-94775e414eb2c3d89e95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9020000000-3ae270aa714aadc44677Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-3700900000-69d2ec81eace8f22cd7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-6900100000-ad2ff302a0c275b9f515Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9300000000-b2fc7b2c08917581b50aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0159-0610900000-30d83a307029a94212acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-4590000000-048c40aacbdb7dc84504Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-9330000000-d9aa2b30226e57e4e68aSpectrum
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 IDHMDB0007004
FooDB IDFDB024198
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24766507
ChEBI ID170122
PubChem Compound ID51040919
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available