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Showing Compound CPA(16:0/0:0) (FDB024197)

Record Information
Version1.0
Creation date2011-09-21 00:41:14 UTC
Update date2015-07-21 06:58:01 UTC
Primary IDFDB024197
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. [HMDB]
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
1-Hexadecanoyl-cycloatidic acidHMDB
1-hexadecanoyl-cyclophosphatidic acidhmdb
1-Palmitoyl-glycero-3-cycloateHMDB
1-palmitoyl-glycero-3-cyclophosphatehmdb
cPA(16:0)hmdb
cPA(16:0/0:0)hmdb
Cyclic atidic acid(16:0)HMDB
Cyclic atidic acid(16:0/0:0)HMDB
Cyclic Phosphatidic acid(16:0)hmdb
Cyclic Phosphatidic acid(16:0/0:0)hmdb
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
Chemical FormulaC19H37O6P
IUPAC name(2-hydroxy-2-oxo-1,3,2λ⁵-dioxaphospholan-4-yl)methyl hexadecanoate
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
Isomeric SMILESCCCCCCCCCCCCCCCC(=O)OCC1COP(O)(=O)O1
Average Molecular Weight392.4672
Monoisotopic Molecular Weight392.232775428
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCPA(16:0/0:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dr-2941000000-a7754b3d4d0b019ecd15Spectrum
Predicted GC-MSCPA(16:0/0:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCPA(16:0/0:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000f-5859000000-3e458c8ea3e85d9bbe452017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-7961000000-376022ff01155f4305442017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000m-6920000000-77c63fe8998476b2c35b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4u-0195000000-72b269827d76881aa8f82017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-2391000000-870f830b62d92cff65472017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9020000000-63a5c62523e8cc061b892017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-0619000000-1210e56060ec93566a5d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-4590000000-d96abd5e1fa5ad56efb02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9520000000-d31380c77196dfd340b52021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-3709000000-85e4fffd82d840924cb52021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-5901000000-3ff44f491b8a9d6e8a742021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9300000000-00f6f81aa8aba1e3fef52021-09-23View Spectrum
NMRNot Available
ChemSpider ID7977702
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID9801940
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB07003
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference