Showing metabocard for PA(P-16:0e/18:2(9Z,12Z)) (BMDB0011155)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:13:45 UTC
Update Date2020-04-22 15:42:59 UTC
BMDB IDBMDB0011155
Secondary Accession Numbers
  • BMDB11155
Metabolite Identification
Common NamePA(P-16:0e/18:2(9Z,12Z))
DescriptionPA(P-16:0/18:2(9Z,12Z)) is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(P-16:0/18:2(9Z,12Z)), in particular, consists of one 1Z-hexadecenyl chain to the C-1 atom, and one 9Z,12Z-octadecadienoyl to the C-2 atom. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(9Z,12Z-Octadecadienoyl)-1-(1Z-hexadecenyl)-sn-glycero-3-phosphateHMDB
1-(1Z-Hexadecenyl)-2-linoleoyl-sn-glycero-3-phosphateHMDB
1-(1Z-Hexadecenyl)-2-linoleoyl-sn-phosphatidic acidHMDB
PA(16:1/18:2)HMDB
PA(34:3)HMDB
PA(O-16:1(1Z)/18:2(9Z,12Z))HMDB
PA(O-16:1(1Z)/18:2N6)HMDB
PA(O-16:1(1Z)/18:2W6)HMDB
PA(P-16:0/18:2N6)HMDB
PA(P-16:0/18:2W6)HMDB
Phosphatidate(16:1/18:2)HMDB
Phosphatidate(34:3)HMDB
Phosphatidate(O-16:1(1Z)/18:2(9Z,12Z))HMDB
Phosphatidate(O-16:1(1Z)/18:2N6)HMDB
Phosphatidate(O-16:1(1Z)/18:2W6)HMDB
Phosphatidate(P-16:0/18:2(9Z,12Z))HMDB
Phosphatidate(P-16:0/18:2N6)HMDB
Phosphatidate(P-16:0/18:2W6)HMDB
Phosphatidic acid(16:1/18:2)HMDB
Phosphatidic acid(34:3)HMDB
Phosphatidic acid(O-16:1(1Z)/18:2(9Z,12Z))HMDB
Phosphatidic acid(O-16:1(1Z)/18:2n6)HMDB
Phosphatidic acid(O-16:1(1Z)/18:2W6)HMDB
Phosphatidic acid(p-16:0/18:2(9Z,12Z))HMDB
Phosphatidic acid(p-16:0/18:2n6)HMDB
Phosphatidic acid(p-16:0/18:2W6)HMDB
PA(P-16:0/18:2(9Z,12Z))HMDB
Chemical FormulaC37H69O7P
Average Molecular Weight656.9133
Monoisotopic Molecular Weight656.478091074
IUPAC Name[(2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphonic acid
Traditional Name(2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCC\C=C/OC[C@]([H])(COP(=O)(O)O)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C37H69O7P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-37(38)44-36(35-43-45(39,40)41)34-42-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h11,13,17,19,31,33,36H,3-10,12,14-16,18,20-30,32,34-35H2,1-2H3,(H2,39,40,41)/b13-11-,19-17-,33-31-/t36-/m1/s1
InChI KeyOLCTYLMZTXKGKH-BBNWHMLASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-(1z-alkenyl),2-acyl-glycerophosphates. These are glycerophosphates that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one 1Z-alkenyl chain attached through an ether linkage at the O1-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct Parent1-(1Z-alkenyl),2-acyl-glycerophosphates
Alternative Parents
Substituents
  • 1-(1z-alkenyl),2-acyl-glycerol-3-phosphate
  • Glycerol vinyl ether
  • Fatty acid ester
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Fatty acyl
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP9.27ALOGPS
logP12.44ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)1.32ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area102.29 ŲChemAxon
Rotatable Bond Count35ChemAxon
Refractivity190.35 m³·mol⁻¹ChemAxon
Polarizability79.89 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9242121000-692d517b782c84adf74fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0bvi-0094024000-d26e3d32b43139cc010cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01vk-1191010000-759b4f1be9058b13ed02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-1190000000-3531949a0e4335a1c5e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-5094104000-9a1389e6629f728fa5beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9030000000-1c805627741e0b7f9ec0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9010000000-057f58ca0a283cf13563View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000009000-a18d16033080fbd91fbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bvj-9041205000-87d1b775d631aa07ef15View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9020000000-749692008f9c19c0a48cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1023192000-d4f59b16aa186b546890View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1028290000-17b2dfdd5baa85347670View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-0932000000-8ec8ba183834e0fc606cView in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0011155
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027930
KNApSAcK IDNot Available
Chemspider ID24766521
KEGG Compound IDC15647
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52929743
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available