Showing metabocard for PA(18:0/18:2(9Z,12Z)) (BMDB0007861)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:45:54 UTC
Update Date2020-05-21 16:27:46 UTC
BMDB IDBMDB0007861
Secondary Accession Numbers
  • BMDB07861
Metabolite Identification
Common NamePA(18:0/18:2(9Z,12Z))
DescriptionPA(18:0/18:2(9Z,12Z)), also known as Pa(18:0/18:2(9z,12z)) or PA(18:0/18:2), belongs to the class of organic compounds known as 1,2-diacylglycerol-3-phosphates. These are glycerol-3-phosphates in which the glycerol moiety is bonded to two aliphatic chains through ester linkages. Thus, PA(18:0/18:2(9Z,12Z)) is considered to be a glycerophosphate lipid molecule. PA(18:0/18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PA(18:0/18:2(9Z,12Z)) exists in all living organisms, ranging from bacteria to humans. PA(18:0/18:2(9Z,12Z)) participates in a number of enzymatic reactions, within cattle. In particular, PA(18:0/18:2(9Z,12Z)) can be biosynthesized from lpa(18:0/0:0) and linoleoyl-CoA; which is mediated by the enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase epsilon. Furthermore, Cytidine triphosphate and PA(18:0/18:2(9Z,12Z)) can be converted into CDP-DG(18:0/18:2(9Z,12Z)); which is catalyzed by the enzyme phosphatidate cytidylyltransferase 2. Furthermore, PA(18:0/18:2(9Z,12Z)) can be biosynthesized from lpa(18:0/0:0) and linoleoyl-CoA; which is mediated by the enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase epsilon. Finally, Cytidine triphosphate and PA(18:0/18:2(9Z,12Z)) can be converted into CDP-DG(18:0/18:2(9Z,12Z)) through its interaction with the enzyme phosphatidate cytidylyltransferase 2. In cattle, PA(18:0/18:2(9Z,12Z)) is involved in a couple of metabolic pathways, which include cardiolipin biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z)) pathway and cardiolipin biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R)-1-(Phosphonooxy)-3-(stearoyloxy)propan-2-yl (9Z,12Z)-octadeca-9,12-dienoateChEBI
1-18:0-2-18:2-Phosphatidic acidChEBI
1-Octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphateChEBI
1-Octadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphateChEBI
18:0-18:2-PAChEBI
PA(18:0/18:2)ChEBI
PA(18:0/18:2N6)ChEBI
PA(18:0/18:2OMEGA6)ChEBI
PA(36:2)ChEBI
Phosphatidic acid(18:0/18:2)ChEBI
Phosphatidic acid(18:0/18:2n6)ChEBI
Phosphatidic acid(18:0/18:2omega6)ChEBI
Phosphatidic acid(36:2)ChEBI
(2R)-1-(Phosphonooxy)-3-(stearoyloxy)propan-2-yl (9Z,12Z)-octadeca-9,12-dienoic acidGenerator
1-18:0-2-18:2-PhosphatidateGenerator
1-Octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphoric acidGenerator
1-Octadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoric acidGenerator
Phosphatidate(18:0/18:2)Generator
Phosphatidate(18:0/18:2N6)Generator
Phosphatidate(18:0/18:2OMEGA6)Generator
Phosphatidate(36:2)Generator
1-Octadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-phosphatidic acidHMDB
1-Stearoyl-2-linoleoyl-sn-glycero-3-phosphateHMDB
PA(18:0/18:2W6)HMDB
Phosphatidic acid(18:0/18:2W6)HMDB
Chemical FormulaC39H73O8P
Average Molecular Weight700.9659
Monoisotopic Molecular Weight700.504305824
IUPAC Name[(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(octadecanoyloxy)propoxy]phosphonic acid
Traditional Name(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(octadecanoyloxy)propoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP(O)(=O)O)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C39H73O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(40)45-35-37(36-46-48(42,43)44)47-39(41)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h12,14,18,20,37H,3-11,13,15-17,19,21-36H2,1-2H3,(H2,42,43,44)/b14-12-,20-18-/t37-/m1/s1
InChI KeyQYYWMYCDFOLKKH-DAKWMOBOSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,2-diacylglycerol-3-phosphates. These are glycerol-3-phosphates in which the glycerol moiety is bonded to two aliphatic chains through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct Parent1,2-diacylglycerol-3-phosphates
Alternative Parents
Substituents
  • 1,2-diacylglycerol-3-phosphate
  • Fatty acid ester
  • Monoalkyl phosphate
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • 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
logP9.14ALOGPS
logP12.93ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)1.32ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area119.36 ŲChemAxon
Rotatable Bond Count38ChemAxon
Refractivity199.21 m³·mol⁻¹ChemAxon
Polarizability85.11 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 (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-1171905400-69c1fb870dc2dc7f674dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-2393505000-7d80d3958dc3cc4c8a77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00vl-0194233000-72a24588ee17dea63d32View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-017j-4090403000-d4941212f149135595b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9050000000-9db11b1be5dca535d31cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-1272fe43292da7553178View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000900-af2da6ae565960d02a74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00i0-0000009900-7e41e59856bf50ddbb3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0773-0000902300-bc749dd94af6446df65aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000009000-55a7c1167cbe0f25b0beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-017j-0060904000-916fe5b246329a558e98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-0090300000-8b54e6cad8c14493034cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0000009500-c84c90ec7d2e858c69f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000007900-6386210cf4e9425daf33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v4i-0000907100-042e00adfff6b52cf41cView 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 Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0007861
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025053
KNApSAcK IDNot Available
Chemspider ID24766515
KEGG Compound IDC00416
BioCyc IDCPD-8267
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24779559
PDB IDNot Available
ChEBI ID77248
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Lipin 1
General function:
Not Available
Specific function:
Not Available
Gene Name:
LPIN1
Uniprot ID:
E1BPE8
Molecular weight:
102857.0
Reactions
PA(18:0/18:2(9Z,12Z)) + Water → DG(18:0/18:2(9Z,12Z)/0:0) + Hydrogen phosphatedetails