Showing metabocard for PA(16:0/18:2(9Z,12Z)) (BMDB0007860)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:45:53 UTC
Update Date2020-05-21 16:27:38 UTC
BMDB IDBMDB0007860
Secondary Accession Numbers
  • BMDB07860
Metabolite Identification
Common NamePA(16:0/18:2(9Z,12Z))
DescriptionPA(16:0/18:2(9Z,12Z)), also known as Pa(16:0/18:2(9z,12z)) or PA(16:0/18:2), 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(16:0/18:2(9Z,12Z)) is considered to be a glycerophosphate lipid molecule. PA(16:0/18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PA(16:0/18:2(9Z,12Z)) exists in all living organisms, ranging from bacteria to humans. PA(16:0/18:2(9Z,12Z)) participates in a number of enzymatic reactions, within cattle. In particular, PA(16:0/18:2(9Z,12Z)) can be biosynthesized from lpa(16:0/0:0) and linoleoyl-CoA through its interaction with the enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase epsilon. In addition, Cytidine triphosphate and PA(16:0/18:2(9Z,12Z)) can be converted into CDP-DG(16:0/18:2(9Z,12Z)) through its interaction with the enzyme phosphatidate cytidylyltransferase 2. In cattle, PA(16:0/18:2(9Z,12Z)) is involved in the metabolic pathway called cardiolipin biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/18:2(9Z,12Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-16:0-2-18:2-Phosphatidic acidChEBI
1-Palmitoyl-2-linoleoyl-sn-glycero-3-phosphateChEBI
16:0-18:2-PAChEBI
2-Linoleoyl-1-palmitoyl-sn-glycero-3-phosphateChEBI
PA(16:0/18:2)ChEBI
PA(16:0/18:2OMEGA6)ChEBI
PA(34:2)ChEBI
Phosphatidic acid(16:0/18:2)ChEBI
Phosphatidic acid(16:0/18:2omega6)ChEBI
Phosphatidic acid(34:2)ChEBI
1-16:0-2-18:2-PhosphatidateGenerator
1-Palmitoyl-2-linoleoyl-sn-glycero-3-phosphoric acidGenerator
2-Linoleoyl-1-palmitoyl-sn-glycero-3-phosphoric acidGenerator
Phosphatidate(16:0/18:2)Generator
Phosphatidate(16:0/18:2OMEGA6)Generator
Phosphatidate(34:2)Generator
1-Hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-phosphatidic acidHMDB
PA(16:0/18:2N6)HMDB
PA(16:0/18:2W6)HMDB
Phosphatidic acid(16:0/18:2n6)HMDB
Phosphatidic acid(16:0/18:2W6)HMDB
Chemical FormulaC37H69O8P
Average Molecular Weight672.9127
Monoisotopic Molecular Weight672.473005696
IUPAC Name[(2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphonic acid
Traditional Name(2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP(O)(=O)O)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C37H69O8P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-37(39)45-35(34-44-46(40,41)42)33-43-36(38)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h11,13,17-18,35H,3-10,12,14-16,19-34H2,1-2H3,(H2,40,41,42)/b13-11-,18-17-/t35-/m1/s1
InChI KeyYQMUIZXKIKXZHD-UMKNCJEQSA-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
logP8.78ALOGPS
logP12.04ChemAxon
logS-6.9ALOGPS
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 Count36ChemAxon
Refractivity190.01 m³·mol⁻¹ChemAxon
Polarizability81.34 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, Positivesplash10-01ot-9472312000-5a0ace43ce559faf6b1aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-022l-0192214000-0ff5badab9b87707949eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p2-1292111000-4a699460a7645a5a2ac2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ds-0392011000-a011b8cc1a3b8c4d40a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05dr-3091102000-a4a318dd2dd7912c0151View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9060000000-f674e5442d2d2e19904cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9010000000-be58bb50c1230574e53cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000009000-6028356bb714d18e544dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-062f-1196606000-8572e410961d7f243448View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-0090200000-7fcea8001e422200fee2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0000009000-4c1c2d930aa8ce64404aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fr-0000059000-4ff73b97ce6c9126eb82View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ou-0006693000-acbbee6d58a28139e3c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000009000-f21c401a141e9540f901View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000099000-734455b81d5b79583fa4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kk-0000923000-1bab141842de7a393a0aView 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 IDHMDB0007860
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025052
KNApSAcK IDNot Available
Chemspider ID7826110
KEGG Compound IDC00416
BioCyc IDCPD-8265
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9547167
PDB IDNot Available
ChEBI ID73259
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(16:0/18:2(9Z,12Z)) + Water → DG(16:0/18:2(9Z,12Z)/0:0) + Hydrogen phosphatedetails