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
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