Showing metabocard for PA(18:1(11Z)/18:1(9Z)) (BMDB0007863)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:45:57 UTC
Update Date2020-05-21 16:27:48 UTC
BMDB IDBMDB0007863
Secondary Accession Numbers
  • BMDB07863
Metabolite Identification
Common NamePA(18:1(11Z)/18:1(9Z))
DescriptionPA(18:1(11Z)/18:1(9Z)), also known as pa(18:1(11z)/18:1(9z)), 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. PA(18:1(11Z)/18:1(9Z)) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). PA(18:1(11Z)/18:1(9Z)) exists in all living species, ranging from bacteria to humans. PA(18:1(11Z)/18:1(9Z)) participates in a number of enzymatic reactions, within cattle. In particular, PA(18:1(11Z)/18:1(9Z)) can be biosynthesized from lpa(18:1(11Z)/0:0) and oleoyl-CoA; which is mediated by the enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase. Furthermore, PA(18:1(11Z)/18:1(9Z)) can be converted into DG(18:1(11Z)/18:1(9Z)/0:0) through its interaction with the enzyme phosphatidate phosphatase. Furthermore, PA(18:1(11Z)/18:1(9Z)) can be biosynthesized from lpa(18:1(11Z)/0:0) and oleoyl-CoA; which is mediated by the enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase. Furthermore, PA(18:1(11Z)/18:1(9Z)) can be converted into DG(18:1(11Z)/18:1(9Z)/0:0); which is mediated by the enzyme phosphatidate phosphatase. Furthermore, PA(18:1(11Z)/18:1(9Z)) can be biosynthesized from lpa(18:1(11Z)/0:0) and oleoyl-CoA; which is mediated by the enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase. Finally, PA(18:1(11Z)/18:1(9Z)) can be converted into DG(18:1(11Z)/18:1(9Z)/0:0) through its interaction with the enzyme phosphatidate phosphatase. In cattle, PA(18:1(11Z)/18:1(9Z)) is involved in a few metabolic pathways, which include de novo triacylglycerol biosynthesis TG(18:1(11Z)/18:1(9Z)/20:0) pathway, de novo triacylglycerol biosynthesis TG(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)) pathway, and de novo triacylglycerol biosynthesis TG(18:1(11Z)/18:1(9Z)/22:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
GlycerophosphateHMDB
1-(11Z-Octadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phosphateHMDB
Glycerophosphate(18:1(11Z)/18:1(9Z))HMDB
Chemical FormulaC39H73O8P
Average Molecular Weight700.979
Monoisotopic Molecular Weight700.504306309
IUPAC Name[(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphonic acid
Traditional Name(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCC\C=C/CCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC
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/h13,15,18,20,37H,3-12,14,16-17,19,21-36H2,1-2H3,(H2,42,43,44)/b15-13-,20-18-/t37-/m1/s1
InChI KeyIIMFLKINUHKKSA-SLLMOJSDSA-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 DescriptorsNot Available
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
logP9.12ALOGPS
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
Polarizability85.46 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 IDHMDB0007863
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478603
PDB IDNot Available
ChEBI ID89527
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(18:1(11Z)/18:1(9Z)) + Water → DG(18:1(11Z)/18:1(9Z)/0:0) + Hydrogen phosphatedetails