Showing metabocard for PA(16:0/18:1(9Z)) (BMDB0007859)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:45:52 UTC
Update Date2020-05-21 16:28:08 UTC
BMDB IDBMDB0007859
Secondary Accession Numbers
  • BMDB07859
Metabolite Identification
Common NamePA(16:0/18:1(9Z))
DescriptionPA(16:0/18:1(9Z)) 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(16:0/18:1(9Z)), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one 9Z-octadecenoyl 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
(2R)-1-(Palmitoyloxy)-3-(phosphonooxy)propan-2-yl (9Z)-octadec-9-enoateChEBI
1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphateChEBI
1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol 3-phosphateChEBI
1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-phosphatidic acidChEBI
PA(16:0/18:1)ChEBI
PA(16:0/18:1OMEGA9)ChEBI
PA(34:1)ChEBI
Phosphatidic acid(16:0/18:1)ChEBI
Phosphatidic acid(16:0/18:1omega9)ChEBI
Phosphatidic acid(34:1)ChEBI
(2R)-1-(Palmitoyloxy)-3-(phosphonooxy)propan-2-yl (9Z)-octadec-9-enoic acidGenerator
1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoric acidGenerator
1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol 3-phosphoric acidGenerator
1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-phosphatidateGenerator
Phosphatidate(16:0/18:1)Generator
Phosphatidate(16:0/18:1OMEGA9)Generator
Phosphatidate(34:1)Generator
1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphateHMDB
PA(16:0/18:1N9)HMDB
PA(16:0/18:1W9)HMDB
Phosphatidic acid(16:0/18:1n9)HMDB
Phosphatidic acid(16:0/18:1W9)HMDB
Chemical FormulaC37H71O8P
Average Molecular Weight674.941
Monoisotopic Molecular Weight674.488656244
IUPAC Name[(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphonic acid
Traditional Name(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C37H71O8P/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/h17-18,35H,3-16,19-34H2,1-2H3,(H2,40,41,42)/b18-17-/t35-/m1/s1
InChI KeyOPVZUEPSMJNLOM-QEJMHMKOSA-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
logP8.91ALOGPS
logP12.41ChemAxon
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 Count37ChemAxon
Refractivity188.89 m³·mol⁻¹ChemAxon
Polarizability82.83 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 IDHMDB0007859
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025051
KNApSAcK IDNot Available
Chemspider ID4446637
KEGG Compound IDC00416
BioCyc IDPhosphatidates-34-1
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283523
PDB IDNot Available
ChEBI ID64844
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(16:0/18:1(9Z)) + Water → DG(16:0/18:1(9Z)/0:0) + Hydrogen phosphatedetails
Enzyme Details
2. 1-acyl-sn-glycerol-3-phosphate acyltransferase alpha
General function:
Not Available
Specific function:
Converts 1-acyl-sn-glycerol-3-phosphate (lysophosphatidic acid or LPA) into 1,2-diacyl-sn-glycerol-3-phosphate (phosphatidic acid or PA) by incorporating an acyl moiety at the sn-2 position of the glycerol backbone.
Gene Name:
AGPAT1
Uniprot ID:
Q95JH2
Molecular weight:
32005.0
Reactions
LPA(16:0/0:0) + Oleoyl-CoA → Coenzyme A + PA(16:0/18:1(9Z))details
Enzyme Details
3. 1-acyl-sn-glycerol-3-phosphate acyltransferase delta
General function:
Not Available
Specific function:
Converts 1-acyl-sn-glycerol-3-phosphate (lysophosphatidic acid or LPA) into 1,2-diacyl-sn-glycerol-3-phosphate (phosphatidic acid or PA) by incorporating an acyl moiety at the sn-2 position of the glycerol backbone (By similarity). Exhibits high acyl-CoA specificity for polyunsaturated fatty acyl-CoA, especially docosahexaenoyl-CoA (22:6-CoA, DHA-CoA) (By similarity).
Gene Name:
AGPAT4
Uniprot ID:
Q5E9R2
Molecular weight:
43907.0
Reactions
LPA(16:0/0:0) + Oleoyl-CoA → PA(16:0/18:1(9Z)) + Coenzyme Adetails