Showing metabocard for LPA(P-16:0e/0:0) (BMDB0011154)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:13:44 UTC
Update Date2020-04-22 15:42:58 UTC
BMDB IDBMDB0011154
Secondary Accession Numbers
  • BMDB11154
Metabolite Identification
Common NameLPA(P-16:0e/0:0)
DescriptionLysoPA(P-16:0/0:0) is a lysophosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. Lysophosphatidic acids can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. Fatty acids containing 16 and 18 carbons are the most common.LysoPA(P-16:0/0:0), in particular, consists of one 1Z-hexadecenyl chain. Lysophosphatidic acid is the simplest possible glycerophospholipid. It is the biosynthetic precursor of phosphatidic acid. Although it is present at very low levels only in animal tissues, it is extremely important biologically, influencing many biochemical processes.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(1Z-Hexadecenyl)-sn-glycero-3-phosphateHMDB
1-(1Z-Hexadecenyl)-glycero-3-phosphateHMDB
1-(1Z-Hexadecenyl)-lysophosphatidic acidHMDB
LPA(16:1)HMDB
LPA(p-16:0)HMDB
LPA(p-16:0/0:0)HMDB
LysoPA(16:1)HMDB
LysoPA(p-16:0)HMDB
Lysophosphatidic acid(16:1)HMDB
Lysophosphatidic acid(p-16:0)HMDB
Lysophosphatidic acid(p-16:0/0:0)HMDB
LPA(O-16:1(1Z))HMDB
LPA(O-16:1(1Z)/0:0)HMDB
LysoPA(O-16:1(1Z))HMDB
LysoPA(O-16:1(1Z)/0:0)HMDB
Lysophosphatidic acid(O-16:1(1Z))HMDB
Lysophosphatidic acid(O-16:1(1Z)/0:0)HMDB
LysoPA(P-16:0/0:0)HMDB
Chemical FormulaC19H39O6P
Average Molecular Weight394.4831
Monoisotopic Molecular Weight394.248425492
IUPAC Name[(2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-hydroxypropoxy]phosphonic acid
Traditional Name(2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-hydroxypropoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCC\C=C/OC[C@](O)([H])COP(=O)(O)O
InChI Identifier
InChI=1S/C19H39O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-24-17-19(20)18-25-26(21,22)23/h15-16,19-20H,2-14,17-18H2,1H3,(H2,21,22,23)/b16-15-/t19-/m1/s1
InChI KeyLBGSRVIXIVDRQM-OAXWQBPPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycerophosphates. Glycerophosphates are compounds containing a glycerol linked to a phosphate group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct ParentGlycerophosphates
Alternative Parents
Substituents
  • Sn-glycerol-3-phosphate
  • Glycerol vinyl ether
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
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
logP4.81ALOGPS
logP5.35ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)1.51ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity105.32 m³·mol⁻¹ChemAxon
Polarizability45.38 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 LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0011154
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027929
KNApSAcK IDNot Available
Chemspider ID24766520
KEGG Compound IDC15646
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52929772
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Lysophosphatidic acid receptor 1
General function:
Involved in G-protein coupled receptor protein signalin
Specific function:
Receptor for lysophosphatidic acid (LPA). Plays a role in the reorganization of the actin cytoskeleton, cell migration, differentiation and proliferation, and thereby contributes to the responses to tissue damage and infectious agents. Activates downstream signaling cascades via the G(i)/G(o), G(12)/G(13), and G(q) families of heteromeric G proteins. Signaling inhibits adenylyl cyclase activity and decreases cellular cAMP levels. Signaling triggers an increase of cytoplasmic Ca(2+) levels. Activates RALA; this leads to the activation of phospholipase C (PLC) and the formation of inositol 1,4,5-trisphosphate. Signaling mediates activation of down-stream MAP kinases. Contributes to the regulation of cell shape. Promotes Rho-dependent reorganization of the actin cytoskeleton in neuronal cells and neurite retraction. Promotes the activation of Rho and the formation of actin stress fibers. Promotes formation of lamellipodia at the leading edge of migrating cells via activation of RAC1. Through its function as lysophosphatidic acid receptor, plays a role in chemotaxis and cell migration, including responses to injury and wounding. Plays a role in triggering inflammation in response to bacterial lipopolysaccharide (LPS) via its interaction with CD14. Promotes cell proliferation in response to lysophosphatidic acid. Required for normal skeleton development. May play a role in osteoblast differentiation. Required for normal brain development. Required for normal proliferation, survival and maturation of newly formed neurons in the adult dentate gyrus. Plays a role in pain perception and in the initiation of neuropathic pain.
Gene Name:
LPAR1
Uniprot ID:
Q28031
Molecular weight:
41070.0
Enzyme Details
2. Lysophosphatidic acid receptor 5
General function:
Involved in purinergic nucleotide receptor activity, G-
Specific function:
Receptor for lysophosphatidic acid (LPA), a mediator of diverse cellular activities.
Gene Name:
LPAR5
Uniprot ID:
Q3ZC80
Molecular weight:
40639.0