Human Metabolome Database Version 3.5

Showing metabocard for LPA(P-16:0e/0:0) (HMDB11154)

Record Information
Version 3.5
Creation Date 2008-10-29 08:53:30 -0600
Update Date 2013-02-08 17:25:47 -0700
HMDB ID HMDB11154
Secondary Accession Numbers None
Metabolite Identification
Common Name LPA(P-16:0e/0:0)
Description 1-(1Z-hexadecenyl)-sn-glycero-3-phosphate is an intermediate of ether lipid metabolism. Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. 1-(1Z-hexadecenyl)-sn-glycero-3-phosphate is irreversibly produced from 1-(1Z-hexadecenyl)-sn-glycero-3-phosphoethanolamine via the enzyme alkylglycerophosphoethanolamine phosphodiesterase (EC: 3.1.4.39). Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1-(1Z-Hexadecenyl)-sn-glycero-3-phosphate
  2. LysoPA(dm16:0e)
Chemical Formula C19H39O6P
Average Molecular Weight 394.4831
Monoisotopic Molecular Weight 394.248425492
IUPAC Name [(2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-hydroxypropoxy]phosphonic acid
Traditional IUPAC Name (2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-hydroxypropoxyphosphonic acid
CAS Registry Number Not 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 Key LBGSRVIXIVDRQM-OAXWQBPPSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Organophosphorus Compounds
Class Organic Phosphoric Acids and Derivatives
Sub Class Organophosphate Esters
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Enol Ether
  • Organic Hypophosphite
  • Organic Phosphite
  • Secondary Alcohol
Direct Parent Organophosphate Esters
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0033 g/L ALOGPS
LogP 4.81 ALOGPS
LogP 5.35 ChemAxon
LogS -5.08 ALOGPS
pKa (strongest acidic) 1.51 ChemAxon
pKa (strongest basic) -3.4 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 96.22 A2 ChemAxon
Rotatable Bond Count 19 ChemAxon
Refractivity 105.32 ChemAxon
Polarizability 45.38 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB027929
KNApSAcK ID Not Available
Chemspider ID 24766520 Link_out
KEGG Compound ID C15646 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB11154 Link_out
Metagene Link HMDB11154 Link_out
METLIN ID Not Available
PubChem Compound 52929772 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes
Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 2
Reactions: Not Available
Gene Name: ENPP2
Uniprot ID: Q13822 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipid phosphate phosphohydrolase 2
Reactions: Not Available
Gene Name: PPAP2C
Uniprot ID: O43688 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipid phosphate phosphohydrolase 1
Reactions: Not Available
Gene Name: PPAP2A
Uniprot ID: O14494 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipid phosphate phosphohydrolase 3
Reactions: Not Available
Gene Name: PPAP2B
Uniprot ID: O14495 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acyl-CoA:lysophosphatidylglycerol acyltransferase 1
Reactions: Not Available
Gene Name: LPGAT1
Uniprot ID: Q92604 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Focal adhesion kinase 1
Reactions: Not Available
Gene Name: PTK2
Uniprot ID: Q05397 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protein-tyrosine kinase 2-beta
Reactions: Not Available
Gene Name: PTK2B
Uniprot ID: Q14289 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-acyl-sn-glycerol-3-phosphate acyltransferase gamma
Reactions: Not Available
Gene Name: AGPAT3
Uniprot ID: Q9NRZ7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-acyl-sn-glycerol-3-phosphate acyltransferase beta
Reactions: Not Available
Gene Name: AGPAT2
Uniprot ID: O15120 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-acyl-sn-glycerol-3-phosphate acyltransferase alpha
Reactions: Not Available
Gene Name: AGPAT1
Uniprot ID: Q99943 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidic acid receptor 2
Reactions: Not Available
Gene Name: LPAR2
Uniprot ID: Q9HBW0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidic acid receptor 1
Reactions: Not Available
Gene Name: LPAR1
Uniprot ID: Q92633 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-acyl-sn-glycerol-3-phosphate acyltransferase epsilon
Reactions: Not Available
Gene Name: AGPAT5
Uniprot ID: Q9NUQ2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycerol-3-phosphate acyltransferase 4
Reactions: Not Available
Gene Name: AGPAT6
Uniprot ID: Q86UL3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-acyl-sn-glycerol-3-phosphate acyltransferase delta
Reactions: Not Available
Gene Name: AGPAT4
Uniprot ID: Q9NRZ5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidylcholine acyltransferase 1
Reactions: Not Available
Gene Name: LPCAT1
Uniprot ID: Q8NF37 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidylcholine acyltransferase 2
Reactions: Not Available
Gene Name: LPCAT2
Uniprot ID: Q7L5N7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysocardiolipin acyltransferase 1
Reactions: Not Available
Gene Name: LCLAT1
Uniprot ID: Q6UWP7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidic acid receptor 3
Reactions: Not Available
Gene Name: LPAR3
Uniprot ID: Q9UBY5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidic acid receptor 4
Reactions: Not Available
Gene Name: LPAR4
Uniprot ID: Q99677 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidic acid receptor 5
Reactions: Not Available
Gene Name: LPAR5
Uniprot ID: Q9H1C0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophospholipid acyltransferase LPCAT4
Reactions: Not Available
Gene Name: LPCAT4
Uniprot ID: Q643R3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycerol-3-phosphate acyltransferase 3
Reactions: Not Available
Gene Name: AGPAT9
Uniprot ID: Q53EU6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidic acid phosphatase type 6
Reactions: Not Available
Gene Name: ACP6
Uniprot ID: Q9NPH0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidic acid receptor 6
Reactions: Not Available
Gene Name: LPAR6
Uniprot ID: P43657 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipase member H
Reactions: Not Available
Gene Name: LIPH
Uniprot ID: Q8WWY8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipase member I
Reactions: Not Available
Gene Name: LIPI
Uniprot ID: Q6XZB0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipid phosphate phosphatase-related protein type 4
Reactions: Not Available
Gene Name: LPPR4
Uniprot ID: Q7Z2D5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acylglycerol kinase, mitochondrial
Reactions: Not Available
Gene Name: AGK
Uniprot ID: Q53H12 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidic acid receptor 1
Reactions: Not Available
Gene Name: LPAR1
Uniprot ID: B1AP63 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: High-affinity lysophosphatidic acid receptor homolog
Reactions: Not Available
Gene Name: Not Available
Uniprot ID: O43898 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: LPAR1 protein
Reactions: Not Available
Gene Name: LPAR1
Uniprot ID: Q6GPG7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA