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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-10-29 15:02:15 UTC
Update Date2020-02-26 21:34:34 UTC
HMDB IDHMDB0011155
Secondary Accession Numbers
  • HMDB11155
Metabolite Identification
Common NamePA(P-16:0/18:2(9Z,12Z))
Description2-(9Z,12Z-octadecadienoyl)-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. 2-(9Z,12Z-octadecadienoyl)-1-(1Z-hexadecenyl)-sn-glycero-3-phosphate is irreversibly produced from 2-(9Z,12Z-octadecadienoyl)-1-(1Z-hexadecenyl))-sn-glycero-3-phosphoethanolamine via the enzyme phospholipase D (EC: 3.1.4.4). 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
Data?1582752874
Synonyms
ValueSource
2-(9Z,12Z-Octadecadienoyl)-1-(1Z-hexadecenyl)-sn-glycero-3-phosphateHMDB
1-(1Z-Hexadecenyl)-2-linoleoyl-sn-glycero-3-phosphateHMDB
1-(1Z-Hexadecenyl)-2-linoleoyl-sn-phosphatidic acidHMDB
PA(16:1/18:2)HMDB
PA(34:3)HMDB
PA(O-16:1(1Z)/18:2(9Z,12Z))HMDB
PA(O-16:1(1Z)/18:2N6)HMDB
PA(O-16:1(1Z)/18:2W6)HMDB
PA(P-16:0/18:2N6)HMDB
PA(P-16:0/18:2W6)HMDB
Phosphatidate(16:1/18:2)HMDB
Phosphatidate(34:3)HMDB
Phosphatidate(O-16:1(1Z)/18:2(9Z,12Z))HMDB
Phosphatidate(O-16:1(1Z)/18:2N6)HMDB
Phosphatidate(O-16:1(1Z)/18:2W6)HMDB
Phosphatidate(P-16:0/18:2(9Z,12Z))HMDB
Phosphatidate(P-16:0/18:2N6)HMDB
Phosphatidate(P-16:0/18:2W6)HMDB
Phosphatidic acid(16:1/18:2)HMDB
Phosphatidic acid(34:3)HMDB
Phosphatidic acid(O-16:1(1Z)/18:2(9Z,12Z))HMDB
Phosphatidic acid(O-16:1(1Z)/18:2n6)HMDB
Phosphatidic acid(O-16:1(1Z)/18:2W6)HMDB
Phosphatidic acid(p-16:0/18:2(9Z,12Z))HMDB
Phosphatidic acid(p-16:0/18:2n6)HMDB
Phosphatidic acid(p-16:0/18:2W6)HMDB
PA(P-16:0/18:2(9Z,12Z))HMDB
Chemical FormulaC37H69O7P
Average Molecular Weight656.9133
Monoisotopic Molecular Weight656.478091074
IUPAC Name[(2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphonic acid
Traditional Name(2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphonic acid
CAS Registry Number937723-92-7
SMILES
CCCCCCCCCCCCCC\C=C/OC[C@]([H])(COP(=O)(O)O)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C37H69O7P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-37(38)44-36(35-43-45(39,40)41)34-42-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h11,13,17,19,31,33,36H,3-10,12,14-16,18,20-30,32,34-35H2,1-2H3,(H2,39,40,41)/b13-11-,19-17-,33-31-/t36-/m1/s1
InChI KeyOLCTYLMZTXKGKH-BBNWHMLASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-(1z-alkenyl),2-acyl-glycerophosphates. These are glycerophosphates that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one 1Z-alkenyl chain attached through an ether linkage at the O1-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct Parent1-(1Z-alkenyl),2-acyl-glycerophosphates
Alternative Parents
Substituents
  • 1-(1z-alkenyl),2-acyl-glycerol-3-phosphate
  • Glycerol vinyl ether
  • Fatty acid ester
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Fatty acyl
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.3e-05 g/LALOGPS
logP9.27ALOGPS
logP12.44ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)1.32ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area102.29 ŲChemAxon
Rotatable Bond Count35ChemAxon
Refractivity190.35 m³·mol⁻¹ChemAxon
Polarizability79.89 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9242121000-692d517b782c84adf74fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0bvi-0094024000-d26e3d32b43139cc010cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01vk-1191010000-759b4f1be9058b13ed02Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-1190000000-3531949a0e4335a1c5e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-5094104000-9a1389e6629f728fa5beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9030000000-1c805627741e0b7f9ec0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9010000000-057f58ca0a283cf13563Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027930
KNApSAcK IDNot Available
Chemspider ID24766521
KEGG Compound IDC15647
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52929743
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDM00627
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Only showing the first 10 proteins. There are 50 proteins in total.

Enzymes

General function:
Involved in protein binding
Specific function:
May have a role in signal-induced cytoskeletal regulation and/or endocytosis (By similarity).
Gene Name:
PLD2
Uniprot ID:
O14939
Molecular weight:
104656.485
General function:
Involved in diacylglycerol kinase activity
Specific function:
Reverses the normal flow of glycerolipid biosynthesis by phosphorylating diacylglycerol back to phosphatidic acid
Gene Name:
DGKG
Uniprot ID:
P49619
Molecular weight:
89095.3
General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is PA > C-1-P > LPA > S-1-P.
Gene Name:
PPAP2C
Uniprot ID:
O43688
Molecular weight:
32573.435
General function:
Involved in catalytic activity
Specific function:
Broad-specificity phosphohydrolase that dephosphorylates exogenous bioactive glycerolipids and sphingolipids. Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). Pivotal regulator of lysophosphatidic acid (LPA) signaling in the cardiovascular system. Major enzyme responsible of dephosphorylating LPA in platelets, which terminates signaling actions of LPA. May control circulating, and possibly also regulate localized, LPA levels resulting from platelet activation. It has little activity towards ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA > PA > S-1-P > C-1-P. It's down-regulation may contribute to the development of colon adenocarcinoma.
Gene Name:
PPAP2A
Uniprot ID:
O14494
Molecular weight:
32155.715
General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA = PA > C-1-P > S-1-P. May be involved in cell adhesion and in cell-cell interactions.
Gene Name:
PPAP2B
Uniprot ID:
O14495
Molecular weight:
35115.61
General function:
Involved in metal ion binding
Specific function:
Probable phospholipase that hydrolyzes phosphatidic acid. The different isoforms may change the substrate specificity
Gene Name:
DDHD1
Uniprot ID:
Q8NEL9
Molecular weight:
100434.4
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Gene Name:
PDE4D
Uniprot ID:
Q08499
Molecular weight:
91114.1
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP11C
Uniprot ID:
Q8NB49
Molecular weight:
129476.0
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP11A
Uniprot ID:
P98196
Molecular weight:
129754.6
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP10A
Uniprot ID:
O60312
Molecular weight:
167686.6

Only showing the first 10 proteins. There are 50 proteins in total.