Showing metabocard for DHAP(18:0) (BMDB0011133)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:13:22 UTC
Update Date2020-05-21 16:29:07 UTC
BMDB IDBMDB0011133
Secondary Accession Numbers
  • BMDB11133
Metabolite Identification
Common NameDHAP(18:0)
DescriptionDhap(18:0) belongs to the class of organic compounds known as o-acylglycerone-phosphates. These are glycerone-3-phosphates carrying an acyl substituent at the 1-position. Dhap(18:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Dhap(18:0) participates in a number of enzymatic reactions, within cattle. In particular, Dhap(18:0) can be biosynthesized from eicosanoyl-CoA and dihydroxyacetone phosphate through its interaction with the enzyme dihydroxyacetone phosphate acyltransferase and alkyldihydroxyacetonephosphate synthase. In addition, Dhap(18:0) and octadecanol can be converted into dhap(18:0E) and stearic acid; which is mediated by the enzyme dihydroxyacetone phosphate acyltransferase and alkyldihydroxyacetonephosphate synthase. In cattle, dhap(18:0) is involved in the metabolic pathway called plasmalogen synthesis pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Octadecanoyl dhapHMDB
1-Octadecanoyl dihydroxyacetone phosphateHMDB
1-Octadecanoyl-glycerone-3-phosphateHMDB
1-Stearoylglycerone 3-phosphateHMDB
Stearoylglycerone phosphateChEBI
Stearoylglycerone phosphoric acidGenerator
Chemical FormulaC21H41O7P
Average Molecular Weight436.5198
Monoisotopic Molecular Weight436.258990178
IUPAC Name[3-(octadecanoyloxy)-2-oxopropoxy]phosphonic acid
Traditional Namestearoylglycerone phosphate
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCC(=O)OCC(=O)COP(O)(O)=O
InChI Identifier
InChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h2-19H2,1H3,(H2,24,25,26)
InChI KeyGTPATKZCXDKGQS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as o-acylglycerone-phosphates. These are glycerone-3-phosphates carrying an acyl substituent at the 1-position.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentO-acylglycerone-phosphates
Alternative Parents
Substituents
  • O-acylglycerone-phosphate
  • Monosaccharide phosphate
  • Fatty acid ester
  • Alpha-acyloxy ketone
  • Monoalkyl phosphate
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • 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
  • 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
logP5.37ALOGPS
logP6.16ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)1.19ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area110.13 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity113.27 m³·mol⁻¹ChemAxon
Polarizability50.42 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-4940000000-80a1bdc493c6960db777View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ks-7675900000-676315db38479a1f63edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gc9-3962200000-9883bfcb711115c19963View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05tb-9361000000-986bb0d9b34e80238360View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00nr-4190400000-3a38a8b555ccf3f080beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9050000000-f0b48935f26d1c1c1c22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-6c9559d558f5504fffa3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1000900000-07d76159781dbd3ab519View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-6190000000-ea20c91d06ab5293e53bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00si-7490000000-02f0b228c932f2c02daeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0015900000-5fb40fae3c12e8ece799View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0295000000-59cfdee546b25ce5989fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052e-9100000000-3f375f3a3380138127d9View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0011133
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027912
KNApSAcK IDNot Available
Chemspider ID389126
KEGG Compound IDC03805
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440127
PDB IDNot Available
ChEBI ID36476
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Dihydroxyacetone phosphate acyltransferase
General function:
Lipid transport and metabolism
Specific function:
Not Available
Gene Name:
GNPAT
Uniprot ID:
A4IF87
Molecular weight:
77664.0
Reactions
Eicosanoyl-CoA + Dihydroxyacetone phosphate → DHAP(18:0) + Coenzyme Adetails
DHAP(18:0) + Octadecanol → DHAP(18:0e) + Stearic aciddetails
Enzyme Details
2. D-2-hydroxyglutarate dehydrogenase, mitochondrial
General function:
Energy production and conversion
Specific function:
Catalyzes the oxidation of D-2-hydroxyglutarate to alpha-ketoglutarate.
Gene Name:
D2HGDH
Uniprot ID:
Q1JPD3
Molecular weight:
59056.0
Reactions
Eicosanoyl-CoA + Dihydroxyacetone phosphate → DHAP(18:0) + Coenzyme Adetails
DHAP(18:0) + Octadecanol → DHAP(18:0e) + Stearic aciddetails