Back to Compounds

Showing Compound DHAP(18:0) (FDB027912)

Record Information
Version1.0
Creation date2011-09-21 01:31:51 UTC
Update date2018-05-29 01:54:22 UTC
Primary IDFDB027912
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDHAP(18:0)
DescriptionDHAP(18:0) is the octadecanoyl derivative of Dihydroxyacetone phosphate. It is also known as an alkyl-DHAP. This compound is formed by octadecanoic acid reacting with DHAP. Alkyl-DHAPs are intermediates in the synthesis of ether phospholipids. The initial steps of ether phospholipid biosynthesis take place in peroxisomes. Alkyl-dihydroxyacetonephosphate synthase is the peroxisomal enzyme that actually introduces the ether linkage. Levels of Alkyl-DHAP have been found to be strongly reduced in human fibroblasts derived from Zellweger syndrome and rhizomelic chondrodysplasia punctata patients. Four other enzymes are known to be involved in the metabolism of acyl-DHAP and alkyl-DHAP. These include: acyl-DHAP/alkyl-DHAP oxidoreductase, DHAP acyltransferase, alkyl-DHAP phosphohydrolase, and a dinitrofluorobenzene-insensitive acyl-DHAP acylhydrolase. Dihydroxyacetone phosphate (DHAP) is a biochemical compound primarily involved in the glycolysis metabolic pathway. DHAP is also the product of the dehydrogenation of L-glycerol-3-phosphate which is part of the entry of glycerol (sourced from triglycerides) into the glycolytic pathway. Conversely, reduction of glycolysis-derived DHAP to L-glycerol-3-phosphate provides adipose cells with the activated glycerol backbone they require to synthesize new triglycerides. Both reactions are catalyzed by the enzyme glycerol 3-phosphate dehydrogenase with NAD+/NADH as cofactor. DHAP may be referred to as glycerone phosphate in older texts. 1-Octadecyl-glycerone-3-phosphate is an intermediate in Ether lipid metabolism. DHAP(18:0) or 1-Octadecanoyl-glycerone-3-phosphate is the precursor to 1-Octadecyl-glycerone-3-phosphate DHAP(18:0e) which is generated via alkylglycerone phosphate synthase (EC: 2.5.1.26). 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. Ether lipids are called plasmalogens (1-O-1'-alkenyl-2-acylglycerophospholipids) if these are glycerol-containing phospholipids with an unsaturated O-(1-alkenyl) (vinyl ether) group at the first position on the glycerol chain. Plasmalogens as well as some 1-O-alkyl lipids are ubiquitous and sometimes major parts of the cell membranes in mammals and anaerobic bacteria. In archaea, ether lipids are the major polar lipids in the cell envelope and their abundance is one of the major characteristics that separate this group of prokaryotes from the bacteria. In these cells, diphytanylglycerolipids or bipolar macrocyclic tetraethers can form covalently linked 'bilayers'. [HMDB]
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.00085 g/LALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H41O7P
IUPAC name[3-(octadecanoyloxy)-2-oxopropoxy]phosphonic acid
InChI IdentifierInChI=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
Isomeric SMILESCCCCCCCCCCCCCCCCCC(=O)OCC(=O)COP(O)(O)=O
Average Molecular Weight436.5198
Monoisotopic Molecular Weight436.258990178
Classification
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
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSDHAP(18:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-4940000000-80a1bdc493c6960db777Spectrum
Predicted GC-MSDHAP(18:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDHAP(18:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ks-7675900000-676315db38479a1f63ed2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gc9-3962200000-9883bfcb711115c199632017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05tb-9361000000-986bb0d9b34e802383602017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00nr-4190400000-3a38a8b555ccf3f080be2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9050000000-f0b48935f26d1c1c1c222017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-6c9559d558f5504fffa32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1000900000-07d76159781dbd3ab5192021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-6190000000-ea20c91d06ab5293e53b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00si-7490000000-02f0b228c932f2c02dae2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0015900000-5fb40fae3c12e8ece7992021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0295000000-59cfdee546b25ce5989f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052e-9100000000-3f375f3a3380138127d92021-09-24View Spectrum
NMRNot Available
ChemSpider ID389126
ChEMBL IDNot Available
KEGG Compound IDC03805
Pubchem Compound ID440127
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB11133
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference