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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-10-29 13:51:13 UTC
Update Date2020-02-26 21:34:32 UTC
HMDB IDHMDB0011142
Secondary Accession Numbers
  • HMDB11142
Metabolite Identification
Common NameDHAP(O-18:0)
DescriptionDHAP(O-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(O-18:0) or 1-Octadecyl-glycerone-3-phosphate is converted from 1-Octadecanoyl-glycerone-3-phosphate 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'. (Wikipedia).
Structure
Data?1582752872
Synonyms
ValueSource
1-Octadecyl dhapHMDB
1-Octadecyl dihdroxyacetone phosphateHMDB
1-Octadecyl-glycerone-3-phosphateHMDB
Octadecyldihydroxyacetone phosphateMeSH, HMDB
Chemical FormulaC21H43O6P
Average Molecular Weight422.5363
Monoisotopic Molecular Weight422.27972562
IUPAC Name[3-(octadecyloxy)-2-oxopropoxy]phosphonic acid
Traditional Name3-(octadecyloxy)-2-oxopropoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCOCC(=O)COP(O)(O)=O
InChI Identifier
InChI=1S/C21H43O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-26-19-21(22)20-27-28(23,24)25/h2-20H2,1H3,(H2,23,24,25)
InChI KeyDSLZSTBYLRGPIK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as o-alkylglycerone phosphates. These are glycerone-3-phosphates carrying an alkyl substituent at the 1-position.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentO-alkylglycerone phosphates
Alternative Parents
Substituents
  • O-alkylglycerone phosphate
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Ether
  • Dialkyl ether
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0013 g/LALOGPS
logP5.82ALOGPS
logP6.54ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)1.19ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity113.51 m³·mol⁻¹ChemAxon
Polarizability50.65 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+206.68131661259
DarkChem[M-H]-204.36831661259
DeepCCS[M+H]+195.35130932474
DeepCCS[M-H]-192.04530932474
DeepCCS[M-2H]-226.46930932474
DeepCCS[M+Na]+203.09830932474
AllCCS[M+H]+211.632859911
AllCCS[M+H-H2O]+209.632859911
AllCCS[M+NH4]+213.532859911
AllCCS[M+Na]+214.032859911
AllCCS[M-H]-205.232859911
AllCCS[M+Na-2H]-207.132859911
AllCCS[M+HCOO]-209.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DHAP(O-18:0)CCCCCCCCCCCCCCCCCCOCC(=O)COP(O)(O)=O3351.8Standard polar33892256
DHAP(O-18:0)CCCCCCCCCCCCCCCCCCOCC(=O)COP(O)(O)=O2830.3Standard non polar33892256
DHAP(O-18:0)CCCCCCCCCCCCCCCCCCOCC(=O)COP(O)(O)=O3190.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
DHAP(O-18:0),1TMS,isomer #1CCCCCCCCCCCCCCCCCCOCC(=O)COP(=O)(O)O[Si](C)(C)C3126.0Semi standard non polar33892256
DHAP(O-18:0),1TMS,isomer #1CCCCCCCCCCCCCCCCCCOCC(=O)COP(=O)(O)O[Si](C)(C)C2999.0Standard non polar33892256
DHAP(O-18:0),1TMS,isomer #1CCCCCCCCCCCCCCCCCCOCC(=O)COP(=O)(O)O[Si](C)(C)C3901.7Standard polar33892256
DHAP(O-18:0),1TMS,isomer #2CCCCCCCCCCCCCCCCCCOCC(=COP(=O)(O)O)O[Si](C)(C)C3175.4Semi standard non polar33892256
DHAP(O-18:0),1TMS,isomer #2CCCCCCCCCCCCCCCCCCOCC(=COP(=O)(O)O)O[Si](C)(C)C2970.8Standard non polar33892256
DHAP(O-18:0),1TMS,isomer #2CCCCCCCCCCCCCCCCCCOCC(=COP(=O)(O)O)O[Si](C)(C)C4296.2Standard polar33892256
DHAP(O-18:0),1TMS,isomer #3CCCCCCCCCCCCCCCCCCOC=C(COP(=O)(O)O)O[Si](C)(C)C3223.2Semi standard non polar33892256
DHAP(O-18:0),1TMS,isomer #3CCCCCCCCCCCCCCCCCCOC=C(COP(=O)(O)O)O[Si](C)(C)C2960.6Standard non polar33892256
DHAP(O-18:0),1TMS,isomer #3CCCCCCCCCCCCCCCCCCOC=C(COP(=O)(O)O)O[Si](C)(C)C4446.5Standard polar33892256
DHAP(O-18:0),2TMS,isomer #1CCCCCCCCCCCCCCCCCCOCC(=O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3122.9Semi standard non polar33892256
DHAP(O-18:0),2TMS,isomer #1CCCCCCCCCCCCCCCCCCOCC(=O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3048.0Standard non polar33892256
DHAP(O-18:0),2TMS,isomer #1CCCCCCCCCCCCCCCCCCOCC(=O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3373.1Standard polar33892256
DHAP(O-18:0),2TMS,isomer #2CCCCCCCCCCCCCCCCCCOCC(=COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C3233.0Semi standard non polar33892256
DHAP(O-18:0),2TMS,isomer #2CCCCCCCCCCCCCCCCCCOCC(=COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C2978.4Standard non polar33892256
DHAP(O-18:0),2TMS,isomer #2CCCCCCCCCCCCCCCCCCOCC(=COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C3697.1Standard polar33892256
DHAP(O-18:0),2TMS,isomer #3CCCCCCCCCCCCCCCCCCOC=C(COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C3227.1Semi standard non polar33892256
DHAP(O-18:0),2TMS,isomer #3CCCCCCCCCCCCCCCCCCOC=C(COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C2994.3Standard non polar33892256
DHAP(O-18:0),2TMS,isomer #3CCCCCCCCCCCCCCCCCCOC=C(COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C3740.7Standard polar33892256
DHAP(O-18:0),3TMS,isomer #1CCCCCCCCCCCCCCCCCCOCC(=COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3257.1Semi standard non polar33892256
DHAP(O-18:0),3TMS,isomer #1CCCCCCCCCCCCCCCCCCOCC(=COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2981.6Standard non polar33892256
DHAP(O-18:0),3TMS,isomer #1CCCCCCCCCCCCCCCCCCOCC(=COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3219.9Standard polar33892256
DHAP(O-18:0),3TMS,isomer #2CCCCCCCCCCCCCCCCCCOC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3256.7Semi standard non polar33892256
DHAP(O-18:0),3TMS,isomer #2CCCCCCCCCCCCCCCCCCOC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2986.6Standard non polar33892256
DHAP(O-18:0),3TMS,isomer #2CCCCCCCCCCCCCCCCCCOC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3245.3Standard polar33892256
DHAP(O-18:0),1TBDMS,isomer #1CCCCCCCCCCCCCCCCCCOCC(=O)COP(=O)(O)O[Si](C)(C)C(C)(C)C3383.0Semi standard non polar33892256
DHAP(O-18:0),1TBDMS,isomer #1CCCCCCCCCCCCCCCCCCOCC(=O)COP(=O)(O)O[Si](C)(C)C(C)(C)C3153.3Standard non polar33892256
DHAP(O-18:0),1TBDMS,isomer #1CCCCCCCCCCCCCCCCCCOCC(=O)COP(=O)(O)O[Si](C)(C)C(C)(C)C3968.8Standard polar33892256
DHAP(O-18:0),1TBDMS,isomer #2CCCCCCCCCCCCCCCCCCOCC(=COP(=O)(O)O)O[Si](C)(C)C(C)(C)C3440.1Semi standard non polar33892256
DHAP(O-18:0),1TBDMS,isomer #2CCCCCCCCCCCCCCCCCCOCC(=COP(=O)(O)O)O[Si](C)(C)C(C)(C)C3091.1Standard non polar33892256
DHAP(O-18:0),1TBDMS,isomer #2CCCCCCCCCCCCCCCCCCOCC(=COP(=O)(O)O)O[Si](C)(C)C(C)(C)C4280.3Standard polar33892256
DHAP(O-18:0),1TBDMS,isomer #3CCCCCCCCCCCCCCCCCCOC=C(COP(=O)(O)O)O[Si](C)(C)C(C)(C)C3483.4Semi standard non polar33892256
DHAP(O-18:0),1TBDMS,isomer #3CCCCCCCCCCCCCCCCCCOC=C(COP(=O)(O)O)O[Si](C)(C)C(C)(C)C3084.8Standard non polar33892256
DHAP(O-18:0),1TBDMS,isomer #3CCCCCCCCCCCCCCCCCCOC=C(COP(=O)(O)O)O[Si](C)(C)C(C)(C)C4404.2Standard polar33892256
DHAP(O-18:0),2TBDMS,isomer #1CCCCCCCCCCCCCCCCCCOCC(=O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3656.7Semi standard non polar33892256
DHAP(O-18:0),2TBDMS,isomer #1CCCCCCCCCCCCCCCCCCOCC(=O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3286.3Standard non polar33892256
DHAP(O-18:0),2TBDMS,isomer #1CCCCCCCCCCCCCCCCCCOCC(=O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3515.1Standard polar33892256
DHAP(O-18:0),2TBDMS,isomer #2CCCCCCCCCCCCCCCCCCOCC(=COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3674.0Semi standard non polar33892256
DHAP(O-18:0),2TBDMS,isomer #2CCCCCCCCCCCCCCCCCCOCC(=COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3213.8Standard non polar33892256
DHAP(O-18:0),2TBDMS,isomer #2CCCCCCCCCCCCCCCCCCOCC(=COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3786.5Standard polar33892256
DHAP(O-18:0),2TBDMS,isomer #3CCCCCCCCCCCCCCCCCCOC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3689.7Semi standard non polar33892256
DHAP(O-18:0),2TBDMS,isomer #3CCCCCCCCCCCCCCCCCCOC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3235.1Standard non polar33892256
DHAP(O-18:0),2TBDMS,isomer #3CCCCCCCCCCCCCCCCCCOC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3788.4Standard polar33892256
DHAP(O-18:0),3TBDMS,isomer #1CCCCCCCCCCCCCCCCCCOCC(=COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3868.1Semi standard non polar33892256
DHAP(O-18:0),3TBDMS,isomer #1CCCCCCCCCCCCCCCCCCOCC(=COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3317.1Standard non polar33892256
DHAP(O-18:0),3TBDMS,isomer #1CCCCCCCCCCCCCCCCCCOCC(=COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3447.2Standard polar33892256
DHAP(O-18:0),3TBDMS,isomer #2CCCCCCCCCCCCCCCCCCOC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3901.5Semi standard non polar33892256
DHAP(O-18:0),3TBDMS,isomer #2CCCCCCCCCCCCCCCCCCOC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3333.8Standard non polar33892256
DHAP(O-18:0),3TBDMS,isomer #2CCCCCCCCCCCCCCCCCCOC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3450.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - DHAP(O-18:0) GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-2921000000-707e951e2f249a0c84562017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DHAP(O-18:0) GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DHAP(O-18:0) GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DHAP(O-18:0) 10V, Positive-QTOFsplash10-00dj-6236900000-250953ab98daae84461f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DHAP(O-18:0) 20V, Positive-QTOFsplash10-0udi-5986300000-a9594fbed5528bb4c4562017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DHAP(O-18:0) 40V, Positive-QTOFsplash10-0udj-9262000000-9ff6cbd7ba10f45d15602017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DHAP(O-18:0) 10V, Negative-QTOFsplash10-00fr-6120900000-2057f81918546a4619532017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DHAP(O-18:0) 20V, Negative-QTOFsplash10-004i-9010000000-0eafcb7cda2c77ee40732017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DHAP(O-18:0) 40V, Negative-QTOFsplash10-004i-9000000000-51b409ce9fb4be773cf92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DHAP(O-18:0) 10V, Negative-QTOFsplash10-00di-1000900000-ce2f2d0d83bfe0c120a62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DHAP(O-18:0) 20V, Negative-QTOFsplash10-004i-9030100000-aa6fa1c045ef23d13a3d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DHAP(O-18:0) 40V, Negative-QTOFsplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DHAP(O-18:0) 10V, Positive-QTOFsplash10-00di-1103900000-b64c0f89dc9b0ca50c3f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DHAP(O-18:0) 20V, Positive-QTOFsplash10-004i-5349100000-dec5743388f44ec0d5d52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DHAP(O-18:0) 40V, Positive-QTOFsplash10-052b-9100000000-674e3d4eb872c8b7b6d32021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDFDB027917
KNApSAcK IDNot Available
Chemspider ID25996866
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound49791756
PDB IDNot Available
ChEBI ID78163
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
1-acyl-glycerone 3-phosphate + a long-chain alcohol = an alkyl-glycerone 3-phosphate + a long-chain acid anion
Gene Name:
AGPS
Uniprot ID:
O00116
Molecular weight:
72911.2