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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:23:04 UTC
Update Date2022-03-07 03:17:45 UTC
HMDB IDHMDB0060469
Secondary Accession Numbers
  • HMDB60469
Metabolite Identification
Common NameDehydrodolichol diphosphate
DescriptionDehydrodolichol diphosphate belongs to the class of organic compounds known as polyprenyl diphosphates. These are prenol lipids in which the diphosphate group is linked to one end of the polyprenol moiety. Dehydrodolichol diphosphate is a moderately acidic compound (based on its pKa).
Structure
Data?1563866064
Synonyms
ValueSource
Ditrans,dicis-pentaprenyl diphosphateKegg
2-cis,6-cis,10-trans,14-trans-Pentaprenyl diphosphateKegg
2-cis,6-cis,10-trans,14-trans-Geranylfarnesyl diphosphateKegg
Ditrans,dicis-pentaprenyl diphosphoric acidGenerator
2-cis,6-cis,10-trans,14-trans-Pentaprenyl diphosphoric acidGenerator
2-cis,6-cis,10-trans,14-trans-Geranylfarnesyl diphosphoric acidGenerator
Dehydrodolichol diphosphoric acidGenerator
Chemical FormulaC25H44O7P2
Average Molecular Weight518.5602
Monoisotopic Molecular Weight518.256226786
IUPAC Name{[hydroxy({[(2Z,6Z,10E,14E)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaen-1-yl]oxy})phosphoryl]oxy}phosphonic acid
Traditional Namedehydrodolichyl diphosphate
CAS Registry NumberNot Available
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C/CC\C(C)=C/COP(O)(=O)OP(O)(O)=O
InChI Identifier
InChI=1S/C25H44O7P2/c1-21(2)11-7-12-22(3)13-8-14-23(4)15-9-16-24(5)17-10-18-25(6)19-20-31-34(29,30)32-33(26,27)28/h11,13,15,17,19H,7-10,12,14,16,18,20H2,1-6H3,(H,29,30)(H2,26,27,28)/b22-13+,23-15+,24-17-,25-19-
InChI KeyJMVSBFJBMXQNJW-PSTDWBAXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as polyprenyl diphosphates. These are prenol lipids in which the diphosphate group is linked to one end of the polyprenol moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenols
Direct ParentPolyprenyl diphosphates
Alternative Parents
Substituents
  • Polyprenyl diphosphate
  • Polyprenyl monophosphate
  • Sesterterpenoid
  • Organic pyrophosphate
  • Isoprenoid phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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 Solubility0.0012 g/LALOGPS
logP4.88ALOGPS
logP6.94ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity144.34 m³·mol⁻¹ChemAxon
Polarizability55.98 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]+219.52231661259
DarkChem[M-H]-212.93431661259
DeepCCS[M+H]+215.19730932474
DeepCCS[M-H]-212.83930932474
DeepCCS[M-2H]-245.72530932474
DeepCCS[M+Na]+221.2930932474
AllCCS[M+H]+232.732859911
AllCCS[M+H-H2O]+231.032859911
AllCCS[M+NH4]+234.332859911
AllCCS[M+Na]+234.732859911
AllCCS[M-H]-223.032859911
AllCCS[M+Na-2H]-226.032859911
AllCCS[M+HCOO]-229.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dehydrodolichol diphosphateCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C/CC\C(C)=C/COP(O)(=O)OP(O)(O)=O4510.1Standard polar33892256
Dehydrodolichol diphosphateCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C/CC\C(C)=C/COP(O)(=O)OP(O)(O)=O3085.3Standard non polar33892256
Dehydrodolichol diphosphateCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C/CC\C(C)=C/COP(O)(=O)OP(O)(O)=O3648.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dehydrodolichol diphosphate,1TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O[Si](C)(C)C)OP(=O)(O)O3599.5Semi standard non polar33892256
Dehydrodolichol diphosphate,1TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O[Si](C)(C)C)OP(=O)(O)O2917.7Standard non polar33892256
Dehydrodolichol diphosphate,1TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O[Si](C)(C)C)OP(=O)(O)O4512.3Standard polar33892256
Dehydrodolichol diphosphate,1TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O)OP(=O)(O)O[Si](C)(C)C3592.5Semi standard non polar33892256
Dehydrodolichol diphosphate,1TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O)OP(=O)(O)O[Si](C)(C)C2924.8Standard non polar33892256
Dehydrodolichol diphosphate,1TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O)OP(=O)(O)O[Si](C)(C)C4532.7Standard polar33892256
Dehydrodolichol diphosphate,2TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C3557.0Semi standard non polar33892256
Dehydrodolichol diphosphate,2TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C2993.7Standard non polar33892256
Dehydrodolichol diphosphate,2TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C4060.1Standard polar33892256
Dehydrodolichol diphosphate,2TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3561.1Semi standard non polar33892256
Dehydrodolichol diphosphate,2TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2973.4Standard non polar33892256
Dehydrodolichol diphosphate,2TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C4059.2Standard polar33892256
Dehydrodolichol diphosphate,3TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3499.6Semi standard non polar33892256
Dehydrodolichol diphosphate,3TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3041.9Standard non polar33892256
Dehydrodolichol diphosphate,3TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3581.5Standard polar33892256
Dehydrodolichol diphosphate,1TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O3800.4Semi standard non polar33892256
Dehydrodolichol diphosphate,1TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O3062.5Standard non polar33892256
Dehydrodolichol diphosphate,1TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O4589.0Standard polar33892256
Dehydrodolichol diphosphate,1TBDMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C3792.4Semi standard non polar33892256
Dehydrodolichol diphosphate,1TBDMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C3080.5Standard non polar33892256
Dehydrodolichol diphosphate,1TBDMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C4604.2Standard polar33892256
Dehydrodolichol diphosphate,2TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C3920.0Semi standard non polar33892256
Dehydrodolichol diphosphate,2TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C3280.9Standard non polar33892256
Dehydrodolichol diphosphate,2TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C4148.5Standard polar33892256
Dehydrodolichol diphosphate,2TBDMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3924.2Semi standard non polar33892256
Dehydrodolichol diphosphate,2TBDMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3248.1Standard non polar33892256
Dehydrodolichol diphosphate,2TBDMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4176.8Standard polar33892256
Dehydrodolichol diphosphate,3TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4025.3Semi standard non polar33892256
Dehydrodolichol diphosphate,3TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3447.9Standard non polar33892256
Dehydrodolichol diphosphate,3TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3751.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dehydrodolichol diphosphate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fvj-8897540000-8727b5480b3179b9518e2017-09-20Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrodolichol diphosphate 10V, Positive-QTOFsplash10-00ko-1309550000-404a71813930230a64062017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrodolichol diphosphate 20V, Positive-QTOFsplash10-0006-4429100000-9411fb3e4564e1ea92732017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrodolichol diphosphate 40V, Positive-QTOFsplash10-052o-5559000000-150907ec187ca3bdb7672017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrodolichol diphosphate 10V, Negative-QTOFsplash10-014i-0400090000-9f47c79182d3c01be7252017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrodolichol diphosphate 20V, Negative-QTOFsplash10-004i-9201000000-6ee037a3eed233ccad1c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrodolichol diphosphate 40V, Negative-QTOFsplash10-004i-9000000000-9fcecdd44b53bc65fe732017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrodolichol diphosphate 10V, Positive-QTOFsplash10-014i-0102490000-db11104e02e5bcc9eaf62021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrodolichol diphosphate 20V, Positive-QTOFsplash10-002n-1119400000-33d1f9d47cff2aaf5fce2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrodolichol diphosphate 40V, Positive-QTOFsplash10-01yt-2935000000-244031b6c35d30ad5dce2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrodolichol diphosphate 10V, Negative-QTOFsplash10-014i-0000090000-befd6f91805f0ef51f2d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrodolichol diphosphate 20V, Negative-QTOFsplash10-014i-2400290000-a4391592122ec62032d82021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydrodolichol diphosphate 40V, Negative-QTOFsplash10-056r-9400000000-cd37df82a8f7acbc7eda2021-10-12Wishart 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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC17435
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24892764
PDB IDNot Available
ChEBI ID81086
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 References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in transferase activity, transferring alkyl or aryl (other than methyl) groups
Specific function:
Catalyzes cis-prenyl chain elongation to produce the polyprenyl backbone of dolichol, a glycosyl carrier-lipid required for the biosynthesis of several classes of glycoprotein.
Gene Name:
DHDDS
Uniprot ID:
Q86SQ9
Molecular weight:
Not Available
Reactions
Farnesyl pyrophosphate + → Dehydrodolichol diphosphate + details