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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-09 21:13:32 UTC
Update Date2022-03-07 03:17:42 UTC
HMDB IDHMDB0060251
Secondary Accession Numbers
  • HMDB60251
Metabolite Identification
Common Name2-Decaprenyl-6-methoxy-3-methyl-1,4-benzoquinone
Description2-Decaprenyl-6-methoxy-3-methyl-1,4-benzoquinone, also known as 5-demethoxyubiquinone-10, belongs to the class of organic compounds known as polyprenylbenzoquinones. Polyprenylbenzoquinones are compounds containing a polyisoprene chain attached to a quinone at the second ring position. Thus, 2-decaprenyl-6-methoxy-3-methyl-1,4-benzoquinone is considered to be a quinone lipid molecule. 2-Decaprenyl-6-methoxy-3-methyl-1,4-benzoquinone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866035
Synonyms
ValueSource
3-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-Decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-5-methoxy-2-methyl-1,4-benzoquinoneChEBI
5-Demethoxyubiquinone-10ChEBI
Chemical FormulaC58H88O3
Average Molecular Weight833.3175
Monoisotopic Molecular Weight832.673346682
IUPAC Name3-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-5-methoxy-2-methylcyclohexa-2,5-diene-1,4-dione
Traditional Name3-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-5-methoxy-2-methylcyclohexa-2,5-diene-1,4-dione
CAS Registry NumberNot Available
SMILES
COC1=CC(=O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C1=O
InChI Identifier
InChI=1S/C58H88O3/c1-44(2)23-14-24-45(3)25-15-26-46(4)27-16-28-47(5)29-17-30-48(6)31-18-32-49(7)33-19-34-50(8)35-20-36-51(9)37-21-38-52(10)39-22-40-53(11)41-42-55-54(12)56(59)43-57(61-13)58(55)60/h23,25,27,29,31,33,35,37,39,41,43H,14-22,24,26,28,30,32,34,36,38,40,42H2,1-13H3/b45-25+,46-27+,47-29+,48-31+,49-33+,50-35+,51-37+,52-39+,53-41+
InChI KeyDLBRMPAESNEOJM-RGIWONJESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as polyprenylbenzoquinones. Polyprenylbenzoquinones are compounds containing a polyisoprene chain attached to a quinone at the second ring position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentPolyprenylbenzoquinones
Alternative Parents
Substituents
  • Polyterpenoid
  • Polyprenylbenzoquinone
  • Quinone
  • P-benzoquinone
  • Vinylogous ester
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

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 Solubility0.00021 g/LALOGPS
logP10.02ALOGPS
logP17.56ChemAxon
logS-6.6ALOGPS
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count30ChemAxon
Refractivity279.89 m³·mol⁻¹ChemAxon
Polarizability108.6 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+313.65530932474
DeepCCS[M-H]-311.7630932474
DeepCCS[M-2H]-345.57430932474
DeepCCS[M+Na]+319.65330932474
AllCCS[M+H]+294.432859911
AllCCS[M+H-H2O]+294.032859911
AllCCS[M+NH4]+294.932859911
AllCCS[M+Na]+295.032859911
AllCCS[M-H]-246.732859911
AllCCS[M+Na-2H]-249.232859911
AllCCS[M+HCOO]-252.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Decaprenyl-6-methoxy-3-methyl-1,4-benzoquinoneCOC1=CC(=O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C1=O6453.1Standard polar33892256
2-Decaprenyl-6-methoxy-3-methyl-1,4-benzoquinoneCOC1=CC(=O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C1=O5328.2Standard non polar33892256
2-Decaprenyl-6-methoxy-3-methyl-1,4-benzoquinoneCOC1=CC(=O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C1=O5666.0Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Decaprenyl-6-methoxy-3-methyl-1,4-benzoquinone 10V, Positive-QTOFsplash10-00lr-0302021390-4f931f524f65b264c6522017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Decaprenyl-6-methoxy-3-methyl-1,4-benzoquinone 20V, Positive-QTOFsplash10-014i-1656569140-dd696e33ba49c5180ec02017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Decaprenyl-6-methoxy-3-methyl-1,4-benzoquinone 40V, Positive-QTOFsplash10-00kb-3233029810-fc889050b8d26c77cf752017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Decaprenyl-6-methoxy-3-methyl-1,4-benzoquinone 10V, Negative-QTOFsplash10-001i-0000000090-76eb431fa902e3c3e8712017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Decaprenyl-6-methoxy-3-methyl-1,4-benzoquinone 20V, Negative-QTOFsplash10-001i-1100000690-97deff8c087791dd0df22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Decaprenyl-6-methoxy-3-methyl-1,4-benzoquinone 40V, Negative-QTOFsplash10-014i-8200002890-91a9bd302827b2a078962017-10-06Wishart 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 IDNot Available
BioCyc IDCPD-11660
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25010748
PDB IDNot Available
ChEBI ID50772
Food Biomarker OntologyNot Available
VMH ID2DP6MOBQ_ME
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
  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.