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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-09 21:13:19 UTC
Update Date2022-03-07 03:17:42 UTC
HMDB IDHMDB0060248
Secondary Accession Numbers
  • HMDB60248
Metabolite Identification
Common Name2-Decaprenyl-6-methoxy-1,4-benzoquinone
Description2-Decaprenyl-6-methoxy-1,4-benzoquinone 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-1,4-benzoquinone is considered to be a quinone lipid molecule. 2-Decaprenyl-6-methoxy-1,4-benzoquinone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866035
Synonyms
ValueSource
2-[(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]-6-methoxycyclohexa-2,5-diene-1,4-dioneChEBI
Chemical FormulaC57H86O3
Average Molecular Weight819.2909
Monoisotopic Molecular Weight818.657696618
IUPAC Name2-[(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]-6-methoxycyclohexa-2,5-diene-1,4-dione
Traditional Name2-[(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]-6-methoxycyclohexa-2,5-diene-1,4-dione
CAS Registry NumberNot Available
SMILES
COC1=CC(=O)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/C57H86O3/c1-44(2)22-13-23-45(3)24-14-25-46(4)26-15-27-47(5)28-16-29-48(6)30-17-31-49(7)32-18-33-50(8)34-19-35-51(9)36-20-37-52(10)38-21-39-53(11)40-41-54-42-55(58)43-56(60-12)57(54)59/h22,24,26,28,30,32,34,36,38,40,42-43H,13-21,23,25,27,29,31,33,35,37,39,41H2,1-12H3/b45-24+,46-26+,47-28+,48-30+,49-32+,50-34+,51-36+,52-38+,53-40+
InChI KeyPOYJNCVGTDCCPK-RDSVHMIISA-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
Not AvailableNot 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 Solubility0.00022 g/LALOGPS
logP10.13ALOGPS
logP17.17ChemAxon
logS-6.6ALOGPS
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count30ChemAxon
Refractivity275.53 m³·mol⁻¹ChemAxon
Polarizability106.23 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]+307.26830932474
DeepCCS[M-H]-305.37330932474
DeepCCS[M-2H]-339.14230932474
DeepCCS[M+Na]+313.21130932474
AllCCS[M+H]+293.332859911
AllCCS[M+H-H2O]+292.832859911
AllCCS[M+NH4]+293.832859911
AllCCS[M+Na]+293.932859911
AllCCS[M-H]-246.232859911
AllCCS[M+Na-2H]-249.132859911
AllCCS[M+HCOO]-252.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Decaprenyl-6-methoxy-1,4-benzoquinoneCOC1=CC(=O)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=O6502.2Standard polar33892256
2-Decaprenyl-6-methoxy-1,4-benzoquinoneCOC1=CC(=O)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=O5350.5Standard non polar33892256
2-Decaprenyl-6-methoxy-1,4-benzoquinoneCOC1=CC(=O)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=O5676.1Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Decaprenyl-6-methoxy-1,4-benzoquinone 10V, Positive-QTOFsplash10-0gb9-1301121390-890c4de151d02e1e2c382017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Decaprenyl-6-methoxy-1,4-benzoquinone 20V, Positive-QTOFsplash10-0uxu-1756569320-077c7c1ca161bf5b51142017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Decaprenyl-6-methoxy-1,4-benzoquinone 40V, Positive-QTOFsplash10-0udi-3354449310-8fadc08297999a644ba92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Decaprenyl-6-methoxy-1,4-benzoquinone 10V, Negative-QTOFsplash10-014i-0000000090-b0c61590f1581a79b2da2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Decaprenyl-6-methoxy-1,4-benzoquinone 20V, Negative-QTOFsplash10-014i-0000000590-aa1555162cc9447e8d332017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Decaprenyl-6-methoxy-1,4-benzoquinone 40V, Negative-QTOFsplash10-0udi-2200000930-1afcce484029c3e1980e2017-10-06Wishart 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 IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25010761
PDB IDNot Available
ChEBI ID50773
Food Biomarker OntologyNot Available
VMH ID2DP6MOBQ
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.