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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-09 21:13:23 UTC
Update Date2019-07-23 07:13:55 UTC
HMDB IDHMDB0060249
Secondary Accession Numbers
  • HMDB60249
Metabolite Identification
Common Name3-Decaprenyl-4,5-dihydroxybenzoate
Description3-Decaprenyl-4,5-dihydroxybenzoate, also known as 3,4-dihydroxy-5-decaprenylbenzoic acid, belongs to the class of organic compounds known as polyprenylbenzene-1,2-diols. Polyprenylbenzene-1,2-diols are compounds containing a polyisoprene chain attached to a catechol group. 3-Decaprenyl-4,5-dihydroxybenzoate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866035
Synonyms
ValueSource
3,4-Dihydroxy-5-decaprenylbenzoic acidChEBI
3-(3,7,11,15,19,23,27,31,35,39-Decamethyltetracosa-2,6,10,14,18,22,26,30,34,38-decaenyl)-4,5-dihydroxybenzoic acidChEBI
all-trans-3,4-Dihydroxy-5-decaprenylbenzoic acidChEBI
all-trans-3-Decaprenyl-4,5-dihydroxybenzoic acidChEBI
3,4-Dihydroxy-5-decaprenylbenzoateGenerator
3-(3,7,11,15,19,23,27,31,35,39-Decamethyltetracosa-2,6,10,14,18,22,26,30,34,38-decaenyl)-4,5-dihydroxybenzoateGenerator
all-trans-3,4-Dihydroxy-5-decaprenylbenzoateGenerator
all-trans-3-Decaprenyl-4,5-dihydroxybenzoateGenerator
3-Decaprenyl-4,5-dihydroxybenzoic acidGenerator
3-Decaprenyl-4,5-dihydroxybenzoateGenerator
Chemical FormulaC57H86O4
Average Molecular Weight835.2903
Monoisotopic Molecular Weight834.65261124
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]-4,5-dihydroxybenzoic acid
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]-4,5-dihydroxybenzoic acid
CAS Registry NumberNot Available
SMILES
CC(C)=CCC\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\CC1=CC(=CC(O)=C1O)C(O)=O
InChI Identifier
InChI=1S/C57H86O4/c1-43(2)21-12-22-44(3)23-13-24-45(4)25-14-26-46(5)27-15-28-47(6)29-16-30-48(7)31-17-32-49(8)33-18-34-50(9)35-19-36-51(10)37-20-38-52(11)39-40-53-41-54(57(60)61)42-55(58)56(53)59/h21,23,25,27,29,31,33,35,37,39,41-42,58-59H,12-20,22,24,26,28,30,32,34,36,38,40H2,1-11H3,(H,60,61)/b44-23+,45-25+,46-27+,47-29+,48-31+,49-33+,50-35+,51-37+,52-39+
InChI KeyHGWUGDIATLOPBN-BHZQGFRMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as polyprenylbenzene-1,2-diols. Polyprenylbenzene-1,2-diols are compounds containing a polyisoprene chain attached to a catechol group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenylphenols
Direct ParentPolyprenylbenzene-1,2-diols
Alternative Parents
Substituents
  • Polyterpenoid
  • Polyprenylbenzene-1,2-diol
  • Dihydroxybenzoic acid
  • Hydroxybenzoic acid
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzoyl
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00024 g/LALOGPS
logP9.8ALOGPS
logP17.69ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)4.13ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count30ChemAxon
Refractivity275.74 m³·mol⁻¹ChemAxon
Polarizability107.59 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0101011490-b5c632d8c1303c1658fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-1836569850-6e98ef39441085bc2790Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-082i-1936466400-2d1b1eea9c4f056af60bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000390-13caac670cd93e11f72dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0019-0000000950-77da2c15356569030ecfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07or-0300000920-f495d01864a5c70c6ed6Spectrum
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 Compound25010746
PDB IDNot Available
ChEBI ID50775
Food Biomarker OntologyNot Available
VMH 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. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.