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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-09 21:13:36 UTC
Update Date2022-03-07 03:17:42 UTC
HMDB IDHMDB0060252
Secondary Accession Numbers
  • HMDB60252
Metabolite Identification
Common Name3-Decaprenyl-4-hydroxy-5-methoxybenzoate
Description3-Decaprenyl-4-hydroxy-5-methoxybenzoate, also known as 4-hydroxy-3-methoxy-5-decaprenylbenzoic acid, belongs to the class of organic compounds known as polyprenylphenols. Polyprenylphenols are compounds containing a polyisoprene chain attached to a phenol group. 3-Decaprenyl-4-hydroxy-5-methoxybenzoate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866035
Synonyms
ValueSource
4-Hydroxy-3-methoxy-5-decaprenylbenzoic acidChEBI
all-trans-3-Decaprenyl-4-hydroxy-5-methoxybenzoic acidChEBI
all-trans-4-Hydroxy-3-methoxy-5-decaprenylbenzoic acidChEBI
4-Hydroxy-3-methoxy-5-decaprenylbenzoateGenerator
all-trans-3-Decaprenyl-4-hydroxy-5-methoxybenzoateGenerator
all-trans-4-Hydroxy-3-methoxy-5-decaprenylbenzoateGenerator
3-Decaprenyl-4-hydroxy-5-methoxybenzoic acidGenerator
3-Decaprenyl-4-hydroxy-5-methoxybenzoateGenerator
Chemical FormulaC58H88O4
Average Molecular Weight849.3169
Monoisotopic Molecular Weight848.668261304
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-hydroxy-5-methoxybenzoic 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-hydroxy-5-methoxybenzoic acid
CAS Registry NumberNot Available
SMILES
COC1=C(O)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)=CC(=C1)C(O)=O
InChI Identifier
InChI=1S/C58H88O4/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(60)61)43-56(62-12)57(54)59/h22,24,26,28,30,32,34,36,38,40,42-43,59H,13-21,23,25,27,29,31,33,35,37,39,41H2,1-12H3,(H,60,61)/b45-24+,46-26+,47-28+,48-30+,49-32+,50-34+,51-36+,52-38+,53-40+
InChI KeyWCQCNOIKXGNDLX-RDSVHMIISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as polyprenylphenols. Polyprenylphenols are compounds containing a polyisoprene chain attached to a phenol group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenylphenols
Direct ParentPolyprenylphenols
Alternative Parents
Substituents
  • Polyterpenoid
  • 2-polyprenyl-6-methoxyphenol
  • Polyprenylphenol
  • M-methoxybenzoic acid or derivatives
  • Hydroxybenzoic acid
  • Methoxyphenol
  • Benzoic acid or derivatives
  • Benzoic acid
  • Anisole
  • Phenoxy compound
  • Benzoyl
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic 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 Solubility0.00023 g/LALOGPS
logP9.77ALOGPS
logP17.84ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)4.12ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count31ChemAxon
Refractivity280.22 m³·mol⁻¹ChemAxon
Polarizability109.58 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]+314.20830932474
DeepCCS[M-H]-312.31330932474
DeepCCS[M-2H]-346.01430932474
DeepCCS[M+Na]+319.98230932474
AllCCS[M+H]+289.432859911
AllCCS[M+H-H2O]+289.032859911
AllCCS[M+NH4]+289.932859911
AllCCS[M+Na]+290.032859911
AllCCS[M-H]-255.432859911
AllCCS[M+Na-2H]-257.032859911
AllCCS[M+HCOO]-258.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Decaprenyl-4-hydroxy-5-methoxybenzoateCOC1=C(O)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)=CC(=C1)C(O)=O6769.8Standard polar33892256
3-Decaprenyl-4-hydroxy-5-methoxybenzoateCOC1=C(O)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)=CC(=C1)C(O)=O5553.0Standard non polar33892256
3-Decaprenyl-4-hydroxy-5-methoxybenzoateCOC1=C(O)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)=CC(=C1)C(O)=O5860.5Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Decaprenyl-4-hydroxy-5-methoxybenzoate 10V, Positive-QTOFsplash10-001j-0100001090-2470e295c75af5d70a3a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Decaprenyl-4-hydroxy-5-methoxybenzoate 20V, Positive-QTOFsplash10-0uyi-0415256190-1a7e7c69399ed19ea3522017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Decaprenyl-4-hydroxy-5-methoxybenzoate 40V, Positive-QTOFsplash10-0lg0-1956567220-5cad57b76d8c9fec48e62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Decaprenyl-4-hydroxy-5-methoxybenzoate 10V, Negative-QTOFsplash10-0002-0000000090-ff13ea4a4b2815bb94a62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Decaprenyl-4-hydroxy-5-methoxybenzoate 20V, Negative-QTOFsplash10-0uds-0000000490-587088bdf048666140062017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Decaprenyl-4-hydroxy-5-methoxybenzoate 40V, Negative-QTOFsplash10-003i-1200000940-0318521611d4e18ae3e12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Decaprenyl-4-hydroxy-5-methoxybenzoate 10V, Positive-QTOFsplash10-003e-4032220960-d9c92cfc0e8765984fc12021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Decaprenyl-4-hydroxy-5-methoxybenzoate 20V, Positive-QTOFsplash10-001i-3619541310-ba293c1cef5889ebb1902021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Decaprenyl-4-hydroxy-5-methoxybenzoate 40V, Positive-QTOFsplash10-005c-9436610000-b26dcb495f46cc4b08a92021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Decaprenyl-4-hydroxy-5-methoxybenzoate 10V, Negative-QTOFsplash10-0002-0000000090-0ed96e8c7dce444823df2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Decaprenyl-4-hydroxy-5-methoxybenzoate 20V, Negative-QTOFsplash10-000b-0630010290-b7a1936267116d8758ca2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Decaprenyl-4-hydroxy-5-methoxybenzoate 40V, Negative-QTOFsplash10-0019-0691260720-2cefde04a44769a268072021-10-12Wishart 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 IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25010743
PDB IDNot Available
ChEBI ID50776
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. 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.