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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:54 UTC
HMDB IDHMDB0001063
Secondary Accession Numbers
  • HMDB01063
Metabolite Identification
Common Name3-Hexaprenyl-4,5-Dihydroxybenzoic acid
Description3-Hexaprenyl-4,5-Dihydroxybenzoic acid, also known as 3,4-dihydroxy-5-hexaprenylbenzoate or dhhpba, 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-Hexaprenyl-4,5-Dihydroxybenzoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1582752174
Synonyms
ValueSource
3-Hexaprenyl-4,5-dihydroxybenzoateChEBI
3,4-Dihydroxy-5-hexaprenylbenzoateHMDB
3,4-Dihydroxy-5-hexaprenylbenzoic acidHMDB
DhhpbaHMDB
Chemical FormulaC37H54O4
Average Molecular Weight562.8223
Monoisotopic Molecular Weight562.402210216
IUPAC Name3-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-4,5-dihydroxybenzoic acid
Traditional Namedhhpba
CAS Registry Number63975-40-6
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=C(O)C(O)=CC(=C1)C(O)=O
InChI Identifier
InChI=1S/C37H54O4/c1-27(2)13-8-14-28(3)15-9-16-29(4)17-10-18-30(5)19-11-20-31(6)21-12-22-32(7)23-24-33-25-34(37(40)41)26-35(38)36(33)39/h13,15,17,19,21,23,25-26,38-39H,8-12,14,16,18,20,22,24H2,1-7H3,(H,40,41)/b28-15+,29-17+,30-19+,31-21+,32-23+
InChI KeyVEPICJBQCOUQPI-IRVXXIIISA-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
  • Polyprenylbenzene-1,2-diol
  • Sesterterpenoid
  • 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

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
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 Solubility0.00057 g/LALOGPS
logP10(8.41) g/LALOGPS
logP10(11.05) g/LChemAxon
logS10(-6) g/LALOGPS
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 Count18ChemAxon
Refractivity180.53 m³·mol⁻¹ChemAxon
Polarizability70.25 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
DarkChem[M+H]+31661259
DarkChem[M-H]-31661259
AllCCS[M+H]+245.81132859911
AllCCS[M-H]-225.53832859911
DeepCCS[M+H]+234.85530932474
DeepCCS[M-H]-232.45930932474
DeepCCS[M-2H]-265.34430932474
DeepCCS[M+Na]+240.76730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Hexaprenyl-4,5-Dihydroxybenzoic acidCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=C(O)C(O)=CC(=C1)C(O)=O6038.6Standard polar33892256
3-Hexaprenyl-4,5-Dihydroxybenzoic acidCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=C(O)C(O)=CC(=C1)C(O)=O4088.0Standard non polar33892256
3-Hexaprenyl-4,5-Dihydroxybenzoic acidCC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=C(O)C(O)=CC(=C1)C(O)=O4332.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hexaprenyl-4,5-Dihydroxybenzoic acid,1TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC1=CC(C(=O)O)=CC(O)=C1O[Si](C)(C)C4296.8Semi standard non polar33892256
3-Hexaprenyl-4,5-Dihydroxybenzoic acid,1TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC1=CC(C(=O)O)=CC(O[Si](C)(C)C)=C1O4314.7Semi standard non polar33892256
3-Hexaprenyl-4,5-Dihydroxybenzoic acid,1TMS,isomer #3CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C)=CC(O)=C1O4271.4Semi standard non polar33892256
3-Hexaprenyl-4,5-Dihydroxybenzoic acid,2TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C)=CC(O)=C1O[Si](C)(C)C4101.5Semi standard non polar33892256
3-Hexaprenyl-4,5-Dihydroxybenzoic acid,2TMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC1=CC(C(=O)O)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C4202.1Semi standard non polar33892256
3-Hexaprenyl-4,5-Dihydroxybenzoic acid,2TMS,isomer #3CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1O4131.1Semi standard non polar33892256
3-Hexaprenyl-4,5-Dihydroxybenzoic acid,3TMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C4080.3Semi standard non polar33892256
3-Hexaprenyl-4,5-Dihydroxybenzoic acid,1TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC1=CC(C(=O)O)=CC(O)=C1O[Si](C)(C)C(C)(C)C4535.6Semi standard non polar33892256
3-Hexaprenyl-4,5-Dihydroxybenzoic acid,1TBDMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC1=CC(C(=O)O)=CC(O[Si](C)(C)C(C)(C)C)=C1O4551.0Semi standard non polar33892256
3-Hexaprenyl-4,5-Dihydroxybenzoic acid,1TBDMS,isomer #3CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(O)=C1O4525.6Semi standard non polar33892256
3-Hexaprenyl-4,5-Dihydroxybenzoic acid,2TBDMS,isomer #1CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(O)=C1O[Si](C)(C)C(C)(C)C4555.0Semi standard non polar33892256
3-Hexaprenyl-4,5-Dihydroxybenzoic acid,2TBDMS,isomer #2CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC1=CC(C(=O)O)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C4638.0Semi standard non polar33892256
3-Hexaprenyl-4,5-Dihydroxybenzoic acid,2TBDMS,isomer #3CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1O4578.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-000b-3394440000-9ca4e15a8864fbc5776d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-01b9-5375429000-ea197f75d2ee1687f2472017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid GC-MS ("3-Hexaprenyl-4,5-Dihydroxybenzoic acid,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid 10V, Positive-QTOFsplash10-03xs-0212090000-04095cbd227edc49a7a12016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid 20V, Positive-QTOFsplash10-014j-0849150000-639873a7488c1a6960072016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid 40V, Positive-QTOFsplash10-00tb-1769200000-4cbbd0cfab58c6dd37642016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid 10V, Negative-QTOFsplash10-03di-0000090000-a08e91d9fefaf0f162ff2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid 20V, Negative-QTOFsplash10-02t9-0000090000-99d552c5bbb95acff7ff2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid 40V, Negative-QTOFsplash10-0zfs-1702690000-7f58130fe1eabd49d71c2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid 10V, Negative-QTOFsplash10-03di-0000090000-ab699c4e48dd66694a102021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid 20V, Negative-QTOFsplash10-02mi-0801190000-5746ee5667f6804445e32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid 40V, Negative-QTOFsplash10-0fdk-2903720000-6606158339c54cc426d22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid 10V, Positive-QTOFsplash10-03di-1102690000-f4b5588e3e3d17d762622021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid 20V, Positive-QTOFsplash10-00li-1319400000-aa11a41d3c21566813702021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hexaprenyl-4,5-Dihydroxybenzoic acid 40V, Positive-QTOFsplash10-000j-0898400000-2eab6c20b158a56bdbf72021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • 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 IDFDB022402
KNApSAcK IDNot Available
Chemspider ID4444330
KEGG Compound IDC05200
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5976
PubChem Compound5280760
PDB IDNot Available
ChEBI ID18081
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 ReferencesNot Available

Enzymes

General function:
Involved in methyltransferase activity
Specific function:
Not Available
Gene Name:
COQ3
Uniprot ID:
Q9NZJ6
Molecular weight:
41053.76
Reactions
S-Adenosylmethionine + 3-Hexaprenyl-4,5-Dihydroxybenzoic acid → S-Adenosylhomocysteine + 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid + Hydrogen Iondetails