Showing metabocard for 3-Hexaprenyl-4,5-Dihydroxybenzoic acid (BMDB0001063)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:40:36 UTC
Update Date2020-05-19 22:01:09 UTC
BMDB IDBMDB0001063
Secondary Accession Numbers
  • BMDB01063
Metabolite Identification
Common Name3-Hexaprenyl-4,5-Dihydroxybenzoic acid
Description3-Hexaprenyl-4,5-dihydroxybenzoic acid, also known as 3-hexaprenyl-4,5-dihydroxybenzoic acid or 3-hexaprenyl-4,5-dihydroxybenzoic 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-Hexaprenyl-4,5-dihydroxybenzoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3-Hexaprenyl-4,5-dihydroxybenzoic acid exists in all eukaryotes, ranging from yeast to humans. In cattle, 3-hexaprenyl-4,5-dihydroxybenzoic acid is involved in the metabolic pathway called ubiquinone biosynthesis pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP8.41ALOGPS
logP11.05ChemAxon
logS-6ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000b-3394440000-9ca4e15a8864fbc5776dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01b9-5375429000-ea197f75d2ee1687f247View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("3-Hexaprenyl-4,5-Dihydroxybenzoic acid,1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xs-0212090000-04095cbd227edc49a7a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0849150000-639873a7488c1a696007View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00tb-1769200000-4cbbd0cfab58c6dd3764View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000090000-a08e91d9fefaf0f162ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02t9-0000090000-99d552c5bbb95acff7ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfs-1702690000-7f58130fe1eabd49d71cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000090000-ab699c4e48dd66694a10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02mi-0801190000-5746ee5667f6804445e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fdk-2903720000-6606158339c54cc426d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1102690000-f4b5588e3e3d17d76262View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00li-1319400000-aa11a41d3c2156681370View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000j-0898400000-2eab6c20b158a56bdbf7View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001063
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Ubiquinone biosynthesis O-methyltransferase, mitochondrial
General function:
Coenzyme transport and metabolism
Specific function:
O-methyltransferase that catalyzes the 2 O-methylation steps in the ubiquinone biosynthetic pathway.
Gene Name:
COQ3
Uniprot ID:
Q3T131
Molecular weight:
41490.0
Reactions
S-Adenosylmethionine + 3-Hexaprenyl-4,5-Dihydroxybenzoic acid → S-Adenosylhomocysteine + 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic aciddetails