Showing metabocard for 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid (BMDB0000977)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:39:23 UTC
Update Date2020-05-21 16:26:59 UTC
BMDB IDBMDB0000977
Secondary Accession Numbers
  • BMDB00977
Metabolite Identification
Common Name3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid
Description3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid, also known as 3-hexaprenyl-4-hydroxy-5-methoxybenzoic acid, belongs to the class of organic compounds known as 2-polyprenyl-6-methoxyphenols. 2-polyprenyl-6-methoxyphenols are compounds containing a polyisoprene chain attached at the 2-position of a 6-methoxyphenol group. 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid exists in all eukaryotes, ranging from yeast to humans. In cattle, 3-hexaprenyl-4-hydroxy-5-methoxybenzoic acid is involved in the metabolic pathway called ubiquinone biosynthesis pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Hexaprenyl-4-hydroxy-5-methoxybenzoateChEBI
3-Methoxy-4-hydroxy-5-hexaprenylbenzoateHMDB
3-Methoxy-4-hydroxy-5-hexaprenylbenzoic acidHMDB, MeSH
3-MHHBHMDB, MeSH
Hexaprenyl-4-hydroxy-5-methoxybenzoateHMDB
Hexaprenyl-4-hydroxy-5-methoxybenzoic acidHMDB
Chemical FormulaC38H56O4
Average Molecular Weight576.8488
Monoisotopic Molecular Weight576.41786028
IUPAC Name3-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-4-hydroxy-5-methoxybenzoic acid
Traditional Name3-mhhb
CAS Registry Number66551-60-8
SMILES
COC1=CC(=CC(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C1O)C(O)=O
InChI Identifier
InChI=1S/C38H56O4/c1-28(2)14-9-15-29(3)16-10-17-30(4)18-11-19-31(5)20-12-21-32(6)22-13-23-33(7)24-25-34-26-35(38(40)41)27-36(42-8)37(34)39/h14,16,18,20,22,24,26-27,39H,9-13,15,17,19,21,23,25H2,1-8H3,(H,40,41)/b29-16+,30-18+,31-20+,32-22+,33-24+
InChI KeyYSZSVGFMAJXGMQ-FRICUITQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2-polyprenyl-6-methoxyphenols. 2-polyprenyl-6-methoxyphenols are compounds containing a polyisoprene chain attached at the 2-position of a 6-methoxyphenol group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenylphenols
Direct Parent2-polyprenyl-6-methoxyphenols
Alternative Parents
Substituents
  • 2-polyprenyl-6-methoxyphenol
  • Sesterterpenoid
  • M-methoxybenzoic acid or derivatives
  • Hydroxybenzoic acid
  • Methoxyphenol
  • Benzoic acid or derivatives
  • Benzoic acid
  • Methoxybenzene
  • Benzoyl
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • 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
logP8.61ALOGPS
logP11.2ChemAxon
logS-6.2ALOGPS
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 Count19ChemAxon
Refractivity185.01 m³·mol⁻¹ChemAxon
Polarizability72.35 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, Positivesplash10-08g0-2388590000-89e434c77e88e9089ef4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-003r-3147469000-0708567822e5bfd90a9eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("3-Hexaprenyl-4-hydroxy-5-methoxybenzoic 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_2_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_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0059-0212090000-055eaf6bf9bb7f66403fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003s-0739160000-67aa4818a2ec38ef35ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gxt-1359210000-0d48ce3c1daca56ef467View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000090000-a22409cb6dbbb1a464f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00o0-0000090000-dda0834068a4ec0b05d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01b9-2200290000-211ab1bf8b89830eeb7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000090000-37874bf3cdf6a781a33eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-0300090000-a09c79ecaeb909c9402bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0856590000-a0df803dc315dc2ff708View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05e9-2011390000-7b7b6746ebaefb787192View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001r-5925200000-1bbeb139fd4f40c1b6c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001l-9632000000-60f2ecc1d8003b07f78cView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000977
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022347
KNApSAcK IDNot Available
Chemspider ID4444339
KEGG Compound IDC05313
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5915
PubChem Compound5280776
PDB IDNot Available
ChEBI ID16835
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