Showing metabocard for 3-hexaprenyl-4-hydroxybenzoic acid (BMDB0006816)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:26:20 UTC
Update Date2020-05-21 16:28:36 UTC
BMDB IDBMDB0006816
Secondary Accession Numbers
  • BMDB06816
Metabolite Identification
Common Name3-hexaprenyl-4-hydroxybenzoic acid
Description3-Hexaprenyl-4-hydroxybenzoic acid belongs to the class of organic compounds known as polyprenylphenols. Polyprenylphenols are compounds containing a polyisoprene chain attached to a phenol group. 3-Hexaprenyl-4-hydroxybenzoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3-Hexaprenyl-4-hydroxybenzoic acid exists in all eukaryotes, ranging from yeast to humans. In cattle, 3-hexaprenyl-4-hydroxybenzoic acid is involved in the metabolic pathway called ubiquinone biosynthesis pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(all-e)-3-(3,7,11,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaenyl)-4-hydroxybenzoic acidChEBI
all-trans-3-(3,7,11,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaenyl)-4-hydroxybenzoic acidChEBI
(all-e)-3-(3,7,11,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaenyl)-4-hydroxybenzoateGenerator
all-trans-3-(3,7,11,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaenyl)-4-hydroxybenzoateGenerator
3-Hexaprenyl-4-hydroxybenzoateGenerator
3-(3,7,11,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaenyl)-4-hydroxy-benzoateHMDB
3-(3,7,11,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaenyl)-4-hydroxy-benzoic acidHMDB
Chemical FormulaC37H54O3
Average Molecular Weight546.8229
Monoisotopic Molecular Weight546.407295594
IUPAC Name3-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-4-hydroxybenzoic acid
Traditional Name3-hexaprenyl-4-hydroxybenzoate
CAS Registry Number65848-03-5
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=CC(=CC=C1O)C(O)=O
InChI Identifier
InChI=1S/C37H54O3/c1-28(2)13-8-14-29(3)15-9-16-30(4)17-10-18-31(5)19-11-20-32(6)21-12-22-33(7)23-24-34-27-35(37(39)40)25-26-36(34)38/h13,15,17,19,21,23,25-27,38H,8-12,14,16,18,20,22,24H2,1-7H3,(H,39,40)/b29-15+,30-17+,31-19+,32-21+,33-23+
InChI KeyLKMQQQABIGIHGL-LAAQXVIISA-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
  • Polyprenylphenol
  • Sesterterpenoid
  • Hydroxybenzoic acid
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • 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
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
logP8.74ALOGPS
logP11.35ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)4.35ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity178.55 m³·mol⁻¹ChemAxon
Polarizability68.67 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, Positivesplash10-05ai-3496450000-5b468805ae29a5f59a42View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-3222219000-0638b89fa0bde34d7abbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("3-Hexaprenyl-4-hydroxybenzoic acid,1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 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 (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, Positivesplash10-0f92-0111090000-0efba026d858a4ae0c57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ufs-0749360000-6112d4d11f00cf6a1fbdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-2579200000-1a695b7874053d38599aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000090000-451426c2227e9a66c0aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-0000190000-4173c10b0b5d3133deabView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-2112920000-b9b9e484d8dc60509991View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-1102590000-0baf32808b3ddee5f52bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uy0-1629600000-89c41d697dba8ac52603View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbi-0859510000-223193ff35c3e152d619View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000090000-d1b5f9d61cd518fa226bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052b-0900010000-73c408ecbea0457640caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1403900000-b753301bd29d4e9b1925View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006816
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030426
KNApSAcK IDNot Available
Chemspider ID10128306
KEGG Compound IDC13425
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11954011
PDB IDNot Available
ChEBI ID31116
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. 4-hydroxybenzoate polyprenyltransferase, mitochondrial
General function:
Not Available
Specific function:
Catalyzes the prenylation of para-hydroxybenzoate (PHB) with an all-trans polyprenyl group. Mediates the second step in the final reaction sequence of coenzyme Q (CoQ) biosynthesis, which is the condensation of the polyisoprenoid side chain with PHB, generating the first membrane-bound Q intermediate.
Gene Name:
COQ2
Uniprot ID:
Q2KIQ4
Molecular weight:
40628.0
Reactions
4-Hydroxybenzoic acid + All-trans-hexaprenyl diphosphate → 3-hexaprenyl-4-hydroxybenzoic acid + Pyrophosphatedetails