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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:07 UTC
HMDB IDHMDB0000977
Secondary Accession Numbers
  • HMDB00977
Metabolite Identification
Common Name3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid
Description3-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. Based on a literature review a significant number of articles have been published on 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid.
Structure
Data?1582752168
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
Physiological effectNot Available
Disposition
Process
Role
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 Solubility0.00036 g/LALOGPS
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
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]+238.86531661259
DarkChem[M-H]-232.88131661259
AllCCS[M+H]+248.09832859911
AllCCS[M-H]-229.20932859911
DeepCCS[M+H]+243.27230932474
DeepCCS[M-H]-240.87730932474
DeepCCS[M-2H]-273.76130932474
DeepCCS[M+Na]+249.18530932474
AllCCS[M+H]+248.132859911
AllCCS[M+H-H2O]+246.632859911
AllCCS[M+NH4]+249.432859911
AllCCS[M+Na]+249.832859911
AllCCS[M-H]-229.232859911
AllCCS[M+Na-2H]-232.832859911
AllCCS[M+HCOO]-236.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acidCOC1=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)=O6015.5Standard polar33892256
3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acidCOC1=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)=O4006.9Standard non polar33892256
3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acidCOC1=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)=O4282.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid,1TMS,isomer #1COC1=CC(C(=O)O)=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[Si](C)(C)C4259.5Semi standard non polar33892256
3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid,1TMS,isomer #2COC1=CC(C(=O)O[Si](C)(C)C)=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)=C1O4154.6Semi standard non polar33892256
3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid,2TMS,isomer #1COC1=CC(C(=O)O[Si](C)(C)C)=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[Si](C)(C)C4115.8Semi standard non polar33892256
3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid,1TBDMS,isomer #1COC1=CC(C(=O)O)=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[Si](C)(C)C(C)(C)C4485.9Semi standard non polar33892256
3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid,1TBDMS,isomer #2COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=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)=C1O4383.3Semi standard non polar33892256
3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid,2TBDMS,isomer #1COC1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=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[Si](C)(C)C(C)(C)C4535.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-08g0-2388590000-89e434c77e88e9089ef42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-003r-3147469000-0708567822e5bfd90a9e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid GC-MS ("3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid GC-MS (TBDMS_2_1) - 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-hydroxy-5-methoxybenzoic acid 10V, Positive-QTOFsplash10-0059-0212090000-055eaf6bf9bb7f66403f2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid 20V, Positive-QTOFsplash10-003s-0739160000-67aa4818a2ec38ef35ec2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid 40V, Positive-QTOFsplash10-0gxt-1359210000-0d48ce3c1daca56ef4672016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid 10V, Negative-QTOFsplash10-004i-0000090000-a22409cb6dbbb1a464f92016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid 20V, Negative-QTOFsplash10-00o0-0000090000-dda0834068a4ec0b05d82016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid 40V, Negative-QTOFsplash10-01b9-2200290000-211ab1bf8b89830eeb7e2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid 10V, Negative-QTOFsplash10-004i-0000090000-37874bf3cdf6a781a33e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid 20V, Negative-QTOFsplash10-016r-0300090000-a09c79ecaeb909c9402b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid 40V, Negative-QTOFsplash10-014i-0856590000-a0df803dc315dc2ff7082021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid 10V, Positive-QTOFsplash10-05e9-2011390000-7b7b6746ebaefb7871922021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid 20V, Positive-QTOFsplash10-001r-5925200000-1bbeb139fd4f40c1b6c42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid 40V, Positive-QTOFsplash10-001l-9632000000-60f2ecc1d8003b07f78c2021-09-25Wishart 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 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
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