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3-Octaprenyl-4-hydroxybenzoate (M2MDB001578)

Record Information
Version2.0
Creation Date2012-07-30 14:54:44 -0600
Update Date2015-06-03 17:20:47 -0600
Secondary Accession Numbers
  • ECMDB21169
Identification
Name:3-Octaprenyl-4-hydroxybenzoate
Description3-octaprenyl-4-hydroxybenzoate belongs to the class of Tetraterpenes. These are terpene molecules containing 10 consecutively linked isoprene units. (inferred from compound structure)3-octaprenyl-4-hydroxybenzoate is catalyzed by UbiD. 3-octaprenyl-4-hydroxybenzoate decarboxylase (UbiD) is an important enzyme on the pathway and deletion of the ubiD gene in E. coli. (PMID 17033719) 4-Hydroxybenzoate is converted to 3-octaprenyl-4-hydroxybenzoate by 4-hydroxybenzoate octaprenyltransferase. (PMID 1644758)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 3-Octaprenyl-4-hydroxybenzoate
  • 3-Octaprenyl-4-hydroxybenzoic acid
  • 3Oct4HBA
  • 4-Hydroxy-3-octaprenylbenzoate
  • 4-Hydroxy-3-octaprenylbenzoic acid
  • 4-Hydroxy-3-[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-yl]benzoate
  • 4-Hydroxy-3-[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-yl]benzoic acid
Chemical Formula:C47H70O3
Weight:Average: 683.0569
Monoisotopic: 682.532496106
InChI Key:UTIBHEBNILDQKX-LQOKPSQISA-N
InChI:InChI=1S/C47H70O3/c1-36(2)17-10-18-37(3)19-11-20-38(4)21-12-22-39(5)23-13-24-40(6)25-14-26-41(7)27-15-28-42(8)29-16-30-43(9)31-32-44-35-45(47(49)50)33-34-46(44)48/h17,19,21,23,25,27,29,31,33-35,48H,10-16,18,20,22,24,26,28,30,32H2,1-9H3,(H,49,50)/b37-19+,38-21+,39-23+,40-25+,41-27+,42-29+,43-31+
CAS number:Not Available
IUPAC Name:4-hydroxy-3-[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-yl]benzoic acid
Traditional IUPAC Name:4-hydroxy-3-[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-yl]benzoic acid
SMILES:CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=C(O)C=CC(=C1)C(O)=O
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
  • Tetraterpenoid
  • Polyprenylphenol
  • 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
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00025 g/LALOGPS
logP9.55ALOGPS
logP14.67ChemAxon
logS-6.4ALOGPS
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 Count24ChemAxon
Refractivity226.16 m³·mol⁻¹ChemAxon
Polarizability88.57 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
3-Octaprenyl-4-hydroxybenzoate + Hydrogen ion > 2-Octaprenylphenol + Carbon dioxide
4-Hydroxybenzoic acid + Octaprenyl diphosphate > 3-Octaprenyl-4-hydroxybenzoate + Pyrophosphate
3-Octaprenyl-4-hydroxybenzoate <> 2-Octaprenylphenol + Carbon dioxide
Octaprenyl diphosphate + 4-Hydroxybenzoic acid <> 3-Octaprenyl-4-hydroxybenzoate + Pyrophosphate
all-<i>trans</i>-octaprenyl diphosphate + 4-Hydroxybenzoic acid > Pyrophosphate + 3-Octaprenyl-4-hydroxybenzoate
4-Hydroxybenzoic acid + Octaprenyl diphosphate > 3-Octaprenyl-4-hydroxybenzoate
4-Hydroxybenzoic acid + Octaprenyl diphosphate + Octaprenyl diphosphate > Pyrophosphate + 3-Octaprenyl-4-hydroxybenzoate
3 3-Octaprenyl-4-hydroxybenzoate + Hydrogen ion >2 2-Octaprenylphenol + Carbon dioxide
4 4-Hydroxybenzoic acid + Octaprenyl diphosphate >3 3-Octaprenyl-4-hydroxybenzoate + Pyrophosphate
SMPDB Pathways:
Secondary Metabolites: Ubiquinol biosynthesisPW000981 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolites: Ubiquinol biosynthesis 2PW002036 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:
  • ubiquinol-8 biosynthesis (prokaryotic) PWY-6708
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0100019000-e06fd4fbf93e99ecb637View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015i-0323459000-e0c0ced9bd43ef340e33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5i-1954662000-ce0bf6d299b5b24a3ab9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000009000-dfbe0e7c3f7583f36c6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0019-0000009000-41f2bece46470ab24116View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0229-1100029000-76beaba4998c0fc6eed2View in MoNA
References
References:
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Liu, J., Liu, J. H. (2006). "Ubiquinone (coenzyme Q) biosynthesis in Chlamydophila pneumoniae AR39: identification of the ubiD gene." Acta Biochim Biophys Sin (Shanghai) 38:725-730. Pubmed: 17033719
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID1617
HMDB IDNot Available
Pubchem Compound ID54685638
Kegg IDC05809
ChemSpider ID5256806
Wikipedia IDNot Available
BioCyc ID3-OCTAPRENYL-4-HYDROXYBENZOATE
EcoCyc ID3-OCTAPRENYL-4-HYDROXYBENZOATE

Enzymes

Protein Details
1. 4-hydroxybenzoate octaprenyltransferase
General function:
Involved in prenyltransferase activity
Specific function:
Synthesis of 3-octaprenyl-4-hydroxybenzoate
Gene Name:
ubiA
Uniprot ID:
P0AGK1
Molecular weight:
32511
Reactions
4-hydroxybenzoate + farnesylfarnesylgeraniol = 3-octaprenyl-4-hydroxybenzoate.
Protein Details
2. 3-octaprenyl-4-hydroxybenzoate carboxy-lyase
General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the decarboxylation of 3-octaprenyl-4-hydroxy benzoate to 2-octaprenylphenol
Gene Name:
ubiD
Uniprot ID:
P0AAB4
Molecular weight:
55603
Protein Details
3. 3-octaprenyl-4-hydroxybenzoate carboxy-lyase
General function:
Coenzyme transport and metabolism
Specific function:
Specific function unknown
Gene Name:
ubiX
Uniprot ID:
P0AG03
Molecular weight:
20695