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4-Hydroxy-3-polyprenylbenzoate (M2MDB004183)

Record Information
Version2.0
Creation Date2015-06-04 15:13:06 -0600
Update Date2015-08-05 16:22:04 -0600
Secondary Accession Numbers
  • ECMDB23756
Identification
Name:4-Hydroxy-3-polyprenylbenzoate
DescriptionA member of the class of benzoates obtained by deprotonation of the carboxy group of any 4-hydroxy-3-polyprenylbenzoic acid; major species at pH 7.3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 4-Hydroxy-3-polyprenylbenzoic acid
Chemical Formula:C17H22O3
Weight:Average: 274.3548
Monoisotopic: 274.15689457
InChI Key:HKIMBCGCVPYUTJ-NTUHNPAUSA-N
InChI:InChI=1S/C17H22O3/c1-12(2)5-4-6-13(3)7-8-14-11-15(17(19)20)9-10-16(14)18/h5,7,9-11,18H,4,6,8H2,1-3H3,(H,19,20)/b13-7+
CAS number:Not Available
IUPAC Name:3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-4-hydroxybenzoic acid
Traditional IUPAC Name:4-hydroxy-3-polyprenylbenzoate
SMILES:CC(C)=CCC\C(C)=C\CC1=CC(=CC=C1O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAromatic monoterpenoids
Alternative Parents
Substituents
  • Aromatic monoterpenoid
  • Hydroxybenzoic acid
  • Monocyclic monoterpenoid
  • 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
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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 Solubility0.01 g/LALOGPS
logP4.32ALOGPS
logP4.72ChemAxon
logS-4.4ALOGPS
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 Count6ChemAxon
Refractivity83.34 m³·mol⁻¹ChemAxon
Polarizability31.46 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
2-Polyprenylphenol + Carbon dioxide + 4-Hydroxy-3-polyprenylbenzoate <> 4-Hydroxy-3-polyprenylbenzoate + 2-Polyprenylphenol
all-trans-Polyprenyl diphosphate + 4-Hydroxybenzoic acid + Geranyl-PP <> 4-Hydroxy-3-polyprenylbenzoate + Pyrophosphate + 4-Hydroxy-3-polyprenylbenzoate
SMPDB Pathways:Not Available
KEGG Pathways:
  • Metabolic pathways eco01100
  • Ubiquinone and other terpenoid-quinone biosynthesis ec00130
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-066r-8980000000-c5f21b9f2315023b8667View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0uk9-8119600000-af4084cfa0588ff40691View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0290000000-5d0c21c1fa97609e5405View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0adi-2950000000-e585e5a13ccaa004bcc8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ldi-8910000000-63c5d4612f9d7c67e790View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-7f80711f214d202e0cb3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-0090000000-aa0418550a1f9c60fa4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0nou-3690000000-b3f087074c5c3915fcb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-2590000000-39bbee729d92ce577091View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05ar-9800000000-aa69e3364a0f7a35d806View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-7900000000-090695f713cd5a105558View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-0090000000-b909803416c1dfda8bb5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05i0-1590000000-789b13156788008d75edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0900-2920000000-7363aa31358a49cf1043View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID61122
HMDB IDHMDB0060388
Pubchem Compound ID5280844
Kegg IDC05848
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

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