You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
Name4-Hydroxy-3-Methoxybenzoate
Accession NumberDB02130  (EXPT03229)
TypeSmall Molecule
GroupsExperimental
Description

A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13). [PubChem]

Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIIGM8Q3JM2Y8
CAS number121-34-6
WeightAverage: 167.1388
Monoisotopic: 167.034433712
Chemical FormulaC8H7O4
InChI KeyInChIKey=WKOLLVMJNQIZCI-UHFFFAOYSA-M
InChI
InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)/p-1
IUPAC Name
4-hydroxy-3-methoxybenzoate
SMILES
COC1=CC(=CC=C1O)C([O-])=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentM-methoxybenzoic acids and derivatives
Alternative Parents
Substituents
  • M-methoxybenzoic acid or derivatives
  • Methoxyphenol
  • Hydroxybenzoic acid
  • Benzoic acid
  • Methoxybenzene
  • Phenol ether
  • Benzoyl
  • Anisole
  • Phenol
  • Alkyl aryl ether
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Organic anion
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6389
Blood Brain Barrier+0.7594
Caco-2 permeable+0.6847
P-glycoprotein substrateNon-substrate0.6796
P-glycoprotein inhibitor INon-inhibitor0.9532
P-glycoprotein inhibitor IINon-inhibitor0.9228
Renal organic cation transporterNon-inhibitor0.9079
CYP450 2C9 substrateNon-substrate0.7487
CYP450 2D6 substrateNon-substrate0.8752
CYP450 3A4 substrateNon-substrate0.6427
CYP450 1A2 substrateNon-inhibitor0.8746
CYP450 2C9 inhibitorNon-inhibitor0.9293
CYP450 2D6 inhibitorNon-inhibitor0.9648
CYP450 2C19 inhibitorNon-inhibitor0.8995
CYP450 3A4 inhibitorNon-inhibitor0.9701
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9423
Ames testNon AMES toxic0.9434
CarcinogenicityNon-carcinogens0.8991
BiodegradationReady biodegradable0.9774
Rat acute toxicity2.1220 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9731
hERG inhibition (predictor II)Non-inhibitor0.9682
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point211.5 °CPhysProp
water solubility1500 mg/L (at 14 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP1.43HANSCH,C ET AL. (1995)
logS-2.05ADME Research, USCD
pKa4.51 (at 25 °C)SERJEANT,EP & DEMPSEY,B (1979)
Predicted Properties
PropertyValueSource
Water Solubility18.6 mg/mLALOGPS
logP1.04ALOGPS
logP1.17ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)4.16ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.59 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity52.6 m3·mol-1ChemAxon
Polarizability15.34 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
General Function:
Chorismate lyase activity
Specific Function:
Removes the pyruvyl group from chorismate, with concomitant aromatization of the ring, to provide 4-hydroxybenzoate (4HB) for the ubiquinone pathway.
Gene Name:
ubiC
Uniprot ID:
P26602
Molecular Weight:
18776.68 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:17