Vanillic acid

Identification

Name
Vanillic acid
Accession Number
DB02130  (EXPT03229)
Type
Small Molecule
Groups
Experimental
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).

Structure
Thumb
Synonyms
  • 4-Hydroxy-3-methoxybenzoic acid
  • VA
External IDs
FEMA NO. 3988
Categories
Not Available
UNII
GM8Q3JM2Y8
CAS number
121-34-6
Weight
Average: 167.1388
Monoisotopic: 167.034433712
Chemical Formula
C8H7O4
InChI Key
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UChorismate--pyruvate lyaseNot AvailableEscherichia coli (strain K12)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C06672
PubChem Compound
54675858
PubChem Substance
46509049
ChemSpider
21708
BindingDB
50337364
ChEBI
16632
ChEMBL
CHEMBL120568
HET
VNL
Wikipedia
Vanillic_acid
PDB Entries
1xlr / 2ahc / 2y2x / 3sys / 4eyg / 4l6d / 5x1j

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)211.5 °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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
M-methoxybenzoic acids and derivatives
Alternative Parents
Methoxyphenols / Hydroxybenzoic acid derivatives / Benzoic acids / Phenoxy compounds / Methoxybenzenes / Benzoyl derivatives / Anisoles / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / Monocarboxylic acids and derivatives
show 4 more
Substituents
M-methoxybenzoic acid or derivatives / Hydroxybenzoic acid / Methoxyphenol / Benzoic acid / Phenoxy compound / Anisole / Methoxybenzene / Benzoyl / Phenol ether / 1-hydroxy-2-unsubstituted benzenoid
show 12 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monohydroxybenzoate, methoxybenzoate (CHEBI:16632) / an aromatic carboxylate (VANILLATE)

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
Uniprot Name
Chorismate pyruvate-lyase
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]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 14:53