Vanillic acid
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Identification
- Generic Name
- Vanillic acid
- DrugBank Accession Number
- DB02130
- Background
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).
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 167.1388
Monoisotopic: 167.034433712 - Chemical Formula
- C8H7O4
- Synonyms
- 4-Hydroxy-3-methoxybenzoic acid
- VA
- External IDs
- FEMA NO. 3988
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UChorismate--pyruvate lyase Not Available Escherichia 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- 1-hydroxy-2-unsubstituted benzenoid / Alkyl aryl ether / Anisole / Aromatic homomonocyclic compound / Benzoic acid / Benzoyl / Carboxylic acid / Carboxylic acid derivative / Ether / Hydrocarbon derivative show 12 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- monohydroxybenzoate, methoxybenzoate (CHEBI:16632) / an aromatic carboxylate (VANILLATE)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- GM8Q3JM2Y8
- CAS number
- 121-34-6
- 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
References
- General References
- Not Available
- External Links
- KEGG Compound
- C06672
- PubChem Compound
- 54675858
- PubChem Substance
- 46509049
- ChemSpider
- 21708
- BindingDB
- 50337364
- ChEBI
- 16632
- ChEMBL
- CHEMBL120568
- PDBe Ligand
- VNL
- Wikipedia
- Vanillic_acid
- PDB Entries
- 1xlr / 2ahc / 2y2x / 3sys / 4eyg / 4l6d / 5x1j / 5z7b / 6lg2
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 211.5 °C PhysProp water solubility 1500 mg/L (at 14 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 1.43 HANSCH,C ET AL. (1995) logS -2.05 ADME Research, USCD pKa 4.51 (at 25 °C) SERJEANT,EP & DEMPSEY,B (1979) - Predicted Properties
Property Value Source Water Solubility 18.6 mg/mL ALOGPS logP 1.04 ALOGPS logP 1.17 Chemaxon logS -1 ALOGPS pKa (Strongest Acidic) 4.16 Chemaxon pKa (Strongest Basic) -4.9 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 69.59 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 52.6 m3·mol-1 Chemaxon Polarizability 15.34 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.6389 Blood Brain Barrier + 0.7594 Caco-2 permeable + 0.6847 P-glycoprotein substrate Non-substrate 0.6796 P-glycoprotein inhibitor I Non-inhibitor 0.9532 P-glycoprotein inhibitor II Non-inhibitor 0.9228 Renal organic cation transporter Non-inhibitor 0.9079 CYP450 2C9 substrate Non-substrate 0.7487 CYP450 2D6 substrate Non-substrate 0.8752 CYP450 3A4 substrate Non-substrate 0.6427 CYP450 1A2 substrate Non-inhibitor 0.8746 CYP450 2C9 inhibitor Non-inhibitor 0.9293 CYP450 2D6 inhibitor Non-inhibitor 0.9648 CYP450 2C19 inhibitor Non-inhibitor 0.8995 CYP450 3A4 inhibitor Non-inhibitor 0.9701 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9423 Ames test Non AMES toxic 0.9434 Carcinogenicity Non-carcinogens 0.8991 Biodegradation Ready biodegradable 0.9774 Rat acute toxicity 2.1220 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9731 hERG inhibition (predictor II) Non-inhibitor 0.9682
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 138.6359634 predictedDarkChem Lite v0.1.0 [M-H]- 131.43889 predictedDeepCCS 1.0 (2019) [M+H]+ 139.8567634 predictedDarkChem Lite v0.1.0 [M+H]+ 135.0136 predictedDeepCCS 1.0 (2019) [M+Na]+ 138.8605634 predictedDarkChem Lite v0.1.0 [M+Na]+ 143.77205 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsChorismate--pyruvate lyase
- 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
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52