You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameBenzoic Acid
Accession NumberDB03793  (EXPT00675)
TypeSmall Molecule
GroupsExperimental
Description

A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid. [PubChem]

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
Categories
CAS number65-85-0
WeightAverage: 122.1213
Monoisotopic: 122.036779436
Chemical FormulaC7H6O2
InChI KeyWPYMKLBDIGXBTP-UHFFFAOYSA-N
InChI
InChI=1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)
IUPAC Name
benzoic acid
SMILES
OC(=O)C1=CC=CC=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassBenzoic Acid and Derivatives
Direct parentBenzoic Acids
Alternative parentsBenzoyl Derivatives; Enolates; Carboxylic Acids; Polyamines
Substituentsbenzoyl; carboxylic acid; polyamine; carboxylic acid derivative; enolate
Classification descriptionThis compound belongs to the benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
SubstrateEnzymesProduct
Benzoic Acid
Not Available
Benzoyl glucuronide (Benzoic acid)Details
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
Property Value Probability
Human Intestinal Absorption + 0.9886
Blood Brain Barrier + 0.9557
Caco-2 permeable + 0.9187
P-glycoprotein substrate Non-substrate 0.8494
P-glycoprotein inhibitor I Non-inhibitor 0.9914
P-glycoprotein inhibitor II Non-inhibitor 0.9941
Renal organic cation transporter Non-inhibitor 0.9136
CYP450 2C9 substrate Non-substrate 0.8003
CYP450 2D6 substrate Non-substrate 0.9672
CYP450 3A4 substrate Non-substrate 0.8374
CYP450 1A2 substrate Non-inhibitor 0.8532
CYP450 2C9 substrate Non-inhibitor 0.9861
CYP450 2D6 substrate Non-inhibitor 0.957
CYP450 2C19 substrate Non-inhibitor 0.9878
CYP450 3A4 substrate Non-inhibitor 0.9822
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9863
Ames test Non AMES toxic 0.9923
Carcinogenicity Non-carcinogens 0.6024
Biodegradation Ready biodegradable 0.8983
Rat acute toxicity 1.7896 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9708
hERG inhibition (predictor II) Non-inhibitor 0.9882
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point122.4 °CPhysProp
boiling point249.2 °CPhysProp
water solubility3400 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP1.87HANSCH,C ET AL. (1995)
logS-1.55ADME Research, USCD
pKa4.19 (at 25 °C)LIDE,DR (1996)
Predicted Properties
PropertyValueSource
Water Solubility7.08ALOGPS
logP1.72ALOGPS
logP1.63ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)4.08ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity33.31 m3·mol-1ChemAxon
Polarizability11.97 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
References
Synthesis Reference

Ludovicus A. L. Kleintjens, Hubertus M. J. Grooten, “Process for the preparation of benzoic acid.” U.S. Patent US4539425, issued March, 1932.

US4539425
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00038
KEGG CompoundC00180
PubChem Compound243
PubChem Substance46504911
ChEBI30746
ChEMBL
PharmGKBPA448578
HETBEZ
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Hydrogen peroxide-inducible genes activator

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Hydrogen peroxide-inducible genes activator P0ACQ4 Details

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
  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

2. HTH-type transcriptional regulator MalT

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
HTH-type transcriptional regulator MalT P06993 Details

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
  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

3. Tautomerase PptA

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Tautomerase PptA P31992 Details

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
  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

4. D-amino-acid oxidase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
D-amino-acid oxidase P14920 Details

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
  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
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

5. Ribonuclease UK114

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Ribonuclease UK114 P52758 Details

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
  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

6. Chlorocatechol 1,2-dioxygenase

Kind: protein

Organism: Rhodococcus opacus

Pharmacological action: unknown

Components

Name UniProt ID Details
Chlorocatechol 1,2-dioxygenase O67987 Details

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
  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

7. Ras-related protein Rab-9A

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Ras-related protein Rab-9A P51151 Details

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
  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

8. 2-hydroxy-6-oxo-7-methylocta-2,4-dienoate hydrolase

Kind: protein

Organism: Pseudomonas fluorescens

Pharmacological action: unknown

Components

Name UniProt ID Details
2-hydroxy-6-oxo-7-methylocta-2,4-dienoate hydrolase P96965 Details

9. Non-heme chloroperoxidase

Kind: protein

Organism: Streptomyces aureofaciens

Pharmacological action: unknown

Components

Name UniProt ID Details
Non-heme chloroperoxidase O31168 Details

10. Oxygen-insensitive NAD(P)H nitroreductase

Kind: protein

Organism: Enterobacter cloacae

Pharmacological action: unknown

Components

Name UniProt ID Details
Oxygen-insensitive NAD(P)H nitroreductase Q01234 Details

11. Hydroxyquinol 1,2-dioxygenase

Kind: protein

Organism: Nocardioides simplex

Pharmacological action: unknown

Components

Name UniProt ID Details
Hydroxyquinol 1,2-dioxygenase Q5PXQ6 Details

12. Replication protein

Kind: protein

Organism: Pseudomonas syringae

Pharmacological action: unknown

Components

Name UniProt ID Details
Replication protein Q52546 Details

13. Peroxiredoxin-5, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Peroxiredoxin-5, mitochondrial P30044 Details

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
  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

14. Heat-labile enterotoxin B chain

Kind: protein

Organism: Escherichia coli

Pharmacological action: unknown

Components

Name UniProt ID Details
Heat-labile enterotoxin B chain P32890 Details

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
  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

15. Cocaine esterase

Kind: protein

Organism: Rhodococcus sp. (strain MB1 Bresler)

Pharmacological action: unknown

Components

Name UniProt ID Details
Cocaine esterase Q9L9D7 Details

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
  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

Transporters

1. Solute carrier organic anion transporter family member 2B1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier organic anion transporter family member 2B1 O94956 Details

References:

  1. Kobayashi D, Nozawa T, Imai K, Nezu J, Tsuji A, Tamai I: Involvement of human organic anion transporting polypeptide OATP-B (SLC21A9) in pH-dependent transport across intestinal apical membrane. J Pharmacol Exp Ther. 2003 Aug;306(2):703-8. Epub 2003 Apr 30. Pubmed

2. Solute carrier family 22 member 8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 8 Q8TCC7 Details

References:

  1. Ohtsuki S, Asaba H, Takanaga H, Deguchi T, Hosoya K, Otagiri M, Terasaki T: Role of blood-brain barrier organic anion transporter 3 (OAT3) in the efflux of indoxyl sulfate, a uremic toxin: its involvement in neurotransmitter metabolite clearance from the brain. J Neurochem. 2002 Oct;83(1):57-66. Pubmed

3. Monocarboxylate transporter 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Monocarboxylate transporter 1 P53985 Details

References:

  1. Kido Y, Tamai I, Okamoto M, Suzuki F, Tsuji A: Functional clarification of MCT1-mediated transport of monocarboxylic acids at the blood-brain barrier using in vitro cultured cells and in vivo BUI studies. Pharm Res. 2000 Jan;17(1):55-62. Pubmed

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:22