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Identification
Name Benzoic Acid
Accession Number DB03793 (EXPT00675)
Type small molecule
Groups experimental
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names Not Available
Brand mixtures Not Available
Categories
  • Food Preservatives
CAS number 65-85-0
Weight Average: 122.1213
Monoisotopic: 122.036779436
Chemical Formula C7H6O2
InChI Key InChIKey=WPYMKLBDIGXBTP-UHFFFAOYSA-N
InChI
InChI=1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)
Plain Text
IUPAC Name
benzoic acid
SMILES
OC(=O)C1=CC=CC=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication Not Available
Pharmacodynamics Not Available
Mechanism of action Not Available
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Not Available

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate Enzymes Product
Benzoic Acid
    		Benzoyl glucuronide (Benzoic acid) Details
    Route of elimination Not Available
    Half life Not Available
    Clearance Not Available
    Toxicity Not Available
    Affected organisms Not Available
    Pathways Not Available
    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 122.4 °C PhysProp
    boiling point 249.2 °C PhysProp
    water solubility 3400 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
    logP 1.87 HANSCH,C ET AL. (1995)
    logS -1.55 ADME Research, USCD
    pKa 4.19 (at 25 °C) LIDE,DR (1996)
    Predicted Properties
    Property Value Source
    water solubility 7.08e+00 g/l ALOGPS
    logP 1.72 ALOGPS
    logP 1.63 ChemAxon
    logS -1.2 ALOGPS
    pKa (strongest acidic) 4.08 ChemAxon
    physiological charge -1 ChemAxon
    hydrogen acceptor count 2 ChemAxon
    hydrogen donor count 1 ChemAxon
    polar surface area 37.3 ChemAxon
    rotatable bond count 1 ChemAxon
    refractivity 33.31 ChemAxon
    polarizability 11.97 ChemAxon
    References
    Synthesis Reference Not Available
    General Reference Not Available
    External Links
    Resource Link
    KEGG Drug D00038 Link_out
    KEGG Compound C00180 Link_out
    PubChem Compound 243 Link_out
    PubChem Substance 46504911 Link_out
    ChEBI 30746 Link_out
    ChEMBL 30746 Link_out
    PharmGKB PA448578 Link_out
    HET BEZ Link_out
    ATC Codes Not Available
    AHFS Codes Not Available
    PDB Entries
    FDA label Not Available
    MSDS Not Available
    Interactions
    Drug Interactions Not Available
    Food Interactions Not Available
    Targets

    1. Hydrogen peroxide-inducible genes activator

    Pharmacological action: unknown

    Hydrogen peroxide sensor. Activates the expression of a regulon of hydrogen peroxide-inducible genes such as katG, gor, ahpC, ahpF, oxyS (a regulatory RNA), dps, fur and grxA. OxyR expression is negatively autoregulated by binding to a 43 bp region upstream of its own coding sequence. OxyR is inactivated by reduction of its essential disulfide bond by the product of grxA, itself positively regulated by OxyR. Has also a positive regulatory effect on the production of surface proteins that control the colony morphology and auto-aggregation ability

    Organism class: bacterial
    UniProt ID: P0ACQ4 Link_out
    Gene: oxyR
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    SNPs: SNPJam Report Link_out

    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

    Pharmacological action: unknown

    Positively regulates the transcription of the maltose regulon whose gene products are responsible for uptake and catabolism of malto-oligosaccharides. Binds and recognizes a DNA motif (called the malT box):5'-GGA[TG]GA-3'

    Organism class: bacterial
    UniProt ID: P06993 Link_out
    Gene: malT
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    SNPs: SNPJam Report Link_out

    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. Probable tautomerase ydcE

    Pharmacological action: unknown
    Organism class: bacterial
    UniProt ID: P31992 Link_out
    Gene: pptA
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    SNPs: SNPJam Report Link_out

    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

    Pharmacological action: unknown

    Regulates the level of the neuromodulator D-serine in the brain. Has high activity towards D-DOPA and contributes to dopamine synthesis. Could act as a detoxifying agent which removes D-amino acids accumulated during aging. Acts on a variety of D- amino acids with a preference for those having small hydrophobic side chains followed by those bearing polar, aromatic, and basic groups. Does not act on acidic amino acids

    Organism class: human
    UniProt ID: P14920 Link_out
    Gene: DAO Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    SNPs: SNPJam Report Link_out

    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

    Pharmacological action: unknown

    Endoribonuclease responsible for the inhibition of the translation by cleaving mRNA. Inhibits cell-free protein synthesis. Cleaves phosphodiester bonds only in single-stranded RNA

    Organism class: human
    UniProt ID: P52758 Link_out
    Gene: HRSP12 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    SNPs: SNPJam Report Link_out

    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

    Pharmacological action: unknown

    4-chlorocatechol + O(2) = 3-chloro-muconate

    Organism class: bacterial
    UniProt ID: O67987 Link_out
    Gene: clcA
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    SNPs: SNPJam Report Link_out

    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-9

    Pharmacological action: unknown

    Involved in the transport of proteins between the endosomes and the trans Golgi network

    Organism class: human
    UniProt ID: P51151 Link_out
    Gene: RAB9 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    SNPs: SNPJam Report Link_out

    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

    Pharmacological action: unknown
    Organism class: bacterial
    UniProt ID: P96965 Link_out
    Gene: cumD
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    SNPs: SNPJam Report Link_out

    9. Non-heme chloroperoxidase

    Pharmacological action: unknown

    2 RH + 2 Cl(-) + H(2)O(2) = 2 RCl + 2 H(2)O

    Organism class: bacterial
    UniProt ID: O31168 Link_out
    Gene: cpo
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    SNPs: SNPJam Report Link_out

    10. Oxygen-insensitive NAD(P)H nitroreductase

    Pharmacological action: unknown

    Reduction of a variety of nitroaromatic compounds using NADH (and to lesser extent NADPH) as source of reducing equivalents; two electrons are transferred

    Organism class: bacterial
    UniProt ID: Q01234 Link_out
    Gene: nfnB
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    SNPs: SNPJam Report Link_out

    11. Hydroxyquinol 1,2-dioxygenase

    Pharmacological action: unknown

    Catalyzes the ortho-cleavage of the aromatic ring of hydroxyquinol

    Organism class: bacterial
    UniProt ID: Q5PXQ6 Link_out
    Gene: chqB
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    SNPs: SNPJam Report Link_out

    12. Replication protein

    Pharmacological action: unknown
    Organism class: bacterial
    UniProt ID: Q52546 Link_out
    Gene: repA
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    SNPs: SNPJam Report Link_out

    13. Peroxiredoxin-5, mitochondrial

    Pharmacological action: unknown

    Reduces hydrogen peroxide and alkyl hydroperoxides with reducing equivalents provided through the thioredoxin system. Involved in intracellular redox signaling

    Organism class: human
    UniProt ID: P30044 Link_out
    Gene: PRDX5 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    SNPs: SNPJam Report Link_out

    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

    Pharmacological action: unknown

    The biological activity of the toxin is produced by the A chain, which activates intracellular adenyl cyclase

    Organism class: bacterial
    UniProt ID: P32890 Link_out
    Gene: eltB
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    SNPs: SNPJam Report Link_out

    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

    Pharmacological action: unknown

    Hydrolyzes cocaine to benzoate and ecgonine methyl ester, endowing the bacteria with the ability to utilize cocaine as a sole source of carbon and energy for growth, as this bacterium lives in the rhizosphere of coca plants

    Organism class: bacterial
    UniProt ID: Q9L9D7 Link_out
    Gene: cocE
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    SNPs: SNPJam Report Link_out

    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

    Actions: inhibitor

    Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost

    UniProt ID: O94956 Link_out
    Gene: SLCO2B1 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    SNPs: SNPJam Report Link_out

    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

    Actions: inhibitor

    Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone- 3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA)

    UniProt ID: Q8TCC7 Link_out
    Gene: SLC22A8 Link_out
    Protein Sequence: FASTA
    SNPs: SNPJam Report Link_out

    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

    Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate

    UniProt ID: P53985 Link_out
    Gene: SLC16A1 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    SNPs: SNPJam Report Link_out

    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
    Drug created on June 13, 2005 07:24 / Updated on February 20, 2013 17:28