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Human Metabolome Database Version 3.5

Showing metabocard for Benzoic acid (HMDB01870)

• Identification
• Taxonomy
• Ontology
• Physical properties
• Spectra
• Biological properties
• Concentrations
• Links
• References

enzymes (6)

• Blood
• Urine

Record Information
Version	3.5
Creation Date	2006-02-23 04:42:39 -0700
Update Date	2013-02-08 17:10:54 -0700
HMDB ID	HMDB01870
Secondary Accession Numbers	None
Metabolite Identification
Common Name	Benzoic acid
Description	Benzoic acid, C6H5COOH, is a colourless crystalline solid and the simplest aromatic carboxylic acid. Benzoic acid occurs naturally free and bound as benzoic acid esters in many plant and animal species. Appreciable amounts have been found in most berries (around 0.05%). Cranberries contain as much as 300-1300 mg free benzoic acid per kg fruit. Benzoic acid is a fungistatic compound that is widely used as a food preservative. It often is conjugated to glycine in the liver and excreted as hippuric acid. Benzoic acid is a byproduct of phenylalanine metabolism in bacteria. It is also produced when gut bacteria process polyphenols (from ingested fruits or beverages).
Structure	Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure
Synonyms	Benzenecarboxylate Benzenecarboxylic acid Benzeneformate Benzeneformic acid Benzenemethanoate Benzenemethanoic acid Benzenemethonic acid Benzoate Benzoic acid Benzoic acid sodium salt Carboxybenzene Diacylate Diacylic acid Dracylate Dracylic acid Oracylic acid Phenylcarboxylate Phenylcarboxylic acid Phenylformate Phenylformic acid Sodium benzoate Sodium benzoic acid
Chemical Formula	C7H6O2
Average Molecular Weight	122.1213
Monoisotopic Molecular Weight	122.036779436
IUPAC Name	benzoic acid
Traditional IUPAC Name	benzoic acid
CAS Registry Number	65-85-0
SMILES	OC(=O)C1=CC=CC=C1
InChI Identifier	InChI=1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)
InChI Key	WPYMKLBDIGXBTP-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom	Organic Compounds
Super Class	Aromatic Homomonocyclic Compounds
Class	Benzoic Acid and Derivatives
Sub Class	N/A
Other Descriptors	Organic Compounds benzoic acids(ChEBI)
Substituents	Benzoyl Carboxylic Acid
Direct Parent	Benzoic Acid and Derivatives
Ontology
Status	Detected and Quantified
Origin	Food Microbial
Biofunction	Not Available
Application	Not Available
Cellular locations	Cytoplasm Extracellular Endoplasmic reticulum
Physical Properties
State	Solid
Experimental Properties	Property Value Reference Melting Point 122.4 °C Not Available Boiling Point Not Available Not Available Water Solubility 3.4 mg/mL at 25 °C Not Available LogP 1.87 HANSCH,C ET AL. (1995)
Predicted Properties	Property Value Source Water Solubility 7.08 g/L ALOGPS LogP 1.72 ALOGPS LogP 1.63 ChemAxon LogS -1.24 ALOGPS pKa (strongest acidic) 4.08 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 37.3 A2 ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 33.31 ChemAxon Polarizability 11.97 ChemAxon Formal Charge 0 ChemAxon Physiological Charge -1 ChemAxon
Spectra
	Gas-MS Spectrum 1H NMR Spectrum MS/MS Spectrum Quattro_QQQ 10 MS/MS Spectrum Quattro_QQQ 25 MS/MS Spectrum Quattro_QQQ 40 MS/MS Spectrum EI-B (HITACHI RMU-7) MS/MS Spectrum EI-B (HITACHI RMU-6E) MS/MS Spectrum EI-B (HITACHI RMU-7M) MS/MS Spectrum EI-B (HITACHI M-80B) MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10 MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20 MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30 MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40 MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies ) MS/MS Spectrum GC-MS [1H,1H] 2D NMR Spectrum [1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations	Cytoplasm Extracellular Endoplasmic reticulum
Biofluid Locations	Blood Urine
Tissue Location	Bladder Fibroblasts Testes Kidney Liver Skin Stratum Corneum
Pathways	Not Available
Normal Concentrations
	Biofluid Status Value Age Sex Condition Reference Blood Detected and Quantified 14.327 +/- 2.066 uM Adult (>18 years old) Male Normal 19812218 Blood Detected and Quantified 10.783 +/- 2.169 uM Adult (>18 years old) Male Normal 19812218 Blood Detected and Quantified 14.96 +/- 1.994 uM Adult (>18 years old) Male Normal 19812218 Blood Detected and Quantified 10.49 +/- 2.401 uM Adult (>18 years old) Male Normal 19812218 Blood Detected and Quantified 12.082 +/- 2.028 uM Adult (>18 years old) Male Normal 19812218 Blood Detected and Quantified 13.422 +/- 2.406 uM Adult (>18 years old) Male Normal 19812218 Blood Detected and Quantified 12.467 +/- 2.747 uM Adult (>18 years old) Male Normal 19812218 Blood Detected and Quantified 77.746 +/- 67.635 uM Adult (>18 years old) Male Normal 19812218 Urine Expected but not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 427 12771321 Urine Expected but not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 427 19812218 Urine Expected but not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 427 14733499 Urine Detected but not Quantified Not Applicable Adult (>18 years old) Both Normal Bouatra, S. ... Urine Detected and Quantified 106.0 +/- 41.0 umol/mmol creatinine Adult (>18 years old) Both Normal Geigy Scient... Urine Detected and Quantified 4.2 (1.9-6.5) umol/mmol creatinine Adult (>18 years old) Both Normal 2702744 Urine Detected and Quantified 0.1452 +/- 0.133 umol/mmol creatinine Adult (>18 years old) Male Normal 19812218 Urine Detected and Quantified 0.1 umol/mmol creatinine Adult (>18 years old) Both Normal 21388201 Urine Detected and Quantified 3.6 (1.4 -7.5) umol/mmol creatinine Adult (>18 years old) Both Normal Bouatra, S. ... Urine Detected and Quantified 4.7 (1.2-10.5) umol/mmol creatinine Adult (>18 years old) Both Normal Bouatra, S. ... Urine Detected and Quantified 1.374 +/- 0.307 umol/mmol creatinine Adult (>18 years old) Male Normal 19812218 Urine Detected and Quantified 4.042 +/- 0.851 umol/mmol creatinine Adult (>18 years old) Male Normal 19812218 Urine Detected but not Quantified Not Applicable Adult (>18 years old) Both Normal 22284503
Abnormal Concentrations
	Biofluid Status Value Age Sex Condition Reference Urine Detected but not Quantified Not Applicable Adult (>18 years old) Both Breast cancer 22284503
Associated Disorders and Diseases
Disease References	None
Associated OMIM IDs	None
External Links
DrugBank ID	Not Available
DrugBank Metabolite ID	Not Available
Phenol Explorer Compound ID	427
Phenol Explorer Metabolite ID	427
FoodDB ID	FDB008739
KNApSAcK ID	C00000207
Chemspider ID	238
KEGG Compound ID	C00180
BioCyc ID	1-O6-O-DIGALLOYL-BETA-D-GLUCOSE
BiGG ID	34156
Wikipedia Link	Benzoic acid
NuGOwiki Link	HMDB01870
Metagene Link	HMDB01870
METLIN ID	1297
PubChem Compound	243
PDB ID	BEZ
ChEBI ID	30746
References
Synthesis Reference	Hronec, Milan; Mikula, Oldrich; Kopernicky, Ivan; Bucko, Milos; Danilla, Frantisek; Hlinistak, Karol. Process for benzoic acid manufacture. Czech. (1987), 3 pp.
Material Safety Data Sheet (MSDS)	Download (PDF)
General References	Temellini A, Mogavero S, Giulianotti PC, Pietrabissa A, Mosca F, Pacifici GM: Conjugation of benzoic acid with glycine in human liver and kidney: a study on the interindividual variability. Xenobiotica. 1993 Dec;23(12):1427-33. Pubmed: 8135043 Dix KJ, Coleman DP, Jeffcoat AR: Comparative metabolism and disposition of gemfibrozil in male and female Sprague-Dawley rats and Syrian golden hamsters. Drug Metab Dispos. 1999 Jan;27(1):138-46. Pubmed: 9884323 Nathan D, Sakr A, Lichtin JL, Bronaugh RL: In vitro skin absorption and metabolism of benzoic acid, p-aminobenzoic acid, and benzocaine in the hairless guinea pig. Pharm Res. 1990 Nov;7(11):1147-51. Pubmed: 2293213 Parry GE, Bunge AL, Silcox GD, Pershing LK, Pershing DW: Percutaneous absorption of benzoic acid across human skin. I. In vitro experiments and mathematical modeling. Pharm Res. 1990 Mar;7(3):230-6. Pubmed: 2339094 Nielsen NM, Bundgaard H: Glycolamide esters as biolabile prodrugs of carboxylic acid agents: synthesis, stability, bioconversion, and physicochemical properties. J Pharm Sci. 1988 Apr;77(4):285-98. Pubmed: 3379586 Jones MR, Kopple JD, Swendseid ME: Phenylalanine metabolism in uremic and normal man. Kidney Int. 1978 Aug;14(2):169-79. Pubmed: 357810 Downard CD, Roberts LJ 2nd, Morrow JD: Topical benzoic acid induces the increased biosynthesis of prostaglandin D2 in human skin in vivo. Clin Pharmacol Ther. 1995 Apr;57(4):441-5. Pubmed: 7712673 Killackey JJ, Killackey BA, Philp RB: Cyclic nucleotide phosphodiesterase inhibition by a benzoic acid derivative. Agents Actions. 1985 Dec;17(2):192-6. Pubmed: 2420162 Nacht S, Yeung D, Beasley JN Jr, Anjo MD, Maibach HI: Benzoyl peroxide: percutaneous penetration and metabolic disposition. J Am Acad Dermatol. 1981 Jan;4(1):31-7. Pubmed: 7204686 LeBel M, Ferron L, Masson M, Pichette J, Carrier C: Benzyl alcohol metabolism and elimination in neonates. Dev Pharmacol Ther. 1988;11(6):347-56. Pubmed: 3229281

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Enzymes
Name: Lysosomal acid lipase/cholesteryl ester hydrolase Reactions: Not Available Gene Name: LIPA Uniprot ID: P38571 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Liver carboxylesterase 1 Reactions: Cocaine + Water unknown Ecgonine methyl ester + Benzoic acid details Gene Name: CES1 Uniprot ID: P23141 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Cocaine esterase Reactions: Cocaine + Water unknown Ecgonine methyl ester + Benzoic acid details Gene Name: CES2 Uniprot ID: O00748 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Acylphosphatase-2 Reactions: Benzoyl phosphate + Water unknown Benzoic acid + Phosphoric acid details Gene Name: ACYP2 Uniprot ID: P14621 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Acylphosphatase-1 Reactions: Benzoyl phosphate + Water unknown Benzoic acid + Phosphoric acid details Gene Name: ACYP1 Uniprot ID: P07311 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Carboxylesterase 5A Reactions: Not Available Gene Name: CES5A Uniprot ID: Q6NT32 Protein Sequence: FASTA Gene Sequence: FASTA

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