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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 19:18:32 UTC
Update Date2018-05-20 00:06:11 UTC
HMDB IDHMDB0004461
Secondary Accession Numbers
  • HMDB04461
Metabolite Identification
Common NameBenzamide
DescriptionBenzamide is an intermediate in the Benzoate degradation via CoA ligation. Benzamides are a class of chemical compounds derived from Benzamid, the carbonic acid amide of benzoic acid. In psychiatry some substituted benzamides are therapeutically used as neuroleptics and/or antipsychotics (wikipedia).
Structure
Thumb
Synonyms
ValueSource
BenzenecarboxamideChEBI
Benzoic acid amideChEBI
BenzoylamideChEBI
PHC(=O)NH2ChEBI
PHC(O)NH2ChEBI
PhenylcarboxamideChEBI
PhenylcarboxyamideChEBI
Benzoate amideGenerator
Amid kyseliny benzooveHMDB
Benzamide (acd/name 4.0)HMDB
BenzoateHMDB
Benzoic acidHMDB
Phenyl carboxyamideHMDB
TiganHMDB
Trimethobenzamide hydrochlorideHMDB
Chemical FormulaC7H7NO
Average Molecular Weight121.1366
Monoisotopic Molecular Weight121.052763851
IUPAC Namebenzamide
Traditional Namebenzamide
CAS Registry Number55-21-0
SMILES
NC(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C7H7NO/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H2,8,9)
InChI KeyKXDAEFPNCMNJSK-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzamides
Alternative Parents
Substituents
  • Benzamide
  • Benzoyl
  • Primary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point129.1 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility13500 mg/L at 25 °CNot Available
LogP0.818Not Available
Predicted Properties
PropertyValueSource
Water Solubility8.77 g/LALOGPS
logP0.51ALOGPS
logP0.82ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)14.56ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.14 m³·mol⁻¹ChemAxon
Polarizability12.38 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ab9-2900000000-d10a8514e7c0dedd5758View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0kk9-8900000000-a6264ed866860ca71f94View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0adi-7900000000-c79bab8ceedf3b276ae1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fbi-0900000000-e11c600f209e5f1be1fdView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ab9-2900000000-d10a8514e7c0dedd5758View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0kk9-8900000000-a6264ed866860ca71f94View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0adi-7900000000-c79bab8ceedf3b276ae1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fbi-0900000000-e11c600f209e5f1be1fdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pi0-4900000000-24e0b6bee128508783c3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00fr-3900000000-274cc52f0c0c8accad8cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0fb9-9400000000-53a105851fb3f3bfa447View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fb9-9000000000-3fd0ac2c3e583778d4f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0ab9-2900000000-d10a8514e7c0dedd5758View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0kk9-8900000000-6e34f51843ee9cdd8237View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-1900000000-b21069169eafde58c822View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0a6r-8900000000-85f7934fa93d7240804fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-004i-9200000000-e4b0272643ae9f111021View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-004i-9100000000-c34f0e594deb730ca6b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0fb9-9100000000-76a5adf911f1a97ad45bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-1900000000-c6e30a6a9805ba36fc2aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a6r-8900000000-d40d6a968a8a706e6500View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9200000000-e4b0272643ae9f111021View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9100000000-c34f0e594deb730ca6b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0fb9-9100000000-76a5adf911f1a97ad45bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-05i0-3900000000-105f114ff019238e0401View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-b10777bbfb9e15c822c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-4900000000-4401050524c9108d0e36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9600000000-a2aca9e73b19fc5335b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1900000000-cb7510152a09599b3704View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-6900000000-4e21f69e91793514c49eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-a5e23c6893e288e53794View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified0.151 +/- 8.15 uMAdult (>18 years old)BothNormal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified24.3 +/- 12.3 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified24.7 +/- 12.7 uMAdult (>18 years old)BothDental caries
    • Sugimoto et al. (...
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023373
KNApSAcK IDC00042277
Chemspider ID2241
KEGG Compound IDC09815
BioCyc IDSAM
BiGG IDNot Available
Wikipedia LinkBenzamide
METLIN IDNot Available
PubChem Compound2331
PDB IDUNU
ChEBI ID28179
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Chemnitius JM, Haselmeyer KH, Gonska BD, Kreuzer H, Zech R: Indirect parasympathomimetic activity of metoclopramide: reversible inhibition of cholinesterases from human central nervous system and blood. Pharmacol Res. 1996 Jul-Aug;34(1-2):65-72. [PubMed:8981558 ]
  2. Coyle JD, MacKichan JJ, Boudoulas H, Lima JJ: Reversed-phase liquid chromatography method for measurement of procainamide and three metabolites in serum and urine: percent of dose excreted as deethyl metabolites. J Pharm Sci. 1987 May;76(5):402-5. [PubMed:2443639 ]
  3. Chiba R, Ogasawara A, Kubo T, Yamazaki H, Umino M, Ishizuka Y: Direct determination of benzamides in serum by column-switching high-performance liquid chromatography. Anal Sci. 2003 May;19(5):785-9. [PubMed:12769385 ]
  4. Yamamoto T, Hanioka N, Maeda Y, Imazumi K, Hamada K, Matsuo M, Manda T, Mutoh S: Contribution of tachykinin receptor subtypes to micturition reflex in guinea pigs. Eur J Pharmacol. 2003 Sep 23;477(3):253-9. [PubMed:14522364 ]
  5. Gschwend MH, Arnold P, Ring J, Martin W: Selective and sensitive determination of amisulpride in human plasma by liquid chromatography-tandem mass spectrometry with positive electrospray ionisation and multiple reaction monitoring. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Feb 2;831(1-2):132-9. Epub 2005 Dec 28. [PubMed:16386474 ]
  6. de Jong AP, Wittebrood AJ, du Chatinier WM, Bron J: Liquid chromatographic analysis of alizapride and metoclopramide in human plasma and urine using solid-phase extraction. J Chromatogr. 1987 Aug 7;419:233-42. [PubMed:3667781 ]
  7. Jitsufuchi N, Kudo K, Tokunaga H, Imamura T: Selective determination of sultopride in human plasma using high-performance liquid chromatography with ultraviolet detection and particle beam mass spectrometry. J Chromatogr B Biomed Sci Appl. 1997 Mar 7;690(1-2):153-9. [PubMed:9106039 ]
  8. Delarue C, Contesse V, Lefebvre H, Lenglet S, Grumolato L, Kuhn JM, Vaudry H: Pharmacological profile of serotonergic receptors in the adrenal gland. Endocr Res. 1998 Aug-Nov;24(3-4):687-94. [PubMed:9888560 ]