You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:02:10 UTC
Update Date2019-07-23 07:14:19 UTC
HMDB IDHMDB0060428
Secondary Accession Numbers
  • HMDB60428
Metabolite Identification
Common NameAcetylhydrazine
DescriptionThe acetylhydrazine metabolite was found to be much less cytotoxic than hydrazine in this hepatocyte inflammation model. (PMID: 18295292 ) In the pathogenesis of isoniazid-induced hepatic injury, cytochrome P450-dependent metabolic activation of the metabolite, acetylhydrazine (AcHz), is the crucial step. (PMID: 8852701 ) The mechanism of action of acetylphosphabenzide is likely to involve the formation of acetylhydrazine, capable of producing active electrophiles attacking DNA. (PMID: 9589859 )
Structure
Data?1563866059
Synonyms
ValueSource
AcethydrazideChEBI
Acetic acid hydrazideChEBI
Acetic hydrazideChEBI
Acetyl hydrazideChEBI
Ethanehydrazonic acidChEBI
Monoacetyl hydrazineChEBI
MonoacetylhydrazineChEBI
N-AcetylhydrazineChEBI
Acetate hydrazideGenerator
EthanehydrazonateGenerator
AcethydrazineHMDB
Acetylhydrazine monohydrochlorideHMDB
AcetylhydrazideHMDB
Acetylhydrazine, (e)-2-fumarate (1:1)HMDB
AcetylhydrazineChEBI
Chemical FormulaC2H6N2O
Average Molecular Weight74.0818
Monoisotopic Molecular Weight74.048012824
IUPAC Nameacetohydrazide
Traditional Nameacetohydrazide
CAS Registry NumberNot Available
SMILES
CC(O)=NN
InChI Identifier
InChI=1S/C2H6N2O/c1-2(5)4-3/h3H2,1H3,(H,4,5)
InChI KeyOFLXLNCGODUUOT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acetamides. These are organic compounds with the general formula RNHC(=O)CH3, where R= organyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentAcetamides
Alternative Parents
Substituents
  • Acetamide
  • Carboxylic acid hydrazide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility46.4 g/LALOGPS
logP-1.6ALOGPS
logP-1.3ChemAxon
logS0.81ALOGPS
pKa (Strongest Acidic)13.18ChemAxon
pKa (Strongest Basic)3.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area55.12 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity18.95 m³·mol⁻¹ChemAxon
Polarizability7.15 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-9000000000-c0c6a35bac1462ff7d95Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00gi-9300000000-e17deff9b9942fd000e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-cf2f4be4db94a1740dc1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-9000000000-e240ca6a723c0fe333efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066u-9000000000-252f13e42ab532c8fb3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-62fb398f4ac53e9a12ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-9000000000-5bb4307ab62748b28a21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-716ce61fe4c7b1100d2fSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      Phenol Explorer Compound IDNot Available
      FooDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC07447
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound14039
      PDB IDNot Available
      ChEBI ID2422
      Food Biomarker OntologyNot Available
      VMH IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
      2. Morike K, Koch M, Fritz P, Urban W, Eichelbaum M: Identification of N2 as a metabolite of acetylhydrazine in the rat. Arch Toxicol. 1996;70(5):300-5. [PubMed:8852701 ]
      3. Jenner PJ, Ellard GA: Isoniazid-related hepatotoxicity: a study of the effect of rifampicin administration on the metabolism of acetylisoniazid in man. Tubercle. 1989 Jun;70(2):93-101. [PubMed:2617692 ]
      4. Tafazoli S, Mashregi M, O'Brien PJ: Role of hydrazine in isoniazid-induced hepatotoxicity in a hepatocyte inflammation model. Toxicol Appl Pharmacol. 2008 May 15;229(1):94-101. doi: 10.1016/j.taap.2008.01.002. Epub 2008 Jan 17. [PubMed:18295292 ]
      5. Il'inskaia ON, Ivanchenko OB, Trubnikova GG, Valimukhametova DA, Tarasova RI, Bagautdinova DB: [Genotoxic effects of metabolic derivatives of the new drug phosphabenzide]. Genetika. 1998 Feb;34(2):308-12. [PubMed:9589859 ]

      Enzymes

      General function:
      Involved in acetyltransferase activity
      Specific function:
      Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivate several known carcinogens.
      Gene Name:
      NAT1
      Uniprot ID:
      P18440
      Molecular weight:
      33898.445
      Reactions
      Acetyl-CoA + Acetylhydrazine → Coenzyme A + N,N'-Diacetylhydrazinedetails
      General function:
      Involved in acetyltransferase activity
      Specific function:
      Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivate several known carcinogens.
      Gene Name:
      NAT2
      Uniprot ID:
      P11245
      Molecular weight:
      33570.245
      Reactions
      Acetyl-CoA + Acetylhydrazine → Coenzyme A + N,N'-Diacetylhydrazinedetails