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Record Information
Version3.6
Creation Date2013-05-17 01:02:10 UTC
Update Date2016-02-11 08:05:38 UTC
HMDB IDHMDB60428
Secondary Accession NumbersNone
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
Thumb
Synonyms
ValueSource
AcethydrazideChEBI
Acetic acid hydrazideChEBI
Acetic hydrazideChEBI
Acetyl hydrazideChEBI
AcetylhydrazineChEBI
Monoacetyl hydrazineChEBI
MonoacetylhydrazineChEBI
N-AcetylhydrazineChEBI
EthanehydrazonateGenerator
Acetate hydrazideGenerator
Chemical FormulaC2H6N2O
Average Molecular Weight74.0818
Monoisotopic Molecular Weight74.048012824
IUPAC Nameethanehydrazonic acid
Traditional Nameethanehydrazonic acid
CAS Registry NumberNot Available
SMILES
CC(O)=NN
InChI Identifier
InChI=1S/C2H6N2O/c1-2(5)4-3/h3H2,1H3,(H,4,5)
InChI KeyInChIKey=OFLXLNCGODUUOT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydrazones. These are compounds containing an N-Alkylidene derivative of hydrazine. They have the generic structure RNN=C(R')R\
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassHydrazines and derivatives
Sub ClassHydrazones
Direct ParentHydrazones
Alternative Parents
Substituents
  • Hydrazone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locationsNot Available
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 mg/mLALOGPS
logP-0.78ALOGPS
logP-0.51ChemAxon
logS-0.2ALOGPS
pKa (Strongest Acidic)8.05ChemAxon
pKa (Strongest Basic)3.03ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.61 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity19.47 m3·mol-1ChemAxon
Polarizability7.12 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC07447
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60428
Metagene LinkHMDB60428
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M, Consortium U: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [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. [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. [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. [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. [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