Hmdb loader
Record Information
Version5.0
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
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+112.81631661259
DarkChem[M-H]-106.40931661259
DeepCCS[M+H]+116.15130932474
DeepCCS[M-H]-114.25630932474
DeepCCS[M-2H]-149.75430932474
DeepCCS[M+Na]+124.2430932474
AllCCS[M+H]+123.032859911
AllCCS[M+H-H2O]+118.632859911
AllCCS[M+NH4]+127.232859911
AllCCS[M+Na]+128.432859911
AllCCS[M-H]-127.532859911
AllCCS[M+Na-2H]-133.132859911
AllCCS[M+HCOO]-139.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AcetylhydrazineCC(O)=NN1879.8Standard polar33892256
AcetylhydrazineCC(O)=NN1025.5Standard non polar33892256
AcetylhydrazineCC(O)=NN1104.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Acetylhydrazine,1TMS,isomer #1CC(=NN)O[Si](C)(C)C1013.8Semi standard non polar33892256
Acetylhydrazine,1TMS,isomer #2CC(O)=NN[Si](C)(C)C1217.2Semi standard non polar33892256
Acetylhydrazine,2TMS,isomer #1CC(=NN[Si](C)(C)C)O[Si](C)(C)C1172.6Semi standard non polar33892256
Acetylhydrazine,2TMS,isomer #1CC(=NN[Si](C)(C)C)O[Si](C)(C)C1135.2Standard non polar33892256
Acetylhydrazine,2TMS,isomer #1CC(=NN[Si](C)(C)C)O[Si](C)(C)C1424.0Standard polar33892256
Acetylhydrazine,2TMS,isomer #2CC(O)=NN([Si](C)(C)C)[Si](C)(C)C1384.2Semi standard non polar33892256
Acetylhydrazine,2TMS,isomer #2CC(O)=NN([Si](C)(C)C)[Si](C)(C)C1129.9Standard non polar33892256
Acetylhydrazine,2TMS,isomer #2CC(O)=NN([Si](C)(C)C)[Si](C)(C)C1558.4Standard polar33892256
Acetylhydrazine,3TMS,isomer #1CC(=NN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C1321.0Semi standard non polar33892256
Acetylhydrazine,3TMS,isomer #1CC(=NN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C1227.6Standard non polar33892256
Acetylhydrazine,3TMS,isomer #1CC(=NN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C1351.6Standard polar33892256
Acetylhydrazine,1TBDMS,isomer #1CC(=NN)O[Si](C)(C)C(C)(C)C1206.5Semi standard non polar33892256
Acetylhydrazine,1TBDMS,isomer #2CC(O)=NN[Si](C)(C)C(C)(C)C1375.2Semi standard non polar33892256
Acetylhydrazine,2TBDMS,isomer #1CC(=NN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1555.5Semi standard non polar33892256
Acetylhydrazine,2TBDMS,isomer #1CC(=NN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1513.9Standard non polar33892256
Acetylhydrazine,2TBDMS,isomer #1CC(=NN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1592.5Standard polar33892256
Acetylhydrazine,2TBDMS,isomer #2CC(O)=NN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1636.5Semi standard non polar33892256
Acetylhydrazine,2TBDMS,isomer #2CC(O)=NN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1540.7Standard non polar33892256
Acetylhydrazine,2TBDMS,isomer #2CC(O)=NN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1674.5Standard polar33892256
Acetylhydrazine,3TBDMS,isomer #1CC(=NN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1893.5Semi standard non polar33892256
Acetylhydrazine,3TBDMS,isomer #1CC(=NN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1832.8Standard non polar33892256
Acetylhydrazine,3TBDMS,isomer #1CC(=NN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1705.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Acetylhydrazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-9000000000-c0c6a35bac1462ff7d952017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetylhydrazine GC-MS (1 TMS) - 70eV, Positivesplash10-00gi-9300000000-e17deff9b9942fd000e92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetylhydrazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylhydrazine 10V, Positive-QTOFsplash10-004i-9000000000-cf2f4be4db94a1740dc12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylhydrazine 20V, Positive-QTOFsplash10-056r-9000000000-e240ca6a723c0fe333ef2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylhydrazine 40V, Positive-QTOFsplash10-066u-9000000000-252f13e42ab532c8fb3a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylhydrazine 10V, Negative-QTOFsplash10-00di-9000000000-62fb398f4ac53e9a12dd2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylhydrazine 20V, Negative-QTOFsplash10-05fr-9000000000-5bb4307ab62748b28a212017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylhydrazine 40V, Negative-QTOFsplash10-0a4i-9000000000-716ce61fe4c7b1100d2f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylhydrazine 10V, Positive-QTOFsplash10-004i-9000000000-83c14c6a559e41e3fc4a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylhydrazine 20V, Positive-QTOFsplash10-0a7i-9000000000-2ff9a771cebd96ee83102021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylhydrazine 40V, Positive-QTOFsplash10-0a4i-9000000000-03118a48b6476710028b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylhydrazine 10V, Negative-QTOFsplash10-00di-9000000000-87753cf4baa848fb88032021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylhydrazine 20V, Negative-QTOFsplash10-00dl-9000000000-2fa51eccd4ca4be2742b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylhydrazine 40V, Negative-QTOFsplash10-0006-9000000000-c6e9b14dd1c3f7143a152021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
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
MarkerDB IDNot Available
Good Scents 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