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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:02:10 UTC

Update Date

2019-07-23 07:14:19 UTC

HMDB ID

HMDB0060428

Secondary Accession Numbers

HMDB60428

Metabolite Identification

Common Name

Acetylhydrazine

Description

The 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Acethydrazide	ChEBI
Acetic acid hydrazide	ChEBI
Acetic hydrazide	ChEBI
Acetyl hydrazide	ChEBI
Ethanehydrazonic acid	ChEBI
Monoacetyl hydrazine	ChEBI
Monoacetylhydrazine	ChEBI
N-Acetylhydrazine	ChEBI
Acetate hydrazide	Generator
Ethanehydrazonate	Generator
Acethydrazine	HMDB
Acetylhydrazine monohydrochloride	HMDB
Acetylhydrazide	HMDB
Acetylhydrazine, (e)-2-fumarate (1:1)	HMDB
Acetylhydrazine	ChEBI

Chemical Formula

C₂H₆N₂O

Average Molecular Weight

74.0818

Monoisotopic Molecular Weight

74.048012824

IUPAC Name

acetohydrazide

Traditional Name

acetohydrazide

CAS Registry Number

Not Available

SMILES

CC(O)=NN

InChI Identifier

InChI=1S/C2H6N2O/c1-2(5)4-3/h3H2,1H3,(H,4,5)

InChI Key

OFLXLNCGODUUOT-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Acetamides

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 Framework

Aliphatic acyclic compounds

External Descriptors

carbohydrazonic acid (CHEBI:48978 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	46.4 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-1.3	ChemAxon
logS	0.81	ALOGPS
pKa (Strongest Acidic)	13.18	ChemAxon
pKa (Strongest Basic)	3.28	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	55.12 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	18.95 m³·mol⁻¹	ChemAxon
Polarizability	7.15 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	112.816	31661259
DarkChem	[M-H]-	106.409	31661259
DeepCCS	[M+H]+	116.151	30932474
DeepCCS	[M-H]-	114.256	30932474
DeepCCS	[M-2H]-	149.754	30932474
DeepCCS	[M+Na]+	124.24	30932474
AllCCS	[M+H]+	123.0	32859911
AllCCS	[M+H-H2O]+	118.6	32859911
AllCCS	[M+NH4]+	127.2	32859911
AllCCS	[M+Na]+	128.4	32859911
AllCCS	[M-H]-	127.5	32859911
AllCCS	[M+Na-2H]-	133.1	32859911
AllCCS	[M+HCOO]-	139.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Acetylhydrazine	CC(O)=NN	1879.8	Standard polar	33892256
Acetylhydrazine	CC(O)=NN	1025.5	Standard non polar	33892256
Acetylhydrazine	CC(O)=NN	1104.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Acetylhydrazine,1TMS,isomer #1	CC(=NN)O[Si](C)(C)C	1013.8	Semi standard non polar	33892256
Acetylhydrazine,1TMS,isomer #2	CC(O)=NN[Si](C)(C)C	1217.2	Semi standard non polar	33892256
Acetylhydrazine,2TMS,isomer #1	CC(=NN[Si](C)(C)C)O[Si](C)(C)C	1172.6	Semi standard non polar	33892256
Acetylhydrazine,2TMS,isomer #1	CC(=NN[Si](C)(C)C)O[Si](C)(C)C	1135.2	Standard non polar	33892256
Acetylhydrazine,2TMS,isomer #1	CC(=NN[Si](C)(C)C)O[Si](C)(C)C	1424.0	Standard polar	33892256
Acetylhydrazine,2TMS,isomer #2	CC(O)=NN([Si](C)(C)C)[Si](C)(C)C	1384.2	Semi standard non polar	33892256
Acetylhydrazine,2TMS,isomer #2	CC(O)=NN([Si](C)(C)C)[Si](C)(C)C	1129.9	Standard non polar	33892256
Acetylhydrazine,2TMS,isomer #2	CC(O)=NN([Si](C)(C)C)[Si](C)(C)C	1558.4	Standard polar	33892256
Acetylhydrazine,3TMS,isomer #1	CC(=NN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	1321.0	Semi standard non polar	33892256
Acetylhydrazine,3TMS,isomer #1	CC(=NN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	1227.6	Standard non polar	33892256
Acetylhydrazine,3TMS,isomer #1	CC(=NN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	1351.6	Standard polar	33892256
Acetylhydrazine,1TBDMS,isomer #1	CC(=NN)O[Si](C)(C)C(C)(C)C	1206.5	Semi standard non polar	33892256
Acetylhydrazine,1TBDMS,isomer #2	CC(O)=NN[Si](C)(C)C(C)(C)C	1375.2	Semi standard non polar	33892256
Acetylhydrazine,2TBDMS,isomer #1	CC(=NN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1555.5	Semi standard non polar	33892256
Acetylhydrazine,2TBDMS,isomer #1	CC(=NN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1513.9	Standard non polar	33892256
Acetylhydrazine,2TBDMS,isomer #1	CC(=NN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1592.5	Standard polar	33892256
Acetylhydrazine,2TBDMS,isomer #2	CC(O)=NN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1636.5	Semi standard non polar	33892256
Acetylhydrazine,2TBDMS,isomer #2	CC(O)=NN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1540.7	Standard non polar	33892256
Acetylhydrazine,2TBDMS,isomer #2	CC(O)=NN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1674.5	Standard polar	33892256
Acetylhydrazine,3TBDMS,isomer #1	CC(=NN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1893.5	Semi standard non polar	33892256
Acetylhydrazine,3TBDMS,isomer #1	CC(=NN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1832.8	Standard non polar	33892256
Acetylhydrazine,3TBDMS,isomer #1	CC(=NN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1705.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Acetylhydrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-9000000000-c0c6a35bac1462ff7d95	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetylhydrazine GC-MS (1 TMS) - 70eV, Positive	splash10-00gi-9300000000-e17deff9b9942fd000e9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetylhydrazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylhydrazine 10V, Positive-QTOF	splash10-004i-9000000000-cf2f4be4db94a1740dc1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylhydrazine 20V, Positive-QTOF	splash10-056r-9000000000-e240ca6a723c0fe333ef	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylhydrazine 40V, Positive-QTOF	splash10-066u-9000000000-252f13e42ab532c8fb3a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylhydrazine 10V, Negative-QTOF	splash10-00di-9000000000-62fb398f4ac53e9a12dd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylhydrazine 20V, Negative-QTOF	splash10-05fr-9000000000-5bb4307ab62748b28a21	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylhydrazine 40V, Negative-QTOF	splash10-0a4i-9000000000-716ce61fe4c7b1100d2f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylhydrazine 10V, Positive-QTOF	splash10-004i-9000000000-83c14c6a559e41e3fc4a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylhydrazine 20V, Positive-QTOF	splash10-0a7i-9000000000-2ff9a771cebd96ee8310	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylhydrazine 40V, Positive-QTOF	splash10-0a4i-9000000000-03118a48b6476710028b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylhydrazine 10V, Negative-QTOF	splash10-00di-9000000000-87753cf4baa848fb8803	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylhydrazine 20V, Negative-QTOF	splash10-00dl-9000000000-2fa51eccd4ca4be2742b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylhydrazine 40V, Negative-QTOF	splash10-0006-9000000000-c6e9b14dd1c3f7143a15	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C07447

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14039

PDB ID

Not Available

ChEBI ID

2422

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
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 ]
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 ]
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

Enzyme Details

1. Arylamine N-acetyltransferase 1

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'-Diacetylhydrazine	details

Enzyme Details

2. Arylamine N-acetyltransferase 2

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'-Diacetylhydrazine	details

Showing metabocard for Acetylhydrazine (HMDB0060428)

MOL for HMDB0060428 (Acetylhydrazine)

3D MOL for HMDB0060428 (Acetylhydrazine)

3D SDF for HMDB0060428 (Acetylhydrazine)

3D-SDF for HMDB0060428 (Acetylhydrazine)

PDB for HMDB0060428 (Acetylhydrazine)

3D PDB for HMDB0060428 (Acetylhydrazine)

SMILES for HMDB0060428 (Acetylhydrazine)

INCHI for HMDB0060428 (Acetylhydrazine)

Structure for HMDB0060428 (Acetylhydrazine)

3D Structure for HMDB0060428 (Acetylhydrazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions