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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

2012-09-13 11:40:59 UTC

Update Date

2019-07-23 06:35:06 UTC

HMDB ID

HMDB0041821

Secondary Accession Numbers

HMDB41821

Metabolite Identification

Common Name

Acetylisoniazid

Description

Acetylisoniazid belongs to the class of organic compounds known as pyridinecarboxylic acids and derivatives. Pyridinecarboxylic acids and derivatives are compounds containing a pyridine ring bearing a carboxylic acid group or a derivative thereof. Acetylisoniazid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Acetylisoniazid.

Structure

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

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       2.667   6.160   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       2.667   4.620   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    4    7                                                       
CONECT    3    5    7                                                       
CONECT    4    2    9                                                       
CONECT    5    3    9                                                       
CONECT    6    1   10   12                                                  
CONECT    7    2    3    8                                                  
CONECT    8    7   11   13                                                  
CONECT    9    4    5                                                       
CONECT   10    6   11                                                       
CONECT   11    8   10                                                       
CONECT   12    6                                                            
CONECT   13    8                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(N)1-Acetylisoniazid	ChEBI
1-Acetyl-2-isonicotinoylhydrazine	ChEBI
Acetyl isoniazid	ChEBI
N-Acetyl-n'-isonicotinoylhydrazine	ChEBI
N-Acetylisoniazid	ChEBI
N-Acetylisonicotinylhydrazide	ChEBI
N'-acetylpyridine-4-carbohydrazide	HMDB
(N)1-Acetylisoniazid monohydrochloride	HMDB
Acetylisoniazid	ChEBI

Chemical Formula

C₈H₉N₃O₂

Average Molecular Weight

179.176

Monoisotopic Molecular Weight

179.069476547

IUPAC Name

N-(pyridine-4-carbonyl)ethanehydrazonic acid

Traditional Name

acetylisoniazid

CAS Registry Number

1078-38-2

SMILES

CC(O)=NNC(=O)C1=CC=NC=C1

InChI Identifier

InChI=1S/C8H9N3O2/c1-6(12)10-11-8(13)7-2-4-9-5-3-7/h2-5H,1H3,(H,10,12)(H,11,13)

InChI Key

CVBGNAKQQUWBQV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridinecarboxylic acids and derivatives. Pyridinecarboxylic acids and derivatives are compounds containing a pyridine ring bearing a carboxylic acid group or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinecarboxylic acids and derivatives

Direct Parent

Pyridinecarboxylic acids and derivatives

Alternative Parents

Substituents

Pyridine carboxylic acid or derivatives
Heteroaromatic compound
Azacycle
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

carbohydrazide (CHEBI:7207 )

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	1.77 g/L	ALOGPS
logP	0.04	ALOGPS
logP	-0.16	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	6.77	ChemAxon
pKa (Strongest Basic)	3.02	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.58 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	46.37 m³·mol⁻¹	ChemAxon
Polarizability	17.34 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	140.179	31661259
DarkChem	[M-H]-	137.614	31661259
DeepCCS	[M+H]+	136.444	30932474
DeepCCS	[M-H]-	133.959	30932474
DeepCCS	[M-2H]-	169.59	30932474
DeepCCS	[M+Na]+	144.167	30932474
AllCCS	[M+H]+	138.5	32859911
AllCCS	[M+H-H2O]+	134.3	32859911
AllCCS	[M+NH4]+	142.5	32859911
AllCCS	[M+Na]+	143.6	32859911
AllCCS	[M-H]-	138.1	32859911
AllCCS	[M+Na-2H]-	138.9	32859911
AllCCS	[M+HCOO]-	139.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.88 minutes	32390414
Predicted by Siyang on May 30, 2022	9.3312 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.29 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	72.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1103.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	278.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	70.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	158.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	38.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	239.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	373.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	117.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	588.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	41.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	962.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	168.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	180.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	578.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	244.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	161.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Acetylisoniazid	CC(O)=NNC(=O)C1=CC=NC=C1	2340.8	Standard polar	33892256
Acetylisoniazid	CC(O)=NNC(=O)C1=CC=NC=C1	1551.5	Standard non polar	33892256
Acetylisoniazid	CC(O)=NNC(=O)C1=CC=NC=C1	1795.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Acetylisoniazid,1TMS,isomer #1	CC(=NNC(=O)C1=CC=NC=C1)O[Si](C)(C)C	1823.2	Semi standard non polar	33892256
Acetylisoniazid,1TMS,isomer #2	CC(O)=NN(C(=O)C1=CC=NC=C1)[Si](C)(C)C	1800.5	Semi standard non polar	33892256
Acetylisoniazid,2TMS,isomer #1	CC(=NN(C(=O)C1=CC=NC=C1)[Si](C)(C)C)O[Si](C)(C)C	1771.2	Semi standard non polar	33892256
Acetylisoniazid,2TMS,isomer #1	CC(=NN(C(=O)C1=CC=NC=C1)[Si](C)(C)C)O[Si](C)(C)C	1788.2	Standard non polar	33892256
Acetylisoniazid,1TBDMS,isomer #1	CC(=NNC(=O)C1=CC=NC=C1)O[Si](C)(C)C(C)(C)C	2044.6	Semi standard non polar	33892256
Acetylisoniazid,1TBDMS,isomer #2	CC(O)=NN(C(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C	1983.5	Semi standard non polar	33892256
Acetylisoniazid,2TBDMS,isomer #1	CC(=NN(C(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2181.7	Semi standard non polar	33892256
Acetylisoniazid,2TBDMS,isomer #1	CC(=NN(C(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2172.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Acetylisoniazid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-3900000000-5c9a49fca1347ce379b3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetylisoniazid GC-MS (1 TMS) - 70eV, Positive	splash10-0abi-7920000000-aec72e6bb42ac1e86ba6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetylisoniazid 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 - Acetylisoniazid 10V, Positive-QTOF	splash10-001i-0900000000-a3d1c5a0e5ebb2c97ae6	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylisoniazid 20V, Positive-QTOF	splash10-000i-0900000000-b85ff7e45abff69ec78d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylisoniazid 40V, Positive-QTOF	splash10-0a4r-8900000000-681c8051d8867866f800	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylisoniazid 10V, Negative-QTOF	splash10-004i-1900000000-1fd563df0fddf0565220	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylisoniazid 20V, Negative-QTOF	splash10-000i-2900000000-d949ad8af3a1a12d8815	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylisoniazid 40V, Negative-QTOF	splash10-004i-9400000000-36da48ad648b55fdbac6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylisoniazid 10V, Negative-QTOF	splash10-004i-3900000000-9ecadad920c257e51e56	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylisoniazid 20V, Negative-QTOF	splash10-004i-9200000000-b40c808dd07605ed79a9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylisoniazid 40V, Negative-QTOF	splash10-004i-9000000000-832bf8c26347108a5e17	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylisoniazid 10V, Positive-QTOF	splash10-0a4i-0900000000-d4a7a493a9c66a84c747	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylisoniazid 20V, Positive-QTOF	splash10-0a4i-1900000000-647f8a4f62f24f4fd80c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetylisoniazid 40V, Positive-QTOF	splash10-0059-9100000000-970318f02baa4e30444c	2021-09-25	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

64672

KEGG Compound ID

C07585

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71602

PDB ID

Not Available

ChEBI ID

7207

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

Ait Moussa L, Khassouani CE, Hue B, Jana M, Begaud B, Soulaymani R: Determination of the acetylator phenotype in Moroccan tuberculosis patients using isoniazid as metabolic probe. Int J Clin Pharmacol Ther. 2002 Dec;40(12):548-53. [PubMed:12503812 ]

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 + Isoniazid → Coenzyme A + Acetylisoniazid	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 + Isoniazid → Coenzyme A + Acetylisoniazid	details

Showing metabocard for Acetylisoniazid (HMDB0041821)

MOL for HMDB0041821 (Acetylisoniazid)

3D MOL for HMDB0041821 (Acetylisoniazid)

3D SDF for HMDB0041821 (Acetylisoniazid)

3D-SDF for HMDB0041821 (Acetylisoniazid)

PDB for HMDB0041821 (Acetylisoniazid)

3D PDB for HMDB0041821 (Acetylisoniazid)

SMILES for HMDB0041821 (Acetylisoniazid)

INCHI for HMDB0041821 (Acetylisoniazid)

Structure for HMDB0041821 (Acetylisoniazid)

3D Structure for HMDB0041821 (Acetylisoniazid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions