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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (10) Show 10 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2023-02-21 17:18:23 UTC

HMDB ID

HMDB0015086

Secondary Accession Numbers

HMDB15086

Metabolite Identification

Common Name

Isoniazid

Description

Isoniazid is only found in individuals that have used or taken this drug. It is an antibacterial agent used primarily as a tuberculostatic. It remains the treatment of choice for tuberculosis. [PubChem]Isoniazid is a prodrug and must be activated by bacterial catalase. Specficially, activation is associated with reduction of the mycobacterial ferric KatG catalase-peroxidase by hydrazine and reaction with oxygen to form an oxyferrous enzyme complex. Once activated, isoniazid inhibits the synthesis of mycoloic acids, an essential component of the bacterial cell wall. At therapeutic levels isoniazid is bacteriocidal against actively growing intracellular and extracellular Mycobacterium tuberculosis organisms. Specifically isoniazid inhibits InhA, the enoyl reductase from Mycobacterium tuberculosis, by forming a covalent adduct with the NAD cofactor. It is the INH-NAD adduct that acts as a slow, tight-binding competitive inhibitor of InhA.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Pyridinecarbohydrazide	ChEBI
Isonicotinic acid hydrazide	ChEBI
Isonicotinic hydrazide	ChEBI
Isonicotinohydrazide	ChEBI
Isonicotinoylhydrazide	ChEBI
Isonicotinsaeurehydrazid	ChEBI
Pyridine-4-carboxylic acid hydrazide	ChEBI
Laniazid	Kegg
Isonicotinate hydrazide	Generator
Pyridine-4-carboxylate hydrazide	Generator
HIA	HMDB
Hydrazid	HMDB
Hydrazide	HMDB
INH	HMDB
Isohydrazide	HMDB
Isonicotinhydrazid	HMDB
Isonicotinoyl hydrazide	HMDB
Isonicotinyl hydrazide	HMDB
Isonicotinyl hydrazine	HMDB
Isonicotinylhydrazine	HMDB
Hydrazide, isonicotinic acid	HMDB
Isonex	HMDB
Tubazide	HMDB
Vanillylidenehydrazide, isonicotinic acid	HMDB
Acid vanillylidenehydrazide, isonicotinic	HMDB
Isonicotinic acid vanillylidenehydrazide	HMDB
Ftivazide	HMDB
Phthivazide	HMDB
Phthivazid	HMDB
Isoniazid	ChEBI

Chemical Formula

C₆H₇N₃O

Average Molecular Weight

137.1393

Monoisotopic Molecular Weight

137.058911861

IUPAC Name

pyridine-4-carbohydrazide

Traditional Name

isoniazid

CAS Registry Number

54-85-3

SMILES

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

InChI Identifier

InChI=1S/C6H7N3O/c7-9-6(10)5-1-3-8-4-2-5/h1-4H,7H2,(H,9,10)

InChI Key

QRXWMOHMRWLFEY-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
Carboxylic acid hydrazide
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:6030 )
a small molecule (ISONIAZIDE )

Ontology

Physiological effect

Health effect

Observation

Neuropathy (HMDB: HMDB0015086)

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Hepatitis (HMDB: HMDB0015086)

Nervous system disorder

Peripheral nervous system disorder

Peripheral neuropathy (HMDB: HMDB0015086)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0015086)

Source

Exogenous

Exogenous (HMDB: HMDB0015086)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0015086)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	171.4 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	34.9 g/L	Not Available
LogP	-0.8	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	125.559	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000998

Predicted Molecular Properties

Property	Value	Source
Water Solubility	34.9 g/L	ALOGPS
logP	-0.71	ALOGPS
logP	-0.69	ChemAxon
logS	-0.59	ALOGPS
pKa (Strongest Acidic)	13.61	ChemAxon
pKa (Strongest Basic)	3.35	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.01 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	37.46 m³·mol⁻¹	ChemAxon
Polarizability	13.21 Å³	ChemAxon
Number of Rings	1	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]+	128.538	31661259
DarkChem	[M-H]-	125.62	31661259
DeepCCS	[M+H]+	127.07	30932474
DeepCCS	[M-H]-	123.861	30932474
DeepCCS	[M-2H]-	160.839	30932474
DeepCCS	[M+Na]+	136.167	30932474
AllCCS	[M+H]+	129.6	32859911
AllCCS	[M+H-H2O]+	125.0	32859911
AllCCS	[M+NH4]+	134.0	32859911
AllCCS	[M+Na]+	135.3	32859911
AllCCS	[M-H]-	125.6	32859911
AllCCS	[M+Na-2H]-	127.3	32859911
AllCCS	[M+HCOO]-	129.2	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.	1.62 minutes	32390414
Predicted by Siyang on May 30, 2022	9.2107 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.23 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	86.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	857.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	318.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	67.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	180.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	43.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	271.0 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	411.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	301.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	594.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	41.4 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	932.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	189.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	221.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	624.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	335.5 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	221.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isoniazid	NNC(=O)C1=CC=NC=C1	2453.2	Standard polar	33892256
Isoniazid	NNC(=O)C1=CC=NC=C1	1538.8	Standard non polar	33892256
Isoniazid	NNC(=O)C1=CC=NC=C1	1491.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isoniazid,1TMS,isomer #1	C[Si](C)(C)NNC(=O)C1=CC=NC=C1	1675.9	Semi standard non polar	33892256
Isoniazid,1TMS,isomer #1	C[Si](C)(C)NNC(=O)C1=CC=NC=C1	1702.5	Standard non polar	33892256
Isoniazid,1TMS,isomer #1	C[Si](C)(C)NNC(=O)C1=CC=NC=C1	2165.2	Standard polar	33892256
Isoniazid,1TMS,isomer #2	C[Si](C)(C)N(N)C(=O)C1=CC=NC=C1	1551.1	Semi standard non polar	33892256
Isoniazid,1TMS,isomer #2	C[Si](C)(C)N(N)C(=O)C1=CC=NC=C1	1687.6	Standard non polar	33892256
Isoniazid,1TMS,isomer #2	C[Si](C)(C)N(N)C(=O)C1=CC=NC=C1	2411.8	Standard polar	33892256
Isoniazid,2TMS,isomer #1	C[Si](C)(C)N(NC(=O)C1=CC=NC=C1)[Si](C)(C)C	1734.2	Semi standard non polar	33892256
Isoniazid,2TMS,isomer #1	C[Si](C)(C)N(NC(=O)C1=CC=NC=C1)[Si](C)(C)C	1767.8	Standard non polar	33892256
Isoniazid,2TMS,isomer #1	C[Si](C)(C)N(NC(=O)C1=CC=NC=C1)[Si](C)(C)C	2093.8	Standard polar	33892256
Isoniazid,2TMS,isomer #2	C[Si](C)(C)NN(C(=O)C1=CC=NC=C1)[Si](C)(C)C	1634.0	Semi standard non polar	33892256
Isoniazid,2TMS,isomer #2	C[Si](C)(C)NN(C(=O)C1=CC=NC=C1)[Si](C)(C)C	1699.7	Standard non polar	33892256
Isoniazid,2TMS,isomer #2	C[Si](C)(C)NN(C(=O)C1=CC=NC=C1)[Si](C)(C)C	1942.9	Standard polar	33892256
Isoniazid,3TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC=NC=C1)N([Si](C)(C)C)[Si](C)(C)C	1699.5	Semi standard non polar	33892256
Isoniazid,3TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC=NC=C1)N([Si](C)(C)C)[Si](C)(C)C	1786.8	Standard non polar	33892256
Isoniazid,3TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC=NC=C1)N([Si](C)(C)C)[Si](C)(C)C	1929.9	Standard polar	33892256
Isoniazid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NNC(=O)C1=CC=NC=C1	1886.6	Semi standard non polar	33892256
Isoniazid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NNC(=O)C1=CC=NC=C1	1891.7	Standard non polar	33892256
Isoniazid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NNC(=O)C1=CC=NC=C1	2287.1	Standard polar	33892256
Isoniazid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(N)C(=O)C1=CC=NC=C1	1774.1	Semi standard non polar	33892256
Isoniazid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(N)C(=O)C1=CC=NC=C1	1883.4	Standard non polar	33892256
Isoniazid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(N)C(=O)C1=CC=NC=C1	2515.1	Standard polar	33892256
Isoniazid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(NC(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C	2163.5	Semi standard non polar	33892256
Isoniazid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(NC(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C	2130.0	Standard non polar	33892256
Isoniazid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(NC(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C	2276.1	Standard polar	33892256
Isoniazid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NN(C(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C	2049.7	Semi standard non polar	33892256
Isoniazid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NN(C(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C	2095.9	Standard non polar	33892256
Isoniazid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NN(C(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C	2202.1	Standard polar	33892256
Isoniazid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=NC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2345.6	Semi standard non polar	33892256
Isoniazid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=NC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2353.0	Standard non polar	33892256
Isoniazid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=NC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2283.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isoniazid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2900000000-d379ce585203e68cb06a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoniazid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0kdr-9600000000-f04526999a9b68d31861	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoniazid LC-ESI-QQ , negative-QTOF	splash10-000i-0900000000-3cf8f43d0df46334dcd9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoniazid LC-ESI-QQ , negative-QTOF	splash10-052r-7900000000-3d43394feacded48669d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoniazid LC-ESI-QQ , negative-QTOF	splash10-004i-9000000000-263a0bcadf2e21536983	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoniazid LC-ESI-QQ , negative-QTOF	splash10-002f-9000000000-17100430370d37f834ce	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoniazid LC-ESI-QQ , negative-QTOF	splash10-0006-9000000000-9466b9291244c1a61f01	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoniazid LC-ESI-QQ , positive-QTOF	splash10-000i-0900000000-afcf227eec118bec08a4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoniazid LC-ESI-QQ , positive-QTOF	splash10-00di-1900000000-d63af1f463124dbf7b65	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoniazid LC-ESI-QQ , positive-QTOF	splash10-00fr-9600000000-1d50dedb0eea7ff8dccb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoniazid LC-ESI-QQ , positive-QTOF	splash10-004i-9100000000-371fd6d67c48f373e2e5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoniazid LC-ESI-QQ , positive-QTOF	splash10-004i-9000000000-dee0012ebd004444b3d8	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoniazid 10V, Positive-QTOF	splash10-000i-0900000000-2900848c5042f3badc64	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoniazid 20V, Positive-QTOF	splash10-000i-0900000000-aeda0fc92729a2561248	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoniazid 40V, Positive-QTOF	splash10-0zgi-9200000000-8cdf3d4be1d99712a839	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoniazid 10V, Negative-QTOF	splash10-000i-0900000000-0de7d57696bde8b4ad72	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoniazid 20V, Negative-QTOF	splash10-000i-4900000000-8760bef4d7b9a5b3360c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoniazid 40V, Negative-QTOF	splash10-056r-9100000000-7dfda590da30abf9e329	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoniazid 10V, Positive-QTOF	splash10-0a4r-0900000000-37604552ea11c4e9ae14	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoniazid 20V, Positive-QTOF	splash10-0a4i-2900000000-0fe0a0315394b81d8b4e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoniazid 40V, Positive-QTOF	splash10-0fb9-9100000000-3169da9068df634af7d4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoniazid 10V, Negative-QTOF	splash10-002r-7900000000-1e1d0995890b4dca1772	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoniazid 20V, Negative-QTOF	splash10-004i-9000000000-c2850ce6846335b0374d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoniazid 40V, Negative-QTOF	splash10-004i-9000000000-fdff89cf4c9b7fb7a653	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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	Taking drug identified by DrugBank entry DB00951	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00951	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00951

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029229

KNApSAcK ID

Not Available

Chemspider ID

3635

KEGG Compound ID

C07054

BioCyc ID

ISONIAZIDE

BiGG ID

Not Available

Wikipedia Link

Isoniazid

METLIN ID

Not Available

PubChem Compound

3767

PDB ID

NIZ

ChEBI ID

6030

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)

Download (PDF)

General References

Not Available

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

References

Upton AM, Mushtaq A, Victor TC, Sampson SL, Sandy J, Smith DM, van Helden PV, Sim E: Arylamine N-acetyltransferase of Mycobacterium tuberculosis is a polymorphic enzyme and a site of isoniazid metabolism. Mol Microbiol. 2001 Oct;42(2):309-17. [PubMed:11703656 ]

Enzyme Details

3. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

7. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

8. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. [PubMed:19754423 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

9. Cytochrome P450 2C8

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

10. Cytochrome P450 2A6

General function:: Involved in monooxygenase activity
Specific function:: Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:: CYP2A6
Uniprot ID:: P11509
Molecular weight:: 56517.005

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Showing metabocard for Isoniazid (HMDB0015086)

MOL for HMDB0015086 (Isoniazid)

3D MOL for HMDB0015086 (Isoniazid)

3D SDF for HMDB0015086 (Isoniazid)

3D-SDF for HMDB0015086 (Isoniazid)

PDB for HMDB0015086 (Isoniazid)

3D PDB for HMDB0015086 (Isoniazid)

SMILES for HMDB0015086 (Isoniazid)

INCHI for HMDB0015086 (Isoniazid)

Structure for HMDB0015086 (Isoniazid)

3D Structure for HMDB0015086 (Isoniazid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions

References

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