Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:30 UTC

Update Date

2023-02-21 17:16:01 UTC

HMDB ID

HMDB0001978

Secondary Accession Numbers

HMDB01978

Metabolite Identification

Common Name

5-Hydroxypyrazinamide

Description

Pyrazinamide. Pyrazinamide is a drug used to treat tuberculosis in afflicted patients. The drug is largely bacteriostatic, but can be bacteriocidal on actively replicating tuberculosis bacteria. -- Wikipedia; Pyrazinamide is a generic drug and is available in a wide variety of presentations. Pyrazinamide tablets are usually 500mg and form the bulkiest part of the standard tuberculosis treatment regimen. Pyrazinamide tablets are so large that some patients find them impossible to swallow: pyrazinamide syrup is an option for these patients. -- Wikipedia; Pyrazinamide is also available as part of fixed dose combinations with other TB drugs such as isoniazid and rifampicin (Rifater is an example). -- Wikipedia; Pyrazinamide is well absorbed orally. It crosses inflamed meninges and is an essential part of the treatment of tuberculous meningitis. It is metabolised by the liver and the metabolic products are excreted by the kidneys. -- Wikipedia; Pyrazinamide is a pro-drug that stops the growth of Mycobacterium tuberculosis. M. tuberculosis has the enzyme pyrazinamidase which is only active at acidic pH. Pyrazinamidase converts pyrazinamide to the active form, pyrazinoic acid. Pyrazinoic acid inhibits the enzyme fatty acid synthetase I, which is required by the bacterium to synthesise fatty acids. Mutations of the pyrazinamidase gene (pncA) are responsible for pyrazinamide resistance in M. tuberculosis. -- Wikipedia.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-carboxamido-5-Hydroxypyrazine	HMDB
5-Hydroxy-(8ci)-pyrazinecarboxamide	HMDB
5-Hydroxypyrazinecarboxamide	HMDB
5-oxo-4,5-Dihydropyrazine-2-carboximidate	Generator, HMDB
5-Hydroxypyrazinamide	MeSH

Chemical Formula

C₅H₅N₃O₂

Average Molecular Weight

139.1121

Monoisotopic Molecular Weight

139.038176419

IUPAC Name

5-oxo-4,5-dihydropyrazine-2-carboxamide

Traditional Name

5-oxo-4H-pyrazine-2-carboxamide

CAS Registry Number

13924-96-4

SMILES

NC(=O)C1=CNC(=O)C=N1

InChI Identifier

InChI=1S/C5H5N3O2/c6-5(10)3-1-8-4(9)2-7-3/h1-2H,(H2,6,10)(H,8,9)

InChI Key

XENWQEOTDAQROM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrazinecarboxamides. Pyrazinecarboxamides are compounds containing a pyrazine ring which bears a carboxamide.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrazines

Direct Parent

Pyrazinecarboxamides

Alternative Parents

Substituents

Pyrazinecarboxamide
2-heteroaryl carboxamide
Heteroaromatic compound
Vinylogous amide
Carboxamide group
Lactam
Primary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0001978)

Source

Endogenous

Endogenous (HMDB: HMDB0001978)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Biological role

Drug metabolite (HMDB: HMDB0001978)

Physical Properties

State

Solid

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	6.95 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-1.5	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	84.55 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	33.71 m³·mol⁻¹	ChemAxon
Polarizability	12.05 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]+	128.361	31661259
DarkChem	[M-H]-	122.165	31661259
AllCCS	[M+H]+	129.952	32859911
AllCCS	[M-H]-	124.832	32859911
DeepCCS	[M+H]+	126.633	30932474
DeepCCS	[M-H]-	122.804	30932474
DeepCCS	[M-2H]-	160.216	30932474
DeepCCS	[M+Na]+	135.729	30932474
AllCCS	[M+H]+	130.0	32859911
AllCCS	[M+H-H2O]+	125.4	32859911
AllCCS	[M+NH4]+	134.2	32859911
AllCCS	[M+Na]+	135.5	32859911
AllCCS	[M-H]-	124.8	32859911
AllCCS	[M+Na-2H]-	126.5	32859911
AllCCS	[M+HCOO]-	128.4	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.	1.63 minutes	32390414
Predicted by Siyang on May 30, 2022	8.9944 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.54 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	173.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	659.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	329.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	69.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	210.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	49.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	262.1 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	289.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	471.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	592.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	87.8 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	799.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	194.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	220.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	617.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	322.5 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	262.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxypyrazinamide	NC(=O)C1=CNC(=O)C=N1	2157.0	Standard polar	33892256
5-Hydroxypyrazinamide	NC(=O)C1=CNC(=O)C=N1	1442.5	Standard non polar	33892256
5-Hydroxypyrazinamide	NC(=O)C1=CNC(=O)C=N1	1786.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxypyrazinamide,1TMS,isomer #1	C[Si](C)(C)NC(=O)C1=C[NH]C(=O)C=N1	1739.4	Semi standard non polar	33892256
5-Hydroxypyrazinamide,1TMS,isomer #1	C[Si](C)(C)NC(=O)C1=C[NH]C(=O)C=N1	1754.2	Standard non polar	33892256
5-Hydroxypyrazinamide,1TMS,isomer #1	C[Si](C)(C)NC(=O)C1=C[NH]C(=O)C=N1	2619.4	Standard polar	33892256
5-Hydroxypyrazinamide,1TMS,isomer #2	C[Si](C)(C)N1C=C(C(N)=O)N=CC1=O	1731.1	Semi standard non polar	33892256
5-Hydroxypyrazinamide,1TMS,isomer #2	C[Si](C)(C)N1C=C(C(N)=O)N=CC1=O	1744.6	Standard non polar	33892256
5-Hydroxypyrazinamide,1TMS,isomer #2	C[Si](C)(C)N1C=C(C(N)=O)N=CC1=O	2728.7	Standard polar	33892256
5-Hydroxypyrazinamide,2TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=C[NH]C(=O)C=N1)[Si](C)(C)C	1797.0	Semi standard non polar	33892256
5-Hydroxypyrazinamide,2TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=C[NH]C(=O)C=N1)[Si](C)(C)C	1815.2	Standard non polar	33892256
5-Hydroxypyrazinamide,2TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=C[NH]C(=O)C=N1)[Si](C)(C)C	2442.1	Standard polar	33892256
5-Hydroxypyrazinamide,2TMS,isomer #2	C[Si](C)(C)NC(=O)C1=CN([Si](C)(C)C)C(=O)C=N1	1795.5	Semi standard non polar	33892256
5-Hydroxypyrazinamide,2TMS,isomer #2	C[Si](C)(C)NC(=O)C1=CN([Si](C)(C)C)C(=O)C=N1	1892.7	Standard non polar	33892256
5-Hydroxypyrazinamide,2TMS,isomer #2	C[Si](C)(C)NC(=O)C1=CN([Si](C)(C)C)C(=O)C=N1	2485.3	Standard polar	33892256
5-Hydroxypyrazinamide,3TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CN([Si](C)(C)C)C(=O)C=N1)[Si](C)(C)C	1874.2	Semi standard non polar	33892256
5-Hydroxypyrazinamide,3TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CN([Si](C)(C)C)C(=O)C=N1)[Si](C)(C)C	1963.0	Standard non polar	33892256
5-Hydroxypyrazinamide,3TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CN([Si](C)(C)C)C(=O)C=N1)[Si](C)(C)C	2172.5	Standard polar	33892256
5-Hydroxypyrazinamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=C[NH]C(=O)C=N1	1966.4	Semi standard non polar	33892256
5-Hydroxypyrazinamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=C[NH]C(=O)C=N1	1980.1	Standard non polar	33892256
5-Hydroxypyrazinamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=C[NH]C(=O)C=N1	2748.0	Standard polar	33892256
5-Hydroxypyrazinamide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C(C(N)=O)N=CC1=O	1994.6	Semi standard non polar	33892256
5-Hydroxypyrazinamide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C(C(N)=O)N=CC1=O	1936.7	Standard non polar	33892256
5-Hydroxypyrazinamide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C(C(N)=O)N=CC1=O	2806.6	Standard polar	33892256
5-Hydroxypyrazinamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=C[NH]C(=O)C=N1)[Si](C)(C)C(C)(C)C	2251.1	Semi standard non polar	33892256
5-Hydroxypyrazinamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=C[NH]C(=O)C=N1)[Si](C)(C)C(C)(C)C	2242.3	Standard non polar	33892256
5-Hydroxypyrazinamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=C[NH]C(=O)C=N1)[Si](C)(C)C(C)(C)C	2542.1	Standard polar	33892256
5-Hydroxypyrazinamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)C1=CN([Si](C)(C)C(C)(C)C)C(=O)C=N1	2242.0	Semi standard non polar	33892256
5-Hydroxypyrazinamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)C1=CN([Si](C)(C)C(C)(C)C)C(=O)C=N1	2276.9	Standard non polar	33892256
5-Hydroxypyrazinamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)C1=CN([Si](C)(C)C(C)(C)C)C(=O)C=N1	2635.7	Standard polar	33892256
5-Hydroxypyrazinamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CN([Si](C)(C)C(C)(C)C)C(=O)C=N1)[Si](C)(C)C(C)(C)C	2523.3	Semi standard non polar	33892256
5-Hydroxypyrazinamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CN([Si](C)(C)C(C)(C)C)C(=O)C=N1)[Si](C)(C)C(C)(C)C	2554.4	Standard non polar	33892256
5-Hydroxypyrazinamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CN([Si](C)(C)C(C)(C)C)C(=O)C=N1)[Si](C)(C)C(C)(C)C	2444.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 5-Hydroxypyrazinamide EI-B (Non-derivatized)	splash10-004v-9100000000-f3668d75358f611d3aea	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5-Hydroxypyrazinamide EI-B (Non-derivatized)	splash10-004v-9100000000-f3668d75358f611d3aea	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxypyrazinamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-059j-9600000000-eed6c6621ac175ebc06f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxypyrazinamide 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 - 5-Hydroxypyrazinamide 10V, Positive-QTOF	splash10-0006-0900000000-4a9bb4436286b18b224f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxypyrazinamide 20V, Positive-QTOF	splash10-00dj-3900000000-aa768b447648d6760f3d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxypyrazinamide 40V, Positive-QTOF	splash10-0kxr-9000000000-9af022e71bfdc81b06ad	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxypyrazinamide 10V, Negative-QTOF	splash10-000i-2900000000-b93be6c1c350e992bfab	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxypyrazinamide 20V, Negative-QTOF	splash10-01pc-5900000000-08d30dda33dea090dd13	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxypyrazinamide 40V, Negative-QTOF	splash10-0006-9000000000-7932fdb1240ebaf3eef5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxypyrazinamide 10V, Positive-QTOF	splash10-006x-0900000000-f65eddb5dd85983512f2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxypyrazinamide 20V, Positive-QTOF	splash10-0002-9200000000-97da033a62736d0386e8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxypyrazinamide 40V, Positive-QTOF	splash10-00kg-9000000000-493cc79bdf78b0bf3112	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxypyrazinamide 10V, Negative-QTOF	splash10-000b-9500000000-a9e59e0dfcd47dd21c3d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxypyrazinamide 20V, Negative-QTOF	splash10-01pd-9800000000-682ec3f0b7fd06e49819	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxypyrazinamide 40V, Negative-QTOF	splash10-0006-9000000000-90a8705015cfb3328f31	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB022776

KNApSAcK ID

Not Available

Chemspider ID

133812

KEGG Compound ID

C01956

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6413

PubChem Compound

151823

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Moriwaki Y; Yamamoto T; Nasako Y; Takahashi S; Suda M; Hiroishi K; Hada T; Higashino K In vitro oxidation of pyrazinamide and allopurinol by rat liver aldehyde oxidase. Biochemical pharmacology (1993), 46(6), 975-81.

Material Safety Data Sheet (MSDS)

Not Available

General References

Lacroix C, Poncet P, Laine G, Guyonnaud C, Ray M, Menager S, Lafont O: [Microdetermination of pyrazinamide and its metabolites (pyrazinoic acid, 5-hydroxypyrazinoic acid, 5-hydroxypyrazinamide and pyrazinuric acid) in plasma and urine with liquid chromatography]. J Chromatogr. 1987 Nov 27;422:217-25. [PubMed:3437007 ]

Enzymes

Enzyme Details

1. Xanthine dehydrogenase/oxidase

General function:: Involved in oxidoreductase activity
Specific function:: Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:: XDH
Uniprot ID:: P47989
Molecular weight:: 146422.99

References

Yamamoto T, Moriwaki Y, Takahashi S, Hada T, Higashino K: In vitro conversion of pyrazinamide into 5-hydroxypyrazinamide and that of pyrazinoic acid into 5-hydroxypyrazinoic acid by xanthine oxidase from human liver. Biochem Pharmacol. 1987 Oct 1;36(19):3317-8. [PubMed:3663245 ]

Showing metabocard for 5-Hydroxypyrazinamide (HMDB0001978)

MOL for HMDB0001978 (5-Hydroxypyrazinamide)

3D MOL for HMDB0001978 (5-Hydroxypyrazinamide)

3D SDF for HMDB0001978 (5-Hydroxypyrazinamide)

3D-SDF for HMDB0001978 (5-Hydroxypyrazinamide)

PDB for HMDB0001978 (5-Hydroxypyrazinamide)

3D PDB for HMDB0001978 (5-Hydroxypyrazinamide)

SMILES for HMDB0001978 (5-Hydroxypyrazinamide)

INCHI for HMDB0001978 (5-Hydroxypyrazinamide)

Structure for HMDB0001978 (5-Hydroxypyrazinamide)

3D Structure for HMDB0001978 (5-Hydroxypyrazinamide)

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

References