Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 18:57:49 UTC

Update Date

2023-02-21 17:30:14 UTC

HMDB ID

HMDB0060760

Secondary Accession Numbers

HMDB60760

Metabolite Identification

Common Name

4-Carboxypyrazole

Description

4-Carboxypyrazole belongs to the class of organic compounds known as pyrazole carboxylic acids and derivatives. These are heterocyclic compounds containing a pyrazole ring in which a hydrogen atom is replaced by a carboxylic acid group. 4-Carboxypyrazole is an extremely weak basic (essentially neutral) compound (based on its pKa). It may be used alone or in combination with hemodialysis. Fomepizole or 4-methylpyrazole is indicated for use as an antidote in confirmed or suspected methanol or ethylene glycol poisoning. 4-Carboxypyrazole is a metabolite of fomepizole. Apart from medical uses, the role of 4-methylpyrazole in coordination chemistry has been studied.

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-Carboxypyrazole	MeSH
1H-Pyrazole-4-carboxylate	Generator

Chemical Formula

C₄H₄N₂O₂

Average Molecular Weight

112.0868

Monoisotopic Molecular Weight

112.027277382

IUPAC Name

1H-pyrazole-4-carboxylic acid

Traditional Name

1H-pyrazole-4-carboxylic acid

CAS Registry Number

37718-11-9

SMILES

OC(=O)C1=CNN=C1

InChI Identifier

InChI=1S/C4H4N2O2/c7-4(8)3-1-5-6-2-3/h1-2H,(H,5,6)(H,7,8)

InChI Key

IMBBXSASDSZJSX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrazole carboxylic acids and derivatives. These are heterocyclic compounds containing a pyrazole ring in which a hydrogen atom is replaced by a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Pyrazoles

Direct Parent

Pyrazole carboxylic acids and derivatives

Alternative Parents

Substituents

Pyrazole-4-carboxylic acid or derivatives
Heteroaromatic compound
Vinylogous amide
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060760)

Organ

Kidney (HMDB: HMDB0060760)
Liver (HMDB: HMDB0060760)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060760)

Cellular substructure

Cytoplasm (HMDB: HMDB0060760)

Source

Endogenous

Endogenous (HMDB: HMDB0060760)

Process

Not Available

Role

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	75.1 g/L	ALOGPS
logP	-0.25	ALOGPS
logP	-0.065	ChemAxon
logS	-0.17	ALOGPS
pKa (Strongest Acidic)	3.43	ChemAxon
pKa (Strongest Basic)	0.94	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.98 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	27 m³·mol⁻¹	ChemAxon
Polarizability	9.52 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]+	121.514	31661259
DarkChem	[M-H]-	114.11	31661259
DeepCCS	[M+H]+	120.41	30932474
DeepCCS	[M-H]-	117.967	30932474
DeepCCS	[M-2H]-	154.265	30932474
DeepCCS	[M+Na]+	129.036	30932474
AllCCS	[M+H]+	124.8	32859911
AllCCS	[M+H-H2O]+	119.9	32859911
AllCCS	[M+NH4]+	129.3	32859911
AllCCS	[M+Na]+	130.6	32859911
AllCCS	[M-H]-	117.5	32859911
AllCCS	[M+Na-2H]-	120.1	32859911
AllCCS	[M+HCOO]-	122.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Carboxypyrazole	OC(=O)C1=CNN=C1	2721.9	Standard polar	33892256
4-Carboxypyrazole	OC(=O)C1=CNN=C1	1566.2	Standard non polar	33892256
4-Carboxypyrazole	OC(=O)C1=CNN=C1	1450.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Carboxypyrazole,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=C[NH]N=C1	1272.8	Semi standard non polar	33892256
4-Carboxypyrazole,1TMS,isomer #2	C[Si](C)(C)N1C=C(C(=O)O)C=N1	1399.4	Semi standard non polar	33892256
4-Carboxypyrazole,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CN([Si](C)(C)C)N=C1	1418.0	Semi standard non polar	33892256
4-Carboxypyrazole,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CN([Si](C)(C)C)N=C1	1513.4	Standard non polar	33892256
4-Carboxypyrazole,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CN([Si](C)(C)C)N=C1	1686.0	Standard polar	33892256
4-Carboxypyrazole,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=C[NH]N=C1	1558.2	Semi standard non polar	33892256
4-Carboxypyrazole,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C(C(=O)O)C=N1	1673.4	Semi standard non polar	33892256
4-Carboxypyrazole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CN([Si](C)(C)C(C)(C)C)N=C1	1901.0	Semi standard non polar	33892256
4-Carboxypyrazole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CN([Si](C)(C)C(C)(C)C)N=C1	1875.4	Standard non polar	33892256
4-Carboxypyrazole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CN([Si](C)(C)C(C)(C)C)N=C1	1892.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Carboxypyrazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-9500000000-94429e6e60c668ee9708	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Carboxypyrazole GC-MS (1 TMS) - 70eV, Positive	splash10-00xs-9300000000-fb5b3000bb78de3e9031	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Carboxypyrazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Carboxypyrazole 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 - 4-Carboxypyrazole 10V, Positive-QTOF	splash10-03di-5900000000-c95620fb7702b93b97a0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Carboxypyrazole 20V, Positive-QTOF	splash10-014i-9100000000-d90e95a65d0d1704d2f5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Carboxypyrazole 40V, Positive-QTOF	splash10-014i-9000000000-1459d27c4c2927b25e35	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Carboxypyrazole 10V, Negative-QTOF	splash10-03di-2900000000-fdd814e5c2c6357411fa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Carboxypyrazole 20V, Negative-QTOF	splash10-014i-9300000000-f658ca9830473cab1aa4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Carboxypyrazole 40V, Negative-QTOF	splash10-014l-9000000000-e5922deb5a7e9053cc71	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Carboxypyrazole 10V, Positive-QTOF	splash10-03di-3900000000-814e1ff85b94c8ef4862	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Carboxypyrazole 20V, Positive-QTOF	splash10-0002-9000000000-5a64beb3368c07c1d38f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Carboxypyrazole 40V, Positive-QTOF	splash10-0uxr-9000000000-1f16d7370ddb8e0833d6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Carboxypyrazole 10V, Negative-QTOF	splash10-014i-9100000000-2417dad927d8456785f1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Carboxypyrazole 20V, Negative-QTOF	splash10-014i-9000000000-d62018a6f02c7e00f542	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Carboxypyrazole 40V, Negative-QTOF	splash10-014i-9000000000-fd4be05796346b274006	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

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3015937

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

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 4-Carboxypyrazole (HMDB0060760)

MOL for HMDB0060760 (4-Carboxypyrazole)

3D MOL for HMDB0060760 (4-Carboxypyrazole)

3D SDF for HMDB0060760 (4-Carboxypyrazole)

3D-SDF for HMDB0060760 (4-Carboxypyrazole)

PDB for HMDB0060760 (4-Carboxypyrazole)

3D PDB for HMDB0060760 (4-Carboxypyrazole)

SMILES for HMDB0060760 (4-Carboxypyrazole)

INCHI for HMDB0060760 (4-Carboxypyrazole)

Structure for HMDB0060760 (4-Carboxypyrazole)

3D Structure for HMDB0060760 (4-Carboxypyrazole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra