Jump To Section:

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

Show more...Show more...Show more...Show more...

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-18 18:41:54 UTC

Update Date

2023-02-21 17:30:08 UTC

HMDB ID

HMDB0060665

Secondary Accession Numbers

HMDB60665

Metabolite Identification

Common Name

Isonicotinic acid

Description

Isonicotinic acid, also known as 4-carboxypyridine or gamma-picolinic acid, belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. Isonicotinic acid is a moderately basic compound (based on its pKa). Isonicotinic acid is an organic compound with a carboxyl group on a pyridine ring. The carboxyl group for isonicotinic acid is on the 4-position instead of the 3-position for nicotinic acid (Wikipedia ). It is an isomer of nicotinic acid. Isonicotinic acid is a metabolite of isoniazid.

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-Carboxypyridine	ChEBI
4-Pyridinecarboxylic acid	ChEBI
gamma-Picolinic acid	ChEBI
gamma-Pyridinecarboxylic acid	ChEBI
p-Pyridinecarboxylic acid	ChEBI
4-Pyridinecarboxylate	Generator
g-Picolinate	Generator
g-Picolinic acid	Generator
gamma-Picolinate	Generator
Γ-picolinate	Generator
Γ-picolinic acid	Generator
g-Pyridinecarboxylate	Generator
g-Pyridinecarboxylic acid	Generator
gamma-Pyridinecarboxylate	Generator
Γ-pyridinecarboxylate	Generator
Γ-pyridinecarboxylic acid	Generator
p-Pyridinecarboxylate	Generator
Isonicotinate	Generator
Acid, isonicotinic	HMDB
Acids, isonicotinic	HMDB
Isonicotinic acids	HMDB

Chemical Formula

C₆H₅NO₂

Average Molecular Weight

123.1094

Monoisotopic Molecular Weight

123.032028409

IUPAC Name

pyridine-4-carboxylic acid

Traditional Name

isonicotinic acid

CAS Registry Number

55-22-1

SMILES

OC(=O)C1=CC=NC=C1

InChI Identifier

InChI=1S/C6H5NO2/c8-6(9)5-1-3-7-4-2-5/h1-4H,(H,8,9)

InChI Key

TWBYWOBDOCUKOW-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinecarboxylic acids and derivatives

Direct Parent

Pyridinecarboxylic acids

Alternative Parents

Substituents

Pyridine carboxylic acid
Heteroaromatic compound
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

pyridinemonocarboxylic acid (CHEBI:6032 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060665)

Organ

Liver (HMDB: HMDB0060665)
Kidney (HMDB: HMDB0060665)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060665)

Source

Exogenous

Exogenous (HMDB: HMDB0060665)

Endogenous

Endogenous (HMDB: HMDB0060665)

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	68.1 g/L	ALOGPS
logP	0.28	ALOGPS
logP	0.15	ChemAxon
logS	-0.26	ALOGPS
pKa (Strongest Acidic)	3.73	ChemAxon
pKa (Strongest Basic)	2.35	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.19 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	31.16 m³·mol⁻¹	ChemAxon
Polarizability	11.29 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]+	124.976	31661259
DarkChem	[M-H]-	117.433	31661259
DeepCCS	[M+H]+	124.218	30932474
DeepCCS	[M-H]-	121.149	30932474
DeepCCS	[M-2H]-	157.924	30932474
DeepCCS	[M+Na]+	133.049	30932474
AllCCS	[M+H]+	125.4	32859911
AllCCS	[M+H-H2O]+	120.6	32859911
AllCCS	[M+NH4]+	130.0	32859911
AllCCS	[M+Na]+	131.3	32859911
AllCCS	[M-H]-	121.0	32859911
AllCCS	[M+Na-2H]-	123.0	32859911
AllCCS	[M+HCOO]-	125.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isonicotinic acid	OC(=O)C1=CC=NC=C1	1970.9	Standard polar	33892256
Isonicotinic acid	OC(=O)C1=CC=NC=C1	1275.5	Standard non polar	33892256
Isonicotinic acid	OC(=O)C1=CC=NC=C1	1235.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isonicotinic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=NC=C1	1273.1	Semi standard non polar	33892256
Isonicotinic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=NC=C1	1523.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Isonicotinic acid GC-EI-TOF (Non-derivatized)	splash10-053r-0900000000-0e8b37e56297b7672e67	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isonicotinic acid GC-EI-TOF (Non-derivatized)	splash10-0540-0900000000-0673678e5fc7980445bd	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isonicotinic acid GC-EI-TOF (Non-derivatized)	splash10-0569-5900000000-26eb2a99def38d4a22c8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isonicotinic acid GC-EI-TOF (Non-derivatized)	splash10-053r-0900000000-0e8b37e56297b7672e67	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isonicotinic acid GC-EI-TOF (Non-derivatized)	splash10-0540-0900000000-0673678e5fc7980445bd	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isonicotinic acid GC-EI-TOF (Non-derivatized)	splash10-0569-5900000000-26eb2a99def38d4a22c8	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isonicotinic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-7900000000-0cb296f8039d0be2482a	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isonicotinic acid GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-9600000000-b1182d94bed173f36102	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isonicotinic acid 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isonicotinic acid LC-ESI-QTOF , negative-QTOF	splash10-004i-9300000000-5aefad19534388180436	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isonicotinic acid LC-ESI-QQ , positive-QTOF	splash10-0ab9-0900000000-3f8ad29d172aa06e19c6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isonicotinic acid LC-ESI-QQ , positive-QTOF	splash10-00di-4900000000-04ecd2ded01bc6f9b466	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isonicotinic acid LC-ESI-QQ , positive-QTOF	splash10-001j-9100000000-b7a02f2f133138354546	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isonicotinic acid LC-ESI-QQ , positive-QTOF	splash10-003r-9000000000-ee099e60544c0326fdb7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isonicotinic acid LC-ESI-QQ , positive-QTOF	splash10-00os-9000020000-f6daab3d1a982cfd35ec	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isonicotinic acid LC-ESI-QTOF , positive-QTOF	splash10-00di-4900000000-c7fa977839a809bc26c9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isonicotinic acid LC-ESI-QTOF , positive-QTOF	splash10-003s-9100000000-187ccf119a0f683d93d0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isonicotinic acid 30V, Positive-QTOF	splash10-003s-9100000000-187ccf119a0f683d93d0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isonicotinic acid 10V, Positive-QTOF	splash10-00di-0900000000-f4662ceafd587b9b6077	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isonicotinic acid 40V, Positive-QTOF	splash10-0ugi-9000000000-8e1d2e76371c68d4ffd2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isonicotinic acid 20V, Positive-QTOF	splash10-008a-9300000000-b2562aafef5b27aaf06f	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonicotinic acid 10V, Positive-QTOF	splash10-00di-0900000000-86289259e4a7d42b1524	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonicotinic acid 20V, Positive-QTOF	splash10-00di-2900000000-ac2510c19cbda2467e17	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonicotinic acid 40V, Positive-QTOF	splash10-0ue9-9100000000-96f139c16425aa89406b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonicotinic acid 10V, Negative-QTOF	splash10-00di-3900000000-5d743650a7f30a929686	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonicotinic acid 20V, Negative-QTOF	splash10-00b9-9500000000-e02450efac27b686ff39	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonicotinic acid 40V, Negative-QTOF	splash10-004i-9000000000-2a4f9a6c9a5c17833568	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonicotinic acid 10V, Positive-QTOF	splash10-05ai-6900000000-354dfc313106a4b42d69	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonicotinic acid 20V, Positive-QTOF	splash10-0a4i-5900000000-4b667bfa85606aed0c8f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonicotinic acid 40V, Positive-QTOF	splash10-004i-9000000000-a99a61d126a314ed38dd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonicotinic acid 10V, Negative-QTOF	splash10-004i-9000000000-c2850ce6846335b0374d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonicotinic acid 20V, Negative-QTOF	splash10-004i-9000000000-c2850ce6846335b0374d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isonicotinic acid 40V, Negative-QTOF	splash10-004i-9000000000-c2850ce6846335b0374d	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

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

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

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

C07446

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Isonicotinic_Acid

METLIN ID

Not Available

PubChem Compound

5922

PDB ID

Not Available

ChEBI ID

6032

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 Isonicotinic acid (HMDB0060665)

MOL for HMDB0060665 (Isonicotinic acid)

3D MOL for HMDB0060665 (Isonicotinic acid)

3D SDF for HMDB0060665 (Isonicotinic acid)

3D-SDF for HMDB0060665 (Isonicotinic acid)

PDB for HMDB0060665 (Isonicotinic acid)

3D PDB for HMDB0060665 (Isonicotinic acid)

SMILES for HMDB0060665 (Isonicotinic acid)

INCHI for HMDB0060665 (Isonicotinic acid)

Structure for HMDB0060665 (Isonicotinic acid)

3D Structure for HMDB0060665 (Isonicotinic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra