Isonicotinic acid

Details

• Internal ID: f31595d2-fbb3-4d03-af2d-d91d471363ab
• Taxonomy: Organoheterocyclic compounds > Pyridines and derivatives > Pyridinecarboxylic acids and derivatives > Pyridinecarboxylic acids
• IUPAC Name: pyridine-4-carboxylic acid
• SMILES (Canonical): C1=CN=CC=C1C(=O)O
• SMILES (Isomeric): C1=CN=CC=C1C(=O)O
• InChI: InChI=1S/C6H5NO2/c8-6(9)5-1-3-7-4-2-5/h1-4H,(H,8,9)
• InChI Key: TWBYWOBDOCUKOW-UHFFFAOYSA-N
• Popularity: 2,433 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₅NO₂
• Molecular Weight: 123.11 g/mol
• Exact Mass: 123.032028402 g/mol
• Topological Polar Surface Area (TPSA): 50.20 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 0.78
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 55-22-1
• Pyridine-4-carboxylic acid
• 4-Pyridinecarboxylic acid
• 4-Picolinic acid
• 4-Carboxypyridine
• p-Pyridinecarboxylic acid
• gamma-Picolinic acid
• gamma-Pyridinecarboxylic acid
• .gamma.-Picolinic acid
• Acide iso-nicotinique
• 1,4-Dihydroisonicotinic acid
• Acide iso-nicotinique [French]
• MFCD00006429
• AI3-19239
• isonicotinic-d4 acid
• NSC 1483
• NSC-1483
• EINECS 200-228-2
• UNII-Y8SYN761TQ
• Y8SYN761TQ
• .gamma.-pyridinecarboxylic acid
• CHEBI:6032
• DTXSID8020757
• Pyridine-4-carboxylic Acid (Isonicotinic Acid)
• 163751-04-0
• isonicotinicacid
• isonicotinsyre-
• isonicotonic acid
• MN1
• S3V
• .alpha.-Picolinic acid
• Isonicotinic acid, 99%
• 4-pyridine-carboxylic acid
• Biomol-NT_000289
• bmse000133
• D0W5CQ
• SCHEMBL1108
• CHEMBL1203
• Pyridinecarboxylic acid-(4)
• Oprea1_749724
• DTXCID80757
• ISONICOTINIC ACID [MI]
• BPBio1_001365
• NSC1483
• ISONICOTINIC ACID [WHO-DD]
• HY-I0736
• STR00113
• Tox21_200502
• AC8088
• s6014
• STL168892
• AKOS000118918
• AB00757
• AM81318
• BS-3754
• CS-W020040
• LS-7134
• CAS-55-22-1
• NCGC00163295-01
• NCGC00163295-02
• NCGC00258056-01
• SY002246
• ISONIAZID IMPURITY A [EP IMPURITY]
• Isonicotinic acid, purum, >=99.0% (T)
• FT-0627426
• FT-0627428
• FT-0627430
• I0207
• EN300-19169
• C07446
• Isonicotinic acid, SAJ special grade, >=99.0%
• A830537
• AC-907/25014347
• Q410465
• W-105578
• F2191-0075
• InChI=1/C6H5NO2/c8-6(9)5-1-3-7-4-2-5/h1-4H,(H,8,9
• Isonicotinic acid; Isoniazid, 4-pyridinecarboxylic acid, p-pyridinecarboxylic acid, 4-Picolinic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9917	99.17%
Caco-2	+	0.9162	91.62%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.8857	88.57%
Subcellular localzation	Mitochondria	0.7912	79.12%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9779	97.79%
OATP1B3 inhibitior	+	0.9677	96.77%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9380	93.80%
P-glycoprotein inhibitior	-	0.9888	98.88%
P-glycoprotein substrate	-	0.9943	99.43%
CYP3A4 substrate	-	0.8755	87.55%
CYP2C9 substrate	-	0.8533	85.33%
CYP2D6 substrate	-	0.9128	91.28%
CYP3A4 inhibition	-	0.8670	86.70%
CYP2C9 inhibition	-	0.9298	92.98%
CYP2C19 inhibition	-	0.9162	91.62%
CYP2D6 inhibition	-	0.8932	89.32%
CYP1A2 inhibition	-	0.9072	90.72%
CYP2C8 inhibition	-	0.7781	77.81%
CYP inhibitory promiscuity	-	0.9828	98.28%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6655	66.55%
Carcinogenicity (trinary)	Non-required	0.6938	69.38%
Eye corrosion	-	0.6846	68.46%
Eye irritation	+	1.0000	100.00%
Skin irritation	+	0.9749	97.49%
Skin corrosion	+	0.5591	55.91%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9389	93.89%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.6794	67.94%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	-	0.6778	67.78%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.6017	60.17%
Acute Oral Toxicity (c)	IV	0.6635	66.35%
Estrogen receptor binding	-	0.9214	92.14%
Androgen receptor binding	-	0.9263	92.63%
Thyroid receptor binding	-	0.8199	81.99%
Glucocorticoid receptor binding	-	0.9300	93.00%
Aromatase binding	-	0.8272	82.72%
PPAR gamma	-	0.8807	88.07%
Honey bee toxicity	-	0.9912	99.12%
Biodegradation	+	0.7750	77.50%
Crustacea aquatic toxicity	-	0.8900	89.00%
Fish aquatic toxicity	-	0.8808	88.08%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4523354	Q6XQN6	Nicotinate phosphoribosyltransferase	0.75 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293277	O15118	Niemann-Pick C1 protein	93.88%	81.11%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	88.63%	87.67%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	87.47%	96.47%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.32%	86.33%
CHEMBL4040	P28482	MAP kinase ERK2	83.99%	83.82%

Plants that contains it

• Aloe africana
• Aloe ferox
• Aloe spicata
• Aloe vera
• Arabidopsis thaliana

Cross-Links

• PubChem: 5922
• NPASS: NPC114310
• LOTUS: LTS0034414
• wikiData: Q410465