pyridine-2,3-dicarboxylic acid

• ChemBase ID: 1567
• Molecular Formular: C7H5NO4
• Molecular Mass: 167.1189
• Monoisotopic Mass: 167.02185765
• SMILES: OC(=O)c1cccnc1C(=O)O
• Canonical SMILES: OC(=O)c1ncccc1C(=O)O
• InChI: InChI=1S/C7H5NO4/c9-6(10)4-2-1-3-8-5(4)7(11)12/h1-3H,(H,9,10)(H,11,12)
• InChIKey: GJAWHXHKYYXBSV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: pyridine-2,3-dicarboxylic acid
• IUPAC Traditional name: pyridine-2,3-dicarboxylic acid; quinolinic acid
• Synonyms: Pyridine-2,3-dicarboxylic acid; Quinolinic acid; 2,3-Pyridinedicarboxylic acid; 2,3-Pyridinedicarboxylic acid; Pyridine-2,3-dicarboxylic acid; Pyridine-2,3-dicarboxylic Acid; Pyridin-2,3-dicarbonsaeure; NSC 13127; NSC 18836; NSC 403247; 3,4-Pyridinedicarboxylic acid; CINCHOMERONIC ACID; 2,3-PYRIDINEDICARBOXYLIC ACID; Quinolinic Acid; 喹啉酸; 2,3-吡啶二甲酸; 吡啶-2,3-二甲酸

Database IDs

• CAS Number: 490-11-9; 89-00-9
• EC Number: 207-705-4; 201-874-8
• MDL Number: MFCD00006295
• Beilstein Number: 137110
• Merck Index: 148073
• PubChem SID: 24278005; 24853597; 160965024; 46505240
• PubChem CID: 1066
• CHEMBL: 286204
• Wikipedia Title: Quinolinic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.2932245
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -2.5607035
• LogD (pH = 7.4): -5.385913
• Log P: -0.5431572
• Molar Refractivity: 38.0415 cm^3
• Polarizability: 14.278031 Å^3
• Polar Surface Area: 87.49 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.15
• LOG S: -1.61
• Solubility (Water): 4.07e+00 g/l

PROPERTIES

Physical Property

• Solubility: 11 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; Dimethyl Sulfoxide
• Apperance: White To Off-White Solid
• Melting Point: ~185 °C (dec.); >190°C (dec); 185–190 °C (dec.); 188-190 °C (dec.)(lit.); ca 188°C(dec); ca 188°C dec.

Safety Information

• Storage Condition: 0°C
• Storage Warning: IRRITANT
• RTECS: US7967250
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37; 26-37
• TSCA Listed: true; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: rat ... Gria1(50592), Grin2a(24409)

Product Information

• Purity: ≥99.0% (T); 97%; 98%; 99%; 99-100%
• Grade: puriss.
• Ignition Residue: ≤0.05%
• Empirical Formula (Hill Notation): C7H5NO4
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 02150688

Crystalline
Purity: 97%

MP Biomedicals - 02150153

Crystalline
Purity: 99-100%
Inhibits glucose synthesis.

MP Biomedicals - 05217635

MP Biomedicals Rare Chemical collection

DrugBank - DB01796

• Drug Groups: experimental
• Description: A metabolite of tryptophan with a possible role in neurodegenerative disorders. Elevated CSF levels of quinolinic acid are correlated with the severity of neuropsychological deficits in patients who have AIDS. [PubChem]

Toronto Research Chemicals - P991630

An inhibitor of glucose synthesis.

Sigma Aldrich - P63204

Packaging
25, 100 g in poly bottle
Application
Inhibits glucose synthesis.1
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. P63204.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

REFERENCES

• Martirosyan, A., et al.: Biochem. Pharmacol., 68, 1729 (2004)