7-nitro-1H-indole-2-carboxylic acid

• ChemBase ID: 34854
• Molecular Formular: C9H6N2O4
• Molecular Mass: 206.15494
• Monoisotopic Mass: 206.03275668
• SMILES: [nH]1c2c([N+](=O)[O-])cccc2cc1C(=O)O
• Canonical SMILES: [O-][N+](=O)c1cccc2c1[nH]c(c2)C(=O)O
• InChI: InChI=1S/C9H6N2O4/c12-9(13)6-4-5-2-1-3-7(11(14)15)8(5)10-6/h1-4,10H,(H,12,13)
• InChIKey: BIUCOFQROHIAEO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-nitro-1H-indole-2-carboxylic acid
• IUPAC Traditional name: 7-nitro-1H-indole-2-carboxylic acid
• Synonyms: 7-Nitro-1H-indole-2-carboxylic acid; CRT0044876; 7-Nitro-1H-indole-2-carboxylic acid; 7-Nitroindole-2carboxylic acid; NSC 69877; CRT0044876; 7-Nitroindole-2-carboxylic acid 95%+; 7-Nitroindole-2-carboxylic acid; 7-硝基吲哚-2-甲酸

Database IDs

• CAS Number: 6960-45-8
• EC Number: 230-154-6
• MDL Number: MFCD00044720
• PubChem SID: 160998161
• PubChem CID: 81409

CALCULATED PROPERTIES

• Acid pKa: 3.54645
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.3573947
• LogD (pH = 7.4): -1.7712691
• Log P: 1.589576
• Molar Refractivity: 50.5987 cm^3
• Polarizability: 19.784101 Å^3
• Polar Surface Area: 96.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: powder
• Melting Point: 249 - 251°C; 264-266°C
• Hydrophobicity(logP): 2.115

Safety Information

• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; 36-43
• Safety Statements: 26-36/37; 26-37
• TSCA Listed: false; 是
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H319-H335; H319-H334
• GHS Precautionary statements: P261-P305 + P351 + P338-P342 + P311; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: room temp

Pharmacology Properties

• Target: DNA/RNA Synthesis

Product Information

• Purity: ≥98% (HPLC); 90%; 95%; 96%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C9H6N2O4

DETAILS

Sigma Aldrich - C0496

Biochem/physiol Actions
CRT0044876 targets the apurinic endonuclease (APE1) active site and inhibits its 3′-phosphodiesterase and 3′-phosphatase activities-essential steps in excision repair-with minimal effects on endonuclease IV, BamH1 restriction endonuclease, or topoisomerase I even at concentrations as high as 100 μM. At non-cytotoxic concentrations, CRT0044876 potentiates the cytotoxicity of several DNA base-targeting compounds, with accumulation of apurinic sites.