1H-indole-5-carboxamide

• ChemBase ID: 140859
• Molecular Formular: C9H8N2O
• Molecular Mass: 160.17262
• Monoisotopic Mass: 160.06366289
• SMILES: c1cc2c(cc[nH]2)cc1C(=O)N
• Canonical SMILES: NC(=O)c1ccc2c(c1)cc[nH]2
• InChI: InChI=1S/C9H8N2O/c10-9(12)7-1-2-8-6(5-7)3-4-11-8/h1-5,11H,(H2,10,12)
• InChIKey: GQMYQEAXTITUAE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1H-indole-5-carboxamide
• IUPAC Traditional name: indole-5-carboxamide
• Synonyms: 5-(Aminocarbonyl)-1H-indole; 5-Carbamoylindole; 5-Carboxamidoindole; 1H-Indole-5-carboxamide; indole-5-carboxamide; SD-169; SD 169; 1H-Indole-5-carboxamide; 5-(氨基羰基)-1H-吲哚; 5-氨基甲酰吲哚; 5-羧酰氨基吲哚; 1H-吲哚-5-甲酰胺

Database IDs

• CAS Number: 1670-87-7
• MDL Number: MFCD07779486
• PubChem SID: 24885716; 24724600; 162235097
• PubChem CID: 14973220

CALCULATED PROPERTIES

• Acid pKa: 14.530005
• H Acceptors: 1
• H Donor: 2
• LogD (pH = 5.5): 0.922648
• LogD (pH = 7.4): 0.92264813
• Log P: 0.92264813
• Molar Refractivity: 46.2229 cm^3
• Polarizability: 18.373056 Å^3
• Polar Surface Area: 58.88 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ~18 mg/mL; H2O: <2 mg/mL
• Apperance: white solid
• Melting Point: 159-163 °C

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC); 97%
• Empirical Formula (Hill Notation): C9H8N2O

DETAILS

Sigma Aldrich - S0572

Biochem/physiol Actions
SD-169 is an orally active, ATP-competitve, p38α-selective Mitogen-Activated Protein Kinase (MAPK) inhibitor. SD-169 demonstrates 38-fold potency against p38α MAP kinase (IC50 = 3.2 nM) than p38β MAP kinase (IC50 = 122 nM).

Sigma Aldrich - 682497

Packaging
1 g in glass bottle
Application

• Used for preparation of potential fructose bisphosphatase inhibitors1
• Reactant for preparation of (indolylamino)thienopyridine-carbonitriles using substitution and Suzuki cross-coupling as potential protein kinase Cθ inhibitors2
• Reactant for preparation of 5-substituted 3-(1′,2′,5′,6′-tetrahydropyridin-3′-yl) indoles as serotonin receptor binding agents3

Toronto Research Chemicals - I615500

1H-Indole-5-carboxamide (SD-169) is a p38α MAPK-selective inhibitor. 1H-Indole-5-carboxamide (SD-169) prevents the development and progression of diabetes in nonobese diabetic (NOD) mice by inhibiting T cell infiltration and activation.

REFERENCES

• Medicherla, S. et al.: J. Pharmacol. Exp. Therap., 318, 99 (2006)