(6S)-2-chloro-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-6-carboxamide

• ChemBase ID: 153948
• Molecular Formular: C14H15ClN2O
• Molecular Mass: 262.7347
• Monoisotopic Mass: 262.08729079
• SMILES: c1cc2c(cc1Cl)c1c([nH]2)[C@H](CCCC1)C(=O)N
• Canonical SMILES: NC(=O)[C@H]1CCCCc2c1[nH]c1c2cc(cc1)Cl
• InChI: InChI=1S/C14H15ClN2O/c15-8-5-6-12-11(7-8)9-3-1-2-4-10(14(16)18)13(9)17-12/h5-7,10,17H,1-4H2,(H2,16,18)/t10-/m0/s1
• InChIKey: ABIVOOWWGYJNLV-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6S)-2-chloro-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-6-carboxamide
• IUPAC Traditional name: (6S)-2-chloro-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-6-carboxamide
• Synonyms: (6S)-2-Chloro-5,6,7,8,9,10-hexahydro-cyclohept[b]indole-6-carboxamide; Compound (S)-35; CHIC-35

Database IDs

• CAS Number: 848193-72-6
• PubChem SID: 162248087
• PubChem CID: 914268

CALCULATED PROPERTIES

• Acid pKa: 15.252329
• H Acceptors: 1
• H Donor: 2
• LogD (pH = 5.5): 2.9086783
• LogD (pH = 7.4): 2.9086783
• Log P: 2.9086783
• Molar Refractivity: 71.9721 cm^3
• Polarizability: 28.838814 Å^3
• Polar Surface Area: 58.88 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: <2 mg/mL
• Apperance: solid

Safety Information

• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97% (chiral, HPLC)
• Empirical Formula (Hill Notation): C14H15ClN2O

DETAILS

Sigma Aldrich - C8742

Biochem/physiol Actions
CHIC-35 is cell-permeable, metabolically stable, and very potent inhibitor of SIRT1; IC50 of S-isomer is 60 nM; IC50 of mixed isomers is 124 nM. There is no inhibition of SIRT3 or HDAC. The IC50 for SIRT2 is 2.77 μM. Sirtuins are protein deacetylases, which represent a new class of histone deacetylases (HDAC) involved in gene silencing. SIRT modulators are potential therapeutics for cancer, diabetes, muscle differentiation, heart failure, neurodegeneration, and aging.