(2S)-1-[(2R,3S)-5-chloro-3-(2-chlorophenyl)-1-(3,4-dimethoxybenzenesulfonyl)-3-hydroxy-2,3-dihydro-1H-indole-2-carbonyl]pyrrolidine-2-carboxamide

• ChemBase ID: 154569
• Molecular Formular: C28H27Cl2N3O7S
• Molecular Mass: 620.50088
• Monoisotopic Mass: 619.09467658
• SMILES: COc1ccc(cc1OC)S(=O)(=O)N1c2ccc(cc2[C@@]([C@@H]1C(=O)N1CCC[C@H]1C(=O)N)(c1ccccc1Cl)O)Cl
• Canonical SMILES: COc1ccc(cc1OC)S(=O)(=O)N1c2ccc(cc2[C@]([C@@H]1C(=O)N1CCC[C@H]1C(=O)N)(O)c1ccccc1Cl)Cl
• InChI: InChI=1S/C28H27Cl2N3O7S/c1-39-23-12-10-17(15-24(23)40-2)41(37,38)33-21-11-9-16(29)14-19(21)28(36,18-6-3-4-7-20(18)30)25(33)27(35)32-13-5-8-22(32)26(31)34/h3-4,6-7,9-12,14-15,22,25,36H,5,8,13H2,1-2H3,(H2,31,34)/t22-,25-,28+/m0/s1
• InChIKey: CEBYCSRFKCEUSW-NAYZPBBASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2R,3S)-5-chloro-3-(2-chlorophenyl)-1-(3,4-dimethoxybenzenesulfonyl)-3-hydroxy-2,3-dihydro-1H-indole-2-carbonyl]pyrrolidine-2-carboxamide
• IUPAC Traditional name: relcovaptan
• Synonyms: (2S)-1-[[(2R,3S)-5-Chloro-3-(2-chlorophenyl)-1-[(3,4-dimethoxyphenyl)sulfonyl]-2,3-dihydro-3-hydroxy-1H-indol-2-yl]carbonyl]-2-pyrrolidinecarboxamide; SR49059; SR 49059

Database IDs

• CAS Number: 150375-75-0
• MDL Number: MFCD00922133
• PubChem SID: 162248707
• PubChem CID: 60943

CALCULATED PROPERTIES

• Acid pKa: 7.7218375
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 2.824296
• LogD (pH = 7.4): 2.6577735
• Log P: 2.8268921
• Molar Refractivity: 152.1818 cm^3
• Polarizability: 60.006042 Å^3
• Polar Surface Area: 139.47 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: white to off-white powder
• Optical Rotation: [α]/D -160 - 190°

Safety Information

• German water hazard class: nwg
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C28H27Cl2N3O7S

DETAILS

Sigma Aldrich - S5701

Biochem/physiol Actions
SR 49059 is a potent and selective Arginine Vasopressin (AVP) V1a-receptor antagonist. AVP is a hormone that plays an important part in circulatory and water homoeostasis and is important in renal hemodynamic alterations, water retention, and cardiac remodeling in congestive heart failure (CHF). There are three AVP receptor subtypes V1a, V1b, and V2. All belong to the large rhodopsin-like G-protein-coupled receptor family. V(1a) antagonists improve water balance and cardiac hypertrophy in CHF and might be beneficial for the treatment of water retention and cardiac remodeling in CHF. SR 49059 has also shown initial positive results in the treatment of Raynaud′s disease, dysmenorrhoea, and tocolysis.