2-[(3R,6S,9R,12R,17aS)-3-[(2S)-butan-2-yl]-9-(1H-indol-3-ylmethyl)-6-(2-methylpropyl)-1,4,7,10,13-pentaoxo-hexadecahydro-1H-pyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecan-12-yl]acetic acid

• ChemBase ID: 131976
• Molecular Formular: C32H44N6O7
• Molecular Mass: 624.72776
• Monoisotopic Mass: 624.32714778
• SMILES: CC[C@H](C)[C@@H]1C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N2CCC[C@H]2C(=O)N1)CC(=O)O)Cc1c[nH]c2c1cccc2)CC(C)C
• Canonical SMILES: CC[C@@H]([C@H]1NC(=O)[C@@H]2CCCN2C(=O)[C@@H](CC(=O)O)NC(=O)[C@H](NC(=O)[C@@H](NC1=O)CC(C)C)Cc1c[nH]c2c1cccc2)C
• InChI: InChI=1S/C32H44N6O7/c1-5-18(4)27-31(44)35-22(13-17(2)3)28(41)34-23(14-19-16-33-21-10-7-6-9-20(19)21)29(42)36-24(15-26(39)40)32(45)38-12-8-11-25(38)30(43)37-27/h6-7,9-10,16-18,22-25,27,33H,5,8,11-15H2,1-4H3,(H,34,41)(H,35,44)(H,36,42)(H,37,43)(H,39,40)/t18-,22-,23+,24+,25-,27+/m0/s1
• InChIKey: KHRTUHCOJNQEQG-CSXHVWADSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(3R,6S,9R,12R,17aS)-3-[(2S)-butan-2-yl]-9-(1H-indol-3-ylmethyl)-6-(2-methylpropyl)-1,4,7,10,13-pentaoxo-hexadecahydro-1H-pyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecan-12-yl]acetic acid
• IUPAC Traditional name: [(3R,6S,9R,12R,17aS)-3-[(2S)-butan-2-yl]-9-(1H-indol-3-ylmethyl)-6-(2-methylpropyl)-1,4,7,10,13-pentaoxo-dodecahydropyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecan-12-yl]acetic acid
• Synonyms: Cyclo(D-Asp-Pro-D-Ile-Leu-D-Trp); JKC 301

Database IDs

• CAS Number: 136553-96-3
• MDL Number: MFCD00214626
• PubChem SID: 162226253
• PubChem CID: 10651568

CALCULATED PROPERTIES

• Acid pKa: 4.044945
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -0.17686284
• LogD (pH = 7.4): -1.8433999
• Log P: 1.2895211
• Molar Refractivity: 163.1872 cm^3
• Polarizability: 64.88552 Å^3
• Polar Surface Area: 189.8 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - J4125

Biochem/physiol Actions
Endothelin receptor (ETA) antagonist