(3R,6S,9R,12R,17aS)-12-(hydroxymethyl)-9-(1H-indol-3-ylmethyl)-6-(2-methylpropyl)-3-(propan-2-yl)-hexadecahydro-1H-pyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecane-1,4,7,10,13-pentone

• ChemBase ID: 133369
• Molecular Formular: C30H42N6O6
• Molecular Mass: 582.69108
• Monoisotopic Mass: 582.31658309
• SMILES: CC(C)C[C@H]1C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N2CCC[C@H]2C(=O)N[C@@H](C(=O)N1)C(C)C)CO)Cc1c[nH]c2c1cccc2
• Canonical SMILES: OC[C@H]1NC(=O)[C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](NC(=O)[C@H]2N(C1=O)CCC2)C(C)C)Cc1c[nH]c2c1cccc2
• InChI: InChI=1S/C30H42N6O6/c1-16(2)12-21-26(38)32-22(13-18-14-31-20-9-6-5-8-19(18)20)27(39)34-23(15-37)30(42)36-11-7-10-24(36)28(40)35-25(17(3)4)29(41)33-21/h5-6,8-9,14,16-17,21-25,31,37H,7,10-13,15H2,1-4H3,(H,32,38)(H,33,41)(H,34,39)(H,35,40)/t21-,22+,23+,24-,25+/m0/s1
• InChIKey: FLVWONZBLRGQPK-VCDBXAJLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,6S,9R,12R,17aS)-12-(hydroxymethyl)-9-(1H-indol-3-ylmethyl)-6-(2-methylpropyl)-3-(propan-2-yl)-hexadecahydro-1H-pyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecane-1,4,7,10,13-pentone
• IUPAC Traditional name: (3R,6S,9R,12R,17aS)-12-(hydroxymethyl)-9-(1H-indol-3-ylmethyl)-3-isopropyl-6-(2-methylpropyl)-dodecahydropyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecane-1,4,7,10,13-pentone
• Synonyms: cyclo(D-Ser-Pro-D-Val-Leu-D-Trp); JKC 302

Database IDs

• CAS Number: 153982-38-8
• MDL Number: MFCD00270699
• PubChem SID: 162227646
• PubChem CID: 11606713

CALCULATED PROPERTIES

• Acid pKa: 10.627044
• H Acceptors: 6
• H Donor: 6
• LogD (pH = 5.5): 0.4398515
• LogD (pH = 7.4): 0.43962628
• Log P: 0.43985435
• Molar Refractivity: 154.0945 cm^3
• Polarizability: 61.287582 Å^3
• Polar Surface Area: 172.73 Å^2
• Rotatable Bonds: 6
• 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

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - J4250

Biochem/physiol Actions
Endothelin receptor (ETA) antagonist