(3S,6S,9S,15S,20aS)-6-(1H-indol-3-ylmethyl)-9-methyl-3,15-bis(propan-2-yl)-icosahydropyrrolo[1,2-a]1,4,7,10,13,16-hexaazacyclooctadecane-1,4,7,10,13,16-hexone

• ChemBase ID: 177730
• Molecular Formular: C31H43N7O6
• Molecular Mass: 609.71642
• Monoisotopic Mass: 609.32748213
• SMILES: N1C(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H]2N(C(=O)[C@H](NC(=O)CNC(=O)[C@@H]1C)C(C)C)CCC2)C(C)C)Cc1c[nH]c2c1cccc2
• Canonical SMILES: O=C1CNC(=O)[C@H](C)NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H]2N(C(=O)[C@H](N1)C(C)C)CCC2)C(C)C)Cc1c[nH]c2c1cccc2
• InChI: InChI=1S/C31H43N7O6/c1-16(2)25-30(43)35-22(13-19-14-32-21-10-7-6-9-20(19)21)28(41)34-18(5)27(40)33-15-24(39)36-26(17(3)4)31(44)38-12-8-11-23(38)29(42)37-25/h6-7,9-10,14,16-18,22-23,25-26,32H,8,11-13,15H2,1-5H3,(H,33,40)(H,34,41)(H,35,43)(H,36,39)(H,37,42)/t18-,22-,23-,25-,26-/m0/s1
• InChIKey: YVUZOKYOUUCVBV-WJTDBPPMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,6S,9S,15S,20aS)-6-(1H-indol-3-ylmethyl)-9-methyl-3,15-bis(propan-2-yl)-icosahydropyrrolo[1,2-a]1,4,7,10,13,16-hexaazacyclooctadecane-1,4,7,10,13,16-hexone
• IUPAC Traditional name: (3S,6S,9S,15S,20aS)-6-(1H-indol-3-ylmethyl)-3,15-diisopropyl-9-methyl-tetradecahydropyrrolo[1,2-a]1,4,7,10,13,16-hexaazacyclooctadecane-1,4,7,10,13,16-hexone
• Synonyms: Cyclo(L-alanylglycyl-L-valyl-L-prolyl-L-valyl-L-tryptophyl) Trifluoroacetic Acid Salt; Vaccarin D Trifluoroacetic Acid Salt; Segetalin A Trifluoroacetic Acid Salt

Database IDs

• CAS Number: 161875-97-4
• PubChem SID: 164233640
• PubChem CID: 10483858

CALCULATED PROPERTIES

• Acid pKa: 10.557305
• H Acceptors: 6
• H Donor: 6
• LogD (pH = 5.5): 0.014862781
• LogD (pH = 7.4): 0.014598331
• Log P: 0.014866155
• Molar Refractivity: 160.6763 cm^3
• Polarizability: 63.72874 Å^3
• Polar Surface Area: 181.6 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - S243000

A cyclic peptide with estrogen-like activity from seeds of Vaccaria segetalis. The compund have been used to activate blood flow and promote milk secretion and to treat amenorrhea and breast infections.

REFERENCES

• Mazza, G., et al.: J. Agric. Food Chem., 40, 1520 (1992)