methyl (1R,15S,17R,18R,19S,20S)-17-[(4-bromobenzenesulfonyl)oxy]-6,18-dimethoxy-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8-tetraene-19-carboxylate

• ChemBase ID: 162753
• Molecular Formular: C29H33BrN2O7S
• Molecular Mass: 633.55052
• Monoisotopic Mass: 632.11918441
• SMILES: c1c(cc2c(c1)c1c([nH]2)[C@@H]2N(CC1)C[C@@H]1[C@H](C2)[C@@H]([C@H]([C@@H](C1)OS(=O)(=O)c1ccc(cc1)Br)OC)C(=O)OC)OC
• Canonical SMILES: COC(=O)[C@H]1[C@H]2C[C@H]3N(C[C@H]2C[C@H]([C@@H]1OC)OS(=O)(=O)c1ccc(cc1)Br)CCc1c3[nH]c2c1ccc(c2)OC
• InChI: InChI=1S/C29H33BrN2O7S/c1-36-18-6-9-20-21-10-11-32-15-16-12-25(39-40(34,35)19-7-4-17(30)5-8-19)28(37-2)26(29(33)38-3)22(16)14-24(32)27(21)31-23(20)13-18/h4-9,13,16,22,24-26,28,31H,10-12,14-15H2,1-3H3/t16-,22+,24-,25-,26+,28+/m1/s1
• InChIKey: AWSOQGFEQNOXNW-GXTCVXTHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1R,15S,17R,18R,19S,20S)-17-[(4-bromobenzenesulfonyl)oxy]-6,18-dimethoxy-3,13-diazapentacyclo[11.8.0.0^2,^1^0.0^4,^9.0^1^5,^2^0]henicosa-2(10),4,6,8-tetraene-19-carboxylate
• IUPAC Traditional name: methyl (1R,15S,17R,18R,19S,20S)-17-[(4-bromobenzenesulfonyl)oxy]-6,18-dimethoxy-3,13-diazapentacyclo[11.8.0.0^2,^1^0.0^4,^9.0^1^5,^2^0]henicosa-2(10),4,6,8-tetraene-19-carboxylate
• Synonyms: 18β-Hydroxy-11,17α-dimethoxy-3β,20α-yohimban-16β-carboxylic Acid Methyl, p-Bromobenzenesulfonate Ester; p-Bromobenzenesulfonate Reserpic Acid Methyl Ester

Database IDs

• CAS Number: 1262-67-5
• PubChem SID: 162256888
• PubChem CID: 71314216

CALCULATED PROPERTIES

• Acid pKa: 16.290113
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 2.9369953
• LogD (pH = 7.4): 4.2147665
• Log P: 4.328653
• Molar Refractivity: 152.7312 cm^3
• Polarizability: 61.744995 Å^3
• Polar Surface Area: 107.16 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Dimethyl Sulfoxide
• Apperance: Brown Solid

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - B680160

Reserpine (R144600) derivative, an alkaloid found in Rauwolfia.

REFERENCES

• Robison, M. et al.: J. Am. Chem. Soc. 83. 2694 (1961)
• Robison, M. et al.: Experientia 17, 14 (1961)