methyl (1R,15S,17R,18R,19S,20S)-17-hydroxy-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: 177401
• Molecular Formular: C23H30N2O5
• Molecular Mass: 414.4947
• Monoisotopic Mass: 414.21547207
• 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)O)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)O)CCc1c3[nH]c2c1ccc(c2)OC
• InChI: InChI=1S/C23H30N2O5/c1-28-13-4-5-14-15-6-7-25-11-12-8-19(26)22(29-2)20(23(27)30-3)16(12)10-18(25)21(15)24-17(14)9-13/h4-5,9,12,16,18-20,22,24,26H,6-8,10-11H2,1-3H3/t12-,16+,18-,19-,20+,22+/m1/s1
• InChIKey: MDJQWFFIUHUJSB-UQVJXISSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1R,15S,17R,18R,19S,20S)-17-hydroxy-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-hydroxy-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: Methyl reserpate; Methyl reserpinolate; NSC 81464; (3β,16β,17α,18β,20α)-18-Hydroxy-11,17-dimethoxy-yohimban-16-carboxylic Acid Methyl Ester; Reserpic Acid Methyl Ester

Database IDs

• CAS Number: 2901-66-8
• PubChem SID: 164233311
• PubChem CID: 73532

CALCULATED PROPERTIES

• Acid pKa: 14.155962
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.011827561
• LogD (pH = 7.4): 1.3601816
• Log P: 1.5092099
• Molar Refractivity: 112.2069 cm^3
• Polarizability: 45.16397 Å^3
• Polar Surface Area: 84.02 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Dimethyl Sulfoxide; Methanol
• Apperance: Light Yellow Solid

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - R144590

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

REFERENCES

• Itoh, A. et al.: J. Nat. Prod. 68, 848 (2005)