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

• ChemBase ID: 174596
• Molecular Formular: C24H32N2O5
• Molecular Mass: 428.52128
• Monoisotopic Mass: 428.23112213
• 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)OC)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)OC)CCc1c3[nH]c2c1ccc(c2)OC
• InChI: InChI=1S/C24H32N2O5/c1-28-14-5-6-15-16-7-8-26-12-13-9-20(29-2)23(30-3)21(24(27)31-4)17(13)11-19(26)22(16)25-18(15)10-14/h5-6,10,13,17,19-21,23,25H,7-9,11-12H2,1-4H3/t13-,17+,19-,20+,21+,23+/m1/s1
• InChIKey: FPGCYQVKNKEGRQ-SXLQGMKLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1R,15S,17S,18R,19S,20S)-6,17,18-trimethoxy-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,17S,18R,19S,20S)-6,17,18-trimethoxy-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: (3β,16β,17α,18α,20α)-11,17,18-Trimethoxyyohimban-16-carboxylic Acid Methyl Ester; O-Methyl-18-epireserpic Acid Methyl Ester; 18-epi-O-Methylreserpic Acid Methyl Ester; Mepiserpate; Methyl O-Methyl-18-epi-reserpate; Methyl O-Methyl-18-epireserpate; Methyl O-Methylepireserpate; Su 9064; Metoserpate

Database IDs

• CAS Number: 1178-28-5
• PubChem SID: 164230506
• PubChem CID: 66252

CALCULATED PROPERTIES

• Acid pKa: 16.290113
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.3801687
• LogD (pH = 7.4): 1.9103066
• Log P: 2.1523364
• Molar Refractivity: 116.9581 cm^3
• Polarizability: 47.07667 Å^3
• Polar Surface Area: 73.02 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 213-217°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M338810

Reserpine (R144600) derivative as a neuroleptic compound. Reserpine and SU 9064 prolonged the duration for the larva development and only SU 9064 had a mortal effect on larvae.

REFERENCES

• Schafer, E.W., Jr., et al.: Arch. Environ. Contam. Toxicol., 12, 355 (1983)