methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[3,4,5-tris(2H3)methoxybenzoyloxy]-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8-tetraene-19-carboxylate

• ChemBase ID: 177402
• Molecular Formular: C33H40N2O9
• Molecular Mass: 608.6787
• Monoisotopic Mass: 608.27338087
• 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(=O)c1cc(c(c(c1)OC)OC)OC)OC)C(=O)OC)OC
• Canonical SMILES: COc1ccc2c(c1)[nH]c1c2CCN2[C@@H]1C[C@H]1[C@@H](C2)C[C@H]([C@@H]([C@H]1C(=O)OC)OC)OC(=O)c1cc(OC)c(c(c1)OC)OC
• InChI: InChI=1S/C33H40N2O9/c1-38-19-7-8-20-21-9-10-35-16-18-13-27(44-32(36)17-11-25(39-2)30(41-4)26(12-17)40-3)31(42-5)28(33(37)43-6)22(18)15-24(35)29(21)34-23(20)14-19/h7-8,11-12,14,18,22,24,27-28,31,34H,9-10,13,15-16H2,1-6H3/t18-,22+,24-,27-,28+,31+/m1/s1
• InChIKey: QEVHRUUCFGRFIF-MDEJGZGSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[3,4,5-tris(^2H₃)methoxybenzoyloxy]-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)-6,18-dimethoxy-17-[3,4,5-tris(^2H₃)methoxybenzoyloxy]-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,18β,20α)-11,17-Dimethoxy-18-[[3,4,5-tri(methoxy-d3)benzoyl]oxy]yohimban-16-carboxylic Acid Methyl Ester-d9; 3,4,5-Tri(methoxy-d3)benzoyl Methyl Reserpate; Anquil-d9; Apoplon-d9; Rivasin-d9; Serpasil-d9; Temposerpine-d9; Triserpin-d9; Reserpine-d9

Database IDs

• CAS Number: 84759-11-5
• PubChem SID: 164233312
• PubChem CID: 71751998

CALCULATED PROPERTIES

• Acid pKa: 16.290113
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 1.7332709
• LogD (pH = 7.4): 3.2777264
• Log P: 3.531496
• Molar Refractivity: 161.4185 cm^3
• Polarizability: 64.30159 Å^3
• Polar Surface Area: 117.78 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - R144602

Labelled Reserpine (R144600). An indole alkaloid found in Rauwolfia serpentina. Inhibits vesicular uptake of catecholamines and serotonin. Reserpine is reasonably anticipated to be a human carcinogen. Antihypertensive.

REFERENCES

• Muller, J.M., et al.: Experientia, 8, 338 (1952)
• Schirmer, R.E., et al.: Anal. Profiles Drug Subs., 4, 384 (1952)
• Diener, R.M., et al.: Toxicol. Pathol., 8, 1 (1952)