(15S,17R,18R,19S,20S)-6,18-dimethoxy-19-(methoxycarbonyl)-17-(3,4,5-trimethoxybenzoyloxy)-3,13λ5-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(13),2(10),4,6,8-pentaen-13-ylium chloride

• ChemBase ID: 165695
• Molecular Formular: C33H39ClN2O9
• Molecular Mass: 643.12376
• Monoisotopic Mass: 642.23440852
• SMILES: c1c(cc2c(c1)c1c([nH]2)C2=[N+](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.[Cl-]
• Canonical SMILES: COc1ccc2c(c1)[nH]c1c2CC[N+]2=C1C[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.[Cl-]
• InChI: InChI=1S/C33H38N2O9.ClH/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;/h7-8,11-12,14,18,22,27-28,31H,9-10,13,15-16H2,1-6H3;1H/t18-,22+,27-,28+,31+;/m1./s1
• InChIKey: DALXIXVMMSDZQU-FMJIVAGGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (15S,17R,18R,19S,20S)-6,18-dimethoxy-19-(methoxycarbonyl)-17-(3,4,5-trimethoxybenzoyloxy)-3,13λ^5-diazapentacyclo[11.8.0.0^2,^1^0.0^4,^9.0^1^5,^2^0]henicosa-1(13),2(10),4,6,8-pentaen-13-ylium chloride
• IUPAC Traditional name: (15S,17R,18R,19S,20S)-6,18-dimethoxy-19-(methoxycarbonyl)-17-(3,4,5-trimethoxybenzoyloxy)-3,13λ^5-diazapentacyclo[11.8.0.0^2,^1^0.0^4,^9.0^1^5,^2^0]henicosa-1(13),2(10),4,6,8-pentaen-13-ylium chloride
• Synonyms: (16β,17α,18β,20α)-3,4-Didehydro-11,17-dimethoxy-16-(methoxycarbonyl)-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimbanium; 3,4-Dehydroreserpine; 3,4-Didehydroreserpine; 3-Dehydro Reserpine Chloride

Database IDs

• CAS Number: 107052-60-8
• PubChem SID: 162259828
• PubChem CID: 13471259

CALCULATED PROPERTIES

• Acid pKa: 13.509311
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): -0.37094355
• LogD (pH = 7.4): -0.37094384
• Log P: -0.37094355
• Molar Refractivity: 172.0281 cm^3
• Polarizability: 63.784588 Å^3
• Polar Surface Area: 117.55 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D230200

The main degradation product of Reserpine (R144600).

REFERENCES

• Krebs, K.G., et al.: Arzneim.-Forsch., 10, 75 (1960)
• Wright, G., et al.: J. Pharm. Sci., 61, 299 (1960)