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methyl (1S,15R,16S,19S,20S)-6,7-dimethoxy-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8-tetraene-19-carboxylate

HCID 178536699
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Basic information

CAS
5308-79-2
Standard SMILES
COC(=O)[C@@H]1CO[C@@H](C)[C@H]2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)[C@@H]3C[C@@H]21
InChIKey
IHJNYBLSZYDUNY-PXWWSQFUSA-N
Molecular formula
C23H30N2O5
Average molar mass
414.5 g/mol
Monoisotopic mass
414.21547206

Names & identifiers

Preferred name
methyl (1S,15R,16S,19S,20S)-6,7-dimethoxy-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8-tetraene-19-carboxylate
IUPAC
methyl (1S,15R,16S,19S,20S)-6,7-dimethoxy-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8-tetraene-19-carboxylate
English name
10,11-Dimethoxy-19α-methyl-18-oxayohimban-16β-carboxylic acid methyl ester
Molecular formula
C23H30N2O5
Molecular weight
414.49

Names & synonyms

HerbaceinVincaherbininVincaherbinine10,11-Dimethoxy-19α-methyl-18-oxayohimban-16β-carboxylic acid methyl esterOxayohimban-16-carboxylic acid, 10,11-dimethoxy-19-methyl-, methyl ester, (16β,19α)- (9CI)

Database identifiers

CAS
5308-79-2
PubChem CID
12309561
Nikkaji
J141.935H

Properties

Computed structural propertiesFilling in

XLogP
2.5
Topological polar surface area
73 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
6
Rotatable bonds
4
Heavy atoms
30
Formal charge
0
Complexity
647

Physicochemical properties

Melting point
139 · 139-140°C (dec.).

Chemistry & industry

Applications

DescriptionAlso present in Vinca herbacea, this base is laevorotatory having [α]20D - 238°and contains three methoxyl groups. The perchlorate is crystalline and has m.p. 205-7°C (dec.).

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