Eschscholtzidine

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Basic information

CAS: 6451-67-8
Standard SMILES: COc1cc2c(cc1OC)[C@@H]1Cc3cc4c(cc3[C@H](C2)N1C)OCO4
InChIKey: YTZIQRTXKBDFKM-HOTGVXAUSA-N
Molecular formula: C20H21NO4
Average molar mass: 339.4 g/mol
Monoisotopic mass: 339.14705815

Overview

Eschscholtzidine is a heteropentacyclic isoquinoline alkaloid having a tertiary amino bridging group. It is an isoquinoline alkaloid, a tertiary amine and an organic heteropentacyclic compound.

Names & identifiers

Preferred name: Eschscholtzidine
IUPAC: (1S,12S)-15,16-dimethoxy-20-methyl-5,7-dioxa-20-azapentacyclo[10.7.1.02,10.04,8.013,18]icosa-2,4(8),9,13,15,17-hexaene

Names & synonyms

Eschscholtzidine6451-67-8(5S)-5,6,11,12-Tetrahydro-8,9-dimethoxy-14-methyl-benzo[5,6]cycloocta[1,2-f]-1,3-benzodioxol-5,11-imine(1S,12S)-15,16-dimethoxy-20-methyl-5,7-dioxa-20-azapentacyclo[10.7.1.02,10.04,8.013,18]icosa-2,4(8),9,13,15,17-hexaene(5S,11S)-8,9-dimethoxy-14-methyl-5,6,11,12-tetrahydro-5,11-epiminobenzo[5',6']cycloocta[1',2':4,5]benzo[1,2-d][1,3]dioxoleC09426CHEBI:4850CHEMBL1621815SCHEMBL14886118DTXSID30983079NS00094108Q27106505

Show more names

(5S,11S)-8,9-Dimethoxy-14-methyl-5,6,11,12-tetrahydro-2H-5,11-epiminobenzo[5',6']cycloocta[1',2':4,5]benzo[1,2-d][1,3]dioxole8,9-Dimethoxy-14-methyl-5,6,11,12-tetrahydro-2H-5,11-epiminobenzo[5',6']cycloocta[1',2':4,5]benzo[1,2-d][1,3]dioxoleBenzo[5,6]cycloocta[1,2-f]-1,3-benzodioxol-5,11-imine, 5,6,11,12-tetrahydro-8,9-dimethoxy-14-methyl-, (5S,11S)-

Database identifiers

CAS: 6451-67-8
PubChem CID: 442222
DTXSID: DTXSID30983079
ChEMBL: CHEMBL1621815
ChEBI: CHEBI:4850

Properties

Computed structural properties

XLogP: 3.1
Topological polar surface area: 40.2 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 5
Rotatable bonds: 2
Heavy atoms: 25
Formal charge: 0
Complexity: 502

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Compound notes

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