Macarpine

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Basic information

CAS: 23594-80-1
Standard SMILES: COc1cc2c3c(OC)cc4c(c3c[n+](C)c2c2cc3c(cc12)OCO3)OCO4
InChIKey: SBVRPBAVNZNLKX-UHFFFAOYSA-N
Molecular formula: C22H18NO6+
Average molar mass: 392.4 g/mol
Monoisotopic mass: 392.11341229

Overview

Macarpine is a benzophenanthridine alkaloid that is sanguinarine bearing two methoxy substituents. It is an organic cation and a benzophenanthridine alkaloid. It derives from a hydride of a sanguinarine.

Names & identifiers

Preferred name: Macarpine
IUPAC: 11,15-dimethoxy-24-methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(13),2,4(8),9,11,14,16,21,23-nonaene

Names & synonyms

Macarpine23594-80-1CHEBI:1710111,15-dimethoxy-24-methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(13),2,4(8),9,11,14,16,21,23-nonaene5,7-dimethoxy-13-methyl-2H,10H-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridinium11,15-dimethoxy-24-methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo(11.11.0.02,10.04,8.014,22.017,21)tetracosa-1(13),2,4(8),9,11,14,16,21,23-nonaene5,7-dimethoxy-13-methyl-2H,10H-(1,3)dioxolo(4,5-i)(1,3)dioxolo(4',5':4,5)benzo(1,2-c)phenanthridiniumRefChem:154935[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium, 5,7-dimethoxy-13-methyl-C06165CHEMBL5205934SCHEMBL29353594

Show more names

DTXSID20946395Q38419525,7-Dimethoxy-13-methyl-2H,10H-[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridin-13-ium6917-73-3

Database identifiers

CAS: 23594-80-1

Properties

Computed structural properties

XLogP: 4.4
Topological polar surface area: 59.3 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 6
Rotatable bonds: 2
Heavy atoms: 29
Formal charge: 1
Complexity: 620

Related reactions

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Compound notes

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