Basic information
- CAS
73706-32-8- Standard SMILES
CC1=C[C@H]2[C@@H]([C@@H](c3[nH]c4ccccc4c3CCN(C)C)[C@]34CCN(C)[C@]23Nc2ccccc24)C(C)(C)C1- InChIKey
RTHNIWHULJBNTJ-BXFVMDGOSA-N- Molecular formula
- C33H42N4
- Average molar mass
- 494.7 g/mol
- Monoisotopic mass
- 494.34094736
Overview
Auricularine is a pyrroloindole.
Names & identifiers
- Preferred name
- Auricularine
- IUPAC
- N,N-dimethyl-2-[2-[(1S,9R,10S,15R,16R)-12,14,14,19-tetramethyl-8,19-diazapentacyclo[7.7.3.01,9.02,7.010,15]nonadeca-2,4,6,11-tetraen-16-yl]-1H-indol-3-yl]ethanamine
- English name
- Auricularine
- Molecular formula
- C33H42N4
- Molecular weight
- 494.71338
Names & synonyms
Auricularine73706-32-8C09043N,N-dimethyl-2-[2-[(1S,9R,10S,15R,16R)-12,14,14,19-tetramethyl-8,19-diazapentacyclo[7.7.3.01,9.02,7.010,15]nonadeca-2,4,6,11-tetraen-16-yl]-1H-indol-3-yl]ethanamineAC1L9C25CHEBI:2927CHEMBL4165417SCHEMBL31023233DTXSID40331704Q27105884N,N-Dimethyl-2-{2-[(4aS,4bR,9bS,10R,10aR)-1,1,3,13-tetramethyl-2,4a,10,10a-tetrahydro-1H,5H-4b,9b-(epiminoethano)indeno[1,2-b]indol-10-yl]-1H-indol-3-yl}ethan-1-amine
Database identifiers
- CAS
73706-32-8- PubChem CID
- 441990
- DTXSID
DTXSID40331704- ChEMBL
CHEMBL4165417- ChEBI
CHEBI:2927- Nikkaji
- J2.767.852A
Properties
Computed structural properties
- XLogP
- 6.2
- Topological polar surface area
- 34.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 37
- Formal charge
- 0
- Complexity
- 925
Chemistry & industry
Applications
OccurrenceA dimeric alkaloid, auricularine occurs in the basic extract of Hedyotis auricularia. It crystallizes as colourless needles from EtOH and is very sensitive to reagents. The base is dextrorotatory with a specific rotation of [α]D +41 °(c 0.27, CHCl3).
Additional notes
DefinitionChEBI: Auricularine is a pyrroloindole.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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