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2,3-Dihydro-6-hydroxy-4-methoxy-5-methyl-1H-isoindol-1-one

HCID 442849
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Basic information

CAS
114090-43-6
Standard SMILES
COc1c(C)c(O)cc2c1CNC2=O
InChIKey
ICZVDXDXJQCDOJ-UHFFFAOYSA-N
Molecular formula
C10H11NO3
Average molar mass
193.2 g/mol
Monoisotopic mass
193.07389321

Overview

Cichorine is a member of the class of isoindoles that is 6-hydroxy-4-methoxy-5-methyl-2,3-dihydro-1H-isoindol-1-one which is substituted at position 4, 5, and 6 by methoxy, methyl, and hydroxy groups, respectively. A secondary metabolite found in Aspergillus silvativus, Aspergillus nidulans and Alternaria cichorii, it is poisonous to Russian knapweed (Acroptilon repens). It has a role as a mycotoxin. It is a member of isoindoles and a member of phenols.

Names & identifiers

Preferred name
2,3-Dihydro-6-hydroxy-4-methoxy-5-methyl-1H-isoindol-1-one
IUPAC
6-hydroxy-4-methoxy-5-methyl-2,3-dihydroisoindol-1-one

Names & synonyms

Cichorine114090-43-66-hydroxy-4-methoxy-5-methyl-2,3-dihydroisoindol-1-oneCHEBI:64977RefChem:9086252,3-Dihydro-6-hydroxy-4-methoxy-5-methyl-1H-isoindol-1-one6-hydroxy-4-methoxy-5-methyl-2,3-dihydro-1H-isoindol-1-oneSCHEMBL29768755DTXSID30331975Q27104923

Database identifiers

CAS
114090-43-6
PubChem CID
442849
DTXSID
DTXSID30331975
ChEBI
CHEBI:64977
Nikkaji
J2.206.804K

Properties

Computed structural properties

XLogP
0.8
Topological polar surface area
58.6 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
14
Formal charge
0
Complexity
244

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Compound notes

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