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Isatinone A

PubChem CID
46913217
Structure
Isatinone A_small.png
Isatinone A_3D_Structure.png
Molecular Formula
Synonyms
  • isatinone A
  • CHEBI:66087
  • (3E)-3-[methoxy(phenyl)methylidene]-1,3-dihydro-2H-indol-2-one
  • (3E)-3-(methoxy(phenyl)methylidene)-1H-indol-2-one
  • (3E)-3-[methoxy(phenyl)methylidene]-1H-indol-2-one
Molecular Weight
251.28 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2010-10-18
  • Modify:
    2025-01-18
Description
Isatinone A is an indole alkaloid that is 1,3-dihydro-2H-indol-2-one substituted by a methoxy(phenyl)methylidene group at position 3 (the 3E stereoisomer). Isolated from Isatis costata, it exhibits antifungal activity. It has a role as a metabolite and an antifungal agent. It is an indole alkaloid, a member of indolones and an enol ether.
isatinone A has been reported in Isatis costata with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Isatinone A.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3E)-3-[methoxy(phenyl)methylidene]-1H-indol-2-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C16H13NO2/c1-19-15(11-7-3-2-4-8-11)14-12-9-5-6-10-13(12)17-16(14)18/h2-10H,1H3,(H,17,18)/b15-14+
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

VRJYLVZCUCQVBL-CCEZHUSRSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CO/C(=C/1\C2=CC=CC=C2NC1=O)/C3=CC=CC=C3
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C16H13NO2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 ChEBI ID

2.3.2 Metabolomics Workbench ID

2.3.3 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 3-(methoxy(phenyl)methylidene)-1,3-dihydro-2H-indol-2-one
  • isatinone A

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
251.28 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
2.7
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
251.094628657 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
251.094628657 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
38.3 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
19
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
382
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 13C NMR Spectra

Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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6 Literature

6.1 Consolidated References

6.2 NLM Curated PubMed Citations

6.3 Chemical Co-Occurrences in Literature

7 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

8 Classification

8.1 MeSH Tree

8.2 ChEBI Ontology

8.3 LOTUS Tree

8.4 MolGenie Organic Chemistry Ontology

9 Information Sources

  1. ChEBI
  2. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  3. Natural Product Activity and Species Source (NPASS)
  4. Metabolomics Workbench
  5. SpectraBase
    ISATINONE-A;3-[(E)-METHOXYPHENYLMETHYLIDENE]-1,3-DIHYDRO-2H-INDOL-2-ONE
    https://spectrabase.com/spectrum/1HLMbSC1JSc
  6. Wikidata
  7. PubChem
  8. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
    3-(methoxy(phenyl)methylidene)-1,3-dihydro-2H-indol-2-one
    https://www.ncbi.nlm.nih.gov/mesh/67523691
  9. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS