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7-oxobrefeldin A

PubChem CID
6441091
Structure
7-oxobrefeldin A_small.png
7-oxobrefeldin A_3D_Structure.png
7-oxobrefeldin A__Crystal_Structure.png
Molecular Formula
Synonyms
  • 7-Dehydrobrefeldin A
  • 7-oxobrefeldin A
  • (1R,2R,3E,7S,11E,13S)-2-hydroxy-7-methyl-6-oxabicyclo[11.3.0]hexadeca-3,11-diene-5,15-dione
  • 62989-90-6
  • 7-Oxo-bfa
Molecular Weight
278.34 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2006-04-28
  • Modify:
    2025-01-11
Description
7-oxobrefeldin A is a macrolide.
7-Dehydrobrefeldin A has been reported in Penicillium brefeldianum and Alternaria carthami with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
7-oxobrefeldin A.png

1.2 3D Conformer

1.3 Crystal Structures

CCDC Number
Associated Article
Crystal Structure Data
Crystal Structure Depiction
Crystal Structure Depiction

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,2R,3E,7S,11E,13S)-2-hydroxy-7-methyl-6-oxabicyclo[11.3.0]hexadeca-3,11-diene-5,15-dione
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C16H22O4/c1-11-5-3-2-4-6-12-9-13(17)10-14(12)15(18)7-8-16(19)20-11/h4,6-8,11-12,14-15,18H,2-3,5,9-10H2,1H3/b6-4+,8-7+/t11-,12+,14+,15+/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

IKUWMGOXYQGWPC-TWAINWRDSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C[C@H]1CCC/C=C/[C@@H]2CC(=O)C[C@H]2[C@@H](/C=C/C(=O)O1)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C16H22O4
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

62989-90-6

2.3.2 ChEBI ID

2.3.3 Metabolomics Workbench ID

2.3.4 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 7-dehydrobrefeldin A
  • 7-oxo-BFA

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
278.34 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
1.6
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
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
278.15180918 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
278.15180918 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
63.6 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
20
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
424
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
4
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
2
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)

5 Chemical Vendors

6 Literature

6.1 Consolidated References

6.2 NLM Curated PubMed Citations

6.3 Nature Journal References

6.4 Chemical Co-Occurrences in Literature

6.5 Chemical-Gene Co-Occurrences in Literature

6.6 Chemical-Disease Co-Occurrences in Literature

7 Patents

7.1 Depositor-Supplied Patent Identifiers

8 Taxonomy

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

9 Classification

9.1 MeSH Tree

9.2 ChEBI Ontology

9.3 ChemIDplus

9.4 The Natural Products Atlas Classification

9.5 LOTUS Tree

9.6 MolGenie Organic Chemistry Ontology

10 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. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. Metabolomics Workbench
  5. Nature Chemistry
  6. The Cambridge Structural Database
  7. Wikidata
  8. PubChem
  9. 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
  10. The Natural Products Atlas
    LICENSE
    The Natural Products Atlas is licensed under a Creative Commons Attribution 4.0 International License.
    https://www.npatlas.org/terms
    The Natural Products Atlas Classification
    https://www.npatlas.org/
  11. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS