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7-Dehydrobrefeldin A

PubChem CID
100625136
Structure
7-Dehydrobrefeldin A_small.png
7-Dehydrobrefeldin A_3D_Structure.png
Molecular Formula
Synonyms
  • 7-Dehydrobrefeldin A
  • 62989-90-6
  • CHEBI:181103
  • AKOS040734619
  • NCGC00386106-01
Molecular Weight
278.34 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2015-12-11
  • Modify:
    2025-01-18
Description
(1S,2S,3E,7R,11E,13R)-2-Hydroxy-7-methyl 6-oxabicyclo[11.3.0]hexadecane-3,11-diene-5,15-dione is a macrolide.
(1S,2S,3E,7R,11E,13R)-2-Hydroxy-7-methyl 6-oxabicyclo[11.3.0]hexadecane-3,11-diene-5,15-dione has been reported in Neonectria obtusispora and Mallotus nudiflorus with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
7-Dehydrobrefeldin A.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S,2S,3E,7R,11E,13R)-2-hydroxy-7-methyl-6-oxabicyclo[11.3.0]hexadeca-3,11-diene-5,15-dione
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

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+/m1/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.3 InChIKey

IKUWMGOXYQGWPC-ZBDJHBETSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

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 2.1 (PubChem release 2019.06.18)

2.3 Other Identifiers

2.3.1 ChEBI ID

2.3.2 Metabolomics Workbench ID

2.3.3 Nikkaji Number

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 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
1.6
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
278.15180918 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
278.15180918 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
63.6 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
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 3.4.6.11 (PubChem release 2019.06.18)
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 2015.09.10)

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 LC-MS

1 of 2
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M-H2O+H]+
Precursor m/z
261.148
Instrument
Maxis II HD Q-TOF Bruker
Ionization Mode
positive
Top 5 Peaks

91.054085 100

215.142365 62.26

105.070137 52.70

261.145477 47.46

131.083817 41.78

Thumbnail
Thumbnail
2 of 2
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
279.159
Instrument
Maxis II HD Q-TOF Bruker
Ionization Mode
positive
Top 5 Peaks

91.053818 100

117.069855 93.21

131.086304 75.70

121.065536 69.02

145.103638 68.91

Thumbnail
Thumbnail

6 Chemical Vendors

7 Literature

7.1 Consolidated References

7.2 NLM Curated PubMed Citations

7.3 Chemical Co-Occurrences in Literature

7.4 Chemical-Gene Co-Occurrences in Literature

7.5 Chemical-Disease Co-Occurrences in Literature

8 Biological Test Results

8.1 BioAssay Results

9 Taxonomy

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

10 Classification

10.1 MeSH Tree

10.2 ChEBI Ontology

10.3 LOTUS Tree

10.4 MolGenie Organic Chemistry Ontology

11 Information Sources

  1. ChEBI
    (1S,2S,3E,7R,11E,13R)-2-Hydroxy-7-methyl 6-oxabicyclo[11.3.0]hexadecane-3,11-diene-5,15-dione
    https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:181103
  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/
    (1S,2S,3E,7R,11E,13R)-2-Hydroxy-7-methyl 6-oxabicyclo[11.3.0]hexadecane-3,11-diene-5,15-dione
    https://www.wikidata.org/wiki/Q105114960
  3. Japan Chemical Substance Dictionary (Nikkaji)
  4. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
    NCGC00386106-01_C16H22O4_(1R,2E,6S,10E,11aS,14aR)-1-Hydroxy-6-methyl-6,7,8,9,11a,12,14,14a-octahydro-4H-cyclopenta[f]oxacyclotridecine-4,13(1H)-dione
    https://mona.fiehnlab.ucdavis.edu/spectra/browse?query=exists(compound.metaData.name:%27InChIKey%27%20and%20compound.metaData.value:%27IKUWMGOXYQGWPC-ZBDJHBETSA-N%27)
  5. Metabolomics Workbench
  6. Wikidata
    (1S,2S,3E,7R,11E,13R)-2-Hydroxy-7-methyl 6-oxabicyclo[11.3.0]hexadecane-3,11-diene-5,15-dione
    https://www.wikidata.org/wiki/Q105114960
  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
  9. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS