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Wilformine

PubChem CID
44584752
Structure
Wilformine_small.png
Molecular Formula
Synonyms
  • Wilformine
  • Euonine
  • CHEBI:132386
  • 41758-69-4
  • [(1S,3R,15S,18S,19R,20R,21R,22S,23R,24R,25R,26S)-19,20,22,23,25-pentaacetyloxy-26-hydroxy-3,15,26-trimethyl-6,16-dioxo-2,5,17-trioxa-11-azapentacyclo[16.7.1.01,21.03,24.07,12]hexacosa-7(12),8,10-trien-21-yl]methyl acetate
Molecular Weight
805.8 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2010-01-26
  • Modify:
    2024-12-06
Description
Wilformine is a sesquiterpene alkaloid that has been isolated from Tripterygium wilfordii and exhibits immunosuppressive and insecticidal properties. It was found to be identical with euonine, previously isolated from Euonymous sieboldiana. It has a role as a plant metabolite, an immunosuppressive agent and an insecticide. It is an acetate ester, a dihydroagarofuran sesquiterpenoid, a macrolide, a pyridine alkaloid and a sesquiterpene alkaloid.
Wilformine has been reported in Tripterygium wilfordii, Tripterygium hypoglaucum, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Wilformine.png

1.2 3D Status

Conformer generation is disallowed since too many atoms

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(1S,3R,15S,18S,19R,20R,21R,22S,23R,24R,25R,26S)-19,20,22,23,25-pentaacetyloxy-26-hydroxy-3,15,26-trimethyl-6,16-dioxo-2,5,17-trioxa-11-azapentacyclo[16.7.1.01,21.03,24.07,12]hexacosa-7(12),8,10-trien-21-yl]methyl acetate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C38H47NO18/c1-17-12-13-25-24(11-10-14-39-25)34(47)50-15-35(8)26-27(51-19(3)41)31(54-22(6)44)37(16-49-18(2)40)32(55-23(7)45)28(52-20(4)42)30(56-33(17)46)36(9,48)38(37,57-35)29(26)53-21(5)43/h10-11,14,17,26-32,48H,12-13,15-16H2,1-9H3/t17-,26+,27+,28-,29+,30-,31+,32-,35-,36-,37+,38-/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

QIHHQEWWGMEJTH-VWEYKOQISA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C[C@H]1CCC2=C(C=CC=N2)C(=O)OC[C@]3([C@@H]4[C@H]([C@H]([C@@]5([C@H]([C@H]([C@@H]([C@]([C@]5([C@@H]4OC(=O)C)O3)(C)O)OC1=O)OC(=O)C)OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C)C
Computed by OEChem 2.3.0 (PubChem release 2021.10.14)

2.2 Molecular Formula

C38H47NO18
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 ChEBI ID

2.3.2 ChEMBL ID

2.3.3 Metabolomics Workbench ID

2.3.4 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

euonine

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
805.8 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
0.5
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
19
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
13
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
805.27931365 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
805.27931365 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
253Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
57
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1670
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
12
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
0
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 Chemical Co-Occurrences in Literature

6.4 Chemical-Gene Co-Occurrences in Literature

6.5 Chemical-Disease Co-Occurrences in Literature

7 Patents

7.1 Depositor-Supplied Patent Identifiers

7.2 Chemical Co-Occurrences in Patents

7.3 Chemical-Disease Co-Occurrences in Patents

7.4 Chemical-Gene Co-Occurrences in Patents

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
  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. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  4. Natural Product Activity and Species Source (NPASS)
  5. Metabolomics Workbench
  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
  9. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS