Structure via PubChem · Public domain (PubChem)
Hexacyclinol
Sign in to saveHexacyclinol is a natural metabolite of a fungus, Panus rudis. Significant controversy surrounded its proposed structure until its total synthesis by John Porco, Jr. in 2006.
In the Vinony graph
Chemical data
- Formula
- C23H28O7
- Molecular weight
- 416.5 g/mol
- IUPAC name
- (1S,2S,6S,8S,9R,10S,11S,12R,13S,15S,17R)-9-hydroxy-2-(2-methoxypropan-2-yl)-17-(2-methylprop-1-enyl)-7,14,18-trioxahexacyclo[10.4.2.01,11.04,10.06,8.013,15]octadec-3-ene-5,16-dione
- SMILES
- CC(=C[C@@H]1[C@@]23[C@H](C=C4[C@H]([C@@H]2[C@@H](O1)[C@H]5[C@@H](C3=O)O5)[C@H]([C@H]6[C@@H](C4=O)O6)O)C(C)(C)OC)C
- InChIKey
- PFZFRWWDGXFULQ-NHFKQXEKSA-N
- XLogP
- 0.5
- Polar surface area
- 97.9 Ų
- H-bond donors
- 1
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 416.183503
Show 4 more facts
- chemical formula
- C₂₃H₂₈O₇
- Commons category
- Hexacyclinol
- canonical SMILES
- CC(=CC1C23C(C=C4C(C2C(O1)C5C(C3=O)O5)C(C6C(C4=O)O6)O)C(C)(C)OC)C
- isomeric SMILES
- CC(=C[C@@H]1[C@@]23[C@H](C=C4[C@H]([C@@H]2[C@@H](O1)[C@H]5[C@@H](C3=O)O5)[C@H]([C@H]6[C@@H](C4=O)O6)O)C(C)(C)OC)C
Sources (1)
via Wikidata · CC0
~2 min read
Encyclopedic overview
2 sectionsContents
- Controversy over structure
- References
Hexacyclinol is a natural metabolite of a fungus, Panus rudis. Significant controversy surrounded its proposed structure until its total synthesis by John Porco, Jr. in 2006.
==Controversy over structure== left|thumb|(2) The structure of hexacyclinol proposed by Gräfe and purportedly synthesized by La Clair. Natural products chemist Udo Gräfe collected a sample of P. rudis HKI 0254 from a dead log in Siberia from which hexacyclinol was isolated. His group's 2002 paper showed that the compound behaved as an antiproliferative drug against cancer cell lines and proposed a structure (2) for the compound.
Excerpted from Wikipedia’s “Hexacyclinol” article, available under the CC BY-SA 4.0 licence.