Talk:Cheilanthifoline
Add topicLatest comment: 5 months ago by DMacks in topic Accuracy problems
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Accuracy problems
[edit]@DMacks: based on Chemical Abstracts, cheilanthifoline (CAS# 483-44-3) is the (-)-(S)-enantiomer. This enantiomer has 136 references cited in Chemical Abstracts. The other enantiomer (CAS #845513-56-6) appears in a single reference and it is a 20 year old article in a journal that I would consider lower tier, so it's possible (likely?) that it's just an error. Since File:Cheilanthifoline.svg is missing stereochemical information and File:Cheilanthifoline.png is the wrong regioisomer, I have created a new image, File:(-)-(S)-Cheilanthifoline.svg, to represent this compound. Innerstream (talk) 17:30, 1 May 2023 (UTC)
-(S)-Cheilanthifoline.svg){kind=link}
- Thanks! I agree the wrong stereo seemed more of a simple mistake. But the regio actually was a legitimate dispute. File:Cheilanthifoline.png agrees with PubChem 20582 (titled "(S)-Cheilanthifoline") whereas PubChem 590762 (titled "12H-Benzo[a]-1,3-benzodioxolo[4,5-g]quinolizin-9-ol, 6,6a,11,14-tetrahydro-8-methoxy-" with alt names "dl-Cheilanthifoline" and "Isochelianthifoline" matches what you and I found in the lit. PubChem 101277425 appears to be the correct regio and stereo but does not list "Cheilanthifoline" among its names. But its InChI matches. DMacks (talk) 02:10, 2 May 2023 (UTC)
- Just for the record regarding stereochemistry of the most-likely-correct regio according to SciFinder:
- CASNo 845513-56-6, is (+)-(R)-
- CASNo 483-44-3 is (S)-
- CASNo 794529-39-8 is "Available stereochemistry shown" (with no R/S info)
- CASNo 41431-80-5 is silent about stereo
- DMacks (talk) 02:29, 2 May 2023 (UTC)
- DMacks More importantly, CAS at 483-44-3 has the wrong regiochemistry for the OH and OMe substituents of cheilanthifoline. See commons:User_talk:Innerstream#Cheilanthifoline for details. Innerstream has updated the file so all is now well and the other IDs given in our chembox (including the InChIKey) are in line with the literature such as the NPR review at doi:10.1039/D4NP00029C. Mike Turnbull (talk) 13:24, 6 February 2026 (UTC)
- Thanks all for catching that and getting it updated. DMacks (talk) 23:29, 6 February 2026 (UTC)
- DMacks More importantly, CAS at 483-44-3 has the wrong regiochemistry for the OH and OMe substituents of cheilanthifoline. See commons:User_talk:Innerstream#Cheilanthifoline for details. Innerstream has updated the file so all is now well and the other IDs given in our chembox (including the InChIKey) are in line with the literature such as the NPR review at doi:10.1039/D4NP00029C. Mike Turnbull (talk) 13:24, 6 February 2026 (UTC)