User talk:Innerstream

Welcome to Wikimedia Commons, Innerstream!

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-- Wikimedia Commons Welcome (talk) 14:20, 24 March 2021 (UTC)

Chemical SVGs

I see you've been contributing a lot of chemical SVGs. Thanks! 🙇🏾‍♂️ I was wondering if you're working off a list like Top_200_chemistry_images_that_should_use_vector_graphics or how you are choosing them? TSamuel (talk) 11:37, 5 September 2021 (UTC)

Mostly just random choices. I've been creating SVG images when I encounter an image while reading Wikipedia that I think could benefit by being higher quality or having a representation that is easier to interpret. I recently stumbled upon the Top 200 list that you mention and created a few improved versions of the files listed there. Innerstream (talk) 13:46, 5 September 2021 (UTC)

Did you run into yet? I optimized the PNG & added the {ShouldBeText} as a suggestion, but I don't know whether fulfilling the {ShouldBeSVG} is right way to go instead, nor am I good at text-in-SVG. TSamuel (talk) 21:23, 5 September 2021 (UTC)

That seems like an image that isn't necessary. Why not just use plain text? Even if an image is preferred for any reason, File:Iodo-group.png is high enough resolution that creating an SVG hardly seems worth the effort - you'll just end up with something that looks the same for any plausible use. Innerstream (talk) 14:44, 6 September 2021 (UTC)

I agree completely. What befuddles me about it is that it's included ~30×(!) in various places & so is in that top 200 list, where folks seem to disagree w/ us & really want a better representation. How about <svg><text y=12>R — I</text></svg>? TSamuel (talk) 20:46, 6 September 2021 (UTC)

I created a simple SVG file, File:Alkyl iodide.svg. I'm not sure it's really useful, or any better than the PNG or just plain text, but it was quick and easy to create. Innerstream (talk) 16:49, 12 September 2021 (UTC)

I think Inkscape made it too large & complicated, but unsure how to best resolve by hand. Did you try Inkscape's export as minimal SVG? TSamuel (talk) 04:58, 13 September 2021 (UTC)

Sorry, I don't know how to make Inkscape save it with smaller file size. I don't think it would be worth the effort anyway. Innerstream (talk) 23:53, 13 September 2021 (UTC)

I'll give it a shot, then. I just can't get Wikimedia's SVG sandbox working right, so I guess I'll just try uploading & seeing. TSamuel (talk) 02:50, 14 September 2021 (UTC)

I just uploaded my version there. Let me know what you think! 🙇🏾‍♂️ TSamuel (talk) 03:33, 14 September 2021 (UTC)

Looks good to me. Innerstream (talk) 00:42, 15 September 2021 (UTC)

Rifapentine

Hi, I noticed an oxygen was forgotten on the Rifapentine structure by the furanone. New structure looks great otherwise! --Ducctip (talk) 18:31, 25 April 2024 (UTC) — Preceding unsigned comment added by Ducctip (talk • contribs) 16:37, 25 April 2024 (UTC)

@Ducctip: You're right. Thanks for catching that. I have corrected the error. Innerstream (talk) 18:05, 25 April 2024 (UTC)

File:Benzotriazole protonation-deprotonation.svg

Hi there, could you please have a look at this comment that seems to refer to your figure? --Leyo 13:06, 11 January 2022 (UTC)

Hi Leyo. Thank you letting me know about that comment. I recently created that image based on the existing image File:Benzotriazol Protolysegleichgewichte.png. I think the concerns expressed in the comment are valid. It is a clear error to have a hydrogen atom on each of the three nitrogen atoms in the cation. I'll fix that. I will also consider a better, more accurate way of representing both the cation and anion. Innerstream (talk) 00:08, 12 January 2022 (UTC)

@Leyo: I have now uploaded an alternate version, File:Benzotriazole protonation-deprotonation v2.svg, which depicts the cation and anion as further delocalized. I think the first image is reasonable, because the charge is likely to be localized mostly in the triazole, but feel free to replace any use of File:Benzotriazole protonation-deprotonation.svg with the new version if you prefer it. If you have any comments or suggestions on a better way to represent this image, please just let me know. Innerstream (talk) 16:20, 12 January 2022 (UTC)

Thank you. I'm just pinging Steffen 962 who uploaded the PNG version twelve years ago. He might have comments or suggestions. --Leyo 19:50, 12 January 2022 (UTC)

I have looked at the acticle which is cited in the German benzotriazole article (H. Wang, C. Burda, G. Persy, J. Wirz: Photochemistry of 1H-Benzotriazole in Aqueous Solution: A Photolatent Base. In: J. Am. Chem. Soc. 122 (2000), 5849–5855; doi:10.1021/ja994464c.) I have created a new version similar to the scheme in the article File:Benzotriazole protonation-deprotonation V3.svg. From my opinion it represent more the charge delocalisation over the thee nitrogen atoms.--Steffen 962 (talk) 21:38, 12 January 2022 (UTC)

Thank you. That seems like a good way of drawing it. Innerstream (talk) 23:32, 12 January 2022 (UTC)

File:Rhizocarpic acid.svg alkene stereochemistry

Hi Innerstream,

I was looking at your rhizocarpic acid as a starting-point for creating an image for en:Epanorin, a close analog. But I think you have the alkene with the wrong stereochemistry? The original report (doi:10.1021/ja01166a032) and pubchem for both compounds have the alkene Z (carbonyl cis to the lactone oxygen), whereas yours looks E. DMacks (talk) 06:09, 10 April 2022 (UTC)

Interesting. I'm not sure if the state of analytical chemistry in 1950 was sufficient to unambiguously assign the double bond stereochemistry of the compound, but I don't have access to the full article you cite to see if they specifically address the issue. Pubchem is often wrong, so I wouldn't use it a source to resolve any chemical structure uncertainty. Chemical Abstracts defines rhizocarpic acid (CAS#18463-11-1) with the annotation "Double bond geometry unknown". I generally consider Chemical Abstracts to be the most authoritative source for chemical structure identification (though, of course, they are not perfect). I would lean towards going with Chemical Abstracts in this case. Considering that other pulvinic acids are known to have the E double bond stereochemistry that I've drawn in File:Rhizocarpic acid.svg (see Category:Pulvinic acids), I think that's the more plausible of the two options. Either way, perhaps this chemical structure ambiguity is best handled by addressing it within the text of the article. Innerstream (talk) 20:03, 10 April 2022 (UTC)

Good point about 1950s state-of-the-art for this detail. Looking more closely, the doi I cited actually does have it drawn E not Z (brain-tangled by working on too many projects at once:(. It doesn't comment on E/Z, but it does mention that both rhizocarpic acid and epanorin convert to a bis-lactone like 5 of File:Synthesis Pulvinic acid.svg, so that would require at least an equilibrium availability E in some way. I can't find any crystal strucures, even though these are readily-available crystalline solids. Leaving it as-is, with a clear comment in text (or at least an embedded note in the infoboxes) sounds like a good idea. DMacks (talk) 08:34, 11 April 2022 (UTC)

I've left a comment in the file description for File:Rhizocarpic acid.svg regarding stereochemistry. You've drawn File:Epanorin.png exactly as I would. Innerstream (talk) 23:41, 11 April 2022 (UTC)

File:Sinapaldehyde.svg

At en:Sinapaldehyde, Smokefoot noted: "missing the propenyl group". Want me to rename this image to en:Syringaldehyde? DMacks (talk) 21:08, 14 May 2022 (UTC)

Thanks for letting me know and thanks to Smokefoot for catching the error. I have now corrected File:Sinapaldehyde.svg and reuploaded the former version as File:Syringaldehyde skeletal.svg. Innerstream (talk) 14:21, 15 May 2022 (UTC)

File:Fosnetupitant.svg

Hi, File:Fosnetupitant.svg has an error in which a nitrogen is missing from the ring between the amide and the Piperazine group. Check https://www.kegg.jp/entry/D11065 for example. Hopefully you can fix the diagram and then can put it in the English Wikipedia article and wikidata. Graeme Bartlett (talk) 00:10, 9 June 2022 (UTC)

You're right. Good eye. I have fixed the image and added it back into the article. Thank you. Innerstream (talk) 03:49, 9 June 2022 (UTC)

File:Triton X-100.svg

Hi Innerstream, the n seems to stick at the bracket in some resolutions. Could you improve this? Leyo 11:23, 19 September 2022 (UTC)

@Leyo: I wasn't able to see the issue on my browser at any resolution. However, I think I've seen the issue you describe on other files. I've made an adjustment to the file (changed object groupings) that I think will address the issue. Please let me know if it looks ok to you now. Innerstream (talk) 13:35, 19 September 2022 (UTC)

It looks fine now, thank you. --Leyo 15:35, 19 September 2022 (UTC)

Autopatrol rights on pl.wiki

Hi, I'm writing just to inform you that I've enabled autopatrol rights on your account on the Polish Wikipedia, because your edits there are only related to replacing inferior chemical diagrams with better versions and therefore do not require manual reviewing. This change does not require you to take any action, I hope you will continue to make these kind of edits and I thank you for your contributions to Polish Wikipedia. Wostr (talk) 12:44, 27 October 2022 (UTC)

Thank you. Innerstream (talk) 23:43, 27 October 2022 (UTC)

Povarov stereochemistry

Do you have a ref for your File:Povarov example.svg reaction diagram? At en:Povarov reaction, there is a cite:

• Unprecedented regio and stereocontrol in Povarov reaction of benzylidene-(3-nitrophenyl)amine Paul J. Stevenson and Isla Graham Arkivoc AM-717D 2003. (Article)

for the adjacent content. But it starts with a trans alkene rather than cis, and it gives a diastereomeric mixture (not preserving alkene geometry like in normal Diels–Alder). DMacks (talk) 15:21, 6 March 2023 (UTC)

@DMacks: I'm pretty sure that I based that image off the deleted file File:Povarov example.gif. Based on the reference you cite, you're right that the starting material should have trans double bond. I'll make that correction shortly. In that reference, they say the reaction is diastereoselective favoring the stereoisomer shown in my image. So I think it's not wrong, in the sense that it depicts the major product of the reaction. But the reaction is not fully diastereoselective and that seems at odds with text in en:Povarov reaction. I see two options here: 1) keep the image showing one product and use the associated text to note that another diastereomer is also formed to a lesser degree, or 2) add the second product and indicate a 2:1 ratio that is reported in the reference. What do you think? Innerstream (talk) 14:20, 7 March 2023 (UTC)

File:Mirvetuximab soravtansine.svg

I've corrected the structure: there's only one hydroxy group at the oxazinanon ring. NadirSH (talk) 18:21, 4 April 2023 (UTC)

@NadirSH: Thank you for noticing the error and correcting it. I have also corrected File:Soravtansine.svg which had the same error. Innerstream (talk) 14:04, 5 April 2023 (UTC)

File:Fumonisin B1.svg

You seem to have dropped one of the Os in this structure, as well as in File:Fumonisin B4.svg. LegionMammal978 (talk) 23:25, 1 May 2023 (UTC)

Thank you for letting me know. I have now corrected the images. Innerstream (talk) 00:37, 2 May 2023 (UTC)

Amphetamine derivative and myristicin structures.svg

On Amphetamine derivative and myristicin structures.svg the centre-left image labelled "MDMA" should be described as "methylenedioxymethamphetamine". Thanks --Pontificalibus (talk) 06:19, 3 September 2023 (UTC)

@Pontificalibus: You're right. Thank you for letting me know. I have now corrected the image. Innerstream (talk) 14:01, 3 September 2023 (UTC)

Thank you --Pontificalibus (talk) 12:36, 4 September 2023 (UTC)

File:Simnotrelvir.svg

It seems that the paper cited (10.1021/acsptsci.3c00134) flipped the sterochemistry on the left-hand side. The correct molecule should have four chiral centers, all S. The Chinese package insert can be used as the source of truth here. As far as I can tell it's the same as PubChem CID 168476146, but check for yourself. Artoria2e5 contribs 08:51, 2 October 2023 (UTC)

@Artoria2e5: Unfortunately, the link to the Chinese package insert doesn't work for me. Based on my personal experience dealing with Chinese bureaucracy, I'm not sure I would trust it to be free of errors though. ☺ Anyway, for now I've updated the image to match the structure shown on PubChem. Thanks for bringing the issue to my attention. I'll keep an eye on this for awhile and see if the structure turns up in other sources that might provide additional confirmation of the correct structure. Innerstream (talk) 13:30, 4 October 2023 (UTC)

Thanks for the change! Har, har, you aren't wrong about the Chinese bureaucracy. What matters is that the full Chinese systematic name "(S)-N-((S)-1-氰基-2-((S)-2-氧代-3-吡咯烷基)乙基)-7-((S)-3,3-二甲基-2-(2,2,2-三氟乙酰氨基)丁酰基)-1,4-二硫杂-7-氮杂螺[4.4]壬烷-8-甲酰胺" seems to match the PubChem IUPAC "(8S)-N-[(1S)-1-cyano-2-[(3S)-2-oxopyrrolidin-3-yl]ethyl]-7-[(2S)-3,3-dimethyl-2-[(2,2,2-trifluoroacetyl)amino]butanoyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxamide" word by word, save for the omission of numbering. Artoria2e5 contribs 15:07, 4 October 2023 (UTC)

File:Chamaecydin.svg

Could you upgrade this diagram to include stereochemistry? en:Chamaecydin is citedly about a known single stereoisomer. DMacks (talk) 20:24, 23 November 2023 (UTC)

I've added stereochemisty based on the Pubchem listing. Thanks for the suggestion. Innerstream (talk) 21:48, 24 November 2023 (UTC)

File:Seseline.svg

File:Seseline.svg has been listed at Commons:Deletion requests so that the community can discuss whether it should be kept or not. We would appreciate it if you could go to voice your opinion about this at its entry. If you created this file, please note that the fact that it has been proposed for deletion does not necessarily mean that we do not value your kind contribution. It simply means that one person believes that there is some specific problem with it, such as a copyright issue. Please see Commons:But it's my own work! for a guide on how to address these issues. Please remember to respond to and – if appropriate – contradict the arguments supporting deletion. Arguments which focus on the nominator will not affect the result of the nomination. Thank you!

Alfa-ketosav (talk) 10:14, 18 December 2023 (UTC)

File:GABA.svg

File:GABA.svg has been listed at Commons:Deletion requests so that the community can discuss whether it should be kept or not. We would appreciate it if you could go to voice your opinion about this at its entry. If you created this file, please note that the fact that it has been proposed for deletion does not necessarily mean that we do not value your kind contribution. It simply means that one person believes that there is some specific problem with it, such as a copyright issue. Please see Commons:But it's my own work! for a guide on how to address these issues. Please remember to respond to and – if appropriate – contradict the arguments supporting deletion. Arguments which focus on the nominator will not affect the result of the nomination. Thank you!

Alfa-ketosav (talk) 14:54, 31 December 2023 (UTC)

File:Guaijaverin.svg

An IP on enwiki reported a mistake in this image of yours. I annotated it with the detail. File:Guaijaverin.png seems correct. Once the SVG is fixed, that poor PNG can be DR'ed. I have no idea if the current SVG is a chemical of interest worth keeping (at a better filename) or not. DMacks (talk) 22:33, 6 February 2024 (UTC)

Thank you for relaying the information to me. I have now corrected the image and put it back into the article. Innerstream (talk) 00:10, 7 February 2024 (UTC)

File:Olgotrelvir.svg

Hi Innerstream! I noticed you created the chemical structure image for olgotrelvir File:Olgotrelvir.svg. I am by no means an expert in organic chemistry, so I could be completely off-base, but it appears that image may have an error. The image looks different on several different sources. For example, PubChem[1], MedChemExpress[2], and the automated structure derived from the SMILES (CC(C)CC(C(=O)NC(CC1CCNC1=O)C(O)S(=O)(=O)O)NC(=O)C2=CC3=CC=CC=C3N2) on Smi2Depict[3] appear different. For example, the double-bounded oxygen in the amide group coming off the carbon attached to the indole group and the double bond oxygen from the next amide group seem to be facing towards each other in the image you created, while they are not in the other images. Could you double-check when you get a chance? I apologize ahead of time if I am incorrect. Thanks! Wikipedialuva (talk) 02:25, 12 April 2024 (UTC)

Hi Wikipedialuva. Thanks for reviewing the chemical structure. In this case, I believe it is correct. The differences that you observe in various images are actually chemically equivalent because of the possibility of free rotation about the bonds. These are essentially conformational differences. The connectivity of atoms, which is what defines the difference between chemicals such as this, is the same in each visual representation. Innerstream (talk) 12:51, 12 April 2024 (UTC)

Thanks for reviewing and making sure the image was accurate, along with the explanation why; it was very helpful. Wikipedialuva (talk) 07:07, 13 April 2024 (UTC)