Category:PK

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Curacin A (Lyngbya), Shiphonazole (Herpetosiphon), Jamaicamide A (Lyngbya), Cylindrospermopsin (Cylindrospermopsis)
 
Curacin A (Lyngbya), Shiphonazole (Herpetosiphon), Jamaicamide A (Lyngbya), Cylindrospermopsin (Cylindrospermopsis)
  
 +
|}
 +
 +
{|
 +
|-
 +
| [[Image:1,3,8-Trihydroxyaceto-Naphthalene.Mol]]
 +
|-
 +
| [[Image:1,3-Dihydroxy-N-Methylacridone.Mol]]
 +
|-
 +
| [[Image:3,8-Dihydroxy-1-Methylanthraquinone-2-Carboxylic_Acid.Mol]]
 +
|-
 +
| [[Image:4-Hydroxy-2-Quinolone.Mol]]
 +
|-
 +
| [[Image:5,7-Dihydroxy-2-Methylchromone.Mol]]
 +
|-
 +
| [[Image:5-Methylorsellinic_Acid.Mol]]
 +
|-
 +
| [[Image:6-Deoxy-Erythronolide_B.Mol]]
 +
|-
 +
| [[Image:6-Methoxymellein.Mol]]
 +
|-
 +
| [[Image:6-Methyl_Salicylic_Acid.Mol]]
 +
|-
 +
| [[Image:Actinorhodin.Mol]]
 +
|-
 +
| [[Image:Adhyperforin.Mol]]
 +
|-
 +
| [[Image:Aflatoxin_B1.Mol]]
 +
|-
 +
| [[Image:Aflatoxin_B2.Mol]]
 +
|-
 +
| [[Image:Aflatoxin_G1.Mol]]
 +
|-
 +
| [[Image:Aflatoxin_G2.Mol]]
 +
|-
 +
| [[Image:Aflatoxin_M1.Mol]]
 +
|-
 +
| [[Image:Aloe-Emodin.Mol]]
 +
|-
 +
| [[Image:Aloesaponarin_II.Mol]]
 +
|-
 +
| [[Image:Alternapyrone.Mol]]
 +
|-
 +
| [[Image:Alternaric_Acid.Mol]]
 +
|-
 +
| [[Image:Alternariol.Mol]]
 +
|-
 +
| [[Image:Amphotericin_B.Mol]]
 +
|-
 +
| [[Image:Andrimid_.Mol]]
 +
|-
 +
| [[Image:Ascomycin.Mol]]
 +
|-
 +
| [[Image:Aslaniol.Mol]]
 +
|-
 +
| [[Image:Aslanipyrone.Mol]]
 +
|-
 +
| [[Image:Asperlactone.Mol]]
 +
|-
 +
| [[Image:Asperlin.Mol]]
 +
|-
 +
| [[Image:Aspyridone_A.Mol]]
 +
|-
 +
| [[Image:Aspyridone_B.Mol]]
 +
|-
 +
| [[Image:Aspyrone.Mol]]
 +
|-
 +
| [[Image:Asteltoxin.Mol]]
 +
|-
 +
| [[Image:Astepyrone.Mol]]
 +
|-
 +
| [[Image:Atrochrysone.Mol]]
 +
|-
 +
| [[Image:Atrochrysone_Carboxylic_Acid.Mol]]
 +
|-
 +
| [[Image:Aureothin.Mol]]
 +
|-
 +
| [[Image:Austdiol.Mol]]
 +
|-
 +
| [[Image:Avenaciolide.Mol]]
 +
|-
 +
| [[Image:Averantin.Mol]]
 +
|-
 +
| [[Image:Avermectin_B1A.Mol]]
 +
|-
 +
| [[Image:Avermectin_B2A.Mol]]
 +
|-
 +
| [[Image:Averufin.Mol]]
 +
|-
 +
| [[Image:Avilamycin.Mol]]
 +
|-
 +
| [[Image:Barnol.Mol]]
 +
|-
 +
| [[Image:Benzophenone.Mol]]
 +
|-
 +
| [[Image:Bikaverin.Mol]]
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|-
 +
| [[Image:Botryodiplodin.Mol]]
 +
|-
 +
| [[Image:Brefeldin_A.Mol]]
 +
|-
 +
| [[Image:Brevetoxin_A.Mol]]
 +
|-
 +
| [[Image:Brevetoxin_B.Mol]]
 +
|-
 +
| [[Image:C-1027.Mol]]
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|-
 +
| [[Image:Calichemicin_Gamma1.Mol]]
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|-
 +
| [[Image:Cannabidiol.Mol]]
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|-
 +
| [[Image:Cannabigerolic_Acid.Mol]]
 +
|-
 +
| [[Image:Cannabinol.Mol]]
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|-
 +
| [[Image:Cercosporin.Mol]]
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|-
 +
| [[Image:Chlortetracycline.Mol]]
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|-
 +
| [[Image:Chrysomycin_A.Mol]]
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|-
 +
| [[Image:Chrysomycin_B.Mol]]
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|-
 +
| [[Image:Chrysophanol.Mol]]
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|-
 +
| [[Image:Chrysophanol_Anthrone.Mol]]
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|-
 +
| [[Image:Ciguatoxin_I.Mol]]
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|-
 +
| [[Image:Citreomontanin.Mol]]
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|-
 +
| [[Image:Citreoviridin.Mol]]
 +
|-
 +
| [[Image:Citrinin.Mol]]
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|-
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| [[Image:Clavatol.Mol]]
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|-
 +
| [[Image:Coarctatin.Mol]]
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|-
 +
| [[Image:Colletodiol.Mol]]
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|-
 +
| [[Image:Compactin.Mol]]
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|-
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| [[Image:Curvularin.Mol]]
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|-
 +
| [[Image:Deoxyherquienone.Mol]]
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|-
 +
| [[Image:Deoxyradicin.Mol]]
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|-
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| [[Image:Dihydroisocoumarin.Mol]]
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|-
 +
| [[Image:Diplosporin.Mol]]
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|-
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| [[Image:Discodermolide.Mol]]
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|-
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| [[Image:Doramectin.Mol]]
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|-
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| [[Image:Dothistromin.Mol]]
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|-
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| [[Image:Doxorubicin.Mol]]
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|-
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| [[Image:Emodin.Mol]]
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|-
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| [[Image:Emodin_Anthrone.Mol]]
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|-
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| [[Image:Emodin_Dianthrone.Mol]]
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|-
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| [[Image:Endocrocin.Mol]]
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|-
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| [[Image:Endocrocin_Anthrone.Mol]]
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|-
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| [[Image:Enniatin_B.Mol]]
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|-
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| [[Image:Enterocin.Mol]]
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|-
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| [[Image:Epothilone_A.Mol]]
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|-
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| [[Image:Epothilone_B.Mol]]
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|-
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| [[Image:Epothilone_C.Mol]]
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|-
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| [[Image:Epothilone_D.Mol]]
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|-
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| [[Image:Epoxydon.Mol]]
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|-
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| [[Image:Epsilon-Pyrromycinone.Mol]]
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|-
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| [[Image:Erythromycin.Mol]]
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|-
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| [[Image:Flavipin.Mol]]
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|-
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| [[Image:Fumigatin.Mol]]
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|-
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| [[Image:Fumonisin_B1.Mol]]
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|-
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| [[Image:Furanomycin.Mol]]
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|-
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| [[Image:Geldanamycin.Mol]]
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|-
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| [[Image:Griseofulvin.Mol]]
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|-
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| [[Image:Griseophenone_B.Mol]]
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|-
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| [[Image:Griseophenone_C.Mol]]
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|-
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| [[Image:Humulone.Mol]]
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|-
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| [[Image:Hyperforin.Mol]]
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|-
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| [[Image:Hypericin.Mol]]
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|-
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| [[Image:Islandicin.Mol]]
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|-
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| [[Image:Isoepoxydon.Mol]]
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|-
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| [[Image:Isousnic_Acid.Mol]]
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|-
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| [[Image:Ivermectin.Mol]]
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|-
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| [[Image:Khellin.Mol]]
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|-
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| [[Image:Lasalocid.Mol]]
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|-
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| [[Image:Lecanoric_Acid.Mol]]
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|-
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| [[Image:Leucomycin_A1.Mol]]
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|-
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| [[Image:Ll-D253Alpha.Mol]]
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|-
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| [[Image:Lovastatin.Mol]]
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|-
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| [[Image:M-Cresol.Mol]]
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|-
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| [[Image:Melanin.Mol]]
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|-
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| [[Image:Mellein.Mol]]
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|-
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| [[Image:Methylphloracetophenone.Mol]]
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|-
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| [[Image:Mollisin.Mol]]
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|-
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| [[Image:Monensin_A.Mol]]
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|-
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| [[Image:Multicolic_Acid.Mol]]
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|-
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| [[Image:Mycolactone.Mol]]
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|-
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| [[Image:Mycophenolic_Acid.Mol]]
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|-
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| [[Image:Myxalamide.Mol]]
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|-
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| [[Image:Myxothiazol_Z.Mol]]
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|-
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| [[Image:Niddamycin.Mol]]
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|-
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| [[Image:Norsolorinic_Acid.Mol]]
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|-
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| [[Image:Nystatin.Mol]]
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|-
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| [[Image:Ochratoxin_A.Mol]]
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|-
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| [[Image:Ochrephilone.Mol]]
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|-
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| [[Image:Okadaic_Acid.Mol]]
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|-
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| [[Image:Oleandomycin.Mol]]
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|-
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| [[Image:Olivetolic_Acid.Mol]]
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|-
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| [[Image:O-Methylasparvenone.Mol]]
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|-
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| [[Image:Orcinol.Mol]]
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|-
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| [[Image:Orsellinic_Acid.Mol]]
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|-
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| [[Image:Oxytetracycline.Mol]]
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|-
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| [[Image:Palitantin.Mol]]
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|-
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| [[Image:Patulin.Mol]]
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|-
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| [[Image:Penicillic_Acid.Mol]]
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|-
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| [[Image:Phloracetophenone.Mol]]
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|-
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| [[Image:Phlorisobutyrophenone.Mol]]
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|-
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| [[Image:Phlorisovalerophenone.Mol]]
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|-
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| [[Image:Physcion.Mol]]
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|-
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| [[Image:Picromycin.Mol]]
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|-
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| [[Image:Pimaricin.Mol]]
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|-
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| [[Image:Pretetramide.Mol]]
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|-
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| [[Image:Protohypericin.Mol]]
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|-
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| [[Image:Pyochelin.Mol]]
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|-
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| [[Image:Pyoluteorin.Mol]]
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|-
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| [[Image:Radicin.Mol]]
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|-
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| [[Image:Rapamycin.Mol]]
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|-
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| [[Image:Ravenilin.Mol]]
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|-
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| [[Image:Rhein.Mol]]
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|-
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| [[Image:Rifabutin.Mol]]
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|-
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| [[Image:Rifamycin_B.Mol]]
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|-
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| [[Image:Rifapentine.Mol]]
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|-
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| [[Image:Rosellisin.Mol]]
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|-
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| [[Image:Rubrofusarin.Mol]]
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|-
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| [[Image:Rubropunctatin.Mol]]
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|-
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| [[Image:Sclerin.Mol]]
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|-
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| [[Image:Sclerotinin_A.Mol]]
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|-
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| [[Image:Sek4.Mol]]
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|-
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| [[Image:Sek4B.Mol]]
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|-
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| [[Image:Selamectin.Mol]]
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|-
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| [[Image:Sennidin_A.Mol]]
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|-
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| [[Image:Sennidin_B.Mol]]
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|-
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| [[Image:Sennidin_C.Mol]]
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|-
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| [[Image:Sennidin_D.Mol]]
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|-
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| [[Image:Sennosides_A.Mol]]
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|-
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| [[Image:Sennosides_B.Mol]]
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|-
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| [[Image:Sennosides_C.Mol]]
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|-
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| [[Image:Sennosides_D.Mol]]
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|-
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| [[Image:Sepedonin.Mol]]
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|-
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| [[Image:Siccanin.Mol]]
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|-
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| [[Image:Silvaticamide.Mol]]
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|-
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| [[Image:Sma76A.Mol]]
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|-
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| [[Image:Sma76B.Mol]]
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|-
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| [[Image:Sma76C.Mol]]
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|-
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| [[Image:Soraphen_A.Mol]]
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|-
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| [[Image:Spinulosin.Mol]]
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|-
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| [[Image:Spiramycin_I.Mol]]
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|-
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| [[Image:Sterigmatocystin.Mol]]
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|-
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| [[Image:Stigmatellin_A.Mol]]
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|-
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| [[Image:Stipitatonic_Acid.Mol]]
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|-
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| [[Image:Sulochrin.Mol]]
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|-
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| [[Image:Tacrolimus.Mol]]
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|-
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| [[Image:Tajixanthone.Mol]]
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|-
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| [[Image:Tennellin.Mol]]
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|-
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| [[Image:Terrein.Mol]]
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|-
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| [[Image:Terrequinone_A.Mol]]
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|-
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| [[Image:Tetracenomycin_F2.Mol]]
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|-
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| [[Image:Tetracycline.Mol]]
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|-
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| [[Image:Tetrahydro_Cannabinol.Mol]]
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|-
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| [[Image:Tetrahydroxynaphthalene.Mol]]
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|-
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| [[Image:Triacetic_Acid_Lactone.Mol]]
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|-
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| [[Image:T-Toxin.Mol]]
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|-
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| [[Image:Tylactone.Mol]]
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|-
 +
| [[Image:Tylosin.Mol]]
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|-
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| [[Image:Urushiol_III.Mol]]
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|-
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| [[Image:Usnic_Acid.Mol]]
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|-
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| [[Image:Variotin.Mol]]
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|-
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| [[Image:Versicolorin_A.Mol]]
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|-
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| [[Image:Versicolorin_B.Mol]]
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|-
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| [[Image:Versiconal.Mol]]
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|-
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| [[Image:Versiconal_Acetate.Mol]]
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|-
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| [[Image:Visnagin.Mol]]
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|-
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| [[Image:Wa-Naphthopyron.Mol]]
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|-
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| [[Image:Zaragozic_Acids_A.Mol]]
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|-
 +
| [[Image:Zearalenone.Mol]]
 
|}
 
|}

Revision as of 12:30, 6 March 2010

Polyketide (ポリケチド)


Contents

Class Overview

Polyketides are synthesized through the polymerization of acetyl units (β-ketomethylene chain).


Table 1. Polyketide Classification
1st Class
PK4: Four C2 Units

orsellinic acid, 6-methylsalicylic acid, triacetic acid lactone, asperlin, usnic acid, methylphloracetophenone, penicillic acid, patulin

PK5: Five C2 Units

citrinin, aflatoxin, augenone, sepedonin, stipitatonic acid

PK6: Six C2 Units

plumbagin, 7-methyljuglone, juglone, variotin

PK7: Seven and eight C2 Units

Anthraquinone rings
griseofulvin, rubrofusarin, emodin, alizarin, pachybasin, xanthone, versicolorin A, aflatoxin B1, sterigmatocystin, tajixanthone

PK9: Nine C2 Units

Tetracyclines
terramycin, aureomycin, daunomycin

Polyketide Synthase (PKS)

species Actinomycetes Cyanobacteria γ-Proteobacteria Fungi Dinoflagellates
Type-I PKS Ο Ο Ο Χ Ο
Type-II PKS Ο Χ Χ Ο Χ
NRPS Ο Ο Ο Ο Χ
deoxysugar Ο Χ Χ Χ Χ
Terpene Δ Χ Χ Ο Χ

Type I PKS (non-iterative)

  • Multi catalytic domains exist in a single protein
  • Chain length is determined by the number of catalytic domains.
  • Products are non-aromatic and have larger masses.

Ref. Erythromycin biosynthesis in Nat Prod Rep 18, 380 (2001)

Type II PKS (iterative)

  • Three proteins (KSα, KSβ, ACP) are repeatedly used for carbon chain elongation.
  • Chain length is determined by another protein, CLF.
  • In bacteria, products are aromatic (e.g. chiorotetracycline, pradimicin).
  • In fungi, products are both non-aromatic and aromatic.

Non-ribosomal peptide synthase (NRPS)

Coupling with PKS and NRPS

  • vancomycin ()
  • leinamycin (Curr opin chem biol 7:285, 2003)
  • pseurotin (chem bio chem 8:1736-1743, 2007)
  • curacin (curr opin chem biol 13:216, 2009)
  • epothilone
  • rapamycin

PKS in Fungi

  • both aromatic and non-aromatic compounds are generated by iterative PKS
  • methyl branch is transferred from methionine, not methylmalonyl CoA

Ref. Dewick, PM Medicinal Natural Products (2009)


Decoration

deoxysugars

deoxygenation, c-methylation, amination, n-methylation, ketosugar,

Unusual structures

Phoma zaragozic acid, phomoidoride Streptomyces yatakemycin, leinamycin, saframycin, neocarzinostatin, staurosporin, FR182877 Other bacteria PKS-NRPS hybrid type

Curacin A (Lyngbya), Shiphonazole (Herpetosiphon), Jamaicamide A (Lyngbya), Cylindrospermopsin (Cylindrospermopsis)

File:1,3,8-Trihydroxyaceto-Naphthalene.Mol
File:1,3-Dihydroxy-N-Methylacridone.Mol
File:3,8-Dihydroxy-1-Methylanthraquinone-2-Carboxylic Acid.Mol
File:4-Hydroxy-2-Quinolone.Mol
File:5,7-Dihydroxy-2-Methylchromone.Mol
File:5-Methylorsellinic Acid.Mol
File:6-Deoxy-Erythronolide B.Mol
File:6-Methoxymellein.Mol
File:6-Methyl Salicylic Acid.Mol
File:Actinorhodin.Mol
File:Adhyperforin.Mol
File:Aflatoxin B1.Mol
File:Aflatoxin B2.Mol
File:Aflatoxin G1.Mol
File:Aflatoxin G2.Mol
File:Aflatoxin M1.Mol
File:Aloe-Emodin.Mol
File:Aloesaponarin II.Mol
File:Alternapyrone.Mol
File:Alternaric Acid.Mol
File:Alternariol.Mol
File:Amphotericin B.Mol
File:Andrimid .Mol
File:Ascomycin.Mol
File:Aslaniol.Mol
File:Aslanipyrone.Mol
File:Asperlactone.Mol
File:Asperlin.Mol
File:Aspyridone A.Mol
File:Aspyridone B.Mol
File:Aspyrone.Mol
File:Asteltoxin.Mol
File:Astepyrone.Mol
File:Atrochrysone.Mol
File:Atrochrysone Carboxylic Acid.Mol
File:Aureothin.Mol
File:Austdiol.Mol
File:Avenaciolide.Mol
File:Averantin.Mol
File:Avermectin B1A.Mol
File:Avermectin B2A.Mol
File:Averufin.Mol
File:Avilamycin.Mol
File:Barnol.Mol
File:Benzophenone.Mol
File:Bikaverin.Mol
File:Botryodiplodin.Mol
File:Brefeldin A.Mol
File:Brevetoxin A.Mol
File:Brevetoxin B.Mol
File:C-1027.Mol
File:Calichemicin Gamma1.Mol
File:Cannabidiol.Mol
File:Cannabigerolic Acid.Mol
File:Cannabinol.Mol
File:Cercosporin.Mol
File:Chlortetracycline.Mol
File:Chrysomycin A.Mol
File:Chrysomycin B.Mol
File:Chrysophanol.Mol
File:Chrysophanol Anthrone.Mol
File:Ciguatoxin I.Mol
File:Citreomontanin.Mol
File:Citreoviridin.Mol
File:Citrinin.Mol
File:Clavatol.Mol
File:Coarctatin.Mol
File:Colletodiol.Mol
File:Compactin.Mol
File:Curvularin.Mol
File:Deoxyherquienone.Mol
File:Deoxyradicin.Mol
File:Dihydroisocoumarin.Mol
File:Diplosporin.Mol
File:Discodermolide.Mol
File:Doramectin.Mol
File:Dothistromin.Mol
File:Doxorubicin.Mol
File:Emodin.Mol
File:Emodin Anthrone.Mol
File:Emodin Dianthrone.Mol
File:Endocrocin.Mol
File:Endocrocin Anthrone.Mol
File:Enniatin B.Mol
File:Enterocin.Mol
File:Epothilone A.Mol
File:Epothilone B.Mol
File:Epothilone C.Mol
File:Epothilone D.Mol
File:Epoxydon.Mol
File:Epsilon-Pyrromycinone.Mol
File:Erythromycin.Mol
File:Flavipin.Mol
File:Fumigatin.Mol
File:Fumonisin B1.Mol
File:Furanomycin.Mol
File:Geldanamycin.Mol
File:Griseofulvin.Mol
File:Griseophenone B.Mol
File:Griseophenone C.Mol
File:Humulone.Mol
File:Hyperforin.Mol
File:Hypericin.Mol
File:Islandicin.Mol
File:Isoepoxydon.Mol
File:Isousnic Acid.Mol
File:Ivermectin.Mol
File:Khellin.Mol
File:Lasalocid.Mol
File:Lecanoric Acid.Mol
File:Leucomycin A1.Mol
File:Ll-D253Alpha.Mol
File:Lovastatin.Mol
File:M-Cresol.Mol
File:Melanin.Mol
File:Mellein.Mol
File:Methylphloracetophenone.Mol
File:Mollisin.Mol
File:Monensin A.Mol
File:Multicolic Acid.Mol
File:Mycolactone.Mol
File:Mycophenolic Acid.Mol
File:Myxalamide.Mol
File:Myxothiazol Z.Mol
File:Niddamycin.Mol
File:Norsolorinic Acid.Mol
File:Nystatin.Mol
File:Ochratoxin A.Mol
File:Ochrephilone.Mol
File:Okadaic Acid.Mol
File:Oleandomycin.Mol
File:Olivetolic Acid.Mol
File:O-Methylasparvenone.Mol
File:Orcinol.Mol
File:Orsellinic Acid.Mol
File:Oxytetracycline.Mol
File:Palitantin.Mol
File:Patulin.Mol
File:Penicillic Acid.Mol
File:Phloracetophenone.Mol
File:Phlorisobutyrophenone.Mol
File:Phlorisovalerophenone.Mol
File:Physcion.Mol
File:Picromycin.Mol
File:Pimaricin.Mol
File:Pretetramide.Mol
File:Protohypericin.Mol
File:Pyochelin.Mol
File:Pyoluteorin.Mol
File:Radicin.Mol
File:Rapamycin.Mol
File:Ravenilin.Mol
File:Rhein.Mol
File:Rifabutin.Mol
File:Rifamycin B.Mol
File:Rifapentine.Mol
File:Rosellisin.Mol
File:Rubrofusarin.Mol
File:Rubropunctatin.Mol
File:Sclerin.Mol
File:Sclerotinin A.Mol
File:Sek4.Mol
File:Sek4B.Mol
File:Selamectin.Mol
File:Sennidin A.Mol
File:Sennidin B.Mol
File:Sennidin C.Mol
File:Sennidin D.Mol
File:Sennosides A.Mol
File:Sennosides B.Mol
File:Sennosides C.Mol
File:Sennosides D.Mol
File:Sepedonin.Mol
File:Siccanin.Mol
File:Silvaticamide.Mol
File:Sma76A.Mol
File:Sma76B.Mol
File:Sma76C.Mol
File:Soraphen A.Mol
File:Spinulosin.Mol
File:Spiramycin I.Mol
File:Sterigmatocystin.Mol
File:Stigmatellin A.Mol
File:Stipitatonic Acid.Mol
File:Sulochrin.Mol
File:Tacrolimus.Mol
File:Tajixanthone.Mol
File:Tennellin.Mol
File:Terrein.Mol
File:Terrequinone A.Mol
File:Tetracenomycin F2.Mol
File:Tetracycline.Mol
File:Tetrahydro Cannabinol.Mol
File:Tetrahydroxynaphthalene.Mol
File:Triacetic Acid Lactone.Mol
File:T-Toxin.Mol
File:Tylactone.Mol
File:Tylosin.Mol
File:Urushiol III.Mol
File:Usnic Acid.Mol
File:Variotin.Mol
File:Versicolorin A.Mol
File:Versicolorin B.Mol
File:Versiconal.Mol
File:Versiconal Acetate.Mol
File:Visnagin.Mol
File:Wa-Naphthopyron.Mol
File:Zaragozic Acids A.Mol
File:Zearalenone.Mol

Subcategories

This category has only the following subcategory.

P

  • [×] PKS‎ (empty)
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