Naphthomycin A
{{Chembox
| ImageFile = Naphthomycin A.svg
| ImageSize = 250px
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|Section1={{Chembox Identifiers
| CASNo =
| ChEBI = 197824
| ChEMBL = 2172467
| PubChem = 10101379
| ChemSpiderID= 8276911
| SMILES = O=C1c2c3C(=O)/C(=C1/Cl)NC(=O)/C(=C\C=C\C=C/[C@H](C)[C@@H](O)CC(=O)\C(=C/C[C@H](O)\C=C/[C@H](C)[C@H](O)[C@H](\C=C(\C(=O)c2c(O)c(c3)C)C)C)C)C
| StdInChI=1S/C40H46ClNO9/c1-20-11-9-8-10-12-23(4)40(51)42-34-33(41)39(50)31-28(38(34)49)18-26(7)37(48)32(31)36(47)25(6)17-24(5)35(46)22(3)14-16-27(43)15-13-21(2)30(45)19-29(20)44/h8-14,16-18,20,22,24,27,29,35,43-44,46,48H,15,19H2,1-7H3,(H,42,51)/b10-8-,11-9-,16-14-,21-13-,23-12-,25-17-/t20-,22-,24-,27-,29-,35-/m0/s1
| StdInChIKey=AXEGRHYJHHPVDH-GGBROUGNSA-N
}}
|Section2={{Chembox Properties
| C=40 | H=46 | Cl=1 | N=1 | O=9
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|Section3={{Chembox Hazards
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Naphthomycin A is a type of naphthomycin. It was isolated as a yellow pigment from Streptomyces collinus and it shows antibacterial, antifungal, and antitumor activities.{{cite journal|last=Kang|first=Q.|author2=Y. Shenb |author3=L. Bai |journal=Nat. Prod. Rep.|year=2012|volume=29|pages=243–263|doi=10.1039/c2np00019a|title=Biosynthesis of 3,5-AHBA-derived natural products|issue=2|pmid=22193711}} Naphthomycins have the longest ansa aliphatic carbon chain of the ansamycin family.{{cite journal|last=Balerna|first=M.|author2=W. Keller-Schierlein |author3=C. Martius |author4=H. Zahner |journal=Arch. Microbiol.|year=1969|volume=65|pages=303–317|doi=10.1007/BF00412210|title=Stoffwechselprodukte von Mikroorganismen|issue=4 |pmid=4988744|s2cid=31145406}} Biosynthetic origins of the carbon skeleton from PKS1 were investigated by feeding 13C-labeled precursors and subsequent 13C-NMR product analysis. Naphthomycin gene clusters have been cloned and sequenced to confirm involvement in biosynthesis via deletion of a 7.2kb region.{{cite journal|last=Bai|first=L.|author2=Y. Wu |author3=Q. Kang |author4=Y. Shen |author5=Z. Deng |journal=Patent|year=2012|volume=CN: 2012-10300294|pages=225}} Thirty-two genes were identified in the 106kb cluster.{{cite journal|last=August|first=P.R. |author2=L. Tang |author3=Y.J. Yoon |author4=S. Ning |author5=R. MuEller |author6=T.W. Yu |author7=M. Taylor |author8=D. Hoffman |author9=C.G. Kim |author10=X. Zahng |author11=C.R. Hutchinson |author12=H.G. Floss |journal=Chem. Biol.|year=1998|volume=5|pages=69–79|doi=10.1016/S1074-5521(98)90141-7|pmid=9512878|title=Biosynthesis of the ansamycin antibiotic rifamycin: Deductions from the molecular analysis of the rif biosynthetic gene cluster of Amycolatopsis mediterranei S699|issue=2|doi-access=free }}
File:Naphthomycin A 2.pdf{{clear-left}}