NAPHTHOMYCIN A

Naphthomycin A
Identifiers
3D model ( JSmol)	Interactive image;
ChEMBL	ChEMBL2172467;
ChemSpider	8276911;
PubChem CID	10101379;
	InChI InChI=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 Key: AXEGRHYJHHPVDH-GGBROUGNSA-N;
	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;
Properties
Chemical formula	C40H46ClNO9
Molar mass	720.26 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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.^[1] Naphthomycins have the longest ansa aliphatic carbon chain of the ansamycin family.^[2] 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.^[3] Thirty-two genes were identified in the 106kb cluster.^[4]

References

^ Kang, Q.; Y. Shenb; L. Bai (2012). "Biosynthesis of 3,5-AHBA-derived natural products". Nat. Prod. Rep. 29 (2): 243–263. doi: 10.1039/c2np00019a. PMID 22193711.
^ Balerna, M.; W. Keller-Schierlein; C. Martius; H. Zahner (1969). "Stoffwechselprodukte von Mikroorganismen". Arch. Microbiol. 65 (4): 303–317. doi: 10.1007/BF00412210. PMID 4988744. S2CID 31145406.
^ Bai, L.; Y. Wu; Q. Kang; Y. Shen; Z. Deng (2012). Patent. CN: 2012-10300294: 225. {{ cite journal}}: Missing or empty |title= ( help)
^ August, P.R.; L. Tang; Y.J. Yoon; S. Ning; R. MuEller; T.W. Yu; M. Taylor; D. Hoffman; C.G. Kim; X. Zahng; C.R. Hutchinson; H.G. Floss (1998). "Biosynthesis of the ansamycin antibiotic rifamycin: Deductions from the molecular analysis of the rif biosynthetic gene cluster of Amycolatopsis mediterranei S699". Chem. Biol. 5 (2): 69–79. doi: 10.1016/S1074-5521(98)90141-7. PMID 9512878.
^ Kang, Q; Y. Shenb; L. Bai (2012). "Biosynthesis of 3,5-AHBA-derived natural products". Nat. Prod. Rep. 29 (2): 243–263. doi: 10.1039/c2np00019a. PMID 22193711.

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[1] Kang, Q.; Y. Shenb; L. Bai (2012). "Biosynthesis of 3,5-AHBA-derived natural products". Nat. Prod. Rep. 29 (2): 243–263. doi: 10.1039/c2np00019a. PMID 22193711.

[2] Balerna, M.; W. Keller-Schierlein; C. Martius; H. Zahner (1969). "Stoffwechselprodukte von Mikroorganismen". Arch. Microbiol. 65 (4): 303–317. doi: 10.1007/BF00412210. PMID 4988744. S2CID 31145406.

[3] Bai, L.; Y. Wu; Q. Kang; Y. Shen; Z. Deng (2012). Patent. CN: 2012-10300294: 225. {{ cite journal}}: Missing or empty |title= ( help)

[4] August, P.R.; L. Tang; Y.J. Yoon; S. Ning; R. MuEller; T.W. Yu; M. Taylor; D. Hoffman; C.G. Kim; X. Zahng; C.R. Hutchinson; H.G. Floss (1998). "Biosynthesis of the ansamycin antibiotic rifamycin: Deductions from the molecular analysis of the rif biosynthetic gene cluster of Amycolatopsis mediterranei S699". Chem. Biol. 5 (2): 69–79. doi: 10.1016/S1074-5521(98)90141-7. PMID 9512878.

[5] Kang, Q; Y. Shenb; L. Bai (2012). "Biosynthesis of 3,5-AHBA-derived natural products". Nat. Prod. Rep. 29 (2): 243–263. doi: 10.1039/c2np00019a. PMID 22193711.

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Identifiers

3D model ( JSmol)	Interactive image
ChEMBL	ChEMBL2172467
ChemSpider	8276911
PubChem CID	10101379
InChI InChI=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 Key: AXEGRHYJHHPVDH-GGBROUGNSA-N
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
Properties
Chemical formula	C₄₀H₄₆ClNO₉
Molar mass	720.26 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references