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Awamycin

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Awamycin
Category Antibiotics
Catalog number BBF-00234
CAS
Molecular Weight 743.86
Molecular Formula C38H49NO12S

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Fermentation Lab

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

Awamycin is produced by the strain of Streptomyces sp. No. 80-217. It has anti-gram-positive bacteria and antitumor activity.

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Synonyms Antibiotic Tan 528A; Protostreptovaricin I, 10,25-didemethyl-21-hydroxy-10-(methoxycarbonyl)-19-O-methyl-25-(methylthio)-; Protostreptovaricin-31-oic acid, 25-demethyl-21-hydroxy-19-O-methyl-2S-(methylthio)-, methyl ester
IUPAC Name methyl (7Z,18E,20Z)-2,10,12,14,16-pentahydroxy-4-methoxy-3,7,9,11,15,17,21-heptamethyl-25-methylsulfanyl-6,22,26,28-tetraoxo-23-azatricyclo[22.3.1.05,27]octacosa-1(27),2,4,7,18,20,24-heptaene-13-carboxylate
Canonical SMILES CC1C=CC=C(C(=O)NC2=C(C(=O)C3=C(C2=O)C(=C(C(=C3C(=O)C(=CC(C(C(C(C(C(C(C1O)C)O)C(=O)OC)O)C)O)C)C)OC)C)O)SC)C
InChI InChI=1S/C38H49NO12S/c1-15-12-11-13-16(2)37(48)39-26-33(46)23-22(34(47)36(26)52-10)24(35(50-8)21(7)32(23)45)29(42)18(4)14-17(3)28(41)20(6)31(44)25(38(49)51-9)30(43)19(5)27(15)40/h11-15,17,19-20,25,27-28,30-31,40-41,43-45H,1-10H3,(H,39,48)/b12-11+,16-13-,18-14-
InChI Key WZCNXFSCUFEMGW-UMLOSGLNSA-N
Antibiotic Activity Spectrum gram-positive bacterial; neoplastics (Tumor)
Melting Point 177-180 °C
1. Two sulfur-containing ansamycin antibiotics from Streptomyces albolongus
S Tanida, S Shinagwa, M Takizawa, T Takahashi, S Harada, T Hasegawa Experientia. 1986 Oct 15;42(10):1167-70. doi: 10.1007/BF01941296.
Two sulfur-containing ansamycin antibiotics were isolated from the culture broth of Streptomyces albolongus C-46366; the major one was identical with awamycin and the minor one was a new ansamycin antibiotic, ansathiazin. Their structures were elucidated from their reactions and spectroscopic analyses. These antibiotics were active against gram-positive bacteria, acid-fast bacteria and a protozoan.
2. A new antitumor antibiotic, awamycin
I Umezawa, H Oka, K Komiyama, K Hagiwara, S Tomisaka, T Miyano J Antibiot (Tokyo). 1983 Sep;36(9):1144-9. doi: 10.7164/antibiotics.36.1144.
A new antibiotic, awamycin, was isolated from the culture broth of Streptomyces sp. No. 80-217. It appeared to belong to the quinone indicator group from results of physicochemical studies and has the empirical formula C38H49NO12S. This antibiotic possessed antibacterial and antitumor activities against Gram-positive bacteria and experimental murine tumors. The antibiotic also showed direct cytotoxic activity against HeLa cells in vitro.

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