Compound ID | 2736

Update compound information

Siomycin

Class: Antimicrobial peptide

Spectrum of activity: Gram-positive
Details of activity: Active against Staphylococcus aureus, Bacillus anthracis, Diplococcus pneumoniae, Streptococcus haemolyticus, Corynebacterium diphtheriae, Mycobacterium tuberculosis, Mycobacterium smegmatis, and Mycobacterium phlei; protein synthesis inhibitor
Description: Natural product from Streptomyces sioyaensis; strains resistant to thiostrepton are cross-resistant to siomycin (and vice versa)
Institute where first reported: Shionogi Research Laboratory, Amagasaki, Japan
Year first mentioned: 1961
Development status: Experimental
Chemical structure(s):
Click here for structure editor
Molecular weight: 1648.85
Iso. SMILES: C/C=C\1/C2=NC(CS2)C(=O)NC(C3=NC(=CS3)C(=O)NC4C(OC(=O)C5=NC6=C(C=CC(C6O)NC(C(=O)NC(=C)C(=O)NC(=C)C(=O)NC(C(=O)NC7(CCC(=NC7C8=CSC4=N8)C9=NC(=CS9)C(=O)NC(=C)C(=O)NC(=C)C(=O)N)C%10=NC(=CS%10)C(=O)NC(C(=O)N1)C(C)O)C)C(C)C)C(=C5)C(C)O)C)C(C)(C(C)O)O
InChI Key: AKFVOKPQHFBYCA-ASKSIGGCSA-N
Can. SMILES: C/C=C\1/C2=NC(CS2)C(=O)NC(C3=NC(=CS3)C(=O)NC4C(C)OC(=O)C5=NC6=C(C=CC(C6O)NC(C(C)C)C(=O)NC(=C)C(=O)NC(=C)C(=O)NC(C)C(=O)NC7(CCC(=NC7C8=CSC4=N8)C9=NC(=CS9)C(=O)NC(=C)C(=O)NC(=C)C(=O)N)C%10=NC(=CS%10)C(=O)NC(C(C)O)C(=O)N1)C(=C5)C(C)O)C(C)(C(C)O)O
InChI: InChI=1S/C71H81N19O18S5/c1-14-37-64-83-44(22-109-64)61(103)89-52(70(13,107)34(12)93)67-85-43(23-112-67)59(101)88-48-33(11)108-68(106)40-19-36(31(9)91)35-15-16-38(50(94)49(35)79-40)78-46(25(2)3)62(104)77-29(7)56(98)74-27(5)55(97)75-30(8)57(99)90-71(69-86-45(24-113-69)60(102)87-47(32(10)92)63(105)81-37)18-17-39(80-51(71)41-20-111-66(48)82-41)65-84-42(21-110-65)58(100)76-28(6)54(96)73-26(4)53(72)95/h14-16,19-21,23-25,30-34,38,44,46-48,50-52,78,91-94,107H,4-7,17-18,22H2,1-3,8-13H3,(H2,72,95)(H,73,96)(H,74,98)(H,75,97)(H,76,100)(H,77,104)(H,81,105)(H,87,102)(H,88,101)(H,89,103)(H,90,99)/b37-14-
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/25200028
Citations:
  • https://www.jstage.jst.go.jp/article/antibioticsa/14/5/14_255/_pdf/-char/en
  • https://www.jstage.jst.go.jp/article/antibioticsa/14/5/14_255/_pdf/-char/en

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