Compound ID | 2769

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Triostin

Class: Natural product antibiotic

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Antimycobacterial
Mechanism of action: DNA synthesis inhibitor. Binds to DNA
Target Pathogen: Active against Staphylococcus aureus, Diplococcus pneumoniae, Corynebacterium diphtheriae, Streptococcus haemolyticus, and Mycobacterium tuberculosis
Description: Natural product from Streptomyces sp. S-2-210; does not show therapeutic effect in Staphylococcus aureus infected mice; low solubility in aqueous solution
Institute where first reported: Shionogi Research Laboratory, Amagasaki, Japan
Year first mentioned: 1968
Development status: Experimental
Chemical structure(s):
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Molecular weight: 1087.23
Iso. SMILES: C[C@H]1C(=O)N([C@@H]2CSSC[C@H](C(=O)N([C@H](C(=O)OC[C@H](C(=O)N1)NC(=O)C3=NC4=CC=CC=C4N=C3)C(C)C)C)N(C(=O)[C@@H](NC(=O)[C@@H](COC(=O)[C@@H](N(C2=O)C)C(C)C)NC(=O)C5=NC6=CC=CC=C6N=C5)C)C)C
InChI Key: GULVULFEAVZHHC-SZZROTLHSA-N
Can. SMILES: CC(C)[C@H]1C(=O)OC[C@H](C(=O)N[C@@H](C)C(=O)N(C)[C@@H]2CSSC[C@H](C(=O)N1C)N(C)C(=O)[C@H](C)NC(=O)[C@@H](COC(=O)[C@H](C(C)C)N(C)C2=O)NC(=O)C3=CN=C4C=CC=CC4=N3)NC(=O)C5=CN=C6C=CC=CC6=N5
InChI: InChI=1S/C50H62N12O12S2/c1-25(2)39-49(71)73-21-35(57-41(63)33-19-51-29-15-11-13-17-31(29)55-33)43(65)53-28(6)46(68)60(8)38-24-76-75-23-37(47(69)61(39)9)59(7)45(67)27(5)54-44(66)36(22-74-50(72)40(26(3)4)62(10)48(38)70)58-42(64)34-20-52-30-16-12-14-18-32(30)56-34/h11-20,25-28,35-40H,21-24H2,1-10H3,(H,53,65)(H,54,66)(H,57,63)(H,58,64)/t27-,28-,35+,36+,37+,38+,39-,40-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/159284
Citation: https://www.jstage.jst.go.jp/article/antibioticsa/14/6/14_335/_pdf

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