Tuberactin

Synonym(s): Tuberactinomycin  |  Enviomycin

Class: Antimicrobial peptide

Spectrum of activity:	Gram-negative
Details of activity:	Active against Pseudomonas aeruginosa, Escherichia coli, Salmonella paratyphi, Shigella flexneri, Mycobacterium phlei, Mycobacterium avium, and Mycobacterium tuberculosis; protein synthesis inhibitor (binds to ribosome at a similar site to kanamycin and amikacin)
Propensity to select resistant mutants:	Yes
Description:	Natural product from Streptomyces griseoverticillatus var. tuberacticus; progenitor of tuberactinomycin N, which is a derivative with greater potency and reduced toxicity
Institute where first reported:	Research Laboratory, Toyo Jozo Co., Ltd., Ohito-cho, Shizuoka-ken, Japan
Year first mentioned:	1968
Development status:	Experimental
Reason Dropped:	Shows ototoxicity

Chemical structure(s):
Canonical SMILES:	C(CN)[C@H]([C@@H](CC(=O)N[C@H]1CNC(=O)[C@H]([C@H]2CCNC(=N2)N)NC(=O)/C(=C/NC(=O)N)/NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC1=O)N)O
Isomeric SMILES:	C1CNC(=N[C@H]1[C@H]2C(=O)NC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N/C(=C\NC(=O)N)/C(=O)N2)CO)CO)NC(=O)C[C@H]([C@@H](CCN)O)N)N
InChI:	InChI=1S/C25H43N13O10/c26-3-1-16(41)10(27)5-17(42)33-12-6-31-23(47)18(11-2-4-30-24(28)37-11)38-20(44)13(7-32-25(29)48)34-21(45)14(8-39)36-22(46)15(9-40)35-19(12)43/h7,10-12,14-16,18,39-41H,1-6,8-9,26-27H2,(H,31,47)(H,33,42)(H,34,45)(H,35,43)(H,36,46)(H,38,44)(H3,28,30,37)(H3,29,32,48)/b13-7-/t10-,11-,12+,14+,15+,16-,18+/m1/s1
InChI Key:	HPWIIERXAFODPP-GHBBWTPBSA-N
Canonical SMILES:	C(CN)[C@H]([C@@H](CC(=O)N[C@H]1CNC(=O)[C@H]([C@H]2C[C@@H](NC(=N2)N)O)NC(=O)/C(=C/NC(=O)N)/NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC1=O)N)O.C(CN)[C@H]([C@@H](CC(=O)N[C@H]1CNC(=O)[C@H]([C@H]2CCNC(=N2)N)NC(=O)/C(=C/NC(=O)N)/NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC1=O)N)O.C(C[C@@H](CC(=O)N[C@H]1CNC(=O)[C@H]([C@H]2C[C@@H](NC(=N2)N)O)NC(=O)/C(=C/NC(=O)N)/NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC1=O)N)CN
Isomeric SMILES:	C1CNC(=N[C@H]1[C@H]2C(=O)NC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N/C(=C\NC(=O)N)/C(=O)N2)CO)CO)NC(=O)C[C@H]([C@@H](CCN)O)N)N.C1[C@@H](N=C(N[C@H]1O)N)[C@H]2C(=O)NC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N/C(=C\NC(=O)N)/C(=O)N2)CO)CO)NC(=O)C[C@H](CCCN)N.C1[C@@H](N=C(N[C@H]1O)N)[C@H]2C(=O)NC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N/C(=C\NC(=O)N)/C(=O)N2)CO)CO)NC(=O)C[C@H]([C@@H](CCN)O)N
InChI:	InChI=1S/C25H43N13O11.2C25H43N13O10/c26-2-1-15(41)9(27)3-16(42)32-11-5-30-23(48)18(10-4-17(43)37-24(28)36-10)38-20(45)12(6-31-25(29)49)33-21(46)13(7-39)35-22(47)14(8-40)34-19(11)44;26-3-1-16(41)10(27)5-17(42)33-12-6-31-23(47)18(11-2-4-30-24(28)37-11)38-20(44)13(7-32-25(29)48)34-21(45)14(8-39)36-22(46)15(9-40)35-19(12)43;26-3-1-2-10(27)4-16(41)32-12-6-30-23(47)18(11-5-17(42)37-24(28)36-11)38-20(44)13(7-31-25(29)48)33-21(45)14(8-39)35-22(46)15(9-40)34-19(12)43/h6,9-11,13-15,17-18,39-41,43H,1-5,7-8,26-27H2,(H,30,48)(H,32,42)(H,33,46)(H,34,44)(H,35,47)(H,38,45)(H3,28,36,37)(H3,29,31,49);7,10-12,14-16,18,39-41H,1-6,8-9,26-27H2,(H,31,47)(H,33,42)(H,34,45)(H,35,43)(H,36,46)(H,38,44)(H3,28,30,37)(H3,29,32,48);7,10-12,14-15,17-18,39-40,42H,1-6,8-9,26-27H2,(H,30,47)(H,32,41)(H,33,45)(H,34,43)(H,35,46)(H,38,44)(H3,28,36,37)(H3,29,31,48)/b12-6-;2*13-7-/t9-,10-,11+,13+,14+,15-,17+,18+;10-,11-,12+,14+,15+,16-,18+;10-,11+,12-,14-,15-,17-,18-/m110/s1
InChI Key:	NLFFJIIRAGZISV-LKMNLCDCSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/136056704

External links:
Guide to Pharmacology:	enviomycin
Main Source:	https://www.jstage.jst.go.jp/article/antibiotics1968/21/12/21_12_681/_pdf
Citation:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9403184/