Kirromycin, Antibiotic agent

Key facts

CAS number

50935-71-2

Purity

>96%

Source

Streptomyces collinus

Molecular weight

796.9 Da

Molecular formula

C₄₃H₆₀N₂O₁₂

PubChem

54679334

Nature

Native

Biochemical name

CID 54679334

Biological description

Potent antibiotic agent. Selective EF-Tu inhibitor. Protein synthesis inhibitor. Prevents EF-Tu release from the ribosome. Induces EF-Tu-dependent hydrolysis of GTP in the absence of ribosomes. Shows potent bactericidal effects in vivo. Orally active.

Canonical smiles

CCC(C(=O)NCC=CC=C(C)C(C(C)C1C(C(C(O1)C=CC=CC=C(C)C(=C2C(=O)C=CNC2=O)O)O)O)OC)C3(C(C(C(C(O3)C=CC=CC)(C)C)O)O)O

Isomeric smiles

CC[C@H](C(=O)NC/C=C/C=C(\C)/[C@H]([C@@H](C)[C@H]1[C@H]([C@H]([C@H](O1)/C=C/C=C/C=C(\C)/C(=C\2/C(=O)C=CNC2=O)/O)O)O)OC)[C@@]3([C@@H]([C@@H](C([C@@H](O3)/C=C/C=C/C)(C)C)O)O)O

InChi

InChI=1S/C43H60N2O12/c1-9-11-13-21-31-42(6,7)38(50)39(51)43(54,57-31)28(10-2)40(52)44-23-17-16-19-26(4)36(55-8)27(5)37-35(49)34(48)30(56-37)20-15-12-14-18-25(3)33(47)32-29(46)22-24-45-41(32)53/h9,11-22,24,27-28,30-31,34-39,47-51,54H,10,23H2,1-8H3,(H,44,52)(H,45,53)/b11-9+,14-12+,17-16+,20-15+,21-13+,25-18+,26-19+,33-32+/t27-,28-,30-,31+,34+,35+,36-,37+,38+,39-,43-/m1/s1

InChiKey

LWXUPCAADQWXRE-UPMFUDSQSA-N

IUPAC Name

(2S)-N-[(2E,4E,6S,7R)-7-[(2S,3S,4R,5R)-5-[(1E,3E,5E,7E)-7-(2,4-dioxo-1H-pyridin-3-ylidene)-7-hydroxy-6-methylhepta-1,3,5-trienyl]-3,4-dihydroxyoxolan-2-yl]-6-methoxy-5-methylocta-2,4-dienyl]-2-[(2R,3R,4R,6S)-2,3,4-trihydroxy-5,5-dimethyl-6-[(1E,3E)-penta-1,3-dienyl]oxan-2-yl]butanamide