Compound: Bicyclomycin
SMILES: O=C1N[C@]2(OCCC([C@]1(O)NC2=O)=C)[C@@H](O)[C@@](O)(CO)C
InChIKey: WOUDXEYYJPOSNE-VKZDFBPFSA-N
Synonyms: Bicyclomycin, Bicozamycin, Aizumycin, 38129-37-2, Bicozamicina, Bicozamycine, Antibiotic 5879, Bicozamycinum, WS-4545 ANTIBIOTIC, J03U9E2P82, CGP-3543, (1S,6R)-6-hydroxy-5-methylidene-1-[(1S,2S)-1,2,3-trihydroxy-2-methylpropyl]-2-oxa-7,9-diazabicyclo[4.2.2]decane-8,10-dione, NSC-180516, CHEBI:60584, DTXSID8042636, (1S,6R)-6-hydroxy-5-methylidene-1-((1S,2S)-1,2,3-trihydroxy-2-methylpropyl)-2-oxa-7,9-diazabicyclo(4.2.2)decane-8,10-dione, RefChem:119658, DTXCID6022636, (1S,6R)-6-hydroxy-5-methylidene-1-((1R,2S)-1,2,3-trihydroxy-2-methylpropyl)-2-oxa-7,9-diazabicyclo(4.2.2)decane-8,10-dione, 253-795-3, Bacteron, Bicozamycin [INN], Bacfeed, Antibiotic WS 4545, Bicozamycine [INN-French], Bicozamycinum [INN-Latin], Bicozamicina [INN-Spanish], WS-4545, EINECS 253-795-3, NSC 180516, WS 4545, UNII-J03U9E2P82, CGP 354E, (1S,6R)-6-HYDROXY-5-METHYLENE-1-((1S,2S)-1,2,3-TRIHYDROXY-2-METHYLPROPYL)-2-OXA-7,9-DIAZABICYCLO(4.2.2)DECANE-8,10-DIONE, (1S,6R)-6-hydroxy-5-methylene-1-((1S,2S)-1,2,3-trihydroxy-2-methylpropyl)-2-oxa-7,9-diazabicyclo[4.2.2]decane-8,10-dione, FR 1881, BICOZAMYCIN [JAN], BICYCLOMYCIN [MI], BICOZAMYCIN [MART.], (1R*,6S*)-6-Hydroxy-5-methylene-1-((1R*,2R*)-1,2,3-trihydroxy-2-methylpropyl)-2-oxa-7,9-diazabicyclo(4.2.2)decan-8,10-dione, orb1986962, CHEMBL1231250, SCHEMBL29420852, BDBM22600, WOUDXEYYJPOSNE-VKZDFBPFSA-N, CGP-3543/E, AKOS040747971, AB61701, HY-122071, CS-0081609, Q27104872, (1S,6R)-6-hydroxy-5-methylene-1-[(1S,2S)-1,2,3-trihydroxy-2-methyl-propyl]-2-oxa-7,9-diazabicyclo[4.2.2]decane-8,10-dione, 8,10-DIAZA-6-HYDROXY-5-METHYLENE-1-(2-METHYL-1,2,3-TRIHYDROXYPROPYL)-2-OXABICYCLO(4.2.2)DECAN-7,9-DIONE
Theoretical properties:
molecular_formula: C12H18N2O7
molecular_weight: 302.28 g/mol
exact_mass: 302.11140092 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 6
hydrogen_bond_acceptor_count: 7
rotatable_bond_count: 3
heavy_atom_count: 21
topological_polar_surface_area: 148 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Bicozamycin is a commercially important azabicyclic antibiotic obtained from Streptomyces sapporonensis. It inhibits the Rho protein of E. coli. It has a role as an antibacterial agent, an antiinfective agent and an antidiarrhoeal drug. It is a bridged compound and an azabicycloalkane.
chebi: A commercially important azabicyclic antibiotic obtained from <em>Streptomyces sapporonensis</em>. It inhibits the Rho protein of <em>E. coli</em>.
chembl: BICOZAMYCIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Bicyclomycin (Bicozamycin) is a broad spectrum antibiotic active against Gram-negative bacteria and the Gram-positive bacterium, Micrococcus luteus that was isolated from Streptomyces sapporonesis and Streptomyces aizumenses in 1972.  It belongs to a class of naturally occurring 2,5-diketopiperazines, that are among the most numerous of all the naturally occurring peptide antibiotics.
This clinically useful antibiotic is rapidly absorbed in humans when given intramuscularly, has low toxicity and has been used to treat diarrhea in humans and bacterial diarrhea in calves and pigs.