Basic information
- CAS
38129-37-2- Standard SMILES
C=C1CCO[C@]2([C@@H](O)[C@@](C)(O)CO)NC(=O)[C@@]1(O)NC2=O- InChIKey
WOUDXEYYJPOSNE-VKZDFBPFSA-N- Molecular formula
- C12H18N2O7
- Average molar mass
- 302.28 g/mol
- Monoisotopic mass
- 302.11140092
Overview
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.
Names & identifiers
- Preferred name
- Bicyclomycin
- IUPAC
- (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
- English name
- bicozamycin
- Molecular formula
- C12H18N2O7
- Molecular weight
- 302.28
Names & synonyms
BicyclomycinBicozamycinAizumycin38129-37-2BicozamicinaBicozamycineAntibiotic 5879BicozamycinumWS-4545 ANTIBIOTIC(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-dioneJ03U9E2P82CGP-3543
Show more names
C11259WS-4545ICOZAMYCINBicozaMycin benzoateBicozaMycin, AizuMycin, Bacteron, CGP 3543E, WS4545, 5879(1R,6S)-1-hydroxy-2-methylidene-6-[(1S,2S)-1,2,3-trihydroxy-2-methylpropyl]-5-oxa-8,10-diazabicyclo[4.2.2]decane-7,9-dione2-Oxa-7,9-diazabicyclo[4.2.2]decane-8,10-dione, 6-hydroxy-5-methylene-1-[(1S,2S)-1,2,3-trihydroxy-2-methylpropyl]-, (1S,6R)-
NSC-180516CHEBI:60584DTXSID8042636(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-dioneRefChem:119658DTXCID6022636(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-dione253-795-3
Properties
Computed structural properties
- XLogP
- -2.9
- Topological polar surface area
- 148 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 3
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 510
Physicochemical properties
- Melting point
- 188 · 188-191° (dec); mp 187-189° (dec) (Imanaka); mp 166-170° (Nakatsuka et al.)
- alpha
- 23 · D23 +63.5° (methanol)
- Boiling point
- 786.6 · 786.6±60.0 °C(Predicted)
- Density
- 1.57 · 1.57±0.1 g/cm3(Predicted)
- pka
- 9.85 · 9.85±0.60(Predicted)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 3 U9E2P82 · J03U9E2P82
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 300 · H300
- Precautionary statements
- 264 · P264-P270-P301+P310-P321-P330-P405-P501
- Toxicity
- 50 in · LD50 in mice: >4 g/kg (Williams, Durham)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 1 (100%)
Safety data
- Toxicity
- LD50 in mice: >4 g/kg (Williams, Durham)
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- Hazard statements
- H300
- Precautionary statements
- P264-P270-P301+P310-P321-P330-P405-P501
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Miscellaneous agents found useful in the symptomatic treatment of diarrhea. They have no effect on the agent(s) that cause diarrhea, but merely alleviate the condition.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Substances that inhibit the growth or reproduction of BACTERIA.
Applications
UsesBicyclomycin is a polar metabolite first isolated from Streptomyces sapporonensis in 1972. The selective Gram negative profile of bicyclomycin is rare among Streptomyces metabolites. The primary site of action for bicyclomycin is thought to be the rho transcription termination factor.
Suppliers17 total
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
孟成科技（上海）有限公司400-820-6829 · [email protected]
上海维亦特生物科技有限公司15317051735 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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