Basic information
- CAS
11015-37-5- Standard SMILES
C=C(C/C=C(\C)CCC=C(C)C)CCC(C)(C)/C=C/CC/C(C)=C/CCOC(=O)[C@H](O)COP(=O)(O)O[C@H]1O[C@H](C(=O)O)[C@@](C)(O)[C@H](OC(N)=O)[C@H]1O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O[C@@H]2O[C@H](C)[C@@H](O[C@@H]3O[C@H](C(=O)NC4=C(O)CCC4=O)[C@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2NC(C)=O)[C@H](O)[C@H]1NC(C)=O- InChIKey
FUIOWSNNCWZETH-NAMXWVJMSA-N- Molecular formula
- C70H109N4O35P
- Average molar mass
- 1,597.6 g/mol
- Monoisotopic mass
- 1,596.6609982
Overview
Bambermycins are antibiotic complexes which are retrieved from the organism, Streptomyces bambergiensis. They are used as an additive in food ingested by chickens and swine. The bambermycin complex of antibiotics consists primarily of moenomycins A and C.
Names & identifiers
- Preferred name
- Bambermycins
- IUPAC
- (2S,3S,4R,5R,6R)-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-methyl-5-[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-hydroxy-5-oxocyclopenten-1-yl)carbamoyl]oxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-4-carbamoyloxy-3-hydroxy-6-[hydroxy-[(2R)-2-hydroxy-3-oxo-3-[(3E,7E,14E)-4,9,9,15,19-pentamethyl-12-methylideneicosa-3,7,14,18-tetraenoxy]propoxy]phosphoryl]oxy-3-methyloxane-2-carboxylic acid
- English name
- Flavomycin
- Molecular formula
- C69H107N4O35P
- Molecular weight
- 1583.57
Names & synonyms
BambermycinsFlavofosfolipolGainproMenomycinPP922A42V2MoenomycinsFlavophospholipolsFlavomycin 4Bambermycin ConcentrateRefChem:57079Bambermycins, unspecifiedGAINPRO 10
Show more names
BAMBERMYCINMOENOMYCINmoenomycin aFlavomycin PremixMoenoMycin coMplexYUHUNJIFlavomyci
bambermycins Type A medicated article234-246-7(2S,3S,4R,5R,6R)-5-((2S,3R,4R,5S,6R)-3-acetamido-5-((2S,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-methyl-5-((2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-((2-hydroxy-5-oxocyclopenten-1-yl)carbamoyl)oxan-2-yl)oxyoxan-2-yl)oxy-4-hydroxy-6-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxymethyl)oxan-2-yl)oxy-4-carbamoyloxy-3-hydroxy-6-(hydroxy-((2R)-2-hydroxy-3-oxo-3-((3E,7E,14E)-4,9,9,15,19-pentamethyl-12-methylideneicosa-3,7,14,18-tetraenoxy)propoxy)phosphoryl)oxy-3-methyloxane-2-carboxylic acidFlavophospholipolBambermycine [INN-French]Bambermycinum [INN-Latin]Bambermicina [INN-Spanish]Bambermycin [INN]
Properties
Computed structural properties
- XLogP
- -0.5
- Topological polar surface area
- 602 Ų
- Hydrogen bond donors
- 18
- Hydrogen bond acceptors
- 35
- Rotatable bonds
- 39
- Heavy atoms
- 110
- Formal charge
- 0
- Complexity
- 3,390
Experimental & physicochemical properties
Animal DrugsFDA approved animal drugs -> Active ingredient
Physicochemical properties
- Melting point
- 150 ° · >150° (dec.)
- storage temp.
- 0 · 0-6°C
- solubility
- Water (Slightly)
- form
- Solid
- color
- Dark Brown
- InChIKey
- PERZMHJGZKHNGU-XIGAONJHSA-N
- LogP
- 1.983 · 1.983 (est)
- CAS DataBase Reference
- 11015 · 11015-37-5
- FDA 21 CFR
- 556.75 · 556.75; 558.4; 558.95
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 922 A42V2 · PP922A42V2
- EPA Substance Registry System
- Bambermycin (11015-37-5)
- Hazard statements
- 413 · H413
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 1
- rtecs
- QA3020000
- ridadr
- UN 3077 9 / PGIII
- Toxicity
- LD50 in mice (mg/kg): >2000 orally, s.c. and i.p.; 1400 i.v. (Lindner, Wallhuser)
- risk_code
- 53
- Hazard statements
- H413
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Applications
DescriptionMoenomycin complex is a mixture of moenomycins A, A12, C1, C3 and C4, which are antibiotics isolated from several strains of Streptomyces that directly inhibit bacterial peptidoglycan glycosyltransferases. The minimal inhibitory concentration of moenomycin A against various Gram-positive bacteria ranges from 1-100 nM.
UsesMoenomycin complex is an antibiotic and selective inhibitor of the transglycosylation step. Flavomycin (bambermycins) is an antibiotic complex obtained from Streptomyces bambergiensis containing mainly Moenomycins A and C. They are used as feed additives and growth promoters for swine, poultry and cattle.
UsesMoenomycin complex is a mixture of five major components, A, A12, C1, C3 and C4, isolated from several strains of Streptomyces in the 1960s. Moenomycins are high molecular weight phosphoglycolipids with potent antibiotic activity used in animal health. Moenomycins are the only antibiotic known to selectively inhibit the transglycosylation step catalysed by penicillin-binding protein 1b.
General DescriptionFlavophospholipol, formerly called moenomycin, was found in the culture broth of Streptomyces bambergiensis by Hoechst in 1955. This drug is called bambermycin by INN and in the United States. It shows strong activity against gram-positive bacteria and weak activity against gram-negative bacteria. Flavophospholipol has been used as a feed additive for growth promotion in poultry.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…