Avilamycin A
Basic information
- CAS
69787-79-7- Standard SMILES
COC[C@H]1O[C@@H](O[C@@H]2OC[C@@H]3O[C@]4(O[C@H]3[C@H]2OC(=O)C(C)C)O[C@H](C)[C@@](O)(C(C)=O)[C@@H]2OCO[C@H]24)[C@@H](OC)[C@@H](O)[C@@H]1O[C@@H]1O[C@H](C)[C@H](OC)[C@H](O[C@H]2C[C@@]3(C)OC4(C[C@@H](O)[C@H](O[C@H]5C[C@@H](O)[C@H](OC(=O)c6c(C)c(Cl)c(O)c(Cl)c6OC)[C@@H](C)O5)[C@@H](C)O4)O[C@@H]3[C@@H](C)O2)[C@H]1O- InChIKey
XIRGHRXBGGPPKY-FCNCREMHSA-N- Molecular formula
- C61H88Cl2O32
- Average molar mass
- 1,404.2 g/mol
- Monoisotopic mass
- 1,402.463576
Overview
Avilamycin A is an oligosaccharide derivative that is produced by Streptomyces viridochromogenes and exhibits antibiotic properties. It has a role as an antimicrobial agent and a bacterial metabolite. It is a tertiary alpha-hydroxy ketone, a dichlorobenzene, a member of phenols, a benzoate ester, an oxaspiro compound, a cyclic acetal, an oligosaccharide derivative and an ortho ester.
Names & identifiers
- Preferred name
- Avilamycin A
- IUPAC
- [(2R,3S,4R,6S)-6-[(2'R,3'S,3aR,4R,4'R,6S,7aR)-6-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5S,6S)-6-[(2R,3aS,3'aR,6S,6'R,7R,7'S,7aR,7'aR)-7'-acetyl-7'-hydroxy-6'-methyl-7-(2-methylpropanoyloxy)spiro[4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2,4'-6,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran]-6-yl]oxy-4-hydroxy-5-methoxy-2-(methoxymethyl)oxan-3-yl]oxy-3-hydroxy-5-methoxy-6-methyloxan-4-yl]oxy-4'-hydroxy-2',4,7a-trimethylspiro[3a,4,6,7-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2,6'-oxane]-3'-yl]oxy-4-hydroxy-2-methyloxan-3-yl] 3,5-dichloro-4-hydroxy-2-methoxy-6-methylbenzoate
- English name
- avilamycin A
- Molecular formula
- C61H88Cl2O32
- Molecular weight
- 1404.24
Names & synonyms
Avilamycin AFlambamycin, 23-deoxy-69787-79-7NI4I9W2OK6A-2357523-deoxy-flambamycinCHEBI:85646DTXSID401016503RefChem:115787DTXCID401474692UNII-NI4I9W2OK6AVILAMYCIN A [MI]
Show more names
23-Deoxyflambamycinβ-D-Mannopyranoside, O-(1R)-4-C-acetyl-6-deoxy-2,3-O-methylene-D-galactopyranosylidene-(1→3-4)-2-O-(2-methyl-1-oxopropyl)-α-L-lyxopyranosyl O-2,6-dideoxy-4-O-(3,5-dichloro-4-hydroxy-2-methoxy-6-methylbenzoyl)-β-D-arabino-hexopyranosyl-(1→4)-O-2,6-dideoxy-D-arabino-hexopyranosylidene-(1→3-4)-O-2,6-di...D-Mannopyranoside, 4-C-acetyl-6-deoxy-2,3-o-methylenehexopyranosylidene-(1-3-4)-2-o-(2-methyl-1-oxopropyl)-L-lyxopyranosyl o-2,6-dideoxy-4-o-(3,5-dichloro-4-hydroxy-2-methoxy-6-methylbenzoyl)-beta-D-arabino-hexopyranosyl-(1-4)-o-2,6-dideoxy-D-ribo-hexopyranosylidene-(1-3-4)-o-2,6-dideoxy-3-C-methyl-D-arabino-hexopyranosyl-(1-3)-o-6-deoxy-4-o-methyl-beta-D-galactopyranosyl-(1-4)-2,6-di-o-methyl-
Properties
Computed structural properties
- XLogP
- 0.6
- Topological polar surface area
- 385 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 32
- Rotatable bonds
- 20
- Heavy atoms
- 95
- Formal charge
- 0
- Complexity
- 2,660
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
Physicochemical properties
- Density
- 1.5 · 1.50±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- Acetone: slightly soluble; Methanol: slightly, heated
- form
- A solid
- pka
- 4.94 · 4.94±0.35(predicted)
- FDA UNII
- 4 I9W2OK6 · NI4I9W2OK6
Chemistry & industry
Applications
UsesAvilamycin A is an oral active antibiotic. Avilamycin A is active against veterinary isolates of C. perfringens (MICs ≤ 0.06-0.5 mg/L) and B. hyodysenteriae (MICs = 12.5-100 μg/ml)[1].
Additional notes
DefinitionChEBI: An oligosaccharide derivative that is produced by Streptomyces viridochromogenes and exhibits antibiotic properties.
Related reactions
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Compound notes
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