Chloroeremomycin
Basic information
- CAS
118395-73-6- Standard SMILES
CN[C@H](CC(C)C)C(=O)N[C@H]1C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H]2C(=O)N[C@H]3C(=O)N[C@H](C(=O)N[C@H](C(=O)O)c4cc(O)cc(O)c4-c4cc3ccc4O)[C@H](O[C@H]3C[C@](C)(N)[C@@H](O)[C@H](C)O3)c3ccc(c(Cl)c3)Oc3cc2cc(c3O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@H]2C[C@](C)(N)[C@@H](O)[C@H](C)O2)Oc2ccc(cc2Cl)[C@H]1O- InChIKey
XJHXLMVKYIVZTE-LOALFDMRSA-N- Molecular formula
- C73H88Cl2N10O26
- Average molar mass
- 1,592.4 g/mol
- Monoisotopic mass
- 1,590.5248283
Overview
Chloroeremomycin is a complex glycopeptide antibiotic that is isolated from Amycolatopsis orientalis. It has a role as an antimicrobial agent and a bacterial metabolite. It is a glycopeptide and a disaccharide derivative. It is functionally related to a vancomycin aglycone. It is a conjugate base of a chloroeremomycin(2+).
Names & identifiers
- Preferred name
- Chloroeremomycin
- IUPAC
- (1S,2R,18R,19R,22S,25R,28R,40S)-2-[(2R,4S,5R,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-48-[(2S,3R,4S,5S,6R)-3-[(2R,4S,5R,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-22-(2-amino-2-oxoethyl)-5,15-dichloro-18,32,35,37-tetrahydroxy-19-[[(2R)-4-methyl-2-(methylamino)pentanoyl]amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3,5,8,10,12(48),14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid
- English name
- chloroorienticin A
- Molecular formula
- C73H88Cl2N10O26
- Molecular weight
- 1592.44
Names & synonyms
Chloroeremomycin118395-73-6X47SLZ2K7DA-82846BCHEBI:29556PA-45052ADTXSID401316793RefChem:125406DTXCID301746620(2R)-5-hydroxy-2,4-dimethyl-2-((1E)-2-methylbuta-1,3-dienyl)thiophen-3-oneLY-2648268-82846A
Show more names
CBR49/ QTH05chloroorienticin AChloroorienticin A (Standard)(4''R)-22-O-(3-Amino-3-C-methyl-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)vancomycin(4''R)-22-O-(3-Amino-2,3,6-trideoxy-3-C-methyl-α-L-arabino-hexopyranosyl)vancomycinVancomycin,22-O-(3-amino-2,3,6-trideoxy-3-C-methyl-a-L-arabino-hexopyranosyl)-, (4''R)-Vancomycin, 22-O-(3-amino-2,3,6-trideoxy-3-C-methyl-α-L-arabino-hexopyranosyl)-, (4''R)-Vancomycin, 22-O-(3-amino-2,3,6-trideoxy-3-C-methyl-α-L-arabino-hexopyranosyl)-, (4′′R)-
Properties
Computed structural properties
- XLogP
- -2.8
- Topological polar surface area
- 575 Ų
- Hydrogen bond donors
- 20
- Hydrogen bond acceptors
- 29
- Rotatable bonds
- 15
- Heavy atoms
- 111
- Formal charge
- 0
- Complexity
- 3,300
Physicochemical properties
- Density
- 1.61 · 1.61±0.1 g/cm3(Predicted)
- pka
- 2.93 · 2.93±0.70(Predicted)
- InChIKey
- XJHXLMVKYIVZTE-LOALFDMRSA-N
- FDA UNII
- 47 SLZ2K7D · X47SLZ2K7D
Chemistry & industry
Applications
UsesChloroorienticin A (A82846B) is a glycopeptide antibiotic. Chloroorienticin A exhibits excellent activity against staphylococci and streptococci[1].
Additional notes
DefinitionChEBI: A complex glycopeptide antibiotic that is isolated from Amycolatopsis orientalis.
Related reactions
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Compound notes
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