Erythromycin C
Basic information
- CAS
1675-02-1- Standard SMILES
CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(O)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O- InChIKey
MWFRKHPRXPSWNT-QNPWSHAKSA-N- Molecular formula
- C36H65NO13
- Average molar mass
- 719.9 g/mol
- Monoisotopic mass
- 719.44559113
Overview
Erythromycin C is an erythromycin that consists of erythronolide A having 2,6-dideoxy-3-C-methyl-alpha-L-ribo-hexopyranosyl and 3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl residues attahced at positions 4 and 6 respectively. It is functionally related to an erythronolide A. It is a conjugate base of an erythromycin C(1+).
Names & identifiers
- Preferred name
- Erythromycin C
- IUPAC
- (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-4-[(2R,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione
- English name
- (3R,4S,5S,6R,7R,9R,11R,12R,13R,14R)-4-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6 -dimethyl-oxan-2-yl]oxy-6-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-m ethyl-oxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexameth yl-1-oxacyclotetradecane-2,10-dione
- Molecular formula
- C36H65NO13
- Molecular weight
- 719.9
Names & synonyms
Erythromycin C1675-02-1Erythromycin, 3''-O-demethyl-9X2R375YNZ(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-4-[(2R,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dioneCHEBI:64273(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-4-(2,6-dideoxy-3-C-methyl-alpha-L-ribo-hexopyranosyloxy)-14-ethyl-7,12,13-trihydroxy-6-[3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyloxy]-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dioneDTXSID501317437(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-4-((2R,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl)oxy-6-((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl)oxy-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-4-(2,6-dideoxy-3-C-methyl-alpha-L-ribo-hexopyranosyloxy)-14-ethyl-7,12,13-trihydroxy-6-(3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyloxy)-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione
Properties
Computed structural properties
- XLogP
- 2.2
- Topological polar surface area
- 205 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 6
- Heavy atoms
- 50
- Formal charge
- 0
- Complexity
- 1,160
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
Physicochemical properties
- Melting point
- 121 · 121-125 °C
- Boiling point
- 826.2 · 826.2±65.0 °C(Predicted)
- Density
- 1.23 · 1.23±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- DMF: soluble; DMSO: soluble; Ethanol: soluble; Methanol: soluble; Water: limited solubility
- pka
- 13.09 · 13.09±0.70(Predicted)
- FDA UNII
- 9 X2R375YNZ · 9X2R375YNZ
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 305 · P305+P351+P338
- Hazard Codes
- Xi
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
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Drugs used for their effects on the gastrointestinal system, as to control gastric acidity, regulate gastrointestinal motility and water flow, and improve digestion.
Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins.
Substances that inhibit the growth or reproduction of BACTERIA.
Applications
DescriptionErythromycin C is an intermediate in the biosynthesis of erythromycin . It is also a potential impurity found in commercial preparations of erythromycin. Erythromycin C is half as active or less than erythromycin A or B against most Gram-positive and Gram-negative bacteria tested.
UsesErythromycin (E649950) impurity. A related substance in Erythromycin drug.
UsesErythromycin C (3’’-O-demethylerythromycin A) is a minor co-metabolite of erythromycin produced by Saccharopolyspora erythreae. Erythromycin C exhibits a narrower spectrum of antibiotic activity and is much less active than erythromycins A and B.
Additional notes
DefinitionChEBI: Erythromycin C is an erythromycin that consists of erythronolide A having 2,6-dideoxy-3-C-methyl-alpha-L-ribo-hexopyranosyl and 3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl residues attahced at positions 4 and 6 respectively. It is functionally related to an erythronolide A. It is a conjugate base of an erythromycin C(1+).
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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