(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl)oxy-14-ethyl-7,12,13-trihydroxy-10-hydroxyimino-4-((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl)oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one

HCID 6537896

Notes Reactions

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Basic information

CAS: 111321-02-9
Standard SMILES: CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[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(=N\O)[C@H](C)[C@@H](O)[C@]1(C)O
InChIKey: KYTWXIARANQMCA-ZWCWUSBLNA-N
Molecular formula: C37H68N2O13
Average molar mass: 748.9 g/mol
Monoisotopic mass: 748.47214023

Overview

See also: Erythromycin A Oxime (annotation moved to) ... View More ...

Names & identifiers

Preferred name: (3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl)oxy-14-ethyl-7,12,13-trihydroxy-10-hydroxyimino-4-((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl)oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one
IUPAC: (3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-10-hydroxyimino-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one
English name: Erythromycin A Oxime
Molecular formula: C37H68N2O13
Molecular weight: 748.94

Names & synonyms

111321-02-9(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-10-hydroxyimino-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl)oxy-14-ethyl-7,12,13-trihydroxy-10-hydroxyimino-4-((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl)oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-oneRefChem:401092978-456-39(E)-Erythromycin A oximeErythromycin, 9-oximeMFCD08062410(3R,4S,5S,6R,7R,9R,11S,12R,13S,14R)-6-(((2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-ethyl-7,12,13-trihydroxy-4-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-10-(hydroxyimino)-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one(3R,4S,5S,6R,7R,9R,11S,12R,13S,14R,E)-6-(((2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-ethyl-7,12,13-trihydroxy-4-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-10-(hydroxyimino)-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one134931-01-4Erythromycin Impurity J

Show more names

(9E)-ErythroMycin A OxiMeErythromycin A Oxime(E)-Erythromycin oximeERYTHROMYCIN 9-E-OXIMECilnidipine Impurity 23AzithroMycin iMpurity 20Azithromycin Impurity 19Erythromycin Impurity SAzithromycin impurity 09

Erythromycin A-E-Oximeorb1693029SCHEMBL13615734HY-Z8447PD121741NS00003654G79883F568235

Database identifiers

CAS: 111321-02-9
PubChem CID: 6537896
EC Number: 978-456-3

Properties

Computed structural properties

XLogP: 3
Topological polar surface area: 209 Å²
Hydrogen bond donors: 6
Hydrogen bond acceptors: 15
Rotatable bonds: 7
Heavy atoms: 52
Formal charge: 0
Complexity: 1,210

Physicochemical properties

Melting point: 156 · 156-166 °C
Boiling point: 841 · 841.0±65.0 °C(Predicted)
Density: 1.28 · 1.28±0.1 g/cm3(Predicted)
storage temp.: Refrigerator
solubility: Chloroform (Slightly), DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
form: Solid
pka: 11.96 · 11.96±0.70(Predicted)
color: White to Off-White
InChIKey: KYTWXIARANQMCA-ZWCWUSBLNA-N
Symbol(GHS): 9 · GHS09
Hazard statements: 401 · H401-H411
Precautionary statements: 273 · P273-P391-P501

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 · 3 items

H411 (100%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P273, P391, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAquatic Chronic 2 (100%)

Safety data

Symbol(GHS): GHS09
Hazard statements: H401-H411
Precautionary statements: P273-P391-P501

Chemistry & industry

Applications · 4 items

Description(9E)-Erythromycin A oxime is a metabolite of the semisynthetic antibiotic roxithromycin .

UsesIntermediate of Azithromycin. Antibacterial agent.

Uses(9E)-Erythromycin A Oxime is a metabolite of Roxithromycin (R700850) in humans. It has anti-Helicobacter pylori activity

UsesErythromycin A 9-oxime is a semi-synthetic analogue of erythromycin prepared as means of overcoming acid lability and improving oral absorption of erythromycin A while retaining comparable antibacterial and potency. Although not developed as a commercial product, erythromycin oxime was pivotal in the development of the ring expanded aza-erythromycins (e.g. azithromycin) and the oxime ethers (e.g. roxithromycin).

Upstream & downstream products

Downstream products

Azathramycin 2',4''-O-bis(benzoyl)erythromycin A 9-O-benzoyloxime

Suppliers97 total

济南百隆化学有限公司[email protected] · [email protected]

武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]

武汉敬康恩生物医药科技有限公司13720134139 086-15871494362 13720134139 · [email protected]

艾吉析科技（上海）有限公司17717235263 · [email protected]

广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]

Related reactions

1 records

New reaction record

HRID 1282285As productuspto-grants-2002_09

Compound notes

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