N-Demethylerythromycin A

HCID 10010092

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Basic information

CAS: 992-62-1
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](NC)[C@H]2O)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O
InChIKey: TXOOBKBDBNRQCF-QNPWSHAKSA-N
Molecular formula: C36H65NO13
Average molar mass: 719.9 g/mol
Monoisotopic mass: 719.44559114

Names & identifiers

Preferred name: N-Demethylerythromycin A
IUPAC: (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-6-[(2S,3R,4S,6R)-3-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione
English name: N-Demethyl erythromycin a
Molecular formula: C36H65NO13
Molecular weight: 719.9

Names & synonyms

N-Demethylerythromycin A992-62-13'-DemethylerythromyonDes-N-methylerythromycinUNII-5CUO27O3DCErythromyon, 3'-demethyl-5CUO27O3DCClarithromycin Impurity RERYTHROMYCIN, N-DEMETHYL-3''-N-DESMETHYLERYTHROMYCIN ACLARITHROMYCIN IMPURITY R [USP-RS]ERYTHROMYCIN IMPURITY B [EP IMPURITY]

Show more names

Erythromycin Imp BDemethylerythromycinN-DemethylerithromycynN-Demethyl-erythromycinErythromycin impurity 02Erythromycin Impurity 16

ERYTHROMYCIN ESTOLATE IMPURITY B [EP IMPURITY]CLARITHROMYCIN IMPURITY R (USP-RS)ERYTHROMYCIN IMPURITY B (EP IMPURITY)ERYTHROMYCIN ESTOLATE IMPURITY B (EP IMPURITY)RefChem:163210N-Demethyl Erythromycin A(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-6-[(2S,3R,4S,6R)-3-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dioneN-Desmethyl Erythromycin

Database identifiers

CAS: 992-62-1
PubChem CID: 10010092
DTXSID: DTXSID701382585
ChEMBL: CHEMBL2063468
UNII: 5CUO27O3DC
EC Number: 641-787-6

Properties

Computed structural properties

XLogP: 2.2
Topological polar surface area: 203 Å²
Hydrogen bond donors: 6
Hydrogen bond acceptors: 14
Rotatable bonds: 7
Heavy atoms: 50
Formal charge: 0
Complexity: 1,150

Experimental & physicochemical properties

LogP2.21

Physicochemical properties

Melting point: 142 · 142-144°C
Boiling point: 818.1 · 818.1±65.0 °C(Predicted)
Density: 1.21 · 1.21±0.1 g/cm3(Predicted)
storage temp.: -20 °C · -20°C Freezer
solubility: Chloroform (Slightly), Methanol (Slightly)
pka: 13.09 · 13.09±0.70(Predicted)
color: White to Off-White
Major Application: pharmaceutical
InChIKey: TXOOBKBDBNRQCF-MBICAZOWNA-N
SMILES: N(C1C(C(OC(C1)C)OC2C(CC(C(=O)C(C(C(C(OC(=O)C(C(C2C)OC3OC(C(C(C3)(OC)C)O)C)C)CC)(O)C)O)C)C)(O)C)O)C
CAS DataBase Reference: 992 · 992-62-1
FDA UNII: 5 CUO27O3DC · 5CUO27O3DC
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 319 · H319
Precautionary statements: 264 · P264-P280-P305+P351+P338-P337+P313P
WGK Germany: 3 · WGK 3
HS Code: 2941500000 · 2941500000
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H319 (98%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

Aggregated GHS information provided per 49 reports by companies from 2 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesEye Irrit. 2 (98%)

Safety data

wgk: WGK 3
hs_code: 2941500000
Signal word: Warning
Symbol(GHS): GHS07
Storage Class: 11 - Combustible Solids
Hazard statements: H319
Precautionary statements: P264-P280-P305+P351+P338-P337+P313P

Chemistry & industry

Applications · 2 items

UsesN-Demethyl Erythromycin A (Erythromycin EP Impurity B) is a metabolite of Erythromycin (E649950).

UsesN-Demethylerythromycin A is a minor co-metabolite of erythromycin produced by Saccharopolyspora erythreae. N-Demethylerythromycin A exhibits a very narrow spectrum of antibiotic activity and is much less active than erythromycins A, B and C.