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Erythromycin (glutamate)

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Description
Erythromycin glutamate is a macrolide antibiotic produced by actinomycete Streptomyces erythreus with a broad spectrum of antimicrobial activity. Erythromycin glutamate binds to bacterial 50S ribosomal subunits and inhibits RNA-dependent protein synthesis by blockage of transpeptidation and/or translocation reactions, without affecting synthesis of nucleic acid[1][2]. Erythromycin glutamate also exhibits antitumor and neuroprotective effect in different fields of research[3][4].
CAS Number
16667-03-1
UNSPSC
12352005
Target
Antibiotic; Bacterial; DNA/RNA Synthesis
Type
Reference compound
Related Pathways
Anti-infection; Cell Cycle/DNA Damage
Field of Research
Infection; Cancer
Assay Protocol
https://www.medchemexpress.com/erythromycin-glutamate.html
Smiles
OC(CC[C@H](N)C(O)=O)=O.C[C@@H]([C@@H]([C@H](C(O[C@@H]([C@@](O)([C@@H]([C@H](C([C@@H](C[C@]1(O)C)C)=O)C)O)C)CC)=O)C)O[C@H]2C[C@](C)([C@H]([C@@H](O2)C)O)OC)[C@H]1O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O
Molecular Formula
C42H76N2O17
Molecular Weight
881.06
References & Citations
[1]Gribble MJ, et al. Erythromycin. Med Clin North Am. 1982 Jan;66 (1) :79-89.|[2]Nakornchai S, et al. Activity of azithromycin or erythromycin in combination with antimalarial drugs against multidrug-resistant Plasmodium falciparum in vitro. Acta Trop. 2006 Dec;100 (3) :185-91. Epub 2006 Nov 28.|[3]Hamada K, et al. Antitumor effect of erythromycin in mice. Chemotherapy. 1995 Jan-Feb. 41 (1) :59-69. |[4]Katayama Y, et al. Neuroprotective effects of erythromycin on cerebral ischemia reperfusion-injury and cell viability after oxygen-glucose deprivation in cultured neuronal cells. Brain Res. 2014 Nov 7. 1588:159-67.
Shipping Conditions
Room temperature
Scientific Category
Reference compound1
Clinical Information
Phase 4

Chemical Information

Erythromycin glutamate
CAS Number16667-03-1
PubChem CID73456720
IUPAC Name(2S)-2-aminopentanedioic acid;(3R,4S,5S,6R,7R,9R,11R,12R,13S)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione
Molecular FormulaC42H76N2O17
Molecular Weight881.1
Topological Polar Surface Area295
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count19
Rotatable Bond Count11
Heavy Atom Count61
Formal Charge0
Complexity1320
SMILES
CCC1[C@@]([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)O)(C)O.C(CC(=O)O)[C@@H](C(=O)O)N
InChI
InChI=1S/C37H67NO13.C5H9NO4/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26;6-3(5(9)10)1-2-4(7)8/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3;3H,1-2,6H2,(H,7,8)(H,9,10)/t18-,19-,20+,21+,22-,23+,24+,25?,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-;3-/m10/s1
InChIKey
KNOXLRZTEFJWPE-OFWBJVIESA-N
Chemical Structure
2D Structure
2D structure of Erythromycin glutamate
CAS: 16667-03-1
CID: 73456720
Formula: C42H76N2O17
MW: 881.1
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight881.1
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count19
Rotatable Bond Count11
Exact Mass880.51439896
Monoisotopic Mass880.51439896
Topological Polar Surface Area295 Ų
Heavy Atom Count61
Formal Charge0
Complexity1320
Isotope Atom Count0
Defined Atom Stereocenter Count18
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes

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