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 Number	16667-03-1
PubChem CID	73456720
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 Formula	C42H76N2O17
Molecular Weight	881.1
Topological Polar Surface Area	295
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	19
Rotatable Bond Count	11
Heavy Atom Count	61
Formal Charge	0
Complexity	1320

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

CAS: 16667-03-1

CID: 73456720

Formula: C42H76N2O17

MW: 881.1

Interactive 3D Structure

Loading 3D structure...

View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	881.1
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	19
Rotatable Bond Count	11
Exact Mass	880.51439896
Monoisotopic Mass	880.51439896
Topological Polar Surface Area	295 Å²
Heavy Atom Count	61
Formal Charge	0
Complexity	1320
Isotope Atom Count	0
Defined Atom Stereocenter Count	18
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	2
Compound Is Canonicalized	Yes

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Erythromycin (glutamate)

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