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Erythromycin (thiocyanate) (Standard)

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Description
Erythromycin (thiocyanate) (Standard) is the analytical standard of Erythromycin (thiocyanate) . This product is intended for research and analytical applications. Erythromycin thiocyanate is a macrolide antibiotic produced by actinomycete Streptomyces erythreus with a broad spectrum of antimicrobial activity. Erythromycin thiocyanate 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 thiocyanate also exhibits antitumor and neuroprotective effect in different fields of research[3][4].
CAS Number
7704-67-8
UNSPSC
12352005
Target
Antibiotic; Bacterial; DNA/RNA Synthesis; Reference Standards
Related Pathways
Anti-infection; Cell Cycle/DNA Damage; Others
Field of Research
Infection; Cancer
Smiles
C[C@@H]([C@@H]([C@H](C(O[C@@H]1CC)=O)C)O[C@@](O[C@@H](C)[C@@H]2O)([H])C[C@@]2(C)OC)[C@H]([C@](O)(C[C@H](C([C@@H]([C@@H](O)[C@@]1(O)C)C)=O)C)C)O[C@@](O[C@H](C)C[C@@H]3N(C)C)([H])[C@@H]3O.SC#N
Molecular Formula
C38H68N2O13S
Molecular Weight
793.02
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 Standards

Chemical Information

Erythromycin Thiocyanate
CAS Number7704-67-8
PubChem CID83938
IUPAC Name(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-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;thiocyanic acid
Molecular FormulaC38H68N2O13S
Molecular Weight793.0
Topological Polar Surface Area219
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count16
Rotatable Bond Count7
Heavy Atom Count54
Formal Charge0
Complexity1210
SMILES
CC[C@@H]1[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(#N)S
InChI
InChI=1S/C37H67NO13.CHNS/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;2-1-3/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3;3H/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-;/m1./s1
InChIKey
WVRRTEYLDPNZHR-YZPBMOCRSA-N
Chemical Structure
2D Structure
2D structure of Erythromycin Thiocyanate
CAS: 7704-67-8
CID: 83938
Formula: C38H68N2O13S
MW: 793.0
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight793.0
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count16
Rotatable Bond Count7
Exact Mass792.44421140
Monoisotopic Mass792.44421140
Topological Polar Surface Area219 Ų
Heavy Atom Count54
Formal Charge0
Complexity1210
Isotope Atom Count0
Defined Atom Stereocenter Count18
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes

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