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114-07-8 molecular structure
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(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-1-oxacyclotetradecane-2,10-dione

ChemBase ID: 127295
Molecular Formular: C37H67NO13
Molecular Mass: 733.92678
Monoisotopic Mass: 733.46124121
SMILES and InChIs

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]1C[C@@]([C@H]([C@@H](O1)C)O)(C)OC)C)O[C@H]1[C@@H]([C@H](C[C@H](O1)C)N(C)C)O)(C)O)C)C)O)(C)O
Canonical SMILES:
CC[C@@H]1OC(=O)[C@H](C)[C@@H](O[C@@H]2O[C@@H](C)[C@@H]([C@](C2)(C)OC)O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C[C@H](C(=O)[C@@H]([C@H]([C@]1(C)O)O)C)C)(C)O
InChI:
InChI=1S/C37H67NO13/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/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1
InChIKey:
ULGZDMOVFRHVEP-RWJQBGPGSA-N

Cite this record

CBID:127295 http://www.chembase.cn/molecule-127295.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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-1-oxacyclotetradecane-2,10-dione
IUPAC Traditional name
erythromycin
Brand Name
E-mycin, Erythrocin
Synonyms
Erythromycin
Erythromycin
Erythromycinum
红霉素
红霉素
CAS Number
114-07-8
EC Number
204-040-1
MDL Number
MFCD00084654
Beilstein Number
75279
PubChem SID
24869227
162221616
24869225
24894661
PubChem CID
3255
12560
CHEBI ID
42355
ATC CODE
D10AF02
S01AA17
J01FA01
QJ51FA01
CHEMBL
532
Chemspider ID
12041
DrugBank ID
DB00199
IUPHAR ligand ID
1456
KEGG ID
D00140
Unique Ingredient Identifier
63937KV33D
Wikipedia Title
Erythromycin
Medline Plus
a682381

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 12.438841  H Acceptors 13 
H Donor LogD (pH = 5.5) -0.1920999 
LogD (pH = 7.4) 1.5732646  Log P 2.5963888 
Molar Refractivity 186.0371 cm3 Polarizability 75.76136 Å3
Polar Surface Area 193.91 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
ethanol: soluble expand Show data source
Melting Point
133-135 °C expand Show data source
Optical Rotation
[α]20/D -75±4°, c = 2% in ethanol expand Show data source
RTECS
KF437500 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
Admin Routes
oral, iv, im, topical, ophthalmic eye drops expand Show data source
Bioavailability
Depends on the ester type between 30% - 65% expand Show data source
Excretion
bile expand Show data source
Half Life
1.5 hours expand Show data source
Metabolism
liver (under 5% excreted unchanged) expand Show data source
Protein Bound
90% expand Show data source
Legal Status
POM (UK) expand Show data source
Rx-only (US) expand Show data source
S4 (Australia) expand Show data source
Pregnancy Category
A (Australia) expand Show data source
B (US) expand Show data source
Gene Information
human ... ABCB1(5243), CYP3A4(1576), MLNR(2862)mouse ... Abcb1a(18671), Abcb1b(18669) expand Show data source
Purity
≥95.0% (NT) expand Show data source
Grade
Biotechnology Performance Certified expand Show data source
Ph Eur expand Show data source
Suitability
suitable for 1694 per US EPA expand Show data source
Impurities
endotoxin, tested expand Show data source
Pharmacopeia
testing & handling conforms to Pharmacopeia expand Show data source
Pharmacopeia Traceability
traceable to BP 794 expand Show data source
traceable to PhEur E1305000 expand Show data source
traceable to USP 1242000 expand Show data source
Empirical Formula (Hill Notation)
C37H67NO13 expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
Sigma Aldrich - E7904 external link
Biochem/physiol Actions
Mode of Action: Inhibits elongation at transpeptidation step (aminoacyl translocation A-site to P-site). Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Mode of Action: Inhibits elongation at transpeptidation step.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Other Notes
Macrolide antibiotic.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich - 45674 external link
Biochem/physiol Actions
Mode of Action: Inhibits elongation at transpeptidation step.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Mode of Action: Inhibits protein synthesis (elongation) at the level of transpeptidation (aminoacyl translocation A-site to P-site). Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Other Notes
Macrolide antibiotic.
Sigma Aldrich - 16221 external link
Biochem/physiol Actions
Mode of Action: Inhibits elongation at transpeptidation step.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Other Notes
Macrolide antibiotic.
Sigma Aldrich - 45673 external link
Biochem/physiol Actions
Mode of Action: Inhibits elongation at transpeptidation step.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Other Notes
Macrolide antibiotic.
Inhibits bacterial protein synthesis by binding to the ribosomes1; Inducible erythromycin resistance in bacteria2

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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