spiramycin   Click here for help

GtoPdb Ligand ID: 13312

Synonyms: foromacidin | Rovamycine®
Approved drug PDB Ligand
spiramycin is an approved drug
Compound class: Natural product
Comment: Spiramycin is a 16-membered macrolide antimicrobial, produced by Streptomyces ambofaciens and originally isolated from soil samples [3].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 16
Hydrogen bond donors 4
Rotatable bonds 11
Topological polar surface area 195.38
Molecular weight 843.05
XLogP 1.93
No. Lipinski's rules broken 3

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

SMILES / InChI / InChIKey
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Canonical SMILES C[C@@H]1C[C@H](CC=O)[C@@H]([C@H]([C@@H](CC(=O)O[C@H](C)C/C=C/C=C/[C@@H]1O[C@H]2CC[C@@H]([C@@H](C)O2)N(C)C)O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](C)O3)O[C@H]4C[C@](C)([C@H]([C@H](C)O4)O)O)N(C)C)O
Isomeric SMILES C[C@@H]1C/C=C/C=C/[C@@H]([C@@H](C[C@@H]([C@@H]([C@H]([C@@H](CC(=O)O1)O)OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)O)(C)O)N(C)C)O)CC=O)C)O[C@H]4CC[C@@H]([C@H](O4)C)N(C)C
InChI InChI=1S/C43H74N2O14/c1-24-21-29(19-20-46)39(59-42-37(49)36(45(9)10)38(27(4)56-42)58-35-23-43(6,51)41(50)28(5)55-35)40(52-11)31(47)22-33(48)53-25(2)15-13-12-14-16-32(24)57-34-18-17-30(44(7)8)26(3)54-34/h12-14,16,20,24-32,34-42,47,49-51H,15,17-19,21-23H2,1-11H3/b13-12+,16-14+/t24-,25-,26-,27-,28+,29+,30+,31-,32+,34+,35+,36-,37-,38-,39+,40+,41+,42+,43-/m1/s1
InChI Key ACTOXUHEUCPTEW-CEUOBAOPSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

Classification Click here for help
Compound class Natural product
Approved drug? Yes
Approved drug? Yes.
IUPAC Name Click here for help
2-[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-[(2S,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-dimethylamino-3-hydroxy-6-methyloxan-2-yl]oxy-10-[(2R,5S,6R)-5-dimethylamino-6-methyloxan-2-yl]oxy-4-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde
International Nonproprietary Names Click here for help
INN number INN
478 spiramycin
Synonyms Click here for help
foromacidin | Rovamycine®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Spiramycin
Other databases
CAS Registry No. 24916-50-5 (source: Scifinder)
ChEMBL Ligand CHEMBL453514
DrugBank Ligand DB06145
DrugCentral Ligand 2471
GtoPdb PubChem SID 496703282
LIPID MAPS LMPK04000005
PubChem CID 5289394
RCSB PDB Ligand SPR
Search Google for chemical match using the InChIKey ACTOXUHEUCPTEW-CEUOBAOPSA-N
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UniChem Compound Search for chemical match using the InChIKey ACTOXUHEUCPTEW-CEUOBAOPSA-N
UniChem Connectivity Search for chemical match using the InChIKey ACTOXUHEUCPTEW-CEUOBAOPSA-N

Product suppliers

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MedChemExpress
Spiramycin (links to external site)
Cat. No. HY-100593
Spiramycin I (links to external site)
Cat. No. HY-N7141