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].

spiramycin is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were 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/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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/)

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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
Search Google for chemicals with the same backbone ACTOXUHEUCPTEW
Search PubMed clinical trials spiramycin
Search PubMed titles spiramycin
Search PubMed titles/abstracts spiramycin
UniChem Compound Search for chemical match using the InChIKey ACTOXUHEUCPTEW-CEUOBAOPSA-N
UniChem Connectivity Search for chemical match using the InChIKey ACTOXUHEUCPTEW-CEUOBAOPSA-N

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