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oleandomycin   Click here for help

GtoPdb Ligand ID: 13280

Synonyms: amimycin | landomycin | Matromycin® | P.A.105 | Romicil®
Approved drug
oleandomycin is an approved drug
Compound class: Natural product
Comment: Oleandomycin is a 14-membered macrolide antibacterial compound, originally isolated from Streptomyces antibioticus.
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 13
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 165.98
Molecular weight 687.86
XLogP 0.7
No. Lipinski's rules broken 2

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@@]2(CO2)C(=O)[C@H](C)[C@H]([C@@H](C)[C@@H](C)OC(=O)[C@H](C)[C@H]([C@H](C)[C@H]1O[C@H]3[C@@H]([C@H](C[C@@H](C)O3)N(C)C)O)O[C@H]4C[C@@H]([C@H]([C@H](C)O4)O)OC)O
Isomeric SMILES C[C@@H]1C[C@@H]([C@H]([C@@H](O1)O[C@H]2[C@H](C[C@@]3(CO3)C(=O)[C@@H]([C@H]([C@H]([C@H](OC(=O)[C@@H]([C@H]([C@@H]2C)O[C@H]4C[C@@H]([C@H]([C@@H](O4)C)O)OC)C)C)C)O)C)C)O)N(C)C
InChI InChI=1S/C35H61NO12/c1-16-14-35(15-43-35)32(40)19(4)27(37)18(3)22(7)46-33(41)21(6)31(47-26-13-25(42-11)28(38)23(8)45-26)20(5)30(16)48-34-29(39)24(36(9)10)12-17(2)44-34/h16-31,34,37-39H,12-15H2,1-11H3/t16-,17+,18-,19+,20+,21+,22+,23-,24-,25-,26-,27-,28-,29+,30-,31-,34-,35+/m0/s1
InChI Key RZPAKFUAFGMUPI-QESOVKLGSA-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.
IUPAC Name Click here for help
(3R,5S,6S,7R,8S,9R,12R,13R,14S,15R)-6-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-8-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-5,7,9,12,13,15-hexamethyl-1,11-dioxaspiro[2.13]hexadecane-10,16-dione
International Nonproprietary Names Click here for help
INN number INN
665 oleandomycin
Synonyms Click here for help
amimycin | landomycin | Matromycin® | P.A.105 | Romicil®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Oleandomycin
Other databases
BindingDB Ligand 234401
CAS Registry No. 3922-90-5 (source: Scifinder)
ChEBI CHEBI:16869
ChEMBL Ligand CHEMBL606258
DrugBank Ligand DB11442
DrugCentral Ligand 1983
GtoPdb PubChem SID 491300062
LIPID MAPS LMPK04000007
PubChem CID 72493
Search Google for chemical match using the InChIKey RZPAKFUAFGMUPI-QESOVKLGSA-N
Search Google for chemicals with the same backbone RZPAKFUAFGMUPI
Search PubMed clinical trials oleandomycin
Search PubMed titles oleandomycin
Search PubMed titles/abstracts oleandomycin
UniChem Compound Search for chemical match using the InChIKey RZPAKFUAFGMUPI-QESOVKLGSA-N
UniChem Connectivity Search for chemical match using the InChIKey RZPAKFUAFGMUPI-QESOVKLGSA-N