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rokitamycin   Click here for help

GtoPdb Ligand ID: 12879

Synonyms: Ricamycin® | TMS-19-Q
Approved drug
rokitamycin is an approved drug
Compound class: Synthetic organic
Comment: Rokitamycin is a 16-membered semisynthetic macrolide antibacterial compound [3].
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 3
Rotatable bonds 15
Topological polar surface area 206.05
Molecular weight 828
XLogP 2.7
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 CCCC(=O)O[C@H]1[C@H](C)O[C@H](C[C@@]1(C)OC(=O)CC)O[C@@H]2[C@@H](C)O[C@H]([C@@H]([C@H]2N(C)C)O)O[C@H]3[C@@H](CC=O)C[C@@H](C)[C@H](/C=C/C=C/C[C@@H](C)OC(=O)C[C@H]([C@@H]3OC)O)O
Isomeric SMILES CCCC(=O)O[C@H]1[C@@H](O[C@H](C[C@@]1(C)OC(=O)CC)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2N(C)C)O)O[C@H]3[C@H](C[C@H]([C@H](/C=C/C=C/C[C@H](OC(=O)C[C@H]([C@@H]3OC)O)C)O)C)CC=O)C)C
InChI InChI=1S/C42H69NO15/c1-11-16-32(48)55-40-27(6)53-34(23-42(40,7)58-31(47)12-2)56-37-26(5)54-41(36(50)35(37)43(8)9)57-38-28(19-20-44)21-24(3)29(45)18-15-13-14-17-25(4)52-33(49)22-30(46)39(38)51-10/h13-15,18,20,24-30,34-41,45-46,50H,11-12,16-17,19,21-23H2,1-10H3/b14-13+,18-15+/t24-,25-,26-,27+,28+,29+,30-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1
InChI Key VYWWNRMSAPEJLS-MDWYKHENSA-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 Synthetic organic
Approved drug? Yes.
IUPAC Name Click here for help
[(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4,10-dihydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-dimethylamino-5-hydroxy-2-methyloxan-3-yl]oxy-2,4-dimethyl-4-propanoyloxyoxan-3-yl] butanoate
International Nonproprietary Names Click here for help
INN number INN
5681 rokitamycin
Synonyms Click here for help
Ricamycin® | TMS-19-Q
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Rokitamycin
Other databases
CAS Registry No. 74014-51-0 (source: Scifinder)
ChEBI CHEBI:32103
ChEMBL Ligand CHEMBL1908350
DrugBank Ligand DB13409
DrugCentral Ligand 2398
GtoPdb PubChem SID 485206000
PubChem CID 5282211
Search Google for chemical match using the InChIKey VYWWNRMSAPEJLS-MDWYKHENSA-N
Search Google for chemicals with the same backbone VYWWNRMSAPEJLS
Search PubMed clinical trials rokitamycin
Search PubMed titles rokitamycin
Search PubMed titles/abstracts rokitamycin
UniChem Compound Search for chemical match using the InChIKey VYWWNRMSAPEJLS-MDWYKHENSA-N
UniChem Connectivity Search for chemical match using the InChIKey VYWWNRMSAPEJLS-MDWYKHENSA-N