tulathromycin   Click here for help

GtoPdb Ligand ID: 13691

Synonyms: Draxxin® (veterinary) | tulathromycin A
Compound class: Synthetic organic
Comment: Tulathromycin is a macrolide (triamilide subclass) antibacterial that was developed for use in veterinary medicine [3]. It consists of an equilibrated mixture of a 15-membered and a 13-membered ring component in a 9:1 ratio [2]. We show the structure for tulathromycin A, the 15-membered isomer.
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 15
Hydrogen bond donors 7
Rotatable bonds 11
Topological polar surface area 200.9
Molecular weight 806.08
XLogP 2.47
No. Lipinski's rules broken 4

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 CCCNC[C@@]1([C@H](C)O[C@H](C[C@@]1(C)OC)O[C@H]2[C@H](C)[C@H]([C@@](C)(C[C@@H](C)CN[C@H](C)[C@H]([C@@](C)([C@@H](CC)OC(=O)[C@@H]2C)O)O)O)O[C@H]3[C@@H]([C@H](C[C@@H](C)O3)N(C)C)O)O
Isomeric SMILES CCCNC[C@@]1([C@@H](O[C@H](C[C@@]1(C)OC)O[C@H]2[C@@H]([C@H]([C@](C[C@H](CN[C@@H]([C@H]([C@]([C@H](OC(=O)[C@@H]2C)CC)(C)O)O)C)C)(C)O)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)C)C)O
InChI InChI=1S/C41H79N3O12/c1-15-17-42-22-41(50)28(8)53-31(20-39(41,10)51-14)55-33-25(5)35(56-37-32(45)29(44(12)13)18-24(4)52-37)38(9,48)19-23(3)21-43-27(7)34(46)40(11,49)30(16-2)54-36(47)26(33)6/h23-35,37,42-43,45-46,48-50H,15-22H2,1-14H3/t23-,24-,25+,26-,27-,28+,29+,30-,31+,32-,33+,34-,35-,37+,38-,39-,40-,41+/m1/s1
InChI Key GUARTUJKFNAVIK-QPTWMBCESA-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
IUPAC Name Click here for help
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-5-(propylaminomethyl)oxan-2-yl]oxy-3,5,8,10,12,14-hexamethyl-1-oxa-6-azacyclopentadecan-15-one
International Nonproprietary Names Click here for help
INN number INN
8236 tulathromycin
Synonyms Click here for help
Draxxin® (veterinary) | tulathromycin A
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Tulathromycin
Other databases
CAS Registry No. 217500-96-4 (source: Scifinder)
ChEBI CHEBI:182495
DrugBank Ligand DB11474
DrugCentral Ligand 5640
GtoPdb PubChem SID 507750325
PubChem CID 9832301
Search Google for chemical match using the InChIKey GUARTUJKFNAVIK-QPTWMBCESA-N
Search Google for chemicals with the same backbone GUARTUJKFNAVIK
Search PubMed clinical trials tulathromycin
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UniChem Compound Search for chemical match using the InChIKey GUARTUJKFNAVIK-QPTWMBCESA-N
UniChem Connectivity Search for chemical match using the InChIKey GUARTUJKFNAVIK-QPTWMBCESA-N