chlortetracycline

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Ligands
chlortetracycline

GtoPdb Ligand ID: 13537

Synonyms: Aureomycin®

chlortetracycline is an approved drug (FDA (1950))

Comment: Chlortetracycline is a tetracycline antibacterial, originally isolated from Kitasatospora aureofaciens (formerly Streptomyces aureofaciens), and the first compound from this class to be discovered [3-5]. Note that the structure shown here matches the CAS-assigned structure. The PubChem link, provided in the table below, is to their standardized chemical structure (CID 54675777), although this is not an exact structural match.

2D Structure

Physico-chemical Properties

Hydrogen bond acceptors	10
Hydrogen bond donors	6
Rotatable bonds	2
Topological polar surface area	181.62
Molecular weight	478.88
XLogP	-0.21
No. Lipinski's rules broken	1

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

Canonical SMILES	C[C@@]1([C@@]2([H])C[C@@]3([H])[C@@H](C(=C(C(=O)[C@]3(C(=C2C(=O)C4=C1C(=CC=C4O)Cl)O)O)C(=O)N)O)N(C)C)O
Isomeric SMILES	O[C@]12[C@]([C@H](N(C)C)C(O)=C(C(N)=O)C1=O)(C[C@]3(C(=C2O)C(=O)C=4C([C@@]3(C)O)=C(Cl)C=CC4O)[H])[H]
InChI	InChI=1S/C22H23ClN2O8/c1-21(32)7-6-8-15(25(2)3)17(28)13(20(24)31)19(30)22(8,33)18(29)11(7)16(27)12-10(26)5-4-9(23)14(12)21/h4-5,7-8,15,26,28-29,32-33H,6H2,1-3H3,(H2,24,31)/t7-,8-,15-,21-,22-/m0/s1
InChI Key	CYDMQBQPVICBEU-XRNKAMNCSA-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/)