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meclocycline   Click here for help

GtoPdb Ligand ID: 13540

Synonyms: GS-2989 | Meclan®
Approved drug
meclocycline is an approved drug (FDA)
Compound class: Synthetic organic
Comment: Meclocycline is a tetracycline antibacterial compound. 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 54676539), although this is not an exact structural match.
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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Click here for structure editor
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 10
Hydrogen bond donors 6
Rotatable bonds 2
Topological polar surface area 181.62
Molecular weight 476.86
XLogP -0.19
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
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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=C1C2=C(C(=CC=C2Cl)O)C(=O)C3=C([C@]4([C@]([H])([C@@H](C(=C(C4=O)C(=O)N)O)N(C)C)[C@H]([C@]13[H])O)O)O
Isomeric SMILES O[C@]12[C@]([C@H](N(C)C)C(O)=C(C(N)=O)C1=O)([C@@H](O)[C@]3(C(=C2O)C(=O)C=4C(C3=C)=C(Cl)C=CC4O)[H])[H]
InChI InChI=1S/C22H21ClN2O8/c1-6-9-7(23)4-5-8(26)11(9)16(27)12-10(6)17(28)14-15(25(2)3)18(29)13(21(24)32)20(31)22(14,33)19(12)30/h4-5,10,14-15,17,26,28-30,33H,1H2,2-3H3,(H2,24,32)/t10-,14-,15+,17+,22+/m1/s1
InChI Key GGQJXCQBBONZFX-IWVLMIASSA-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. US FDA (0)
IUPAC Name Click here for help
(4S,4aR,5S,5aR,12aS)-7-chloro-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methylidene-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
International Nonproprietary Names Click here for help
INN number INN
1566 meclocycline
Synonyms Click here for help
GS-2989 | Meclan®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Meclocycline
Other databases
CAS Registry No. 2013-58-3 (source: Scifinder)
ChEBI CHEBI:135772
ChEMBL Ligand CHEMBL1237124
DrugBank Ligand DB13092
DrugCentral Ligand 3333
GtoPdb PubChem SID 500839950
PubChem CID 54676539
Search Google for chemical match using the InChIKey GGQJXCQBBONZFX-IWVLMIASSA-N
Search Google for chemicals with the same backbone GGQJXCQBBONZFX
Search PubMed clinical trials meclocycline
Search PubMed titles meclocycline
Search PubMed titles/abstracts meclocycline
UniChem Compound Search for chemical match using the InChIKey GGQJXCQBBONZFX-IWVLMIASSA-N
UniChem Connectivity Search for chemical match using the InChIKey GGQJXCQBBONZFX-IWVLMIASSA-N