demeclocycline   Click here for help

GtoPdb Ligand ID: 10905

Synonyms: Declomycin® | Ledermycin®
Compound class: Synthetic organic
Comment: Demeclocycline is a tetracycline antibacterial which was derived from a mutant strain of Streptomyces aureofaciens.
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 CDK toolkit. 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 9
Hydrogen bond donors 6
Rotatable bonds 2
Topological polar surface area 181.62
Molecular weight 464.1
XLogP 0.77
No. Lipinski's rules broken 1
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.

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Canonical SMILES CN([C@@H]1C(=O)C(=C([C@@]2([C@H]1C[C@H]1C(=C(O)c3c([C@H]1O)c(Cl)ccc3O)C2=O)O)O)C(=O)N)C
Isomeric SMILES CN([C@@H]1C(=O)C(=C([C@@]2([C@H]1C[C@H]1C(=C(O)c3c([C@H]1O)c(Cl)ccc3O)C2=O)O)O)C(=O)N)C
InChI InChI=1S/C21H21ClN2O8/c1-24(2)14-7-5-6-10(16(27)12-9(25)4-3-8(22)11(12)15(6)26)18(29)21(7,32)19(30)13(17(14)28)20(23)31/h3-4,6-7,14-15,25-27,30,32H,5H2,1-2H3,(H2,23,31)/t6-,7-,14-,15-,21-/m0/s1
InChI Key GUXHBMASAHGULD-SEYHBJAFSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(4S,4aS,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
International Nonproprietary Names Click here for help
INN number INN
917 demeclocycline
Synonyms Click here for help
Declomycin® | Ledermycin®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Demeclocycline
Other databases
CAS Registry No. 127-33-3 (source: WHO INN record)
ChEMBL Ligand CHEMBL1591
DrugBank Ligand DB00618
GtoPdb PubChem SID 405560346
PubChem CID 54680690
Search Google for chemical match using the InChIKey GUXHBMASAHGULD-SEYHBJAFSA-N
Search Google for chemicals with the same backbone GUXHBMASAHGULD
Search PubMed clinical trials demeclocycline
Search PubMed titles demeclocycline
Search PubMed titles/abstracts demeclocycline
UniChem Compound Search for chemical match using the InChIKey GUXHBMASAHGULD-SEYHBJAFSA-N
UniChem Connectivity Search for chemical match using the InChIKey GUXHBMASAHGULD-SEYHBJAFSA-N