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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL249837
CHEMBL249837
Compound Name METHACYCLINE
ChEMBL Synonyms MOTC | METHACYCLINE HYDROCHLORIDE | RONDOMYCIN | Methacycline | METACYCLINE | GS-2876
Max Phase 4 (Approved)
Trade Names RONDOMYCIN
Molecular Formula C22H22N2O8

Additional synonyms for CHEMBL249837 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CN(C)[C@H]1[C@@H]2[C@@H](O)[C@@H]3C(=C)c4cccc(O)c4C(=O)C3=C( ...
Download SMILES
Standard InChI InChI=1S/C22H22N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17( ...
Download InChI
Standard InChI Key MHIGBKBJSQVXNH-IWVLMIASSA-N

Sources

  • British National Formulary
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL249837

Molecule Features

CHEMBL249837 compound icon
Drug Type:Natural Product-derived Rule of Five:N First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Discontinued

Mechanism of Action

Mechanism of Action ChEMBL Target References
Bacterial 70S ribosome inhibitor Bacterial 70S ribosome PubMed PubMed PubMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
OsteomyelitisD010019EFO:0003102osteomyelitis0ClinicalTrials
ClinicalTrials
Bacterial InfectionsD001424EFO:0000771bacterial disease4ATC

Clinical Data

ClinicalTrials.gov METHACYCLINE
The Cochrane Collaboration METHACYCLINE

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL249837. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 1.000

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL5990 Breast cancer type 1 susceptibility protein Homo sapiens 1.000
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.956
CHEMBL3401 Pregnane X receptor Homo sapiens 0.944
CHEMBL3834 Tyrosine-protein kinase BMX Homo sapiens 0.817
CHEMBL2980 Arachidonate 5-lipoxygenase Bos taurus 0.697
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.674
CHEMBL1293226 Lysine-specific demethylase 4D-like Homo sapiens 0.480
CHEMBL1806 DNA topoisomerase II alpha Homo sapiens 0.346

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
442.4 442.1376 -0.44 2 181.62 ZWITTERION


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
9 6 1 10 7 1


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
4.5 10.73 1.35 -1.56 1 32 0.33

Structural Alerts

There are 3 structural alerts for CHEMBL249837. To view alerts please click here.

Compound Cross References

ATC J - ANTIINFECTIVES FOR SYSTEMIC USE
J01 - ANTIBACTERIALS FOR SYSTEMIC USE
J01A - TETRACYCLINES
J01AA - Tetracyclines
J01AA05 - metacycline

ChemSpider ChemSpider:MHIGBKBJSQVXNH-IWVLMIASSA-N
Wikipedia Metacycline

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL249837



ACToR 914-00-1
ChEBI 6805
DrugBank DB00931
DrugCentral 1727
eMolecules 2725962
EPA CompTox Dashboard DTXSID2023272
FDA SRS IR235I7C5P
KEGG Ligand C07654
Mcule MCULE-8490229191
Metabolights MTBLC6805
Nikkaji J7.166H
PubChem: Thomson Pharma 15143534
SureChEMBL SCHEMBL4014
ZINC ZINC000085650610

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/MHIGBKBJSQVXNH-IWVLMIASSA-N spacer
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