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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL416
CHEMBL416
Compound Name METHOXSALEN
ChEMBL Synonyms XANTHOTOXIN | 8-MOP | UVADEX | MELADININE | OXSORALEN | PUVASORALEN-8 | DELTASORALEN | METHOXSALEN | OXSORALEN-ULTRA | 8-METHOXYPSORALEN
Max Phase 4 (Approved)
Trade Names OXSORALEN | METHOXSALEN | OXSORALEN-ULTRA | 8-MOP | UVADEX | MELADININE | DELTASORALEN | PUVASORALEN-8
Molecular Formula C12H8O4

Additional synonyms for CHEMBL416 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES COc1c2OC(=O)C=Cc2cc3ccoc13
Standard InChI InChI=1S/C12H8O4/c1-14-12-10-8(4-5-15-10)6-7-2-3-9(13)16-11( ...
Download InChI
Standard InChI Key QXKHYNVANLEOEG-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • DrugMatrix
  • 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


CHEMBL416

Molecule Features

CHEMBL416 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:Y Topical:Y Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
DNA inhibitor DNA DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Crohn DiseaseD003424EFO:0000384Crohn's disease2ClinicalTrials
Mycosis FungoidesD009182EFO:1001051mycosis fungoides3ClinicalTrials
Epidermolysis Bullosa AcquisitaD016107EFO:1000691epidermolysis bullosa acquisita2ClinicalTrials
LymphomaD008223EFO:0000574lymphoma3ClinicalTrials
Hematologic NeoplasmsD019337EFO:0001642lymphoid neoplasm1ClinicalTrials
Graft vs Host DiseaseD006086EFO:0004599acute graft vs. host disease3ClinicalTrials
Arthritis, RheumatoidD001172EFO:0000685rheumatoid arthritis2ClinicalTrials

Clinical Data

ClinicalTrials.gov METHOXSALEN
The Cochrane Collaboration METHOXSALEN

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 CHEMBL416. 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
CHEMBL4633 Voltage-gated potassium channel subunit Kv1.3 Homo sapiens 1.000
CHEMBL3356 Cytochrome P450 1A2 Homo sapiens 0.971
CHEMBL4159 Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens 0.948
CHEMBL1293226 Lysine-specific demethylase 4D-like Homo sapiens 0.908
CHEMBL2026 Beta-lactamase AmpC Escherichia coli K-12 0.847
CHEMBL6110 Thioredoxin glutathione reductase Schistosoma mansoni 0.815
CHEMBL2231 Cytochrome P450 1A1 Homo sapiens 0.793
CHEMBL1293231 Nuclear receptor ROR-gamma Mus musculus 0.739
CHEMBL5514 Huntingtin Homo sapiens 0.710
CHEMBL1293224 Microtubule-associated protein tau Homo sapiens 0.692
CHEMBL2392 DNA polymerase beta Homo sapiens 0.640
CHEMBL3594 Carbonic anhydrase IX Homo sapiens 0.569
CHEMBL4878 Cytochrome P450 1B1 Homo sapiens 0.477
CHEMBL5282 Cytochrome P450 2A6 Homo sapiens 0.460
CHEMBL3242 Carbonic anhydrase XII Homo sapiens 0.303
CHEMBL1963 Thyroid stimulating hormone receptor Homo sapiens 0.246
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.207



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL4633 Voltage-gated potassium channel subunit Kv1.3 Homo sapiens 1.000
CHEMBL2326 Carbonic anhydrase VII Homo sapiens 0.997
CHEMBL4818 Voltage-gated potassium channel subunit Kv1.3 Mus musculus 0.995
CHEMBL4159 Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens 0.994
CHEMBL3912 Carbonic anhydrase XIII Homo sapiens 0.979
CHEMBL1293226 Lysine-specific demethylase 4D-like Homo sapiens 0.974
CHEMBL1293255 15-hydroxyprostaglandin dehydrogenase [NAD+] Homo sapiens 0.933
CHEMBL6110 Thioredoxin glutathione reductase Schistosoma mansoni 0.917
CHEMBL4878 Cytochrome P450 1B1 Homo sapiens 0.906
CHEMBL2903 Arachidonate 15-lipoxygenase Homo sapiens 0.902
CHEMBL2392 DNA polymerase beta Homo sapiens 0.811
CHEMBL1293277 Niemann-Pick C1 protein Homo sapiens 0.772
CHEMBL1293231 Nuclear receptor ROR-gamma Mus musculus 0.699
CHEMBL3577 Aldehyde dehydrogenase 1A1 Homo sapiens 0.670
CHEMBL5514 Huntingtin Homo sapiens 0.656
CHEMBL5508 Dual specificity tyrosine-phosphorylation-regulated kinase 1A Rattus norvegicus 0.610
CHEMBL2186 Carbonic anhydrase XIII Mus musculus 0.603
CHEMBL3356 Cytochrome P450 1A2 Homo sapiens 0.601
CHEMBL2026 Beta-lactamase AmpC Escherichia coli K-12 0.593
CHEMBL1963 Thyroid stimulating hormone receptor Homo sapiens 0.571

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
216.2 216.0423 2.55 1 52.58 -


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
4 0 0 4 0 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- - 1.52 1.52 3 16 0.59

Structural Alerts

There are 6 structural alerts for CHEMBL416. To view alerts please click here.

Compound Cross References

ATC D - DERMATOLOGICALS
D05 - ANTIPSORIATICS
D05A - ANTIPSORIATICS FOR TOPICAL USE
D05AD - Psoralens for topical use
D05AD02 - methoxsalen

D - DERMATOLOGICALS
D05 - ANTIPSORIATICS
D05B - ANTIPSORIATICS FOR SYSTEMIC USE
D05BA - Psoralens for systemic use
D05BA02 - methoxsalen

ChemSpider ChemSpider:QXKHYNVANLEOEG-UHFFFAOYSA-N
DailyMed methoxsalen
PubChem SID: 104171301 SID: 11112313 SID: 144203983 SID: 144208965 SID: 144213133 SID: 170465041 SID: 17389831 SID: 174006539 SID: 26752292 SID: 4255217 SID: 50105146 SID: 99459
Wikipedia Methoxsalen

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL416



ACToR 12692-94-3 298-81-7
BindingDB 50041234
Brenda 144111 7629 30509
ChEBI 18358
ChemicalBook CB6733540
DrugBank DB00553
DrugCentral 30
eMolecules 533332
EPA CompTox Dashboard DTXSID8020830
FDA SRS U4VJ29L7BQ
Human Metabolome Database HMDB0014693
IBM Patent System CDD82F0F925C5316644B5DD974B7859E
KEGG Ligand C01864
LINCS LSM-3410
Mcule MCULE-2500932325
Metabolights MTBLC18358
MolPort MolPort-000-696-480
NIH Clinical Collection SAM002548974
Nikkaji J2.983A
PDBe 8MO
PharmGKB PA450433
PubChem 4114
PubChem: Thomson Pharma 14822550
Rhea 18358
Selleck Methoxsalen(Oxsoralen)
SureChEMBL SCHEMBL19168
ZINC ZINC000002548959

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