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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL313972
CHEMBL313972
Compound Name MASOPROCOL
ChEMBL Synonyms CHX-100 | MESO-NORDIHYDROGUAIARETIC ACID | Actinex | INSM-18 | MASOPROCOL | MESO-NDGA
Max Phase 4 (Approved)
Trade Names Actinex
Molecular Formula C18H22O4

Additional synonyms for CHEMBL313972 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES C[C@H](Cc1ccc(O)c(O)c1)[C@@H](C)Cc2ccc(O)c(O)c2
Standard InChI InChI=1S/C18H22O4/c1-11(7-13-3-5-15(19)17(21)9-13)12(2)8-14- ...
Download InChI
Standard InChI Key HCZKYJDFEPMADG-TXEJJXNPSA-N

Sources

  • Orange Book
  • PubChem BioAssays
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL313972

Molecule Features

CHEMBL313972 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:N Parenteral:N Topical:Y Black Box:N Availability Type:Discontinued

Mechanism of Action

Mechanism of Action ChEMBL Target References
Unknown Not Available PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
NeoplasmsD009369EFO:0000616neoplasm4ATC

Clinical Data

ClinicalTrials.gov MASOPROCOL
The Cochrane Collaboration MASOPROCOL

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 CHEMBL313972. 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
CHEMBL312 Arachidonate 5-lipoxygenase Rattus norvegicus 1.000
CHEMBL210 Beta-2 adrenergic receptor Homo sapiens 0.992
CHEMBL2903 Arachidonate 15-lipoxygenase Homo sapiens 0.979
CHEMBL321 Matrix metalloproteinase 9 Homo sapiens 0.956
CHEMBL246 Beta-3 adrenergic receptor Homo sapiens 0.915
CHEMBL333 Matrix metalloproteinase-2 Homo sapiens 0.887
CHEMBL215 Arachidonate 5-lipoxygenase Homo sapiens 0.881
CHEMBL5414 Beta-2 adrenergic receptor Cavia porcellus 0.868
CHEMBL3510 Carbonic anhydrase XIV Homo sapiens 0.775
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.608
CHEMBL3369 Neprilysin Rattus norvegicus 0.561
CHEMBL3687 Arachidonate 12-lipoxygenase Homo sapiens 0.554
CHEMBL4159 Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens 0.471
CHEMBL270 Mu opioid receptor Rattus norvegicus 0.407
CHEMBL213 Beta-1 adrenergic receptor Homo sapiens 0.297
CHEMBL1944 Neprilysin Homo sapiens 0.268
CHEMBL243 Human immunodeficiency virus type 1 protease Human immunodeficiency virus 1 0.229
CHEMBL1860 Thyroid hormone receptor alpha Homo sapiens 0.217



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL312 Arachidonate 5-lipoxygenase Rattus norvegicus 0.999
CHEMBL210 Beta-2 adrenergic receptor Homo sapiens 0.993
CHEMBL321 Matrix metalloproteinase 9 Homo sapiens 0.967
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.930
CHEMBL333 Matrix metalloproteinase-2 Homo sapiens 0.925
CHEMBL215 Arachidonate 5-lipoxygenase Homo sapiens 0.879
CHEMBL246 Beta-3 adrenergic receptor Homo sapiens 0.874
CHEMBL4586 Seed lipoxygenase-1 Glycine max 0.859
CHEMBL5414 Beta-2 adrenergic receptor Cavia porcellus 0.770
CHEMBL3687 Arachidonate 12-lipoxygenase Homo sapiens 0.745
CHEMBL3510 Carbonic anhydrase XIV Homo sapiens 0.730
CHEMBL2903 Arachidonate 15-lipoxygenase Homo sapiens 0.720
CHEMBL332 Matrix metalloproteinase-1 Homo sapiens 0.663
CHEMBL3402 Alkaline phosphatase placental-like Homo sapiens 0.654
CHEMBL3471 Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 0.528
CHEMBL3369 Neprilysin Rattus norvegicus 0.482
CHEMBL4393 Matrix metalloproteinase 12 Homo sapiens 0.432
CHEMBL270 Mu opioid receptor Rattus norvegicus 0.338
CHEMBL243 Human immunodeficiency virus type 1 protease Human immunodeficiency virus 1 0.262
CHEMBL2980 Arachidonate 5-lipoxygenase Bos taurus 0.247

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
302.4 302.1518 3.57 5 80.92 NEUTRAL


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


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
9.56 - 3.52 3.51 2 22 0.64

Structural Alerts

There are 2 structural alerts for CHEMBL313972. To view alerts please click here.

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01X - OTHER ANTINEOPLASTIC AGENTS
L01XX - Other antineoplastic agents
L01XX10 - masoprocol

ChemSpider ChemSpider:HCZKYJDFEPMADG-TXEJJXNPSA-N
PubChem SID: 11111540 SID: 11111541 SID: 124891671 SID: 144203761 SID: 50100292 SID: 50106727 SID: 50106728 SID: 90341429
Wikipedia Masoprocol

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL313972



BindingDB 22372
Brenda 143361
ChEBI 73468
DrugBank DB00179
DrugCentral 1637
EPA CompTox Dashboard DTXSID5045178
FDA SRS 7BO8G1BYQU
Human Metabolome Database HMDB0014325
IBM Patent System D72112E0E997DDEA6E2665605B9129DA
KEGG Ligand C10719
Metabolights MTBLC73468
Nikkaji J257.424A
PharmGKB PA164746493
PubChem 71398
PubChem: Drugs of the Future 12014519
PubChem: Thomson Pharma 136913921 14825338
SureChEMBL SCHEMBL3818
ZINC ZINC000000012342

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