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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL187709
CHEMBL187709
Compound Name TRIPARANOL
ChEMBL Synonyms Triparanol
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names
Molecular Formula C27H32ClNO2

Additional synonyms for CHEMBL187709 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CCN(CC)CCOc1ccc(cc1)C(O)(Cc2ccc(Cl)cc2)c3ccc(C)cc3
Standard InChI InChI=1S/C27H32ClNO2/c1-4-29(5-2)18-19-31-26-16-12-24(13-17- ...
Download InChI
Standard InChI Key SYHDSBBKRLVLFF-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • Withdrawn Drugs

Alternate Forms of Compound in ChEMBL


CHEMBL187709

Molecule Features

CHEMBL187709 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:N First In Class:N Chirality:Racemic Mixture Prodrug:N Oral:N Parenteral:N Topical:N Black Box:N Availability Type:Withdrawn

Withdrawal Information

Year 1962
Country France; United States
Reason Cataracts, Alopecia, lchthyosis
Class Dermatological toxicity; Opthalmic toxicity

Mechanism of Action

Mechanism of Action ChEMBL Target References
Delta(24)-sterol reductase inhibitor Delta(24)-sterol reductase PubMed

Clinical Data

ClinicalTrials.gov TRIPARANOL
The Cochrane Collaboration TRIPARANOL

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 CHEMBL187709. 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
CHEMBL245 Muscarinic acetylcholine receptor M3 Homo sapiens 0.997
CHEMBL4931 3-beta-hydroxysteroid-delta(8),delta(7)-isomerase Homo sapiens 0.993
CHEMBL344 Melanin-concentrating hormone receptor 1 Homo sapiens 0.987
CHEMBL3593 Lanosterol synthase Homo sapiens 0.940
CHEMBL211 Muscarinic acetylcholine receptor M2 Homo sapiens 0.929
CHEMBL240 HERG Homo sapiens 0.793
CHEMBL1821 Muscarinic acetylcholine receptor M4 Homo sapiens 0.645
CHEMBL1075228 Melanin-concentrating hormone receptor 1 Rattus norvegicus 0.590
CHEMBL264 Histamine H3 receptor Homo sapiens 0.555
CHEMBL2128 Peroxisome proliferator-activated receptor alpha Mus musculus 0.539
CHEMBL2731 Galanin receptor 3 Homo sapiens 0.500
CHEMBL216 Muscarinic acetylcholine receptor M1 Homo sapiens 0.357



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL245 Muscarinic acetylcholine receptor M3 Homo sapiens 0.994
CHEMBL344 Melanin-concentrating hormone receptor 1 Homo sapiens 0.991
CHEMBL3593 Lanosterol synthase Homo sapiens 0.975
CHEMBL211 Muscarinic acetylcholine receptor M2 Homo sapiens 0.972
CHEMBL4931 3-beta-hydroxysteroid-delta(8),delta(7)-isomerase Homo sapiens 0.972
CHEMBL2128 Peroxisome proliferator-activated receptor alpha Mus musculus 0.945
CHEMBL264 Histamine H3 receptor Homo sapiens 0.770
CHEMBL1075228 Melanin-concentrating hormone receptor 1 Rattus norvegicus 0.434
CHEMBL240 HERG Homo sapiens 0.278

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
438 437.2122 5.85 10 32.7 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
3 1 1 3 1 1


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
13.44 9.62 5.93 3.77 3 31 0.43

Structural Alerts

There are 1 structural alerts for CHEMBL187709. To view alerts please click here.

Compound Cross References

ChemSpider ChemSpider:SYHDSBBKRLVLFF-UHFFFAOYSA-N
PubChem SID: 144205821 SID: 170466640 SID: 29217665 SID: 50111719

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL187709



ACToR 78-41-1
BindingDB 50170637
Brenda 4575 78077
ChEBI 135714
DrugCentral 2761
eMolecules 7387946
EPA CompTox Dashboard DTXSID6046507
IBM Patent System CB27722066A3524EB2F59D188A0DBC78
MolPort MolPort-006-110-249
Nikkaji J5.241H
PubChem 6536
PubChem: Thomson Pharma 16858634
SureChEMBL SCHEMBL133384

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