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Compound Detail

CHEMBL187709

TRIPARANOL
💊 Approved Drug
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💊 Approved Drug
CCN(CC)CCOc1ccc(C(O)(Cc2ccc(Cl)cc2)c2ccc(C)cc2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL187709
Name TRIPARANOL
Phase Approved
Structure Type MOL
InChI Key SYHDSBBKRLVLFF-UHFFFAOYSA-N

Known Names

NSC-65345 Triparanol
6
Targets
16
Activities
2
Assay Types
0
PK Parameters
17
Publications
2
Known Names
1
Mechanisms

Molecular Properties

438.0
MW (Da)
5.85
ALogP
3
HBA
1
HBD
32.7
PSA (Ų)
0.43
QED
1
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Racemic

Flags

Withdrawn Natural Product

Extended Properties

Molecular Formula C27H32ClNO2
MW 438.01
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -0.91

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Delta(24)-sterol reductase inhibitor INHIBITOR Delta(24)-sterol reductase ✓ ✓

Drug Warnings

Withdrawn
dermatological toxicity
Cataracts, Alopecia, lchthyosis
Country: France; United States   Year: 1962
Withdrawn
dermatological toxicity
Cataracts, Alopecia, lchthyosis
Country: France; United States   Year: 1962
Withdrawn
occular toxicity
Cataracts, Alopecia, lchthyosis
Country: France; United States   Year: 1962

Activity Summary

IC50 13 meas. best 6.53
Ki 3 meas. best 8.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
C-8 sterol isomerase ERG2
CHEMBL3224
 Ki 8.7 8.7 2.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 8.1 8.1 8.0 1
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase
CHEMBL4931
 Ki 7.96 7.96 11.0 1
Unchecked
CHEMBL612545
 IC50 6.53 5.4033 298.7 9
SARS-CoV-2
CHEMBL4303835
 IC50 5.33 5.2233 4680.0 3
HL-60
CHEMBL383
 IC50 5.0 5.0 10000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
C-8 sterol isomerase ERG2 Ki = 2.0 nM 8.7 Affinity for ERG2 of Saccharomyces cerevisiae using [3H]ifenprodil or (+)-[3H]pe... 16033255
Sigma non-opioid intracellular receptor 1 Ki = 8.0 nM 8.1 Affinity for sigma receptor type 1 of guinea pig using [3H]ifenprodil or (+)-[3H... 16033255
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase Ki = 11.0 nM 7.96 Affinity for human EMP expressed in ERG2 deficient strain of Saccharomyces cerev... 16033255
Unchecked IC50 = 298.7 nM 6.53 PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: conf... -
Unchecked IC50 = 2457.7 nM 5.61 PubChem BioAssay. SNU-C1 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Unchecked IC50 = 3166.5 nM 5.5 PubChem BioAssay. HT-29 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 3210.4 nM 5.49 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area de... -
Unchecked IC50 = 3737.2 nM 5.43 PubChem BioAssay. GSK3B-pretreated HCT116 viability from Cell TiterGlo-IC50. (... -
Unchecked IC50 = 3759.2 nM 5.42 PubChem BioAssay. SW480 viability from Cell TiterGlo-IC50. (Class of assay: co... -
SARS-CoV-2 IC50 = 4680.0 nM 5.33 IC50 determination at MOI 0.004 using CellTiter- Glo (CTG) assay, performed 3 da... -
SARS-CoV-2 IC50 = 6410.0 nM 5.19 IC50 determination at MOI 0.01 using CellTiter- Glo (CTG) assay, performed 3 day... -
Unchecked IC50 = 6976.63 nM 5.16 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture nuclear area decrease (vi... -
SARS-CoV-2 IC50 = 7050.0 nM 5.15 Antiviral activity against SARS-CoV-2 (viral titer) measured by plaque assay in ... -
Unchecked IC50 = 8992.8 nM 5.05 PubChem BioAssay. Colo320 viability from Cell TiterGlo-IC50. (Class of assay: ... -
HL-60 IC50 = 10000.0 nM 5.0 Cytotoxicity in human HL60 cells by MTT assay 28964935
Unchecked IC50 = 36106.78 nM 4.44 PubChem BioAssay. GLP1 secretion from NCI-H716 cells-IC50. (Class of assay: co... -

Literature References

PubMed DOI Target Context # Activities
28964935 10.1016/j.ejmech.2017.08.011 HL-60 6
17428028 10.1021/ci6004542 Phospholipidosis 3
- 10.1101/2020.03.25.008482 ADMET 2
- 10.1101/2020.03.25.008482 Vero C1008 2
- 10.1101/2020.03.25.008482 SARS-CoV-2 2
26789657 10.1021/acs.jmedchem.5b01696 Delta(24)-sterol reductase 1
- 10.1101/2020.03.20.999730 ADMET 1
- 10.1101/2020.03.20.999730 Vero 1
- 10.1101/2020.03.20.999730 SARS-CoV-2 1
28964935 10.1016/j.ejmech.2017.08.011 Delta(24)-sterol reductase 1
16033255 10.1021/jm049073+ 3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase 1
26789657 10.1021/acs.jmedchem.5b01696 3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase 1
- 10.6019/CHEMBL3301361 No relevant target 1
20020916 10.1080/15376510701857262 Phospholipidosis 1
20799726 10.1021/mp100103e Phospholipidosis 1
16033255 10.1021/jm049073+ C-8 sterol isomerase ERG2 1
16033255 10.1021/jm049073+ Sigma non-opioid intracellular receptor 1 1

Data from ChEMBL 36 via Core Engine