TRIPARANOL

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Search structure


Synonyms	NSC-65345 Triparanol
Status
Molecule Category	Free-form
UNII	63S8C3RXGS
EPA CompTox	DTXSID6046507


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	SYHDSBBKRLVLFF-UHFFFAOYSA-N
Smiles	CCN(CC)CCOc1ccc(C(O)(Cc2ccc(Cl)cc2)c2ccc(C)cc2)cc1
InChI	InChI=1S/C27H32ClNO2/c1-4-29(5-2)18-19-31-26-16-12-24(13-17-26)27(30,23-10-6-21(3)7-11-23)20-22-8-14-25(28)15-9-22/h6-17,30H,4-5,18-20H2,1-3H3

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C27H32ClNO2
Molecular Weight	438.01
AlogP	5.85
Hydrogen Bond Acceptor	3.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	10.0
Polar Surface Area	32.7
Molecular species	BASE
Aromatic Rings	3.0
Heavy Atoms	31.0

Bioactivity

Mechanism of Action	Action	Reference
Delta(24)-sterol reductase inhibitor	INHIBITOR	PubMed Wikipedia


Protein: Delta(24)-sterol reductase Description: Delta(24)-sterol reductase Organism : Homo sapiens Q15392 ENSG00000116133

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Isomerase	-	-	-	11	-
Membrane receptor	-	-	-	8	-

Assay Description	Organism	Bioactivity	Reference
Affinity for ERG2 of Saccharomyces cerevisiae using [3H]ifenprodil or (+)-[3H]pentazocine radioligand	Saccharomyces cerevisiae	2.0 nM
Affinity for sigma receptor type 1 of guinea pig using [3H]ifenprodil or (+)-[3H]pentazocine radioligand	Cavia porcellus	8.0 nM
Affinity for human EMP expressed in ERG2 deficient strain of Saccharomyces cerevisiae using [3H]ifenprodil or (+)-[3H]pentazocine as radioligand	Homo sapiens	11.0 nM
PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: confirmatory)	None	298.7 nM

Cross References

Resources	Reference
ChEBI	135714
ChEMBL	CHEMBL187709
DrugCentral	2761
FDA SRS	63S8C3RXGS
PubChem	6536
SureChEMBL	SCHEMBL133384

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).