ID: ALA187709

Max Phase: Approved

Molecular Formula: C27H32ClNO2

Molecular Weight: 438.01

Molecule Type: Small molecule

Representations

Synonyms (2): Triparanol | NSC-65345
Synonyms from Alternative Forms(2):

Canonical SMILES:  CCN(CC)CCOc1ccc(C(O)(Cc2ccc(Cl)cc2)c2ccc(C)cc2)cc1

Standard 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

Standard InChI Key:  SYHDSBBKRLVLFF-UHFFFAOYSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 438.01

Molecular Weight (Monoisotopic): 437.2122

AlogP: 5.85

#Rotatable Bonds: 10

Polar Surface Area: 32.70

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.31

CX Basic pKa: 9.32

CX LogP: 6.48

CX LogD: 4.57

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.43

Np Likeness Score: -0.91

References

1. Laggner C, Schieferer C, Fiechtner B, Poles G, Hoffmann RD, Glossmann H, Langer T, Moebius FF..  (2005)  Discovery of high-affinity ligands of sigma1 receptor, ERG2, and emopamil binding protein by pharmacophore modeling and virtual screening.,  48  (15): [PMID:16033255] [10.1021/jm049073+]

2. PubChem BioAssay data set, 

3. PubChem BioAssay data set, 

4. Pelletier DJ, Gehlhaar D, Tilloy-Ellul A, Johnson TO, Greene N..  (2007)  Evaluation of a published in silico model and construction of a novel Bayesian model for predicting phospholipidosis inducing potential.,  47  (1): [PMID:17428028] [10.1021/ci6004542]

5. Cerep in vitro phospholipidosis assay data, 

6. Lowe R, Glen RC, Mitchell JB..  (2010)  Predicting phospholipidosis using machine learning.,  7  (5): [PMID:20799726] [10.1021/mp100103e]

7. Kruhlak NL, Choi SS, Contrera JF, Weaver JL, Willard JM, Hastings KL, Sancilio LF..  (2008)  Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.,  18  (2): [PMID:20020916] [10.1080/15376510701857262]

8. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

9. PubChem BioAssay data set, 

10. PubChem BioAssay data set, 

11. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

12. Unpublished dataset, 

13. Korade Z, Kim HY, Tallman KA, Liu W, Koczok K, Balogh I, Xu L, Mirnics K, Porter NA..  (2016)  The Effect of Small Molecules on Sterol Homeostasis: Measuring 7-Dehydrocholesterol in Dhcr7-Deficient Neuro2a Cells and Human Fibroblasts.,  59  (3): [PMID:26789657] [10.1021/acs.jmedchem.5b01696]

14. Müller C, Hemmers S, Bartl N, Plodek A, Körner A, Mirakaj V, Giera M, Bracher F..  (2017)  New chemotype of selective and potent inhibitors of human delta 24-dehydrocholesterol reductase.,  140  [PMID:28964935] [10.1016/j.ejmech.2017.08.011]

15. Sangeun Jeon, Meehyun Ko, Jihye Lee, Inhee Choi, Soo Young Byun, Soonju Park, David Shum, Seungtaek Kim.  (2020)  Identification of antiviral drug candidates against SARS-CoV-2 from FDA-approved drugs,  [10.1101/2020.03.20.999730]

16. Stuart Weston, Christopher M. Coleman, Rob Haupt, James Logue, Krystal Matthews and Matthew B. Frieman.  (2020)  Broad anti-coronaviral activity of FDA approved drugs against SARS-CoV-2 in vitro and SARS-CoV in vivo,  [10.1101/2020.03.25.008482]

Source

Source(6):

• Scientific Literature
• PubChem BioAssays
• USP Dictionary of USAN and International Drug Names
• AstraZeneca Deposited Data
• Withdrawn Drugs
• SARS-CoV-2 Screening Data 2020-21