ID: ALA75880

Max Phase: Approved

First Approval: 1974

Molecular Formula: C19H35N

Molecular Weight: 277.50

Molecule Type: Small molecule

Representations

Synonyms (1): Perhexiline
Synonyms from Alternative Forms(1):

Canonical SMILES:  C1CCC(C(CC2CCCCN2)C2CCCCC2)CC1

Standard InChI:  InChI=1S/C19H35N/c1-3-9-16(10-4-1)19(17-11-5-2-6-12-17)15-18-13-7-8-14-20-18/h16-20H,1-15H2

Standard InChI Key:  CYXKNKQEMFBLER-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

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: 277.50

Molecular Weight (Monoisotopic): 277.2770

AlogP: 5.30

#Rotatable Bonds: 4

Polar Surface Area: 12.03

Molecular Species: BASE

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 1

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa: 10.58

CX LogP: 5.53

CX LogD: 2.62

Aromatic Rings: 0

Heavy Atoms: 20

QED Weighted: 0.74

Np Likeness Score: 0.31

References

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2. Keserü GM..  (2003)  Prediction of hERG potassium channel affinity by traditional and hologram qSAR methods.,  13  (16): [PMID:12873512] [10.1016/s0960-894x(03)00492-x]

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4. Leclerc G, Decker N, Schwartz J..  (1982)  Synthesis and cardiovascular activity of a new series of cyclohexylaralkylamine derivatives related to perhexiline.,  25  (6): [PMID:6124638] [10.1021/jm00348a019]

5. Rajamani R, Tounge BA, Li J, Reynolds CH..  (2005)  A two-state homology model of the hERG K+ channel: application to ligand binding.,  15  (6): [PMID:15745831] [10.1016/j.bmcl.2005.01.008]

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9. 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]

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11. Sinha N, Sen S..  (2011)  Predicting hERG activities of compounds from their 3D structures: development and evaluation of a global descriptors based QSAR model.,  46  (2): [PMID:21185626] [10.1016/j.ejmech.2010.11.042]

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26. Unpublished dataset, 

27. Unpublished dataset, 

28. Unpublished dataset, 

29. Unpublished dataset, 

30. Biour M, Ben Salem C, Chazouillères O, Grangé JD, Serfaty L, Poupon R..  (2004)  [Drug-induced liver injury; fourteenth updated edition of the bibliographic database of liver injuries and related drugs].,  28  (8-9): [PMID:15646539] [10.1016/s0399-8320(04)95062-2]

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38. Tseng CC, Noordali H, Sani M, Madhani M, Grant DM, Frenneaux MP, Zanda M, Greig IR..  (2017)  Development of Fluorinated Analogues of Perhexiline with Improved Pharmacokinetic Properties and Retained Efficacy.,  60  (7): [PMID:28277663] [10.1021/acs.jmedchem.6b01592]

39. Unpublished dataset, 

40. 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]

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Source

Source(10):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• Open TG-GATEs
• DrugMatrix
• Gene Expression Atlas Compounds
• AstraZeneca Deposited Data
• WHO Anatomical Therapeutic Chemical Classification
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6