ID: ALA37744

Max Phase: Approved

Molecular Formula: C16H17BrN2

Molecular Weight: 317.23

Molecule Type: Small molecule

Representations

Synonyms (4): Cis-zimelidine | Normud | Zelmid | Zimelidine
Synonyms from Alternative Forms(4):

Canonical SMILES:  CN(C)C/C=C(/c1ccc(Br)cc1)c1cccnc1

Standard InChI:  InChI=1S/C16H17BrN2/c1-19(2)11-9-16(14-4-3-10-18-12-14)13-5-7-15(17)8-6-13/h3-10,12H,11H2,1-2H3/b16-9-

Standard InChI Key:  OYPPVKRFBIWMSX-SXGWCWSVSA-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: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 317.23

Molecular Weight (Monoisotopic): 316.0575

AlogP: 3.84

#Rotatable Bonds: 4

Polar Surface Area: 16.13

Molecular Species: BASE

HBA: 2

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 8.62

CX LogP: 3.51

CX LogD: 2.27

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.85

Np Likeness Score: -0.70

References

1. Högberg T, Ulff B, Renyi AL, Ross SB..  (1981)  Synthesis of pyridylallylamines related to zimelidine and their inhibition of neuronal monoamine uptake.,  24  (12): [PMID:6458703] [10.1021/jm00144a025]

2. Welch WM, Kraska AR, Sarges R, Koe BK..  (1984)  Nontricyclic antidepressant agents derived from cis- and trans-1-amino-4-aryltetralins.,  27  (11): [PMID:6492080] [10.1021/jm00377a021]

3. McNeal ET, Lewandowski GA, Daly JW, Creveling CR..  (1985)  [3H]Batrachotoxinin A 20 alpha-benzoate binding to voltage-sensitive sodium channels: a rapid and quantitative assay for local anesthetic activity in a variety of drugs.,  28  (3): [PMID:2579237] [10.1021/jm00381a019]

4. Högberg T, Ross SB, Ström P, Grunewald GL, Creese MW, Bunce JD..  (1988)  Homoallylic amines related to zimeldine. A comparative study on neuronal serotonin and norepinephrine reuptake based on conformational analysis.,  31  (5): [PMID:2966246] [10.1021/jm00400a005]

5. 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]

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. PubChem BioAssay data set, 

9. PubChem BioAssay data set, 

10. Chen M, Vijay V, Shi Q, Liu Z, Fang H, Tong W..  (2011)  FDA-approved drug labeling for the study of drug-induced liver injury.,  16  (15-16): [PMID:21624500] [10.1016/j.drudis.2011.05.007]

11. Liu Z, Shi Q, Ding D, Kelly R, Fang H, Tong W..  (2011)  Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).,  7  (12): [PMID:22194678] [10.1371/journal.pcbi.1002310]

12. Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW..  (2002)  Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs.,  303  (1): [PMID:12438524] [10.1124/jpet.102.039255]

13. 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]

14. WHO Anatomical Therapeutic Chemical Classification, 

15. Warner DJ, Chen H, Cantin LD, Kenna JG, Stahl S, Walker CL, Noeske T..  (2012)  Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.,  40  (12): [PMID:22961681] [10.1124/dmd.112.047068]

16. Chen M, Suzuki A, Thakkar S, Yu K, Hu C, Tong W..  (2016)  DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.,  21  (4): [PMID:26948801] [10.1016/j.drudis.2016.02.015]

17. Rana P, Will Y, Nadanaciva S, Jones LH..  (2016)  Development of a cell viability assay to assess drug metabolite structure-toxicity relationships.,  26  (16): [PMID:27397500] [10.1016/j.bmcl.2016.06.088]

18. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

19. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]

Source

Source(5):

• Scientific Literature
• PubChem BioAssays
• TP-search Transporter Database
• WHO Anatomical Therapeutic Chemical Classification
• Fraunhofer HDAC6