ID: ALA87379

Max Phase: Preclinical

Molecular Formula: C21H25NO

Molecular Weight: 307.44

Molecule Type: Small molecule

Representations

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

Canonical SMILES:  O[C@@H]1Cc2ccccc2C[C@H]1N1CCC(c2ccccc2)CC1

Standard InChI:  InChI=1S/C21H25NO/c23-21-15-19-9-5-4-8-18(19)14-20(21)22-12-10-17(11-13-22)16-6-2-1-3-7-16/h1-9,17,20-21,23H,10-15H2/t20-,21-/m1/s1

Standard InChI Key:  UUCLSDHQYDLBNN-NHCUHLMSSA-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: 307.44

Molecular Weight (Monoisotopic): 307.1936

AlogP: 3.39

#Rotatable Bonds: 2

Polar Surface Area: 23.47

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 9.70

CX LogP: 3.94

CX LogD: 1.67

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.92

Np Likeness Score: 0.26

References

1. Efange SM, Khare AB, Foulon C, Akella SK, Parsons SM..  (1994)  Spirovesamicols: conformationally restricted analogs of 2-(4-phenylpiperidino)cyclohexanol (vesamicol, AH5183) as potential modulators of presynaptic cholinergic function.,  37  (16): [PMID:8057300] [10.1021/jm00042a010]

2. Efange SM, Kamath AP, Khare AB, Kung MP, Mach RH, Parsons SM..  (1997)  N-hydroxyalkyl derivatives of 3 beta-phenyltropane and 1-methylspiro[1H-indoline-3,4'-piperidine]: vesamicol analogues with affinity for monoamine transporters.,  40  (24): [PMID:9397171] [10.1021/jm970326r]

3. Szymoszek A, Wenzel B, Scheunemann M, Steinbach J, Schüürmann G..  (2008)  First CoMFA characterization of vesamicol analogs as ligands for the vesicular acetylcholine transporter.,  51  (7): [PMID:18324757] [10.1021/jm700961r]

4. Tu Z, Efange SM, Xu J, Li S, Jones LA, Parsons SM, Mach RH..  (2009)  Synthesis and in vitro and in vivo evaluation of 18F-labeled positron emission tomography (PET) ligands for imaging the vesicular acetylcholine transporter.,  52  (5): [PMID:19203271] [10.1021/jm8012344]

5. Efange SM, Khare AB, von Hohenberg K, Mach RH, Parsons SM, Tu Z..  (2010)  Synthesis and in vitro biological evaluation of carbonyl group-containing inhibitors of vesicular acetylcholine transporter.,  53  (7): [PMID:20218624] [10.1021/jm9017916]

6. Tu Z, Wang W, Cui J, Zhang X, Lu X, Xu J, Parsons SM..  (2012)  Synthesis and evaluation of in vitro bioactivity for vesicular acetylcholine transporter inhibitors containing two carbonyl groups.,  20  (14): [PMID:22739089] [10.1016/j.bmc.2012.05.045]

7. Barthel C, Sorger D, Deuther-Conrad W, Scheunemann M, Schweiger S, Jäckel P, Roghani A, Steinbach J, Schüürmann G, Sabri O, Brust P, Wenzel B..  (2015)  New systematically modified vesamicol analogs and their affinity and selectivity for the vesicular acetylcholine transporter - A critical examination of the lead structure.,  100  [PMID:26071858] [10.1016/j.ejmech.2015.05.033]

Source

Source(1):

• Scientific Literature