4'-((1R,3r)-3-((R)-2-methylpyrrolidin-1-yl)cyclobutyl)biphenyl-4-carbonitrile

ID: ALA4516622

PubChem CID: 11973711

Max Phase: Preclinical

Molecular Formula: C22H24N2

Molecular Weight: 316.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@@H]1CCCN1[C@H]1C[C@H](c2ccc(-c3ccc(C#N)cc3)cc2)C1

Standard InChI:  InChI=1S/C22H24N2/c1-16-3-2-12-24(16)22-13-21(14-22)20-10-8-19(9-11-20)18-6-4-17(15-23)5-7-18/h4-11,16,21-22H,2-3,12-14H2,1H3/t16-,21-,22-/m1/s1

Standard InChI Key:  DQUUMUHVZGIZNI-NPFVIJTESA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   22.0191   -3.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0179   -3.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7327   -4.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4491   -3.9893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4462   -3.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7309   -2.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1562   -2.7449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8724   -3.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5849   -2.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5821   -1.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8611   -1.5064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1517   -1.9233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3060   -4.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5093   -4.1843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2952   -4.9811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0919   -5.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5803   -5.3930    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8279   -5.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2754   -5.6716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6874   -6.3864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4944   -6.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6563   -4.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2914   -1.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0038   -1.0857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  5  7  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 13  1  0
 13  2  1  1
 15 17  1  6
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 17  1  0
 18 22  1  1
 23 24  3  0
 10 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4516622

   4'-{3[(2R)-2-Methyl-pyrrolidin-1-yl]-cis-cyclobutyl}-biphenyl-4-carbonitrile

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 316.45

Molecular Weight (Monoisotopic): 316.1939

AlogP: 4.96

#Rotatable Bonds: 3

Polar Surface Area: 27.03

Molecular Species: BASE

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.06

CX LogP: 4.85

CX LogD: 2.25

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.80

Np Likeness Score: -0.45

References

1. Łażewska D, Kaleta M, Schwed JS, Karcz T, Mogilski S, Latacz G, Olejarz A, Siwek A, Kubacka M, Lubelska A, Honkisz E, Handzlik J, Filipek B, Stark H, Kieć-Kononowicz K..  (2017)  Biphenyloxy-alkyl-piperidine and azepane derivatives as histamine H₃ receptor ligands.,  25  (20): [PMID:28797771] [10.1016/j.bmc.2017.07.058]

Source

Source(1):

• Scientific Literature