(-)-1-[(1R,2R)-2-(5-Fluoro-2-methoxyphenyl)cyclopropyl]-N-(2-methoxybenzyl)methanamine Hydrochloride

ID: ALA4101194

PubChem CID: 137660307

Max Phase: Preclinical

Molecular Formula: C19H23ClFNO2

Molecular Weight: 315.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1CNC[C@@H]1C[C@H]1c1cc(F)ccc1OC.Cl

Standard InChI:  InChI=1S/C19H22FNO2.ClH/c1-22-18-6-4-3-5-13(18)11-21-12-14-9-16(14)17-10-15(20)7-8-19(17)23-2;/h3-8,10,14,16,21H,9,11-12H2,1-2H3;1H/t14-,16+;/m0./s1

Standard InChI Key:  KNTRIIJGIFKPED-KUARMEPBSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   22.3339   -9.8411    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.0081   -8.3291    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.7202   -8.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7081   -9.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4160   -9.9995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1402   -9.5968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8481  -10.0193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8360  -10.8445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1482   -8.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8682   -8.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6935   -8.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2908   -7.6609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4013   -8.7994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1213   -8.3967    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8335   -8.8193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5535   -8.4165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2614   -8.8391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9814   -8.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9936   -7.6112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2814   -7.1886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5614   -7.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8536   -7.1688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8657   -6.3436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4402   -8.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
 10  9  1  6
 10 11  1  0
 11 12  1  0
 10 12  1  0
 11 13  1  1
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
  9 24  2  0
  3 24  1  0
M  END

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

Calculated Properties

Molecular Weight: 315.39

Molecular Weight (Monoisotopic): 315.1635

AlogP: 3.74

#Rotatable Bonds: 7

Polar Surface Area: 30.49

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.05

CX LogP: 3.56

CX LogD: 1.91

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.84

Np Likeness Score: -0.45

References

1. Zhang G, Cheng J, McCorvy JD, Lorello PJ, Caldarone BJ, Roth BL, Kozikowski AP..  (2017)  Discovery of N-Substituted (2-Phenylcyclopropyl)methylamines as Functionally Selective Serotonin 2C Receptor Agonists for Potential Use as Antipsychotic Medications.,  60  (14): [PMID:28657744] [10.1021/acs.jmedchem.7b00584]

Source

Source(1):

• Scientific Literature