2-[[[[2-(5-Fluoro-2-methoxyphenyl)cyclopropyl]methyl]-amino]methyl]benzamide Hydrochloride

ID: ALA4094054

PubChem CID: 137655187

Max Phase: Preclinical

Molecular Formula: C19H22ClFN2O2

Molecular Weight: 328.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(F)cc1C1CC1CNCc1ccccc1C(N)=O.Cl

Standard InChI:  InChI=1S/C19H21FN2O2.ClH/c1-24-18-7-6-14(20)9-17(18)16-8-13(16)11-22-10-12-4-2-3-5-15(12)19(21)23;/h2-7,9,13,16,22H,8,10-11H2,1H3,(H2,21,23);1H

Standard InChI Key:  LNVGCSONTIIPNA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    7.9554  -16.8241    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9488  -15.0334    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.6639  -15.4459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6615  -16.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3766  -16.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0902  -16.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8053  -16.6879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8029  -17.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0926  -15.4461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8062  -15.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6312  -15.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2188  -14.3226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3464  -15.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0599  -15.0446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7751  -15.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4886  -15.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2038  -15.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9173  -15.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9198  -14.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2046  -13.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4911  -14.2197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7759  -13.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0624  -14.2154    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7784  -12.9780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3775  -15.0335    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
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 12  1  0
 11 13  1  0
 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
 22 24  2  0
  9 25  2  0
  3 25  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: 328.39

Molecular Weight (Monoisotopic): 328.1587

AlogP: 2.83

#Rotatable Bonds: 7

Polar Surface Area: 64.35

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.20

CX LogP: 2.57

CX LogD: 0.78

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.82

Np Likeness Score: -0.42

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