US8476267, 2

ID: ALA3659493

PubChem CID: 46181100

Max Phase: Preclinical

Molecular Formula: C22H20ClN3O

Molecular Weight: 377.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N1CCC2(c3c[nH]c4ncccc34)CC12)C1(c2ccc(Cl)cc2)CC1

Standard InChI:  InChI=1S/C22H20ClN3O/c23-15-5-3-14(4-6-15)21(7-8-21)20(27)26-11-9-22(12-18(22)26)17-13-25-19-16(17)2-1-10-24-19/h1-6,10,13,18H,7-9,11-12H2,(H,24,25)

Standard InChI Key:  KXCFQRTUSWKVDX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 32  0  0  0  0  0  0  0  0999 V2000
   -5.1678  -13.4068    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.4410  -12.4519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9531  -12.6418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0446  -11.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6240  -10.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1120   -9.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0205  -11.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7170   -8.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6540   -9.7582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4666   -8.2700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2988   -7.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4895   -7.3351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3940   -6.2908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1057   -6.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6007   -4.9081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6928   -4.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8528   -3.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8257   -4.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114   -2.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4133   -1.7530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10  8  1  0
  8 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 13  1  0
 18 16  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 19  1  0
 27 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3659493

   [1-(4-chlorophenyl)cyclopropyl]-[5-(1H-pyrrolo[2,3-b]pyridin-3-yl)-2-azabicyclo[3.1.0]hexan-2-yl]methanone

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: 377.88

Molecular Weight (Monoisotopic): 377.1295

AlogP: 4.19

#Rotatable Bonds: 3

Polar Surface Area: 48.99

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.33

CX LogP: 3.61

CX LogD: 3.61

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.74

Np Likeness Score: -0.55

References

1.  (2013)  Fused pyrrolidino-cyclopropane derivatives as selective 11-beta-hydroxysteroid dehydrogenase type 1 inhibitors, 

Source

Source(1):

• BindingDB Database