US9169205, 1.82

ID: ALA3983789

PubChem CID: 118473451

Max Phase: Preclinical

Molecular Formula: C23H25N3O4

Molecular Weight: 407.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@@H](C)c1ccc(OC2CCN(c3cc4c(cc3C#N)OCCO4)C2)cc1

Standard InChI:  InChI=1S/C23H25N3O4/c1-15(25-16(2)27)17-3-5-19(6-4-17)30-20-7-8-26(14-20)21-12-23-22(11-18(21)13-24)28-9-10-29-23/h3-6,11-12,15,20H,7-10,14H2,1-2H3,(H,25,27)/t15-,20?/m0/s1

Standard InChI Key:  SVPQZVZSORDUBU-OOJLDXBWSA-N

Molfile:  

     RDKit          2D

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    1.2539   -9.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8547  -10.8801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9647  -12.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4451  -13.1883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2278  -11.9552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1438   -8.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6348   -8.4606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5226   -7.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9195   -5.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8054   -4.6666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2010   -3.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9531   -1.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9511   -0.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987   -1.5004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343   -2.9815    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
    0.0000    3.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2991    3.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    1.5000    0.0000 O   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
    0.0000   -3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.2008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4285   -5.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5407   -6.9229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  2  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 19  2  0
 24 25  1  0
 25 26  2  0
 26 17  1  0
 26 27  1  0
 27 28  3  0
 10 29  1  0
 29 30  2  0
 30  7  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3983789

   N-[(1S)-1-[4-[1-(7-cyano-2,3-dihydro-1,4-benzodioxin-6-yl)pyrrolidin-3-yl]oxyphenyl]ethyl]acetamide

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: 407.47

Molecular Weight (Monoisotopic): 407.1845

AlogP: 3.18

#Rotatable Bonds: 5

Polar Surface Area: 83.82

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.40

CX LogD: 2.40

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.82

Np Likeness Score: -1.00

References

1.  (2015)  Pyrrolidine derivatives, pharmaceutical compositions and uses thereof, 

Source

Source(1):

• BindingDB Database