exo-2,3-dihydro-3,3-dimethyl-N-[(hexahydro-lH-pyrrolizin-1S-yl)methyl]-2-oxo-1H-indole-1-carboxamide

ID: ALA371883

PubChem CID: 11537858

Max Phase: Preclinical

Molecular Formula: C19H25N3O2

Molecular Weight: 327.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)C(=O)N(C(=O)NC[C@@H]2CCN3CCC[C@@H]23)c2ccccc21

Standard InChI:  InChI=1S/C19H25N3O2/c1-19(2)14-6-3-4-7-16(14)22(17(19)23)18(24)20-12-13-9-11-21-10-5-8-15(13)21/h3-4,6-7,13,15H,5,8-12H2,1-2H3,(H,20,24)/t13-,15-/m0/s1

Standard InChI Key:  CXPIFHGPZZDWIL-ZFWWWQNUSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  1  0  0  0  0  0999 V2000
   11.1841   -8.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1903   -7.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7049   -8.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9760   -7.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9700   -8.7393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7529   -9.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2428   -8.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7626   -7.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9380   -6.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1317   -6.6945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8794   -5.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0730   -5.7347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4335   -5.2978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7446   -5.8727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4577   -6.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9188   -5.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7384   -4.9835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0748   -4.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5928   -3.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7705   -3.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4378   -4.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5421   -7.1081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0250   -5.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5250   -6.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9823   -6.9142    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
  2  3  1  0
 11 12  1  0
  3  1  1  0
 11 13  2  0
 12 17  1  0
  5  6  1  0
  6  7  1  0
 16 14  1  0
 14 15  1  0
 15 12  1  0
  7  8  1  0
  4  8  1  0
 16 17  2  0
  4  5  1  0
 17 18  1  0
 18 19  2  0
  1  5  1  0
 19 20  1  0
  2  9  1  1
 20 21  2  0
 21 16  1  0
 15 22  2  0
  9 10  1  0
 14 23  1  0
  4  2  1  0
 14 24  1  0
  4 25  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA371883

   N-[[(1S,8S)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-yl]methyl]-3,3-dimethyl-2-oxoindole-1-carboxamide

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: 327.43

Molecular Weight (Monoisotopic): 327.1947

AlogP: 2.50

#Rotatable Bonds: 2

Polar Surface Area: 52.65

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.98

CX LogP: 2.24

CX LogD: -0.29

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.91

Np Likeness Score: -0.16

References

1. Becker DP, Flynn DL, Moormann AE, Nosal R, Villamil CI, Loeffler R, Gullikson GW, Moummi C, Yang DC..  (2006)  Pyrrolizidine esters and amides as 5-HT4 receptor agonists and antagonists.,  49  (3): [PMID:16451077] [10.1021/jm0509501]

Source

Source(1):

• Scientific Literature