4-Amino-N-(5-aza-tricyclo[3.2.1.0*2,7*]oct-1-yl)-5-chloro-2-methoxy-benzamide

ID: ALA1907770

PubChem CID: 57391435

Max Phase: Preclinical

Molecular Formula: C15H18ClN3O2

Molecular Weight: 307.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(N)c(Cl)cc1C(=O)N[C@]12CN3CCC1C2C3

Standard InChI:  InChI=1S/C15H18ClN3O2/c1-21-13-5-12(17)11(16)4-8(13)14(20)18-15-7-19-3-2-9(15)10(15)6-19/h4-5,9-10H,2-3,6-7,17H2,1H3,(H,18,20)/t9?,10?,15-/m1/s1

Standard InChI Key:  VQZUPPBUGNMRJI-HKJQSTPSSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    6.2209   -6.3071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9799   -6.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2740   -6.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8852   -4.8953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1888   -5.2137    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4605   -5.6012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4777   -4.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4791   -7.9426    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7116   -4.8953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8235   -7.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4103   -7.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9024   -3.4663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1247   -4.1836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7173   -3.4663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9469   -7.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8737   -6.3242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5437   -8.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1247   -2.7546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9224   -4.3902    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -4.1722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2382   -3.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5380   -7.3422    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7467   -5.8275    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  6  1  0
  1  5  1  1
  6  5  1  0
  7  4  1  0
  8 10  1  0
  9  4  2  0
 10  1  1  0
 11  2  1  0
 12  7  2  0
 13  9  1  0
 14 13  2  0
 15  3  1  0
 16  6  2  0
 17  8  1  0
 18 14  1  0
 19 13  1  0
 20  7  1  0
 21 20  1  0
  3  2  1  0
  8 11  1  0
 17 15  1  0
 14 12  1  0
  2 22  1  0
  3 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1907770

   4-amino-N-[(1R)-5-azatricyclo[3.2.1.02,7]octan-1-yl]-5-chloro-2-methoxybenzamide

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: 307.78

Molecular Weight (Monoisotopic): 307.1088

AlogP: 1.36

#Rotatable Bonds: 3

Polar Surface Area: 67.59

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.51

CX LogP: 0.45

CX LogD: 0.09

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.83

Np Likeness Score: -0.36

References

1. Flynn DL, Zabrowski DL, Becker DP, Nosal R, Villamil CI, Gullikson GW, Moummi C, Yang DC..  (1992)  SC-53116: the first selective agonist at the newly identified serotonin 5-HT4 receptor subtype.,  35  (8): [PMID:1573641] [10.1021/jm00086a019]

Source

Source(1):

• Scientific Literature