C-[3-(2-Dimethylamino-ethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide

ID: ALA159825

PubChem CID: 44374544

Max Phase: Preclinical

Molecular Formula: C15H20ClN3O2

Molecular Weight: 309.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(N)c(Cl)cc1C(=O)NC1CCN2CCC1C2

Standard InChI:  InChI=1S/C15H20ClN3O2/c1-21-14-7-12(17)11(16)6-10(14)15(20)18-13-3-5-19-4-2-9(13)8-19/h6-7,9,13H,2-5,8,17H2,1H3,(H,18,20)

Standard InChI Key:  DTTGUKXBOVDIES-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    4.2167   -2.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167   -2.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167   -3.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167   -3.0417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3125   -3.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2292   -2.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7167   -3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7500   -3.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292   -1.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0167   -2.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7500   -3.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7167   -3.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1292   -2.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7500   -2.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2292   -3.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3292   -3.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167   -2.4792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0375   -1.4500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2042   -3.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042   -4.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  2  1  0
  5  1  1  0
  6  3  1  0
  7  8  1  0
  8  4  1  0
  9 16  1  0
 10  5  2  0
 11 10  1  0
 12  7  1  0
 13  8  1  0
 14  2  2  0
 15  7  1  0
 16 13  1  0
 17 15  1  0
 18 11  1  0
 19 10  1  0
 20  3  1  0
 21 20  1  0
 11  6  2  0
 12  9  1  0
  9 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA159825

   RENZAPRIDE

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: 309.80

Molecular Weight (Monoisotopic): 309.1244

AlogP: 1.75

#Rotatable Bonds: 3

Polar Surface Area: 67.59

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.82

CX LogP: 0.70

CX LogD: -1.69

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.83

Np Likeness Score: -0.59

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]

2. Flynn DL, Becker DP, Spangler DP, Nosal R, Gullikson GW, Moummi C, Yang D.  (1992)  New aza(nor)adamantanes are agonists at the newly identified serotonin 5-HT4 receptor and antagonists at the 5-HT3 receptor,  2  (12): [10.1016/S0960-894X(00)80441-2]

3. Baxter G, Boyland P, Gaster L, King F.  (1993)  Quaternised renzapride as a potent and selective 5-HT4 receptor agonist,  3  (4): [10.1016/S0960-894X(01)81243-9]

4. King FD, Hadley MS, Joiner KT, Martin RT, Sanger GJ, Smith DM, Smith GE, Smith P, Turner DH, Watts EA..  (1993)  Substituted benzamides with conformationally restricted side chains. 5. Azabicyclo[x.y.z] derivatives as 5-HT4 receptor agonists and gastric motility stimulants.,  36  (6): [PMID:8459397] [10.1021/jm00058a004]

5. King FD, Hadley MS, Joiner KT, Martin RT, Sanger GJ, Smith DM, Smith GE, Smith P, Turner DH, Watts EA..  (1993)  Substituted benzamides with conformationally restricted side chains. 5. Azabicyclo[x.y.z] derivatives as 5-HT4 receptor agonists and gastric motility stimulants.,  36  (6): [PMID:8459397] [10.1021/jm00058a004]

6. King FD, Hadley MS, Joiner KT, Martin RT, Sanger GJ, Smith DM, Smith GE, Smith P, Turner DH, Watts EA..  (1993)  Substituted benzamides with conformationally restricted side chains. 5. Azabicyclo[x.y.z] derivatives as 5-HT4 receptor agonists and gastric motility stimulants.,  36  (6): [PMID:8459397] [10.1021/jm00058a004]

7. Hirokawa Y, Fujiwara I, Suzuki K, Harada H, Yoshikawa T, Yoshida N, Kato S..  (2003)  Synthesis and structure-affinity relationships of novel N-(1-ethyl-4-methylhexahydro-1,4-diazepin-6-yl)pyridine-3-carboxamides with potent serotonin 5-HT3 and dopamine D2 receptor antagonistic activity.,  46  (5): [PMID:12593651] [10.1021/jm020270n]

Source

Source(1):

• Scientific Literature