3-(2-Amino-ethyl)-5-hydroxy-1H-indole-2-carbonitrile

ID: ALA337592

PubChem CID: 15681427

Max Phase: Preclinical

Molecular Formula: C11H11N3O

Molecular Weight: 201.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1[nH]c2ccc(O)cc2c1CCN

Standard InChI:  InChI=1S/C11H11N3O/c12-4-3-8-9-5-7(15)1-2-10(9)14-11(8)6-13/h1-2,5,14-15H,3-4,12H2

Standard InChI Key:  YXXOHKFHHPGTPN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 15 16  0  0  0  0  0  0  0  0999 V2000
    6.0792   -9.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2542   -9.2000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4167   -8.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8000   -7.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0792   -8.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917  -10.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9000  -10.7167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8000   -7.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3667   -7.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0875   -6.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1292   -8.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3667   -7.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5542   -8.1292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0917   -5.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8417   -8.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  3  1  0
  5  2  1  0
  6  1  1  0
  7  6  3  0
  8  4  2  0
  9  5  2  0
 10  8  1  0
 11  3  1  0
 12  9  1  0
 13 15  1  0
 14 10  1  0
 15 11  1  0
  5  4  1  0
 10 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA337592

   3-(2-aminoethyl)-5-hydroxy-1H-indole-2-carbonitrile

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: 201.23

Molecular Weight (Monoisotopic): 201.0902

AlogP: 1.25

#Rotatable Bonds: 2

Polar Surface Area: 85.83

Molecular Species: BASE

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.99

CX Basic pKa: 9.81

CX LogP: 0.13

CX LogD: -1.10

Aromatic Rings: 2

Heavy Atoms: 15

QED Weighted: 0.68

Np Likeness Score: 0.11

References

1. Blum E, Buchheit K, Buescher H, Gamse R, Kloeppner E, Meigel H, Papageorgiou C, Waelchli R, Revesz L.  (1992)  Design and synthesis of novel ligands for the 5-HT3 and the 5-HT4 receptor,  2  (5): [10.1016/S0960-894X(00)80170-5]

Source

Source(1):

• Scientific Literature