(R)-N-[(7-Nitro-1H-indol-2-yl)methyl]-1-(1-naphthyl)ethanamine

ID: ALA3753306

PubChem CID: 127036924

Max Phase: Preclinical

Molecular Formula: C21H19N3O2

Molecular Weight: 345.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](NCc1cc2cccc([N+](=O)[O-])c2[nH]1)c1cccc2ccccc12

Standard InChI:  InChI=1S/C21H19N3O2/c1-14(18-10-4-7-15-6-2-3-9-19(15)18)22-13-17-12-16-8-5-11-20(24(25)26)21(16)23-17/h2-12,14,22-23H,13H2,1H3/t14-/m1/s1

Standard InChI Key:  VFNKRNJLVCWDAT-CQSZACIVSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   -1.2896    2.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3263    3.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0131    3.7434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0200    5.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4761    7.4707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3227    5.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6465    5.3679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6674    6.4577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1709    6.4182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9455    7.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2184    9.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6990    9.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9403    7.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9643   10.3710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5760   11.4034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7644   10.3849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1
  1  3  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  4 13  2  0
  8 13  1  0
  1  4  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 15 23  1  0
 18 23  2  0
 24 25  2  0
 24 26  1  0
 22 24  1  0
 14 16  1  0
  3 14  1  0
M  CHG  2  24   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3753306

   ---

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: 345.40

Molecular Weight (Monoisotopic): 345.1477

AlogP: 5.08

#Rotatable Bonds: 5

Polar Surface Area: 70.96

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.19

CX Basic pKa: 8.77

CX LogP: 4.62

CX LogD: 3.24

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.39

Np Likeness Score: -1.12

References

1. Kiefer L, Beaumard F, Gorojankina T, Faure H, Ruat M, Dodd RH..  (2016)  Design and synthesis of calindol derivatives as potent and selective calcium sensing receptor agonists.,  24  (4): [PMID:26752095] [10.1016/j.bmc.2015.12.019]

Source

Source(1):

• Scientific Literature