Calindol

ID: ALA1801356

Max Phase: Preclinical

Molecular Formula: C21H20N2

Molecular Weight: 300.41

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Calindol

Canonical SMILES:  C[C@@H](NCc1cc2ccccc2[nH]1)c1cccc2ccccc12

Standard InChI:  InChI=1S/C21H20N2/c1-15(19-11-6-9-16-7-2-4-10-20(16)19)22-14-18-13-17-8-3-5-12-21(17)23-18/h2-13,15,22-23H,14H2,1H3/t15-/m1/s1

Standard InChI Key:  JLPWXRZETODYFC-OAHLLOKOSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   -2.2076    4.1153    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1366    3.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8846    2.9749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0097    4.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4302    3.5910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4255    2.0688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7112    1.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4223    2.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4388    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4388   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4076    5.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2590    3.5923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1372    1.9803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2450    5.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6655    4.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  1  5  1  0
  4  6  2  0
  3  7  1  0
  5  7  2  0
  4  9  1  0
  8  9  1  0
  2 10  1  0
  8 10  1  0
  6 11  1  0
  4 12  1  0
  6 13  1  0
 12 14  2  0
  5 15  1  0
  7 16  1  0
 11 17  2  0
 14 17  1  0
 11 18  1  0
  9 19  1  6
 13 20  2  0
 15 21  2  0
 16 22  2  0
 21 22  1  0
 18 23  2  0
 20 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1801356

   CALINDOL

2. Alternative Forms:

   

   ALA1801356

   Calindol hydrochloride

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: 300.41

Molecular Weight (Monoisotopic): 300.1626

AlogP: 5.17

#Rotatable Bonds: 4

Polar Surface Area: 27.82

Molecular Species: BASE

HBA: 1

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.87

CX LogP: 4.68

CX LogD: 3.20

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.53

Np Likeness Score: -0.79

References

1. Kiefer L, Gorojankina T, Dauban P, Faure H, Ruat M, Dodd RH..  (2010)  Design and synthesis of cyclic sulfonamides and sulfamates as new calcium sensing receptor agonists.,  20  (24): [PMID:21041081] [10.1016/j.bmcl.2010.10.006]

2. 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