N-{4-[(1-Allyl-6-fluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-methyl]-cyclohexylmethyl}-benzenesulfonamide

ID: ALA3084890

Max Phase: Preclinical

Molecular Formula: C27H35FN2O2S

Molecular Weight: 470.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCC1c2ccc(F)cc2CCC1NC[C@H]1CC[C@H](CNS(=O)(=O)c2ccccc2)CC1

Standard InChI:  InChI=1S/C27H35FN2O2S/c1-2-6-26-25-15-14-23(28)17-22(25)13-16-27(26)29-18-20-9-11-21(12-10-20)19-30-33(31,32)24-7-4-3-5-8-24/h2-5,7-8,14-15,17,20-21,26-27,29-30H,1,6,9-13,16,18-19H2/t20-,21-,26?,27?

Standard InChI Key:  ZIYDLWAHMHYRTG-VNJSAXHHSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  1  0  0  0  0  0999 V2000
   12.3038   -4.3563    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.7608   -6.8913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7608   -7.7134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4987   -4.4077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4802   -6.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1259   -4.3220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2695   -3.5341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0586   -6.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3551   -5.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9018   -6.4802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1996   -6.8913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0586   -8.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4973   -8.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1996   -7.7134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7779   -5.2298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7779   -4.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3392   -7.7134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3392   -6.8913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9190   -5.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4802   -5.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6198   -8.1074    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.6383   -5.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0771   -4.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3577   -3.9966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6383   -4.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0771   -5.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3577   -5.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0916   -5.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6700   -5.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1602   -6.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7385   -6.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4750   -6.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  3 13  1  0
  4  1  1  0
  5 11  1  0
  6  1  2  0
  7  1  2  0
  8  2  2  0
  9  1  1  0
 10 20  1  0
 11 10  1  0
 12  3  2  0
 13 14  1  0
 14 11  1  0
 15 21  1  0
 16 15  2  0
 17 12  1  0
 18  4  1  0
 19  8  1  0
 23 20  1  1
 21  5  1  0
 22 17  1  0
 23 28  1  0
 24 18  1  6
 25 24  1  0
 26 25  1  0
 27 24  1  0
 28 27  1  0
 29  9  1  0
 30  9  2  0
 31 29  2  0
 32 30  1  0
 33 32  2  0
 33 31  1  0
 23 26  1  0
  3  2  1  0
 17 19  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3084890

   ---

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: 470.65

Molecular Weight (Monoisotopic): 470.2403

AlogP: 5.17

#Rotatable Bonds: 9

Polar Surface Area: 58.20

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.10

CX Basic pKa: 10.95

CX LogP: 5.03

CX LogD: 2.84

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.50

Np Likeness Score: -0.65

References

1. Youngman MA, McNally JJ, Lovenberg TW, Reitz AB, Willard NM, Nepomuceno DH, Wilson SJ, Crooke JJ, Rosenthal D, Vaidya AH, Dax SL..  (2000)  alpha-Substituted N-(sulfonamido)alkyl-beta-aminotetralins: potent and selective neuropeptide Y Y5 receptor antagonists.,  43  (3): [PMID:10669561] [10.1021/jm990468g]

Source

Source(1):

• Scientific Literature