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

ID: ALA3084889

Max Phase: Preclinical

Molecular Formula: C27H36N2O3S

Molecular Weight: 468.66

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C27H36N2O3S/c1-2-6-26-25-15-14-23(30)17-22(25)13-16-27(26)28-18-20-9-11-21(12-10-20)19-29-33(31,32)24-7-4-3-5-8-24/h2-5,7-8,14-15,17,20-21,26-30H,1,6,9-13,16,18-19H2/t20-,21-,26?,27?

Standard InChI Key:  PAQODBFVSXXTHF-VNJSAXHHSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  1  0  0  0  0  0999 V2000
    7.1996   -1.3760    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6566   -3.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6566   -4.7331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3945   -1.4274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3760   -3.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0456   -3.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2510   -2.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7976   -3.4999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0954   -3.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3760   -2.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9729   -1.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5341   -2.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2535   -2.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2535   -1.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5341   -1.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9729   -2.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4844   -5.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9875   -2.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5658   -2.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0560   -3.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6343   -3.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3709   -3.8425    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 18  1  6
 23 24  1  0
 24 27  1  0
 25 22  1  0
 26 25  1  0
 27 22  1  0
 28 17  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:

   

   ALA3084889

   ---

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: 468.66

Molecular Weight (Monoisotopic): 468.2447

AlogP: 4.74

#Rotatable Bonds: 9

Polar Surface Area: 78.43

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.83

CX Basic pKa: 11.13

CX LogP: 4.25

CX LogD: 2.43

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.46

Np Likeness Score: -0.10

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