rac-N-(6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-yl)-3-methoxybenzamide

ID: ALA549486

PubChem CID: 11153783

Max Phase: Preclinical

Molecular Formula: C20H19BrN2O2

Molecular Weight: 399.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(C(=O)NC2CCCc3c2[nH]c2ccc(Br)cc32)c1

Standard InChI:  InChI=1S/C20H19BrN2O2/c1-25-14-5-2-4-12(10-14)20(24)23-18-7-3-6-15-16-11-13(21)8-9-17(16)22-19(15)18/h2,4-5,8-11,18,22H,3,6-7H2,1H3,(H,23,24)

Standard InChI Key:  KXORNHGXMBLSKZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    6.6603   -1.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9152   -2.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3632   -3.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8533   -1.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3013   -2.1846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5562   -2.9692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4763   -2.1846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2213   -2.9692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4144   -3.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8623   -2.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1173   -1.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9243   -1.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2123   -1.1299    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.3525   -4.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0975   -4.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8004   -3.4838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6496   -5.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3946   -6.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5876   -6.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0356   -5.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2906   -5.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2286   -6.0092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0263   -6.7938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8888   -3.4541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1594   -3.9254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  7  5  1  0
  7  8  2  0
  7 12  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  1 13  1  0
 14 15  1  0
 14 16  2  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 15  1  0
 20 22  1  0
 22 23  1  0
  1  2  2  0
  6 24  1  0
 24  8  1  0
  9 25  1  0
 25 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA549486

   N-(6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-yl)-3-methoxybenzamide

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: 399.29

Molecular Weight (Monoisotopic): 398.0630

AlogP: 4.75

#Rotatable Bonds: 3

Polar Surface Area: 54.12

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.39

CX LogD: 4.39

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.67

Np Likeness Score: -0.69

References

1. Gudmundsson KS, Boggs SD, Sebahar PR, Richardson LD, Spaltenstein A, Golden P, Sethna PB, Brown KW, Moniri K, Harvey R, Romines KR..  (2009)  Tetrahydrocarbazole amides with potent activity against human papillomaviruses.,  19  (15): [PMID:19556128] [10.1016/j.bmcl.2009.06.001]

Source

Source(1):

• Scientific Literature