1,1-dimethyl-7-(phenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridine

ID: ALA1935593

PubChem CID: 57391729

Max Phase: Preclinical

Molecular Formula: C19H19NO3S

Molecular Weight: 341.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)NCCc2c1oc1cc(S(=O)(=O)c3ccccc3)ccc21

Standard InChI:  InChI=1S/C19H19NO3S/c1-19(2)18-16(10-11-20-19)15-9-8-14(12-17(15)23-18)24(21,22)13-6-4-3-5-7-13/h3-9,12,20H,10-11H2,1-2H3

Standard InChI Key:  UJGWKHGEWIJNQV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    6.2779   -3.7661    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8637   -4.4795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6887   -4.4815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5090   -2.8594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5910   -3.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2609   -3.1989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9959   -2.5279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9934   -3.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7075   -3.7694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7084   -2.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4232   -2.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4221   -3.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2077   -3.6096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2095   -2.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6922   -2.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8495   -2.1080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3668   -1.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5436   -1.5200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5645   -3.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5704   -2.5284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8577   -2.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1413   -2.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1419   -3.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8551   -3.7648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
 13 15  1  0
 14 11  1  0
 14 15  2  0
  7  8  2  0
  8  9  1  0
  9 12  2  0
  2  1  2  0
 14 18  1  0
 15  4  1  0
  4 16  1  0
 16 17  1  0
 17 18  1  0
  8  1  1  0
 11 10  2  0
  1 19  1  0
 10  7  1  0
 19 20  2  0
 11 12  1  0
 20 21  1  0
  1  3  2  0
 21 22  2  0
  5  4  1  0
 22 23  1  0
  4  6  1  0
 23 24  2  0
 24 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1935593

   7-(benzenesulfonyl)-1,1-dimethyl-3,4-dihydro-2H-[1]benzofuro[2,3-c]pyridine

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: 341.43

Molecular Weight (Monoisotopic): 341.1086

AlogP: 3.65

#Rotatable Bonds: 2

Polar Surface Area: 59.31

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.48

CX LogP: 3.30

CX LogD: 2.19

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.77

Np Likeness Score: -0.19

References

1. Sundar BG, Bailey TR, Dunn DD, Bacon ER, Salvino JM, Morton GC, Aimone LD, Zeqi H, Mathiasen JR, Dicamillo A, Huffman MJ, McKenna BA, Kopec K, Lu LD, Brown R, Qian J, Angeles T, Connors T, Spais C, Holskin B, Galinis D, Duzic E, Schaffhauser H, Rosse GC..  (2012)  Novel brain penetrant benzofuropiperidine 5-HT₆ receptor antagonists.,  22  (1): [PMID:22153937] [10.1016/j.bmcl.2011.11.050]

Source

Source(1):

• Scientific Literature