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

ID: ALA1935588

PubChem CID: 57400477

Max Phase: Preclinical

Molecular Formula: C17H15NO3S

Molecular Weight: 313.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(c1ccccc1)c1ccc2oc3c(c2c1)CCNC3

Standard InChI:  InChI=1S/C17H15NO3S/c19-22(20,12-4-2-1-3-5-12)13-6-7-16-15(10-13)14-8-9-18-11-17(14)21-16/h1-7,10,18H,8-9,11H2

Standard InChI Key:  ILUMPMYJXUWNQS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   -2.7708    2.2041    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3458    2.9109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1704    2.9256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4419    1.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0641    1.7790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0803    0.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3734    0.5263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3451    2.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6375    1.7567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6523    0.9306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1289    0.6613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1527    1.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6241    1.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946    2.1351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3232    2.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4990    2.7444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4924    1.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1947    2.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9157    1.8339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9309    1.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2192    0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5011    0.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12  9  1  0
 12 13  2  0
  6  7  1  0
  7 10  2  0
  2  1  2  0
  9  8  2  0
  8  5  1  0
 12 16  1  0
 13  4  1  0
  4 14  1  0
 14 15  1  0
 15 16  1  0
  5  1  1  0
  9 10  1  0
  1 17  1  0
  1  3  2  0
 17 18  2  0
  5  6  2  0
 18 19  1  0
 19 20  2  0
 10 11  1  0
 20 21  1  0
 11 13  1  0
 21 22  2  0
 22 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1935588

   6-(Benzenesulfonyl)-1,2,3,4-tetrahydro-[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: 313.38

Molecular Weight (Monoisotopic): 313.0773

AlogP: 2.91

#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: 8.26

CX LogP: 2.61

CX LogD: 1.69

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.79

Np Likeness Score: -0.76

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