cis-7-(3-isopropoxy-5-methoxyphenylsulfonyl)-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridine hydrochloride

ID: ALA1949930

PubChem CID: 57396812

Max Phase: Preclinical

Molecular Formula: C21H26ClNO5S

Molecular Weight: 403.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC(C)C)cc(S(=O)(=O)c2ccc3c(c2)O[C@H]2CNCC[C@@H]32)c1.Cl

Standard InChI:  InChI=1S/C21H25NO5S.ClH/c1-13(2)26-15-8-14(25-3)9-17(10-15)28(23,24)16-4-5-18-19-6-7-22-12-21(19)27-20(18)11-16;/h4-5,8-11,13,19,21-22H,6-7,12H2,1-3H3;1H/t19-,21-;/m0./s1

Standard InChI Key:  IKXSPLZKOZXPFB-RQBPZYBGSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   12.0373  -22.2377    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.9697  -26.1014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5617  -25.3893    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.1490  -26.0987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2806  -24.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2794  -24.9793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9938  -25.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9920  -23.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7070  -24.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7073  -24.9793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4972  -25.2358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4968  -23.8920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9854  -24.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8080  -24.4790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1485  -23.7209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6600  -23.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8309  -23.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9061  -23.3030    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5676  -25.1477    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8496  -24.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8562  -24.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1449  -23.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4279  -24.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4267  -24.9710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1386  -25.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1492  -22.9088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8654  -22.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8697  -21.6758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5774  -22.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7121  -25.3824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9986  -24.9693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  6  3  1  0
  3  2  2  0
 12 18  1  1
  5  6  2  0
 13 19  1  1
  4  3  2  0
  3 20  1  0
 10 11  1  0
 20 21  2  0
 11 13  1  0
 21 22  1  0
 12  9  1  0
 22 23  2  0
 12 13  1  0
 23 24  1  0
  6  7  1  0
 24 25  2  0
 25 20  1  0
  7 10  2  0
 22 26  1  0
 26 27  1  0
  9  8  2  0
 27 28  1  0
  8  5  1  0
 27 29  1  0
  9 10  1  0
 24 30  1  0
 12 17  1  0
 30 31  1  0
M  END

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: 403.50

Molecular Weight (Monoisotopic): 403.1453

AlogP: 3.15

#Rotatable Bonds: 5

Polar Surface Area: 73.86

Molecular Species: BASE

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.16

CX LogP: 2.86

CX LogD: 1.10

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.83

Np Likeness Score: -0.10

References

1. Tripathy R, McHugh RJ, Bacon ER, Salvino JM, Morton GC, Aimone LD, Huang Z, Mathiasen JR, DiCamillo A, Huffman MJ, McKenna BA, Kopec K, Lu LD, Qian J, Angeles TS, Connors T, Spais C, Holskin B, Duzic E, Schaffhauser H, Rossé GC..  (2012)  Discovery of 7-arylsulfonyl-1,2,3,4, 4a,9a-hexahydro-benzo[4,5]furo[2,3-c]pyridines: identification of a potent and selective 5-HT₆ receptor antagonist showing activity in rat social recognition test.,  22  (3): [PMID:22226656] [10.1016/j.bmcl.2011.12.026]

2. Tripathy R, McHugh RJ, Bacon ER, Salvino JM, Morton GC, Aimone LD, Huang Z, Mathiasen JR, DiCamillo A, Huffman MJ, McKenna BA, Kopec K, Lu LD, Qian J, Angeles TS, Connors T, Spais C, Holskin B, Duzic E, Schaffhauser H, Rossé GC..  (2012)  Discovery of 7-arylsulfonyl-1,2,3,4, 4a,9a-hexahydro-benzo[4,5]furo[2,3-c]pyridines: identification of a potent and selective 5-HT₆ receptor antagonist showing activity in rat social recognition test.,  22  (3): [PMID:22226656] [10.1016/j.bmcl.2011.12.026]

Source

Source(1):

• Scientific Literature