N-{(R)-2-[4'-((S)-2-Methanesulfonylamino-1-methyl-ethyl)-biphenyl-4-yl]-propyl}-methanesulfonamide

ID: ALA1277002

PubChem CID: 16731393

Max Phase: Preclinical

Molecular Formula: C20H28N2O4S2

Molecular Weight: 424.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](CNS(C)(=O)=O)c1ccc(-c2ccc([C@@H](C)CNS(C)(=O)=O)cc2)cc1

Standard InChI:  InChI=1S/C20H28N2O4S2/c1-15(13-21-27(3,23)24)17-5-9-19(10-6-17)20-11-7-18(8-12-20)16(2)14-22-28(4,25)26/h5-12,15-16,21-22H,13-14H2,1-4H3/t15-,16+

Standard InChI Key:  ZESUARCHWPARIF-IYBDPMFKSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   14.4974   -8.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4963   -8.9699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2111   -9.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9275   -8.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9247   -8.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2093   -7.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7834   -9.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0689   -8.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3546   -9.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3535  -10.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0727  -10.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7841  -10.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6376   -7.7237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3536   -8.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0665   -7.7183    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7825   -8.1281    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.4954   -7.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3700   -8.8426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3659   -8.7115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6345   -6.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6393  -10.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9246  -10.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2103  -10.6181    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4957  -10.2060    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.7814  -10.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9042   -9.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0750   -9.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6397  -11.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  2  0
 12  7  1  0
  2  7  1  0
  5 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 16 19  2  0
 13 20  1  1
  1  2  2  0
  2  3  1  0
  3  4  2  0
 10 21  1  0
  4  5  1  0
 21 22  1  0
  5  6  2  0
 22 23  1  0
  6  1  1  0
 23 24  1  0
  7  8  2  0
 24 25  1  0
  8  9  1  0
 24 26  2  0
  9 10  2  0
 24 27  2  0
 10 11  1  0
 21 28  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1277002

   N-[(2R)-2-[4-[4-[(2S)-1-(methanesulfonamido)propan-2-yl]phenyl]phenyl]propyl]methanesulfonamide

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: 424.59

Molecular Weight (Monoisotopic): 424.1490

AlogP: 2.66

#Rotatable Bonds: 9

Polar Surface Area: 92.34

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.95

CX Basic pKa: ┄

CX LogP: 1.81

CX LogD: 1.81

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.65

Np Likeness Score: -0.55

References

1. Grove SJ, Jamieson C, Maclean JK, Morrow JA, Rankovic Z..  (2010)  Positive allosteric modulators of the α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor.,  53  (20): [PMID:20839777] [10.1021/jm1000419]

Source

Source(1):

• Scientific Literature