(2R,3S,5R)-2-(2,5-difluorophenyl)-5-(2-(ethylsulfonyl)pyrrolo[3,4-c]pyrazol-5(2H,4H,6H)-yl)tetrahydro-2H-pyran-3-amine

ID: ALA3735281

PubChem CID: 127035240

Max Phase: Preclinical

Molecular Formula: C18H22F2N4O3S

Molecular Weight: 412.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCS(=O)(=O)n1cc2c(n1)CN([C@H]1CO[C@H](c3cc(F)ccc3F)[C@@H](N)C1)C2

Standard InChI:  InChI=1S/C18H22F2N4O3S/c1-2-28(25,26)24-8-11-7-23(9-17(11)22-24)13-6-16(21)18(27-10-13)14-5-12(19)3-4-15(14)20/h3-5,8,13,16,18H,2,6-7,9-10,21H2,1H3/t13-,16+,18-/m1/s1

Standard InChI Key:  GEWSELRSYBADTB-RPVQJOFSSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    6.4140    2.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1942    0.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7992    0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6284    1.1358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8440    2.6219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2389    3.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4148    4.3604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1968    0.6852    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9876    1.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7333   -0.7256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2217   -0.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2419    0.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7333    0.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1968   -0.7054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9876   -1.5720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8096    2.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9833    1.8588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3791    2.4081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6013    3.8916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4277    4.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0319    4.2764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3180    1.6608    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.0930    5.0238    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6167   -1.1834    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7433   -0.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8532   -2.3599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7537   -1.5670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8806   -0.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  6
  4  8  1  6
  8  9  1  0
  9 12  1  0
 11 10  1  0
 10  8  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 11  2  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  1 16  1  1
 18 22  1  0
 21 23  1  0
 14 24  1  0
 24 25  1  0
 24 26  2  0
 24 27  2  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3735281

   ---

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: 412.46

Molecular Weight (Monoisotopic): 412.1381

AlogP: 1.53

#Rotatable Bonds: 4

Polar Surface Area: 90.45

Molecular Species: BASE

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.81

CX LogP: 0.61

CX LogD: -0.81

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.82

Np Likeness Score: -0.76

References

1. Chen P, Feng D, Qian X, Apgar J, Wilkening R, Kuethe JT, Gao YD, Scapin G, Cox J, Doss G, Eiermann G, He H, Li X, Lyons KA, Metzger J, Petrov A, Wu JK, Xu S, Weber AE, Yan Y, Roy RS, Biftu T..  (2015)  Structure-activity-relationship of amide and sulfonamide analogs of omarigliptin.,  25  (24): [PMID:26546218] [10.1016/j.bmcl.2015.10.070]

Source

Source(1):

• Scientific Literature