5-(((3S)-4-(4-(S-Cyclopropylsulfonimidoyl)phenyl)-3-(1-propyn-1-yl)-1-piperazinyl)sulfonyl)-2-pyridinamine

ID: ALA3238300

PubChem CID: 73332122

Max Phase: Preclinical

Molecular Formula: C21H25N5O3S2

Molecular Weight: 459.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC#C[C@H]1CN(S(=O)(=O)c2ccc(N)nc2)CCN1c1ccc(S(=N)(=O)C2CC2)cc1

Standard InChI:  InChI=1S/C21H25N5O3S2/c1-2-3-17-15-25(31(28,29)20-10-11-21(22)24-14-20)12-13-26(17)16-4-6-18(7-5-16)30(23,27)19-8-9-19/h4-7,10-11,14,17,19,23H,8-9,12-13,15H2,1H3,(H2,22,24)/t17-,30?/m0/s1

Standard InChI Key:  VOWDKMQSGVDLAG-ZRYJOUNDSA-N

Molfile:  

     RDKit          2D

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   13.3748  -14.5745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   14.4997  -15.6952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8245  -20.6272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4075  -17.4453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.9955  -18.1536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7914  -15.2869    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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    8.8243  -21.4480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2344  -16.5143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5293  -17.7511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0775  -15.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6560  -18.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0764  -16.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2370  -18.1550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6560  -16.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9119  -16.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3202  -15.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0
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 24 28  1  0
  1  8  2  0
 18 27  1  0
  6 14  1  0
 17 21  1  0
 26  6  3  0
 17 26  1  1
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  7 12  1  0
 28 17  1  0
 11 12  2  0
 12 15  2  0
 19 16  2  0
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 20 29  1  0
 27 25  2  0
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  4  7  2  0
  8 10  1  0
 25 16  1  0
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  5 20  2  0
 12 24  1  0
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 29 18  2  0
 25  5  1  0
 16  9  1  0
 30  9  1  0
 31 30  1  0
  9 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3238300

   5-[(3S)-4-[4-(cyclopropylsulfonimidoyl)phenyl]-3-prop-1-ynylpiperazin-1-yl]sulfonylpyridin-2-amine

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: 459.60

Molecular Weight (Monoisotopic): 459.1399

AlogP: 2.13

#Rotatable Bonds: 5

Polar Surface Area: 120.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.54

CX LogP: 2.06

CX LogD: 2.06

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.66

Np Likeness Score: -0.80

References

1. Nishimura N, Norman MH, Liu L, Yang KC, Ashton KS, Bartberger MD, Chmait S, Chen J, Cupples R, Fotsch C, Helmering J, Jordan SR, Kunz RK, Pennington LD, Poon SF, Siegmund A, Sivits G, Lloyd DJ, Hale C, St Jean DJ..  (2014)  Small molecule disruptors of the glucokinase-glucokinase regulatory protein interaction: 3. Structure-activity relationships within the aryl carbinol region of the N-arylsulfonamido-N'-arylpiperazine series.,  57  (7): [PMID:24611879] [10.1021/jm5000497]

Source

Source(1):

• Scientific Literature