(2R)-2-(6-((2S)-4-((6-Amino-3-pyridinyl)-sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)-3-pyridinyl)-3,3,3-trifluoro-1,2-propanediol

ID: ALA3238314

PubChem CID: 89762388

Max Phase: Preclinical

Molecular Formula: C20H22F3N5O4S

Molecular Weight: 485.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC#C[C@H]1CN(S(=O)(=O)c2ccc(N)nc2)CCN1c1ccc([C@@](O)(CO)C(F)(F)F)cn1

Standard InChI:  InChI=1S/C20H22F3N5O4S/c1-2-3-15-12-27(33(31,32)16-5-6-17(24)25-11-16)8-9-28(15)18-7-4-14(10-26-18)19(30,13-29)20(21,22)23/h4-7,10-11,15,29-30H,8-9,12-13H2,1H3,(H2,24,25)/t15-,19-/m0/s1

Standard InChI Key:  XZAJRLOTZNWGPU-KXBFYZLASA-N

Molfile:  

     RDKit          2D

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    7.1140  -20.4007    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.5742  -26.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5389  -20.4000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.5373  -21.2141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667  -24.0951    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6934  -24.4954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6927  -22.0431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8618  -26.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1482  -25.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5713  -25.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1138  -22.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2759  -22.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9873  -23.2707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  7 33  1  0
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 28 22  2  0
  2 29  1  0
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  1 12  1  6
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  8  7  1  0
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  9 10  1  0
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  1 24  1  0
  5 20  1  0
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  3 14  1  0
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 29 15  2  0
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M  END

Alternative Forms

1. Parent:

   

   ALA3238314

   (2R)-2-[6-[(2S)-4-(6-aminopyridin-3-yl)sulfonyl-2-prop-1-ynylpiperazin-1-yl]pyridin-3-yl]-3,3,3-trifluoropropane-1,2-diol

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: 485.49

Molecular Weight (Monoisotopic): 485.1345

AlogP: 0.70

#Rotatable Bonds: 5

Polar Surface Area: 132.88

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.80

CX Basic pKa: 5.67

CX LogP: 1.29

CX LogD: 1.29

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.53

Np Likeness Score: -1.08

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