(2S)-N-[4-[3-Cyano-1-(tetrahydropyran-4-ylmethyl)indol-5-yl]oxyphenyl]pyrrolidine-2-carboxamide

ID: ALA3422672

PubChem CID: 118735786

Max Phase: Preclinical

Molecular Formula: C26H28N4O3

Molecular Weight: 444.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1cn(CC2CCOCC2)c2ccc(Oc3ccc(NC(=O)[C@@H]4CCCN4)cc3)cc12

Standard InChI:  InChI=1S/C26H28N4O3/c27-15-19-17-30(16-18-9-12-32-13-10-18)25-8-7-22(14-23(19)25)33-21-5-3-20(4-6-21)29-26(31)24-2-1-11-28-24/h3-8,14,17-18,24,28H,1-2,9-13,16H2,(H,29,31)/t24-/m0/s1

Standard InChI Key:  OIUUHNYUJDUUHX-DEOSSOPVSA-N

Molfile:  

     RDKit          2D

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   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1783    2.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5503    3.7690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6187    1.4919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1855   -2.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3417    9.7472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5992   12.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0992   12.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5581   10.6031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6552   -2.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1295   -4.3524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5991   -4.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5944   -3.5310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1201   -2.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6506   -1.8071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
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  5  4  2  0
  4  1  1  0
  5  6  1  0
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  9  5  1  0
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 19 20  1  0
 23 20  1  1
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  7 22  1  0
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 24 25  1  0
 25 26  1  0
 26 27  1  0
 23 27  1  0
 22 28  1  0
 28 29  1  0
 28 33  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3422672

   ---

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: 444.54

Molecular Weight (Monoisotopic): 444.2161

AlogP: 4.42

#Rotatable Bonds: 6

Polar Surface Area: 88.31

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.71

CX Basic pKa: 9.49

CX LogP: 3.44

CX LogD: 1.38

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.59

Np Likeness Score: -1.14

References

1. Boyd S, Brookfield JL, Critchlow SE, Cumming IA, Curtis NJ, Debreczeni J, Degorce SL, Donald C, Evans NJ, Groombridge S, Hopcroft P, Jones NP, Kettle JG, Lamont S, Lewis HJ, MacFaull P, McLoughlin SB, Rigoreau LJ, Smith JM, St-Gallay S, Stock JK, Turnbull AP, Wheatley ER, Winter J, Wingfield J..  (2015)  Structure-Based Design of Potent and Selective Inhibitors of the Metabolic Kinase PFKFB3.,  58  (8): [PMID:25849762] [10.1021/acs.jmedchem.5b00352]

Source

Source(1):

• Scientific Literature