US8552202, Compound 15

ID: ALA3648413

PubChem CID: 58101963

Max Phase: Preclinical

Molecular Formula: C25H29FN4O4

Molecular Weight: 468.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1CC[C@H]([C@H](NC(=O)c2cccc(-n3ccnc3)c2)C(=O)N2C[C@H](F)[C@H]3OCC(=O)[C@H]32)CC1

Standard InChI:  InChI=1S/C25H29FN4O4/c1-15-5-7-16(8-6-15)21(25(33)30-12-19(26)23-22(30)20(31)13-34-23)28-24(32)17-3-2-4-18(11-17)29-10-9-27-14-29/h2-4,9-11,14-16,19,21-23H,5-8,12-13H2,1H3,(H,28,32)/t15-,16-,19-,21-,22+,23+/m0/s1

Standard InChI Key:  GXCSFFZWKWHFDR-YKHRXLODSA-N

Molfile:  

     RDKit          2D

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    4.9527    2.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4610    1.8724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8514    0.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2253   -0.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9888   -2.0397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3873   -4.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8791   -4.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6332   -2.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1470   -3.3397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -1.0323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2135    0.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4760    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2135    0.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7115    0.3949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1750   -1.0317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9615   -1.9133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9612   -3.1133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
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  5  4  1  6
  5  6  1  0
  6  7  1  0
  7  2  1  0
  5  8  1  0
  8  9  1  6
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 10 11  2  0
 10 12  1  0
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 13 14  1  0
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 15 16  1  0
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 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 18  1  0
  8 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27 29  1  0
 29 30  1  6
 30 31  1  0
 31 32  1  0
 32 33  2  0
 34 32  1  6
 34 25  1  0
 34 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3648413

   N-[(1S)-2-[(3aS,6S,6aS)-6-fluoro-3-oxo-3a,5,6,6a-tetrahydrofuro[3,2-b]pyrrol-4-yl]-1-(4-methylcyclohexyl)-2-oxoethyl]-3-imidazol-1-ylbenzamide

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: 468.53

Molecular Weight (Monoisotopic): 468.2173

AlogP: 2.31

#Rotatable Bonds: 5

Polar Surface Area: 93.53

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.05

CX LogP: 2.37

CX LogD: 2.35

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.73

Np Likeness Score: -0.86

References

1.  (2013)  Furo[3, 2-B] pyrrol-3-ones as cathespin S inhibitors, 

Source

Source(1):

• BindingDB Database