6-((3-Fluorobenzyl)thio)-2-(oxetan-3-yl)-5-phenyl-2H-pyrazolo-[3,4-d]pyrimidin-4(5H)-one

ID: ALA4210115

PubChem CID: 132258507

Max Phase: Preclinical

Molecular Formula: C21H17FN4O2S

Molecular Weight: 408.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1c2cn(C3COC3)nc2nc(SCc2cccc(F)c2)n1-c1ccccc1

Standard InChI:  InChI=1S/C21H17FN4O2S/c22-15-6-4-5-14(9-15)13-29-21-23-19-18(10-25(24-19)17-11-28-12-17)20(27)26(21)16-7-2-1-3-8-16/h1-10,17H,11-13H2

Standard InChI Key:  IBYYWHNJSYBLSJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    7.0034   -5.7492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7087   -5.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7087   -4.5276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0034   -4.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0034   -3.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4158   -5.7544    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.1241   -5.3468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8312   -5.7564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4140   -4.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1208   -4.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8292   -4.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8320   -3.3116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1205   -2.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4150   -3.3093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8271   -6.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5334   -6.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2427   -6.5735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2412   -5.7521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5344   -5.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9481   -5.3420    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.2982   -5.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2982   -4.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5210   -4.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0406   -4.9362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5210   -5.5973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2180   -4.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6402   -4.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0624   -4.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6402   -5.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 22  4  1  0
 21  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  3  9  1  0
  8 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19  8  1  0
 18 20  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 21  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 26  1  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4210115

   ---

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: 408.46

Molecular Weight (Monoisotopic): 408.1056

AlogP: 3.58

#Rotatable Bonds: 5

Polar Surface Area: 61.94

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.66

CX LogD: 4.66

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.37

Np Likeness Score: -1.82

References

1. Huddle BC, Grimley E, Buchman CD, Chtcherbinine M, Debnath B, Mehta P, Yang K, Morgan CA, Li S, Felton J, Sun D, Mehta G, Neamati N, Buckanovich RJ, Hurley TD, Larsen SD..  (2018)  Structure-Based Optimization of a Novel Class of Aldehyde Dehydrogenase 1A (ALDH1A) Subfamily-Selective Inhibitors as Potential Adjuncts to Ovarian Cancer Chemotherapy.,  61  (19): [PMID:30221940] [10.1021/acs.jmedchem.8b00930]

2. Huddle BC, Grimley E, Chtcherbinine M, Buchman CD, Takahashi C, Debnath B, McGonigal SC, Mao S, Li S, Felton J, Pan S, Wen B, Sun D, Neamati N, Buckanovich RJ, Hurley TD, Larsen SD..  (2021)  Development of 2,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one inhibitors of aldehyde dehydrogenase 1A (ALDH1A) as potential adjuncts to ovarian cancer chemotherapy.,  211  [PMID:33341649] [10.1016/j.ejmech.2020.113060]

Source

Source(1):

• Scientific Literature