1-methyl-5-(4-(2-(methylamino)ethyl)phenyl)-6-((1-phenylethyl)thio)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one

ID: ALA4854678

PubChem CID: 164611285

Max Phase: Preclinical

Molecular Formula: C23H25N5OS

Molecular Weight: 419.55

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNCCc1ccc(-n2c(SC(C)c3ccccc3)nc3c(cnn3C)c2=O)cc1

Standard InChI:  InChI=1S/C23H25N5OS/c1-16(18-7-5-4-6-8-18)30-23-26-21-20(15-25-27(21)3)22(29)28(23)19-11-9-17(10-12-19)13-14-24-2/h4-12,15-16,24H,13-14H2,1-3H3

Standard InChI Key:  WYEFYTRRGYXTGL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   25.0291  -15.6321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   26.4468  -15.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4440  -14.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7353  -14.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3176  -16.0425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.6069  -15.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6114  -17.2714    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3194  -16.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6083  -14.8100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8952  -16.8606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8960  -16.0363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1123  -15.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6271  -16.4473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1110  -17.1145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8578  -17.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0272  -17.2674    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.0277  -18.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7356  -18.4928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7310  -19.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4381  -19.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1466  -19.3073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1434  -18.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4358  -18.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3202  -18.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1501  -14.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8594  -14.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5655  -14.3924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2748  -14.7983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  6  1  1  0
  2  7  1  0
  7  8  1  0
  8 13  1  0
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  9 10  2  0
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  8 11  2  0
 12 13  2  0
 13 14  1  0
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 15 16  1  0
 16 12  1  0
 16 17  1  0
 10 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 19 26  1  0
  5 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4854678

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 419.55

Molecular Weight (Monoisotopic): 419.1780

AlogP: 3.73

#Rotatable Bonds: 7

Polar Surface Area: 64.74

Molecular Species: BASE

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.07

CX LogP: 4.33

CX LogD: 1.76

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.37

Np Likeness Score: -1.63

References

1. 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