7-methyl-3-(3-(4-sulfamoylphenethyl)ureido)pyrazolo[1,5-a]pyrimidine-6-carboxylic acid

ID: ALA4875979

PubChem CID: 164626349

Max Phase: Preclinical

Molecular Formula: C17H18N6O5S

Molecular Weight: 418.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1c(C(=O)O)cnc2c(NC(=O)NCCc3ccc(S(N)(=O)=O)cc3)cnn12

Standard InChI:  InChI=1S/C17H18N6O5S/c1-10-13(16(24)25)8-20-15-14(9-21-23(10)15)22-17(26)19-7-6-11-2-4-12(5-3-11)29(18,27)28/h2-5,8-9H,6-7H2,1H3,(H,24,25)(H2,18,27,28)(H2,19,22,26)

Standard InChI Key:  NMDVARAMHFVDHU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   20.7435   -1.9315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5359   -1.7211    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.9574   -1.1400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8796  -10.2314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5849  -10.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2902  -10.2314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2902   -9.4142    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8774   -9.4103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5849   -9.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4148   -8.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6020   -8.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2699   -8.8637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1731  -10.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5849  -11.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8772  -11.8617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2926  -11.8617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9614   -7.5947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7086   -6.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2553   -6.2101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9092   -6.6480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0025   -5.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5491   -4.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2963   -4.0485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8440   -3.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5918   -2.6690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7916   -2.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2441   -3.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4992   -3.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0836   -1.1138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  8  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  9  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
  4 13  1  0
  5 14  1  0
 14 15  2  0
 14 16  1  0
 10 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 26  2  1  0
  2 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4875979

   ---

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: 418.44

Molecular Weight (Monoisotopic): 418.1059

AlogP: 0.75

#Rotatable Bonds: 6

Polar Surface Area: 168.78

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.46

CX Basic pKa: 0.59

CX LogP: 0.26

CX LogD: -3.13

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.46

Np Likeness Score: -1.83

References

1. Gumus A, Bozdag M, Angeli A, Peat TS, Carta F, Supuran CT, Selleri S..  (2021)  Privileged scaffolds in medicinal chemistry: Studies on pyrazolo[1,5-a]pyrimidines on sulfonamide containing Carbonic Anhydrase inhibitors.,  49  [PMID:34371130] [10.1016/j.bmcl.2021.128309]

Source

Source(1):

• Scientific Literature