(R)-benzyl (4-methyl-1-oxo-1-((4-sulfamoylphenethyl)amino)pentan-2-yl)carbamate

ID: ALA5198932

PubChem CID: 168286462

Max Phase: Preclinical

Molecular Formula: C22H29N3O5S

Molecular Weight: 447.56

Names and Identifiers

Canonical SMILES:  CC(C)C[C@@H](NC(=O)OCc1ccccc1)C(=O)NCCc1ccc(S(N)(=O)=O)cc1

Standard InChI:  InChI=1S/C22H29N3O5S/c1-16(2)14-20(25-22(27)30-15-18-6-4-3-5-7-18)21(26)24-13-12-17-8-10-19(11-9-17)31(23,28)29/h3-11,16,20H,12-15H2,1-2H3,(H,24,26)(H,25,27)(H2,23,28,29)/t20-/m1/s1

Standard InChI Key:  UDSLZFAOQYIGJL-HXUWFJFHSA-N

Molfile:  

 
     RDKit          2D

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    3.5180    1.4452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2299    1.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2299    0.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5198   -0.2036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8034    0.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9445    1.4459    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9445    2.2711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3579    0.7299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7697    1.4459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0886   -0.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3742    0.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6595   -0.2081    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0551    0.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7695   -0.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0551    1.0296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4843    0.2044    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1990   -0.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9135    0.2044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6282   -0.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3429    0.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1990   -1.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0577   -0.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7697    0.2039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7697    1.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0595    1.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3429    1.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7695   -1.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0551   -1.4459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0551   -2.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6595   -1.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  3  7  1  0
  7  8  1  0
  7  9  2  0
  7 10  2  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 18 22  2  0
 23 21  2  0
 24 23  1  0
 25 24  2  0
 26 25  1  0
 27 26  2  0
 21 27  1  0
 15 28  1  1
 28 29  1  0
 29 30  1  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5198932

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 447.56

Molecular Weight (Monoisotopic): 447.1828

AlogP: 2.33

#Rotatable Bonds: 10

Polar Surface Area: 127.59

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.22

CX Basic pKa: ┄

CX LogP: 2.87

CX LogD: 2.87

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.52

Np Likeness Score: -0.80

References

1. Kumar S, Rulhania S, Jaswal S, Monga V..  (2021)  Recent advances in the medicinal chemistry of carbonic anhydrase inhibitors.,  209  [PMID:33121862] [10.1016/j.ejmech.2020.112923]

Source

Source(1):

• Scientific Literature