(R)-Benzyl 4-((4-((2-(hydroxycarbamoyl)pyrrolidin-1-yl)sulfonyl)phenyl)carbamoyl)benzylcarbamate

ID: ALA4531635

PubChem CID: 155546617

Max Phase: Preclinical

Molecular Formula: C20H22N2O6S

Molecular Weight: 418.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(S(=O)(=O)C2CCC[C@@H]2C(=O)NO)cc1)OCc1ccccc1

Standard InChI:  InChI=1S/C20H22N2O6S/c23-19(22-25)17-7-4-8-18(17)29(26,27)16-11-9-15(10-12-16)21-20(24)28-13-14-5-2-1-3-6-14/h1-3,5-6,9-12,17-18,25H,4,7-8,13H2,(H,21,24)(H,22,23)/t17-,18?/m0/s1

Standard InChI Key:  YKYLIBIHPXSXED-ZENAZSQFSA-N

Molfile:  

 
     RDKit          2D

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   23.2280  -12.4312    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.9425  -12.8361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9279  -11.7668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7493  -11.7668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0036  -10.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   21.6737  -10.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7887  -10.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3993  -11.2802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   24.7413   -9.6737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   22.0776  -13.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7402  -14.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2240  -14.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0449  -14.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3744  -13.8378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8918  -15.4256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3722  -16.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0400  -16.8415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1890  -16.0053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6736  -16.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4904  -16.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9687  -17.2509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7848  -17.1657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1220  -16.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6328  -15.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8184  -15.8358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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 27 28  1  0
 28 29  2  0
 29 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4531635

   ---

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: 418.47

Molecular Weight (Monoisotopic): 418.1199

AlogP: 2.88

#Rotatable Bonds: 6

Polar Surface Area: 121.80

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.86

CX Basic pKa: ┄

CX LogP: 2.62

CX LogD: 2.61

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.49

Np Likeness Score: -0.73

References

1. Lenci E, Innocenti R, Di Francescantonio T, Menchi G, Bianchini F, Contini A, Trabocchi A..  (2019)  Identification of highly potent and selective MMP2 inhibitors addressing the S1' subsite with d-proline-based compounds.,  27  (9): [PMID:30926311] [10.1016/j.bmc.2019.03.043]

Source

Source(1):

• Scientific Literature