(2S,4R)-N-[(2-chlorophenyl)methyl]-4-hydroxy-1-[2-(3-methylisoxazol-5-yl)acetyl]pyrrolidine-2-carboxamide

ID: ALA4639001

PubChem CID: 57382178

Max Phase: Preclinical

Molecular Formula: C18H20ClN3O4

Molecular Weight: 377.83

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(CC(=O)N2C[C@H](O)C[C@H]2C(=O)NCc2ccccc2Cl)on1

Standard InChI:  InChI=1S/C18H20ClN3O4/c1-11-6-14(26-21-11)8-17(24)22-10-13(23)7-16(22)18(25)20-9-12-4-2-3-5-15(12)19/h2-6,13,16,23H,7-10H2,1H3,(H,20,25)/t13-,16+/m1/s1

Standard InChI Key:  UGZKBQSCCGQTLZ-CJNGLKHVSA-N

Molfile:  

 
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   21.4757  -16.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7318  -15.5661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5530  -15.5661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8090  -16.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   24.1908  -15.9798    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.9886  -16.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5726  -15.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3593  -14.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9375  -14.2308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7355  -14.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9499  -15.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3711  -15.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5847  -16.6220    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   23.8203  -17.3617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3171  -14.8529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1423  -17.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8597  -18.0712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4292  -18.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4292  -18.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0955  -19.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8395  -20.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0147  -20.1651    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7629  -19.3813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2543  -20.8783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0
  3  4  1  0
  4  5  1  0
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  5  6  1  1
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  9 14  1  0
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  6 16  2  0
  3 17  1  6
  1 18  1  0
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 23 24  2  0
 24 25  1  0
 25 21  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4639001

   (2S,4R)-N-[(2-chlorophenyl)methyl]-4-hydroxy-1-[2-(3-methyl-1,2-oxazol-5-yl)acetyl]pyrrolidine-2-carboxamide

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: 377.83

Molecular Weight (Monoisotopic): 377.1142

AlogP: 1.46

#Rotatable Bonds: 5

Polar Surface Area: 95.67

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.42

CX Basic pKa: 0.54

CX LogP: 0.36

CX LogD: 0.36

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.82

Np Likeness Score: -1.53

References

1. Blaquiere N, Villemure E, Staben ST..  (2020)  Medicinal Chemistry of Inhibiting RING-Type E3 Ubiquitin Ligases.,  63  (15): [PMID:32142281] [10.1021/acs.jmedchem.9b01451]

Source

Source(1):

• Scientific Literature