(S)-1-(5,6-dihydroxybenzofuran-2-carbonyl)-N-phenylpyrrolidine-2-carboxamide

ID: ALA4875563

PubChem CID: 164625724

Max Phase: Preclinical

Molecular Formula: C20H18N2O5

Molecular Weight: 366.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccccc1)[C@@H]1CCCN1C(=O)c1cc2cc(O)c(O)cc2o1

Standard InChI:  InChI=1S/C20H18N2O5/c23-15-9-12-10-18(27-17(12)11-16(15)24)20(26)22-8-4-7-14(22)19(25)21-13-5-2-1-3-6-13/h1-3,5-6,9-11,14,23-24H,4,7-8H2,(H,21,25)/t14-/m0/s1

Standard InChI Key:  LZGLYQJZXIDNFD-AWEZNQCLSA-N

Molfile:  

 
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   33.1166  -28.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1148  -27.0867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   36.3094  -28.6081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.3089  -27.1927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.1239  -27.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   38.4710  -27.5386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.0190  -28.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7653  -28.9214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3126  -29.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1125  -29.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3623  -28.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8133  -27.9710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA4875563

   ---

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: 366.37

Molecular Weight (Monoisotopic): 366.1216

AlogP: 3.09

#Rotatable Bonds: 3

Polar Surface Area: 103.01

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.33

CX Basic pKa: ┄

CX LogP: 2.27

CX LogD: 2.23

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.62

Np Likeness Score: -0.90

References

1. Maus H, Barthels F, Hammerschmidt SJ, Kopp K, Millies B, Gellert A, Ruggieri A, Schirmeister T..  (2021)  SAR of novel benzothiazoles targeting an allosteric pocket of DENV and ZIKV NS2B/NS3 proteases.,  47  [PMID:34509861] [10.1016/j.bmc.2021.116392]

Source

Source(1):

• Scientific Literature