(S)-N-(1-(5,6-dihydroxybenzo[d]thiazol-2-ylamino)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)benzamide

ID: ALA4877369

PubChem CID: 164626227

Max Phase: Preclinical

Molecular Formula: C23H19N3O5S

Molecular Weight: 449.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H](Cc1ccc(O)cc1)C(=O)Nc1nc2cc(O)c(O)cc2s1)c1ccccc1

Standard InChI:  InChI=1S/C23H19N3O5S/c27-15-8-6-13(7-9-15)10-17(24-21(30)14-4-2-1-3-5-14)22(31)26-23-25-16-11-18(28)19(29)12-20(16)32-23/h1-9,11-12,17,27-29H,10H2,(H,24,30)(H,25,26,31)/t17-/m0/s1

Standard InChI Key:  AVYZDYVFRJSUDS-KRWDZBQOSA-N

Molfile:  

 
     RDKit          2D

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    3.6080  -21.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1080  -21.1944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5936  -20.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1075  -19.8572    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1798  -19.7041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4181  -19.0963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0686  -20.5246    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8313  -21.2396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6537  -22.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0658  -23.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8916  -23.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3037  -22.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8892  -21.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0702  -17.6701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6582  -16.9562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8323  -16.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4202  -17.6757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8346  -18.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4186  -16.2423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  8 12  1  0
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 14 16  1  0
 14 17  1  6
 17 18  1  0
 16 19  1  0
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 19 21  2  0
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 26 20  1  0
 18 27  2  0
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 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 18  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4877369

   ---

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: 449.49

Molecular Weight (Monoisotopic): 449.1045

AlogP: 3.39

#Rotatable Bonds: 6

Polar Surface Area: 131.78

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.62

CX Basic pKa: 0.18

CX LogP: 4.10

CX LogD: 3.89

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.29

Np Likeness Score: -0.89

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