(S)-3,4-dichloro-N-(2-(((5-hydroxy-4-oxo-4H-pyran-2-yl)methyl)amino)-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)-5-methyl-1H-pyrrole-2-carboxamide

ID: ALA5284544

Max Phase: Preclinical

Molecular Formula: C19H18Cl2N4O4S

Molecular Weight: 469.35

Names and Identifiers

Canonical SMILES:  Cc1[nH]c(C(=O)N[C@H]2CCc3nc(NCc4cc(=O)c(O)co4)sc3C2)c(Cl)c1Cl

Standard InChI:  InChI=1S/C19H18Cl2N4O4S/c1-8-15(20)16(21)17(23-8)18(28)24-9-2-3-11-14(4-9)30-19(25-11)22-6-10-5-12(26)13(27)7-29-10/h5,7,9,23,27H,2-4,6H2,1H3,(H,22,25)(H,24,28)/t9-/m0/s1

Standard InChI Key:  MKUONPTVXORDMA-VIFPVBQESA-N

Molfile:  

 
     RDKit          2D

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    4.8129   -0.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8025   -1.2960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2192   -0.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4326    0.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2295    0.2976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4431    1.0945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4223   -0.9261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8389   -0.3428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0421   -0.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0773   -1.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6606   -1.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4575   -1.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6710   -0.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0877   -0.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2908   -0.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4010   -0.0371    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4679   -0.6427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6814    0.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0980    0.7375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4783    0.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1456   -0.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8129    0.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6098    0.1541    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.5580    1.1522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9705    1.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7332    1.1522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1456   -0.9421    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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  3  2  2  0
  4  3  1  0
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 15 14  1  0
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 17 16  1  0
 18 17  1  0
 13 18  2  0
 18 19  1  0
 19 11  1  0
 16 20  1  6
 21 20  1  0
 21 22  2  0
 23 21  1  0
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 24 25  1  0
 25 26  1  0
 25 27  2  0
 27 28  1  0
 27 29  1  0
 29 23  1  0
 24 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5284544

   ---

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: 469.35

Molecular Weight (Monoisotopic): 468.0426

AlogP: 3.64

#Rotatable Bonds: 5

Polar Surface Area: 120.25

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.88

CX Basic pKa: 3.32

CX LogP: 2.85

CX LogD: 2.84

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.45

Np Likeness Score: -1.07

References

1. He M, Fan M, Peng Z, Wang G..  (2021)  An overview of hydroxypyranone and hydroxypyridinone as privileged scaffolds for novel drug discovery.,  221  [PMID:34023737] [10.1016/j.ejmech.2021.113546]

Source

Source(1):

• Scientific Literature