3,4-Dichlorophenyl 3-o-((5-carboxy)1H-benzo[d]imidazole-2-ylmethyl)-1-thio-alpha-D-galactopyranoside

ID: ALA4872829

PubChem CID: 164624352

Max Phase: Preclinical

Molecular Formula: C21H20Cl2N2O7S

Molecular Weight: 515.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc2nc(CO[C@@H]3[C@@H](O)[C@@H](Sc4ccc(Cl)c(Cl)c4)O[C@H](CO)[C@@H]3O)[nH]c2c1

Standard InChI:  InChI=1S/C21H20Cl2N2O7S/c22-11-3-2-10(6-12(11)23)33-21-18(28)19(17(27)15(7-26)32-21)31-8-16-24-13-4-1-9(20(29)30)5-14(13)25-16/h1-6,15,17-19,21,26-28H,7-8H2,(H,24,25)(H,29,30)/t15-,17+,18-,19+,21-/m1/s1

Standard InChI Key:  ULXYWOSGYPHZDE-RMMBEPAUSA-N

Molfile:  

 
     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   15.5720  -17.2229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5720  -18.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2773  -18.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9826  -18.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9826  -17.2229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2773  -16.8102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2773  -19.2618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8649  -18.4497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6915  -16.8164    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.8631  -16.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8607  -15.9992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6897  -18.4497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3980  -17.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5696  -19.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5696  -20.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9127  -20.9704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2349  -20.9704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9825  -21.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1683  -21.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7628  -22.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1704  -23.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9876  -23.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3895  -22.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3997  -23.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9946  -24.5675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2169  -23.8538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3940  -18.0453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0997  -18.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8096  -18.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8094  -17.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1031  -16.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5166  -18.4590    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.5168  -16.8189    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  3  7  1  1
  2  8  1  1
  5  9  1  6
  1 10  1  1
 10 11  1  0
  4 12  1  6
  9 13  1  0
  7 14  1  0
 14 15  1  0
 15 16  2  0
 16 19  1  0
 18 17  1  0
 17 15  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 22 24  1  0
 24 25  2  0
 24 26  1  0
 13 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 13  1  0
 29 32  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4872829

   ---

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: 515.37

Molecular Weight (Monoisotopic): 514.0368

AlogP: 2.68

#Rotatable Bonds: 7

Polar Surface Area: 145.13

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.96

CX Basic pKa: 4.96

CX LogP: 1.16

CX LogD: -0.88

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.32

Np Likeness Score: -0.23

References

1. Hassan M, van Klaveren S, Håkansson M, Diehl C, Kovačič R, Baussière F, Sundin AP, Dernovšek J, Walse B, Zetterberg F, Leffler H, Anderluh M, Tomašič T, Jakopin Ž, Nilsson UJ..  (2021)  Benzimidazole-galactosides bind selectively to the Galectin-8 N-Terminal domain: Structure-based design and optimisation.,  223  [PMID:34225180] [10.1016/j.ejmech.2021.113664]

Source

Source(1):

• Scientific Literature