Methyl 3-O((4-methylcarboxyphenyl)-1,2,3-triazol-4-ylmethyl)-beta-D-galactopyranoside

ID: ALA4864732

PubChem CID: 164622685

Max Phase: Preclinical

Molecular Formula: C18H23N3O8

Molecular Weight: 409.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(-n2cc(CO[C@H]3[C@@H](O)[C@@H](CO)O[C@@H](OC)[C@@H]3O)nn2)cc1

Standard InChI:  InChI=1S/C18H23N3O8/c1-26-17(25)10-3-5-12(6-4-10)21-7-11(19-20-21)9-28-16-14(23)13(8-22)29-18(27-2)15(16)24/h3-7,13-16,18,22-24H,8-9H2,1-2H3/t13-,14+,15-,16+,18-/m1/s1

Standard InChI Key:  PEVGVNKWBXYLCS-RIUYPTKQSA-N

Molfile:  

 
     RDKit          2D

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   40.4918  -14.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1970  -14.0078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1970  -13.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4918  -12.7779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.4918  -15.2295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.0794  -14.4174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.9059  -12.7841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.0776  -12.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   42.6125  -13.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7841  -15.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7841  -16.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1272  -16.9381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3797  -17.7153    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.1969  -17.7153    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.4493  -16.9381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.9016  -18.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0879  -18.2882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6077  -18.9485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9401  -19.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7573  -19.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2338  -19.1180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4606  -20.3578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6478  -20.2734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.7940  -21.1039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.3145  -21.7656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3  7  1  1
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  5  9  1  1
  1 10  1  1
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  4 12  1  6
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  7 14  1  0
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 26 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4864732

   ---

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: 409.40

Molecular Weight (Monoisotopic): 409.1485

AlogP: -0.98

#Rotatable Bonds: 7

Polar Surface Area: 145.39

Molecular Species: NEUTRAL

HBA: 11

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.28

CX Basic pKa: ┄

CX LogP: -0.13

CX LogD: -0.13

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.49

Np Likeness Score: 0.17

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