3,4-Dichlorophenyl 3-deoxy-3-(3-methoxyphenylamino)-1-thio-alpha-D-galactopyranoside

ID: ALA4557916

PubChem CID: 155554696

Max Phase: Preclinical

Molecular Formula: C19H21Cl2NO5S

Molecular Weight: 446.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cccc(N[C@@H]2[C@@H](O)[C@@H](Sc3ccc(Cl)c(Cl)c3)O[C@H](CO)[C@@H]2O)c1

Standard InChI:  InChI=1S/C19H21Cl2NO5S/c1-26-11-4-2-3-10(7-11)22-16-17(24)15(9-23)27-19(18(16)25)28-12-5-6-13(20)14(21)8-12/h2-8,15-19,22-25H,9H2,1H3/t15-,16+,17+,18-,19-/m1/s1

Standard InChI Key:  XRWPMSSCPKNFEZ-ICBNADEASA-N

Molfile:  

 
     RDKit          2D

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   25.4774  -13.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4774  -14.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1868  -14.5237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8962  -14.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8962  -13.2979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1868  -12.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1868  -12.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7644  -12.8873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7661  -14.5289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.1868  -15.3450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4750  -11.6512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0589  -14.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0637  -13.3015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3573  -12.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6482  -13.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6499  -14.1216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3570  -14.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6028  -14.5298    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   28.3116  -14.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0150  -14.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7234  -14.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7260  -13.3095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0144  -12.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3090  -13.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4298  -14.5384    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   30.4343  -12.9019    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   23.3586  -12.0751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0669  -11.6676    0.0000 C   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
  6  7  1  1
  1  8  1  1
  2  9  1  1
  3 10  1  6
  7 11  1  0
  9 12  1  0
 12 13  2  0
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 15 16  1  0
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  4 18  1  6
 18 19  1  0
 19 20  2  0
 20 21  1  0
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 22 23  1  0
 23 24  2  0
 24 19  1  0
 21 25  1  0
 22 26  1  0
 14 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4557916

   ---

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: 446.35

Molecular Weight (Monoisotopic): 445.0517

AlogP: 3.01

#Rotatable Bonds: 6

Polar Surface Area: 91.18

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.96

CX Basic pKa: 2.62

CX LogP: 2.81

CX LogD: 2.81

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.54

Np Likeness Score: -0.30

References

1. Mahanti M, Pal KB, Sundin AP, Leffler H, Nilsson UJ..  (2020)  Epimers Switch Galectin-9 Domain Selectivity: 3N-Aryl Galactosides Bind the C-Terminal and Gulosides Bind the N-Terminal.,  11  (1): [PMID:31938460] [10.1021/acsmedchemlett.9b00396]

Source

Source(1):

• Scientific Literature