(2R,3R,4S,5R,6R)-4-(3-chloroanilino)-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-3,5-diol

ID: ALA4570596

PubChem CID: 155563008

Max Phase: Preclinical

Molecular Formula: C13H18ClNO5

Molecular Weight: 303.74

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](Nc2cccc(Cl)c2)[C@H]1O

Standard InChI:  InChI=1S/C13H18ClNO5/c1-19-13-12(18)10(11(17)9(6-16)20-13)15-8-4-2-3-7(14)5-8/h2-5,9-13,15-18H,6H2,1H3/t9-,10+,11+,12-,13-/m1/s1

Standard InChI Key:  JAERMUMTOKHESY-KSSYENDESA-N

Molfile:  

 
     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   24.3300  -11.9483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3300  -12.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0394  -13.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7488  -12.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7488  -11.9483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0394  -11.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0394  -10.7102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6170  -11.5377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6188  -13.1793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.0394  -13.9954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4601  -13.1793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4589  -14.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3276  -10.3016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9115  -12.7699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9164  -11.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2099  -11.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5008  -11.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5026  -12.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2096  -13.1775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2112  -10.7255    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
  6  7  1  1
  1  8  1  1
  2  9  1  1
  3 10  1  6
  4 11  1  1
 11 12  1  0
  7 13  1  0
  9 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 16 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4570596

   ---

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: 303.74

Molecular Weight (Monoisotopic): 303.0874

AlogP: 0.21

#Rotatable Bonds: 4

Polar Surface Area: 91.18

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.66

CX Basic pKa: 2.54

CX LogP: 0.28

CX LogD: 0.28

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.64

Np Likeness Score: 0.57

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