Methyl 3-((2-amino-6-(4-bromophenyl)-pyrimidin-4-yl)methyl)-beta-D-galactopyranoside

ID: ALA4475931

PubChem CID: 155538005

Max Phase: Preclinical

Molecular Formula: C18H22BrN3O6

Molecular Weight: 456.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](OCc2cc(-c3ccc(Br)cc3)nc(N)n2)[C@H]1O

Standard InChI:  InChI=1S/C18H22BrN3O6/c1-26-17-15(25)16(14(24)13(7-23)28-17)27-8-11-6-12(22-18(20)21-11)9-2-4-10(19)5-3-9/h2-6,13-17,23-25H,7-8H2,1H3,(H2,20,21,22)/t13-,14+,15-,16+,17-/m1/s1

Standard InChI Key:  BAXHMZFTOFKHCY-BPKGMFCQSA-N

Molfile:  

 
     RDKit          2D

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   14.5650   -3.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2744   -4.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9838   -3.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9838   -3.1037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2744   -2.6910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6968   -2.6972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2744   -5.1549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8537   -4.3387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8520   -2.6972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8496   -1.8758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4075   -3.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6950   -4.3387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5667   -5.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5667   -6.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8558   -6.7860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8555   -7.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5637   -8.0118    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2738   -7.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2706   -6.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1476   -8.0107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9792   -8.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9808   -8.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6891   -9.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3963   -8.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3908   -7.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6819   -7.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1060   -9.2210    0.0000 Br  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
  5  7  1  1
  3  8  1  1
  2  9  1  1
  1 10  1  1
 10 11  1  0
  7 12  1  0
  4 13  1  6
  8 14  1  0
 14 15  1  0
 15 16  2  0
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 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 17 21  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 19 22  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4475931

   ---

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: 456.29

Molecular Weight (Monoisotopic): 455.0692

AlogP: 0.46

#Rotatable Bonds: 6

Polar Surface Area: 140.18

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.28

CX Basic pKa: 4.03

CX LogP: 0.89

CX LogD: 0.89

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.49

Np Likeness Score: 0.66

References

1. Dahlqvist A, Zetterberg FR, Leffler H, Nilsson UJ..  (2019)  Aminopyrimidine-galactose hybrids are highly selective galectin-3 inhibitors.,  10  (6): [PMID:31303989] [10.1039/C9MD00183B]

Source

Source(1):

• Scientific Literature