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

ID: ALA4576450

PubChem CID: 155551949

Max Phase: Preclinical

Molecular Formula: C18H22ClN3O6

Molecular Weight: 411.84

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H22ClN3O6/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:  RNGXGXAJHZLJRH-BPKGMFCQSA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    5.1301  -14.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1301  -15.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8396  -15.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5490  -15.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5490  -14.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8396  -13.9046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2620  -13.9108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8396  -16.3686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4189  -15.5524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4171  -13.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4147  -13.0895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9726  -14.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2602  -15.5524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1318  -16.7772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1318  -17.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4210  -17.9997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4206  -18.8161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1289  -19.2255    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8389  -18.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8358  -17.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7127  -19.2243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5444  -19.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5459  -20.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2542  -20.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9615  -20.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9559  -19.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2471  -18.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6712  -20.4347    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
  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
 16 17  1  0
 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:

   

   ALA4576450

   ---

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: 411.84

Molecular Weight (Monoisotopic): 411.1197

AlogP: 0.35

#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: 4.04

CX LogP: 0.72

CX LogD: 0.72

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.53

Np Likeness Score: 0.56

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