3-O-[(7-Methoxycarbonyl-quinolin-2-yl)-methyl]-D-galactal

ID: ALA4873509

PubChem CID: 164622076

Max Phase: Preclinical

Molecular Formula: C18H19NO6

Molecular Weight: 345.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc2ccc(CO[C@@H]3C=CO[C@H](CO)[C@@H]3O)nc2c1

Standard InChI:  InChI=1S/C18H19NO6/c1-23-18(22)12-3-2-11-4-5-13(19-14(11)8-12)10-25-15-6-7-24-16(9-20)17(15)21/h2-8,15-17,20-21H,9-10H2,1H3/t15-,16-,17-/m1/s1

Standard InChI Key:  RGQUDGLEAUKLIE-BRWVUGGUSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   12.2042  -23.1950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2042  -24.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9136  -24.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6230  -24.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6230  -23.1950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9136  -22.7823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4953  -22.7885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4929  -21.9672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4971  -24.4301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9136  -25.2463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2018  -25.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2018  -26.4762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4873  -26.8835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4870  -27.7040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9093  -26.8813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9125  -27.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2005  -28.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2028  -28.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9164  -29.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6291  -28.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6232  -28.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3406  -29.3304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3461  -30.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0455  -28.9170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6412  -30.5610    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  2  0
  5  6  1  0
  1  7  1  1
  7  8  1  0
  2  9  1  1
  3 10  1  1
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 17  2  0
 16 15  2  0
 15 12  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 22 23  1  0
 22 24  2  0
 20 22  1  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4873509

   ---

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: 345.35

Molecular Weight (Monoisotopic): 345.1212

AlogP: 1.17

#Rotatable Bonds: 5

Polar Surface Area: 98.11

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.05

CX Basic pKa: 2.04

CX LogP: 0.97

CX LogD: 0.97

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.79

Np Likeness Score: 0.52

References

1. Hassan M, Baussière F, Guzelj S, Sundin AP, Håkansson M, Kovačič R, Leffler H, Tomašič T, Anderluh M, Jakopin Ž, Nilsson UJ..  (2021)  Structure-Guided Design of d-Galactal Derivatives with High Affinity and Selectivity for the Galectin-8 N-Terminal Domain.,  12  (11.0): [PMID:34795863] [10.1021/acsmedchemlett.1c00371]

Source

Source(1):

• Scientific Literature