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

ID: ALA4860496

PubChem CID: 162368307

Max Phase: Preclinical

Molecular Formula: C17H17NO6

Molecular Weight: 331.32

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H17NO6/c19-8-15-16(20)14(5-6-23-15)24-9-12-4-3-10-1-2-11(17(21)22)7-13(10)18-12/h1-7,14-16,19-20H,8-9H2,(H,21,22)/t14-,15-,16-/m1/s1

Standard InChI Key:  ZGVBVJVFIXTFPT-BZUAXINKSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   18.2135  -23.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2135  -24.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9229  -24.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6323  -24.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6323  -23.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9229  -23.2115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5046  -23.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5022  -22.3964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5063  -24.8593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9229  -25.6755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2110  -26.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2110  -26.9054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4966  -27.3127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4962  -28.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9185  -27.3105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9217  -28.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2097  -28.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2121  -29.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9256  -29.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6383  -29.3551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6325  -28.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3498  -29.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3554  -30.5768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0547  -29.3462    0.0000 O   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
M  END

Alternative Forms

1. Parent:

   

   ALA4860496

   ---

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: 331.32

Molecular Weight (Monoisotopic): 331.1056

AlogP: 1.08

#Rotatable Bonds: 5

Polar Surface Area: 109.11

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.63

CX Basic pKa: 1.06

CX LogP: 0.63

CX LogD: -2.71

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.75

Np Likeness Score: 0.64

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