3-(4-hydroxyphenyl)-1-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxyphenyl]propan-1-one

ID: ALA4552590

PubChem CID: 155556004

Max Phase: Preclinical

Molecular Formula: C21H24O8

Molecular Weight: 404.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CCc1ccc(O)cc1)c1ccccc1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C21H24O8/c22-11-17-18(25)19(26)20(27)21(29-17)28-16-4-2-1-3-14(16)15(24)10-7-12-5-8-13(23)9-6-12/h1-6,8-9,17-23,25-27H,7,10-11H2/t17-,18-,19+,20-,21-/m1/s1

Standard InChI Key:  UAFIADONBJJDTB-YMQHIKHWSA-N

Molfile:  

 
     RDKit          2D

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    9.5224   -6.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2307   -6.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2307   -7.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5249   -7.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8144   -7.3044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5224   -5.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8143   -4.8418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2304   -4.8418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9426   -5.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6507   -4.8418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6510   -4.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3566   -3.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0691   -4.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0672   -4.8388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3631   -5.2561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7772   -3.6175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1063   -6.0726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3941   -6.4803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3941   -7.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6861   -7.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9780   -7.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9780   -6.4803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6860   -6.0726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2699   -6.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2699   -5.2532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2699   -7.7074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6861   -8.5268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1063   -7.7074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  2  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 12 11  2  0
 13 12  1  0
 14 13  2  0
 15 14  1  0
 16 15  2  0
 11 16  1  0
 14 17  1  0
  1 18  1  0
 19 18  1  1
 20 19  1  0
 21 20  1  0
 22 21  1  0
 23 22  1  0
 24 23  1  0
 19 24  1  0
 23 25  1  1
 25 26  1  0
 22 27  1  6
 21 28  1  1
 20 29  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4552590

   ---

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: 404.42

Molecular Weight (Monoisotopic): 404.1471

AlogP: 0.39

#Rotatable Bonds: 7

Polar Surface Area: 136.68

Molecular Species: NEUTRAL

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.50

CX Basic pKa: ┄

CX LogP: 0.93

CX LogD: 0.93

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.42

Np Likeness Score: 1.25

References

1. Romero FA, Jones CT, Xu Y, Fenaux M, Halcomb RL..  (2020)  The Race to Bash NASH: Emerging Targets and Drug Development in a Complex Liver Disease.,  63  (10): [PMID:31930920] [10.1021/acs.jmedchem.9b01701]

Source

Source(1):

• Scientific Literature