Methyl-6-O-(8-hydroxynaphthalene-1,4-dione-2-yl)-alpha-D-glucopyranoside

ID: ALA3236761

PubChem CID: 90671097

Max Phase: Preclinical

Molecular Formula: C17H18O9

Molecular Weight: 366.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@H]1O[C@H](COC2=CC(=O)c3cccc(O)c3C2=O)[C@@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C17H18O9/c1-24-17-16(23)15(22)14(21)11(26-17)6-25-10-5-9(19)7-3-2-4-8(18)12(7)13(10)20/h2-5,11,14-18,21-23H,6H2,1H3/t11-,14-,15+,16-,17+/m1/s1

Standard InChI Key:  HAZQMRTXWQGCHZ-UFRBAHOGSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   10.4940   -4.5969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7745   -7.2165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4580   -2.9510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0622   -5.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6209   -5.5520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4867   -5.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0805   -5.4527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1914   -4.7383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9103   -5.9680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7726   -5.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2031   -8.0338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3304   -5.9620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8040   -5.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9150   -6.7964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0634   -4.6312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2342   -5.8259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2014   -7.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5107   -5.4277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7536   -3.3773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4874   -6.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8226   -6.6779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7705   -4.1987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2007   -4.1737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1958   -5.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0611   -6.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7701   -4.7494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 22 19  1  6
 18 16  1  1
  1 23  1  6
  4 25  1  0
  7 12  1  1
  9 24  1  0
 24  6  1  0
 20 17  1  0
 13  7  1  0
 19  3  1  0
 17 11  2  0
 10  4  2  0
 17 14  1  0
 24  8  2  0
  2 20  1  0
  6 20  2  0
  1 18  1  0
  5 12  1  0
 15 22  1  0
  7 15  1  0
 25  2  2  0
  9  5  1  0
  6 10  1  0
 22  1  1  0
 13 21  1  6
 18 13  1  0
 14  9  2  0
 10 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3236761

   8-hydroxy-2-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methoxy]naphthalene-1,4-dione

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 366.32

Molecular Weight (Monoisotopic): 366.0951

AlogP: -0.87

#Rotatable Bonds: 4

Polar Surface Area: 142.75

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.09

CX Basic pKa: ┄

CX LogP: -0.34

CX LogD: -0.42

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.53

Np Likeness Score: 2.17

References

1. Pelageev DN, Dyshlovoy SA, Pokhilo ND, Denisenko VA, Borisova KL, Keller-von Amsberg G, Bokemeyer C, Fedorov SN, Honecker F, Anufriev VP..  (2014)  Quinone-carbohydrate nonglucoside conjugates as a new type of cytotoxic agents: synthesis and determination of in vitro activity.,  77  [PMID:24631733] [10.1016/j.ejmech.2014.03.006]

Source

Source(1):

• Scientific Literature