Methyl-6-O-(5-hydroxynaphthalene-1,4-dione-2-yl)-alpha-D-glucopyranoside

ID: ALA3236760

PubChem CID: 90671096

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)c3c(O)cccc3C2=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)12-7(13(10)20)3-2-4-8(12)18/h2-5,11,14-18,21-23H,6H2,1H3/t11-,14-,15+,16-,17+/m1/s1

Standard InChI Key:  FKBLMGDBUJPMMF-UFRBAHOGSA-N

Molfile:  

     RDKit          2D

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   15.3047   -5.3749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7518   -6.1713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7853   -7.8235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3737   -8.6755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6145   -6.6288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3216   -6.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0451   -6.5945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0618   -7.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3551   -7.8485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6316   -7.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1720   -7.5496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6133   -7.9762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6122   -8.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3256   -9.2141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3237   -7.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0378   -7.9726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0385   -8.7978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7525   -9.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4661   -8.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4614   -7.9656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7469   -7.5593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3275  -10.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7425   -6.7359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7542  -10.0314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8815   -7.9596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0091   -4.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 25  1  1
  6  1  1  6
  7  2  1  6
  8  3  1  1
  9  4  1  6
 12 13  1  0
 13 14  2  0
 14 17  1  0
 16 15  1  0
 15 12  2  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 16  1  0
 14 22  1  0
 21 23  2  0
 18 24  2  0
 20 11  1  0
 11 25  1  0
  1 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3236760

   5-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: 8.18

CX Basic pKa: ┄

CX LogP: -0.34

CX LogD: -0.40

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.53

Np Likeness Score: 2.14

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