Methyl-6-O-(5,8-dihydroxynaphthalene-1,4-dione-2-yl)-alpha-D-glucopyranoside

ID: ALA3236759

PubChem CID: 90671095

Max Phase: Preclinical

Molecular Formula: C17H18O10

Molecular Weight: 382.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@H]1O[C@H](COC2=CC(=O)c3c(O)ccc(O)c3C2=O)[C@@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C17H18O10/c1-25-17-16(24)15(23)14(22)10(27-17)5-26-9-4-8(20)11-6(18)2-3-7(19)12(11)13(9)21/h2-4,10,14-19,22-24H,5H2,1H3/t10-,14-,15+,16-,17+/m1/s1

Standard InChI Key:  CRCUZMYCSZHCEV-AUMBKBSLSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    6.1512   -5.5909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5982   -6.3872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6319   -8.0393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2203   -8.8913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4612   -6.8448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1681   -6.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8916   -6.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9083   -7.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2018   -8.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4782   -7.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0187   -7.7655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4602   -8.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4590   -9.0178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1724   -9.4299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1706   -7.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8845   -8.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8854   -9.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5992   -9.4238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3129   -9.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3081   -8.1815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5937   -7.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1743  -10.2533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5892   -6.9518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6009  -10.2472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1682   -6.9568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7282   -8.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8557   -5.1646    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 26  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
 15 25  1  0
 20 11  1  0
 11 26  1  0
  1 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3236759

   methyl 6-O-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-alpha-d-glucopyranoside

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: 382.32

Molecular Weight (Monoisotopic): 382.0900

AlogP: -1.17

#Rotatable Bonds: 4

Polar Surface Area: 162.98

Molecular Species: NEUTRAL

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.38

CX Basic pKa: ┄

CX LogP: 0.01

CX LogD: -0.03

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.40

Np Likeness Score: 2.15

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