7-O-galloyl-2,3-dehydrosilybin

ID: ALA4527061

PubChem CID: 132519867

Max Phase: Preclinical

Molecular Formula: C32H24O14

Molecular Weight: 632.53

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(C2Oc3cc(-c4oc5cc(OC(=O)c6cc(O)c(O)c(O)c6)cc(O)c5c(=O)c4O)ccc3OC2CO)ccc1O

Standard InChI:  InChI=1S/C32H24O14/c1-42-22-8-13(2-4-17(22)34)30-25(12-33)44-21-5-3-14(9-23(21)45-30)31-29(40)28(39)26-18(35)10-16(11-24(26)46-31)43-32(41)15-6-19(36)27(38)20(37)7-15/h2-11,25,30,33-38,40H,12H2,1H3

Standard InChI Key:  WYVRNHJWFHVFAT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 46 51  0  0  0  0  0  0  0  0999 V2000
    3.7172   -5.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7161   -6.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4241   -7.1675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4223   -5.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1309   -5.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1343   -6.7606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8467   -7.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5603   -6.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5569   -5.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8399   -5.5177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8489   -7.9852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0094   -5.5306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4227   -7.9847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2633   -5.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9715   -5.9273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9615   -4.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2584   -4.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6754   -4.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6752   -5.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3806   -5.9256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0906   -5.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0908   -4.6994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3809   -4.2874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7990   -4.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8000   -3.4745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7977   -5.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7928   -6.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4990   -7.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2083   -6.7471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2070   -5.9257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5002   -5.5197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9159   -7.1559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9139   -5.5157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6224   -5.9229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2691   -7.1615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0092   -4.7134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3014   -4.3050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7168   -4.3047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3024   -3.4870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5954   -3.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8879   -3.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8933   -4.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5972   -4.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1788   -3.0814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5953   -2.2615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1873   -4.7205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  7 11  2  0
  1 12  1  0
  3 13  1  0
  9 14  1  0
 14 15  2  0
 15 19  1  0
 18 16  1  0
 16 17  2  0
 17 14  1  0
 18 19  2  0
 18 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 21 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 29 32  1  0
 30 33  1  0
 33 34  1  0
  8 35  1  0
 12 36  1  0
 36 37  1  0
 36 38  2  0
 37 39  2  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 42 43  2  0
 43 37  1  0
 41 44  1  0
 40 45  1  0
 42 46  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4527061

   ---

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: 632.53

Molecular Weight (Monoisotopic): 632.1166

AlogP: 3.79

#Rotatable Bonds: 6

Polar Surface Area: 225.81

Molecular Species: NEUTRAL

HBA: 14

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 14

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 6.66

CX Basic pKa: ┄

CX LogP: 4.02

CX LogD: 3.08

Aromatic Rings: 5

Heavy Atoms: 46

QED Weighted: 0.08

Np Likeness Score: 1.40

References

1. Karas D, Gažák R, Valentová K, Chambers CS, Pivodová V, Biedermann D, Křenková A, Oborná I, Kuzma M, Cvačka J, Ulrichová J, Křen V..  (2016)  Effects of 2,3-Dehydrosilybin and Its Galloyl Ester and Methyl Ether Derivatives on Human Umbilical Vein Endothelial Cells.,  79  (4): [PMID:27015547] [10.1021/acs.jnatprod.5b00905]

Source

Source(1):

• Scientific Literature