Silibinin

ID: ALA3739556

PubChem CID: 127038404

Max Phase: Preclinical

Molecular Formula: C25H22O10

Molecular Weight: 482.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc([C@H]2Oc3cc([C@H]4Oc5cc(O)c(O)cc5C(=O)[C@@H]4O)ccc3O[C@@H]2CO)ccc1O

Standard InChI:  InChI=1S/C25H22O10/c1-32-19-6-11(2-4-14(19)27)24-21(10-26)33-17-5-3-12(7-20(17)35-24)25-23(31)22(30)13-8-15(28)16(29)9-18(13)34-25/h2-9,21,23-29,31H,10H2,1H3/t21-,23+,24-,25-/m1/s1

Standard InChI Key:  PEMNNSUBNJRXIZ-RVFVQDDPSA-N

Molfile:  

     RDKit          2D

 35 39  0  0  0  0  0  0  0  0999 V2000
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9086    1.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2105    0.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5102    1.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9053    3.0146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1960    3.7730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4984    3.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7892    3.7930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7774    5.2900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4749    6.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1842    5.2700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2229   -0.4368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5559    0.9487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4657    7.2285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8119    5.8981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8911   -1.5017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8894   -2.7017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8926    1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8951    2.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1953    3.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4931    2.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4907    1.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1905    0.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1946    5.2478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1555    5.8480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5333    3.5932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 11 12  1  0
 11 14  1  0
 12 13  1  0
 13 16  1  0
 15 14  1  0
 11  2  1  6
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 12 21  1  1
 13 22  2  0
 19 23  1  0
 18 24  1  0
  8 25  1  1
 25 26  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
  9 27  1  6
 33 34  1  0
 29 33  1  0
 30 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3739556

   ---

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: 482.44

Molecular Weight (Monoisotopic): 482.1213

AlogP: 2.36

#Rotatable Bonds: 4

Polar Surface Area: 155.14

Molecular Species: NEUTRAL

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.79

CX Basic pKa: ┄

CX LogP: 1.98

CX LogD: 1.83

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.35

Np Likeness Score: 1.81

References

1. Zemanova L, Hofman J, Novotna E, Musilek K, Lundova T, Havrankova J, Hostalkova A, Chlebek J, Cahlikova L, Wsol V..  (2015)  Flavones Inhibit the Activity of AKR1B10, a Promising Therapeutic Target for Cancer Treatment.,  78  (11): [PMID:26529431] [10.1021/acs.jnatprod.5b00616]

Source

Source(1):

• Scientific Literature