7-O-Methylisosilybin A

ID: ALA2397728

PubChem CID: 71713316

Max Phase: Preclinical

Molecular Formula: C26H24O10

Molecular Weight: 496.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(O)c2c(c1)O[C@H](c1ccc3c(c1)O[C@H](CO)[C@@H](c1ccc(O)c(OC)c1)O3)[C@@H](O)C2=O

Standard InChI:  InChI=1S/C26H24O10/c1-32-14-9-16(29)22-20(10-14)36-26(24(31)23(22)30)13-4-6-17-19(8-13)34-21(11-27)25(35-17)12-3-5-15(28)18(7-12)33-2/h3-10,21,24-29,31H,11H2,1-2H3/t21-,24+,25-,26-/m1/s1

Standard InChI Key:  MYYFXVDERGWZEA-GGLXGSTNSA-N

Molfile:  

     RDKit          2D

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   24.0179   -9.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7327  -10.0068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7309   -8.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4463   -8.7629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   26.8892   -9.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8858   -8.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   27.5979   -8.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   29.0245   -7.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   26.1711  -10.8322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3044   -8.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.1684   -7.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1670   -8.7555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1657   -9.5805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8778   -7.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5922   -7.1089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   33.3081   -5.8705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   23.3043   -7.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  5  4  2  0
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 15 13  1  0
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  9 11  1  6
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 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  8 21  1  1
  3 22  1  0
  7 23  2  0
  1 24  1  0
 19 25  1  6
 18 26  1  1
 26 27  1  0
 25 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 25  1  0
 30 33  1  0
 29 34  1  0
 34 35  1  0
 24 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2397728

   (2R,3R)-3,5-dihydroxy-2-[(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-7-methoxy-2,3-dihydrochromen-4-one

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: 496.47

Molecular Weight (Monoisotopic): 496.1369

AlogP: 2.67

#Rotatable Bonds: 5

Polar Surface Area: 144.14

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.55

CX Basic pKa: ┄

CX LogP: 2.78

CX LogD: 2.75

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.42

Np Likeness Score: 1.76

References

1. Althagafy HS, Graf TN, Sy-Cordero AA, Gufford BT, Paine MF, Wagoner J, Polyak SJ, Croatt MP, Oberlies NH..  (2013)  Semisynthesis, cytotoxicity, antiviral activity, and drug interaction liability of 7-O-methylated analogues of flavonolignans from milk thistle.,  21  (13): [PMID:23673225] [10.1016/j.bmc.2013.04.017]

Source

Source(1):

• Scientific Literature