7-O-Methylisosilybin B

ID: ALA2397729

PubChem CID: 71713317

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+/m0/s1

Standard InChI Key:  MYYFXVDERGWZEA-CPPMQADQSA-N

Molfile:  

     RDKit          2D

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   17.4604  -17.9248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   18.8868  -15.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  8 21  1  1
  3 22  1  0
  7 23  2  0
  1 24  1  0
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 34 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2397729

   (2R,3R)-3,5-dihydroxy-2-[(2S,3S)-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