7-O-Methylisosilychristin

ID: ALA2397732

PubChem CID: 73349003

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](c1ccc(O)c3c1[C@@H](CO)[C@H](c1ccc(O)c(OC)c1)O3)[C@@H](O)C2=O

Standard InChI:  InChI=1S/C26H24O10/c1-33-12-8-17(30)21-19(9-12)35-25(23(32)22(21)31)13-4-6-16(29)26-20(13)14(10-27)24(36-26)11-3-5-15(28)18(7-11)34-2/h3-9,14,23-25,27-30,32H,10H2,1-2H3/t14-,23+,24+,25-/m1/s1

Standard InChI Key:  VVQOMYSMOUXQNI-VEIHWBNBSA-N

Molfile:  

     RDKit          2D

 36 40  0  0  0  0  0  0  0  0999 V2000
   22.7024  -27.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7013  -28.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4162  -28.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4144  -27.0328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1297  -27.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1331  -28.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8522  -28.6862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5727  -28.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5692  -27.4360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8455  -27.0200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2814  -27.0216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9974  -27.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7078  -27.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2882  -28.6795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4147  -29.5107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8546  -29.5112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9879  -27.0332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7093  -26.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2775  -26.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9868  -25.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8097  -24.9797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9907  -24.8999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6619  -25.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4222  -25.7764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5727  -24.1886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9838  -23.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5665  -22.7629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7407  -22.7688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3339  -23.4915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7535  -24.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3217  -22.0581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9738  -22.0455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7988  -22.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8563  -25.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2995  -25.2230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9877  -26.2082    0.0000 C   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  1  0
  9 10  1  0
 11 12  2  0
 12 13  1  0
 19 11  1  0
  9 11  1  6
 18 13  2  0
  8 14  1  1
  3 15  1  0
  7 16  2  0
  1 17  1  0
 20 18  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 19  1  0
 18 24  1  0
 22 25  1  6
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 28 31  1  0
 27 32  1  0
 32 33  1  0
 23 34  1  1
 34 35  1  0
 17 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2397732

   (2R,3R)-3,5-dihydroxy-2-[(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-4-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: 2.71

#Rotatable Bonds: 5

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: 8.53

CX Basic pKa: ┄

CX LogP: 2.44

CX LogD: 2.41

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.36

Np Likeness Score: 1.87

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