Isosilychristin

ID: ALA2397731

Cas Number: 77182-66-2

PubChem CID: 21589839

Max Phase: Preclinical

Molecular Formula: C25H22O10

Molecular Weight: 482.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc([C@@H]2Oc3c(O)ccc([C@H]4Oc5cc(O)cc(O)c5C(=O)[C@@H]4O)c3[C@H]2CO)ccc1O

Standard InChI:  InChI=1S/C25H22O10/c1-33-17-6-10(2-4-14(17)28)23-13(9-26)19-12(3-5-15(29)25(19)35-23)24-22(32)21(31)20-16(30)7-11(27)8-18(20)34-24/h2-8,13,22-24,26-30,32H,9H2,1H3/t13-,22+,23+,24-/m1/s1

Standard InChI Key:  QYCJAWYDGRZSTO-IRLTUAEKSA-N

Molfile:  

     RDKit          2D

 35 39  0  0  0  0  0  0  0  0999 V2000
   13.8859  -27.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8848  -28.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5995  -28.6524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5977  -26.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3132  -27.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3166  -28.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0357  -28.6529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7561  -28.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7527  -27.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0289  -26.9867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4648  -26.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1809  -27.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8913  -26.9873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4717  -28.6462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5981  -29.4774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0380  -29.4779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1713  -26.9998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8927  -26.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4609  -26.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1703  -25.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9931  -24.9463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1741  -24.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8453  -25.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6056  -25.7431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7561  -24.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1673  -23.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7499  -22.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9241  -22.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5173  -23.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9370  -24.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5052  -22.0248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1573  -22.0121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9823  -22.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0397  -25.7985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4830  -25.1896    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  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
M  END

Alternative Forms

1. Parent:

   

   ALA2397731

   ISOSILYCHRISTIN

Molecule Features

Natural Product: Yes

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: 2.40

#Rotatable Bonds: 4

Polar Surface Area: 166.14

Molecular Species: NEUTRAL

HBA: 10

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.75

CX Basic pKa: ┄

CX LogP: 2.30

CX LogD: 2.13

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.33

Np Likeness Score: 2.07

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]

2. Biedermann D, Buchta M, Holečková V, Sedlák D, Valentová K, Cvačka J, Bednárová L, Křenková A, Kuzma M, Škuta C, Peikerová Ž, Bartůněk P, Křen V..  (2016)  Silychristin: Skeletal Alterations and Biological Activities.,  79  (12): [PMID:28006905] [10.1021/acs.jnatprod.6b00750]

Source

Source(1):

• Scientific Literature