(2R,3R)-3,5,7-Trihydroxy-2-[(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-3-hydroxymethyl-2,3-dihydro-benzofuran-5-yl]-chroman-4-one

ID: ALA4802105

PubChem CID: 12442781

Max Phase: Phase

Molecular Formula: C25H22O10

Molecular Weight: 482.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C2Oc3c(O)cc([C@H]4Oc5cc(O)cc(O)c5C(=O)[C@@H]4O)cc3C2CO)ccc1O

Standard InChI:  InChI=1S/C25H22O10/c1-33-18-6-10(2-3-15(18)28)23-14(9-26)13-4-11(5-17(30)25(13)35-23)24-22(32)21(31)20-16(29)7-12(27)8-19(20)34-24/h2-8,14,22-24,26-30,32H,9H2,1H3/t14?,22-,23?,24+/m0/s1

Standard InChI Key:  BMLIIPOXVWESJG-CMIZNHKFSA-N

Molfile:  

     RDKit          2D

 35 39  0  0  0  0  0  0  0  0999 V2000
   -3.0812   -0.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3667   -1.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4912    0.4484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4912    1.2734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3667    0.4484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2758    1.5284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0812    0.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6522    0.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6522   -0.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7607    0.8609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2758    0.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9377    0.4484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7956   -1.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2233    0.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5857    0.8609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2233    1.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9377    1.2734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7956    0.4484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5101   -0.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9982    0.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8232    0.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3667   -2.0266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5101    0.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2357    0.8609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9982    1.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8232    1.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9377   -1.2016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7956   -2.0266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2233    2.5109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5308   -0.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2357   -0.5680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0607    0.8609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2246    0.4484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9787   -1.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0607   -0.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3 14  1  0
  4 16  1  0
  5  7  1  0
  6  4  1  0
  7  1  2  0
  8  5  1  0
  9  2  1  0
 10 11  1  0
 11  3  1  0
  8 12  1  6
 13  1  1  0
 14 12  2  0
 10 15  1  0
 16 17  2  0
 17 12  1  0
 18  7  1  0
 19 13  2  0
 20 15  2  0
 21 20  1  0
 22  2  2  0
 23 19  1  0
 24 26  1  0
 25 15  1  0
 26 25  2  0
  9 27  1  1
 28 13  1  0
 29 16  1  0
 11 30  1  0
 31 21  1  0
 32 24  1  0
 33 23  1  0
 34 30  1  0
 35 31  1  0
  9  8  1  0
 18 23  2  0
  3  4  2  0
  6 10  1  0
 21 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4802105

   SILICRISTIN

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: Yes

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: 2.29

References

1. Checa A, Ortiz AR, de Pascual-Teresa B, Gago F..  (1997)  Assessment of solvation effects on calculated binding affinity differences: trypsin inhibition by flavonoids as a model system for congeneric series.,  40  (25): [PMID:9406602] [10.1021/jm970245v]

2. Parellada J, Guinea M..  (1995)  Flavonoid inhibitors of trypsin and leucine aminopeptidase: a proposed mathematical model for IC50 estimation.,  58  (6): [PMID:7673925] [10.1021/np50120a001]

3. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

4. 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]

5. Pferschy-Wenzig EM, Atanasov AG, Malainer C, Noha SM, Kunert O, Schuster D, Heiss EH, Oberlies NH, Wagner H, Bauer R, Dirsch VM..  (2014)  Identification of isosilybin a from milk thistle seeds as an agonist of peroxisome proliferator-activated receptor gamma.,  77  (4): [PMID:24597776] [10.1021/np400943b]

6. Köck K, Xie Y, Hawke RL, Oberlies NH, Brouwer KL..  (2013)  Interaction of silymarin flavonolignans with organic anion-transporting polypeptides.,  41  (5): [PMID:23401473] [10.1124/dmd.112.048272]

7. 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(2):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names