ID: ALA4802105

Max Phase: Phase

Molecular Formula: C25H22O10

Molecular Weight: 482.44

Molecule Type: Small molecule

Representations

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

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

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