ID: ALA38464

Max Phase: Preclinical

Molecular Formula: C25H20O10

Molecular Weight: 480.43

Molecule Type: Small molecule

Representations

Synonyms (3): 2,3-Dehydrosilybin | Dehydrosilybin | Dehydrosilylbin
Synonyms from Alternative Forms(3):

Canonical SMILES:  COc1cc(C2Oc3cc(-c4oc5cc(O)cc(O)c5c(=O)c4O)ccc3OC2CO)ccc1O

Standard InChI:  InChI=1S/C25H20O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,24,26-29,31H,10H2,1H3

Standard InChI Key:  BVKQRAYKLBRNIK-UHFFFAOYSA-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: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 480.43

Molecular Weight (Monoisotopic): 480.1056

AlogP: 3.16

#Rotatable Bonds: 4

Polar Surface Area: 159.05

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 6.38

CX Basic pKa:

CX LogP: 2.97

CX LogD: 1.84

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.29

Np Likeness Score: 1.85

References

1. Maitrejean M, Comte G, Barron D, El Kirat K, Conseil G, Di Pietro A..  (2000)  The flavanolignan silybin and its hemisynthetic derivatives, a novel series of potential modulators of P-glycoprotein.,  10  (2): [PMID:10673101] [10.1016/s0960-894x(99)00636-8]

2. Häcker HG, Leyers S, Wiendlocha J, Gütschow M, Wiese M..  (2009)  Aromatic 2-(thio)ureidocarboxylic acids as a new family of modulators of multidrug resistance-associated protein 1: synthesis, biological evaluation, and structure-activity relationships.,  52  (15): [PMID:19580319] [10.1021/jm900688v]

3. Yang LX, Huang KX, Li HB, Gong JX, Wang F, Feng YB, Tao QF, Wu YH, Li XK, Wu XM, Zeng S, Spencer S, Zhao Y, Qu J..  (2009)  Design, synthesis, and examination of neuron protective properties of alkenylated and amidated dehydro-silybin derivatives.,  52  (23): [PMID:19673490] [10.1021/jm900735p]

4. Zarrelli A, Sgambato A, Petito V, De Napoli L, Previtera L, Di Fabio G..  (2011)  New C-23 modified of silybin and 2,3-dehydrosilybin: synthesis and preliminary evaluation of antioxidant properties.,  21  (15): [PMID:21737270] [10.1016/j.bmcl.2011.06.049]

5. PubChem BioAssay data set, 

6. Zhang S, Vue B, Huang M, Zhang X, Lee T, Chen G, Zhang Q, Zheng S, Wang G, Chen QH..  (2016)  3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.,  26  (14): [PMID:27261177] [10.1016/j.bmcl.2016.05.069]

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]

8. Karas D, Gažák R, Valentová K, Chambers CS, Pivodová V, Biedermann D, Křenková A, Oborná I, Kuzma M, Cvačka J, Ulrichová J, Křen V..  (2016)  Effects of 2,3-Dehydrosilybin and Its Galloyl Ester and Methyl Ether Derivatives on Human Umbilical Vein Endothelial Cells.,  79  (4): [PMID:27015547] [10.1021/acs.jnatprod.5b00905]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays