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Chemistry

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Also known as: Silymarin, Zinc4016719, N1711
Molecular Formula
C25H22O10
Molecular Weight
482.4  g/mol
InChI Key
SEBFKMXJBCUCAI-VDVKDMFPSA-N

AC1OFCT7
A mixture of flavonoids extracted from seeds of the MILK THISTLE, Silybum marianum. It consists primarily of silybin and its isomers, silicristin and silidianin. Silymarin displays antioxidant and membrane stabilizing activity. It protects various tissues and organs against chemical injury, and shows potential as an antihepatoxic agent.
1 2D Structure

AC1OFCT7

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S,3R)-3,5,7-trihydroxy-2-[(2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
2.1.2 InChI
InChI=1S/C25H22O10/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/h2-9,20,23-29,31H,10H2,1H3/t20-,23-,24-,25-/m0/s1
2.1.3 InChI Key
SEBFKMXJBCUCAI-VDVKDMFPSA-N
2.1.4 Canonical SMILES
COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O
2.1.5 Isomeric SMILES
COC1=C(C=CC(=C1)[C@H]2[C@@H](OC3=C(O2)C=C(C=C3)[C@H]4[C@H](C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Carsil

2. Karsil

3. Legalon

4. Silimarin

5. Silymarin

2.2.2 Depositor-Supplied Synonyms

1. Silymarin

2. Zinc4016719

3. N1711

2.3 Create Date
2006-07-29
3 Chemical and Physical Properties
Molecular Weight 482.4 g/mol
Molecular Formula C25H22O10
XLogP32.4
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count10
Rotatable Bond Count4
Exact Mass482.12129689 g/mol
Monoisotopic Mass482.12129689 g/mol
Topological Polar Surface Area155 Ų
Heavy Atom Count35
Formal Charge0
Complexity750
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Antioxidants

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)


Protective Agents

Synthetic or natural substances which are given to prevent a disease or disorder or are used in the process of treating a disease or injury due to a poisonous agent. (See all compounds classified as Protective Agents.)


4.2 ATC Code

A - Alimentary tract and metabolism

A05 - Bile and liver therapy

A05B - Liver therapy, lipotropics

A05BA - Liver therapy

A05BA03 - Silymarin


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