ContaminantDB: Silybin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 03:59:55 UTC

Update Date

2016-11-09 01:15:32 UTC

Accession Number

CHEM017188

Identification

Common Name

Silybin

Class

Small Molecule

Description

A flavonolignan isolated from milk thistle, Silybum marianum, that has been shown to exhibit antioxidant and antineoplastic activities.

Contaminant Sources

FooDB Chemicals
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Flavobin	ChEBI
Karsil	ChEBI
Silibinina	ChEBI
Silibinine	ChEBI
Silibininum	ChEBI
Silybin	ChEBI
Silymarin	ChEBI
Silymarin I	Kegg
Legalon	Kegg
Silybin b	MeSH
Hepar pasc	MeSH
Ardeyhepan	MeSH
Cefasilymarin	MeSH
Hepa-merz sil	MeSH
Hepa-loges	MeSH
Legalon forte	MeSH
Silibinin b	MeSH
2,3 Dehydrosilybin	MeSH
Silibinin a	MeSH
Hepar-pasc	MeSH
Lagosa	MeSH
Silybinin	MeSH
Silybin a	MeSH
Heplant	MeSH
Alepa forte	MeSH
Alepa-forte	MeSH
HepaBesch	MeSH
2,3-Dehydrosilybin	MeSH
Durasilymarin	MeSH
Silibin	MeSH
Hepa loges	MeSH
Heparsyx	MeSH
Hepa merz sil	MeSH
Silibinin	MeSH
Hepatos	MeSH

Chemical Formula

C₂₅H₂₂O₁₀

Average Molecular Mass

482.441 g/mol

Monoisotopic Mass

482.121 g/mol

CAS Registry Number

22888-70-6

IUPAC Name

(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

silibinin

SMILES

[H][C@@]1(OC2=C(O[C@@H]1CO)C=CC(=C2)[C@@]1([H])OC2=C(C(O)=CC(O)=C2)C(=O)[C@@H]1O)C1=CC(OC)=C(O)C=C1

InChI Identifier

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-/m1/s1

InChI Key

SEBFKMXJBCUCAI-HKTJVKLFSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Styrene
Benzenoid
Monocyclic benzene moiety
Aromatic hydrocarbon
Cyclic olefin
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

stilbene (CHEBI:36007 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.093 g/L	ALOGPS
logP	2.35	ALOGPS
logP	2.63	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	7.75	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	120.29 m³·mol⁻¹	ChemAxon
Polarizability	48.41 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0gvk-2952100000-c3d2a818a44f51b39801	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0ue9-0943800000-af015f0adf79e0968a5a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0gvk-2952100000-c3d2a818a44f51b39801	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0f7k-0931200000-a04a951f896c0248d2fe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0230900000-300bc825bbe98458b2bf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f79-0741900000-d501c9b910b2d5fdab53	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uk9-0920000000-fa7604cbd3962727b9f7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0101900000-89dc501a9aa86eeb6450	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0wpi-0632900000-9280d934e31287af1255	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fs9-1930000000-cb4cf324a6790d4133c7	Spectrum