ContaminantDB: 2,3-Dehydrosilybin

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

Record Information

Version

1.0

Creation Date

2016-05-26 04:21:29 UTC

Update Date

2016-11-09 01:20:59 UTC

Accession Number

CHEM033693

Identification

Common Name

2,3-Dehydrosilybin

Class

Small Molecule

Description

2,3-Dehydrosilybin is found in coffee and coffee products. 2,3-Dehydrosilybin is a constituent of Silybum marianum (milk thistle).

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Dehydrosilybin	ChEMBL, HMDB
23-Dehydrosilybin	ChEMBL, HMDB
Hepa-merz sil	MeSH, HMDB
Hepatos	MeSH, HMDB
Lagosa	MeSH, HMDB
Durasilymarin	MeSH, HMDB
Heplant	MeSH, HMDB
Legalon forte	MeSH, HMDB
Silibin	MeSH, HMDB
Silibinin	MeSH, HMDB
Silybinin	MeSH, HMDB
Silybin	MeSH, HMDB
Alepa-forte	MeSH, HMDB
Ardeyhepan	MeSH, HMDB
Cefasilymarin	MeSH, HMDB
HepaBesch	MeSH, HMDB
Hepar-pasc	MeSH, HMDB
Heparsyx	MeSH, HMDB
Hepa-loges	MeSH, HMDB
Silybin b	MeSH
2,3-Dehydrosilybin	MeSH
Silybin a	MeSH
Hepar pasc	MeSH
Silibinin a	MeSH
2,3 Dehydrosilybin	MeSH
Alepa forte	MeSH
Hepa merz sil	MeSH
Hepa loges	MeSH
Silibinin b	MeSH

Chemical Formula

C₂₅H₂₀O₁₀

Average Molecular Mass

480.420 g/mol

Monoisotopic Mass

480.106 g/mol

CAS Registry Number

25166-14-7

IUPAC Name

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

Traditional Name

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

SMILES

COC1=C(O)C=CC(=C1)C1OC2=C(OC1CO)C=CC(=C2)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

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

InChI Key

BVKQRAYKLBRNIK-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as flavonolignans. These are non-conventional lignans that derived from flavonoids. They are characterized by a p-dioxin ring substituted at one carbon atom by a C3C6 (phenylpropan) group and fused to the B-ring of the 2-phenylchromene moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Flavonolignans

Sub Class

Not Available

Direct Parent

Flavonolignans

Alternative Parents

Substituents

Flavonolignan
3-hydroxyflavone
3-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
2-phenylbenzo-1,4-dioxane
Phenylbenzodioxane
Chromone
Benzo-1,4-dioxane
Benzodioxane
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Phenol
Pyranone
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Para-dioxin
Pyran
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	0.021 g/L	ALOGPS
logP	2.8	ALOGPS
logP	2.97	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	6.44	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	122.55 m³·mol⁻¹	ChemAxon
Polarizability	47.84 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uds-0500900000-56c1ffdd487032e6550d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-001i-0000009000-7578df2242c1dfa9bfd4	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0120900000-de60f08d2a03d1a527cd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0210900000-ff9d1c5d560f401da1c5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uy0-0950100000-4effdc8a32bf2e4e1e53	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000900000-e6f80131ca3aa2d3119b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-0210900000-e3ed41ab7917edead850	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-2890200000-2e4a737ea62863bdea05	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000900000-f2c2d8b84dce71fc9486	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0500900000-74cd390bce1dd7dabf64	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uy0-2923500000-1bed6f66ddab2b045fa3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000900000-3724d7f1c090543b5c7e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0000900000-448dd11750c5e850cab6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uyi-2910200000-24cf0a0fe0c4d789d082	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0040513

FooDB ID

FDB020279

Phenol Explorer ID

Not Available

KNApSAcK ID

C00054112

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

4578204

ChEBI ID

172705

PubChem Compound ID

5467200

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

2,3-Dehydrosilybin (CHEM033693)

Structure for CHEM033693: 2,3-Dehydrosilybin