ChemFOnt: Showing chemical card for Diarctigenin (CFc000281575)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:33:06 UTC

Chemfont ID

CFc000281575

Molecule Identification

Common Name

Diarctigenin

Definition

Diarctigenin is a member of the class of compounds known as dibenzylbutyrolactone lignans. Dibenzylbutyrolactone lignans are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. Diarctigenin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Diarctigenin can be found in burdock, which makes diarctigenin a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₄₂H₄₆O₁₂

Average Molecular Weight

742.8074

Monoisotopic Molecular Weight

742.298926936

IUPAC Name

(3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-{[3-(5-{[(3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-2-oxooxolan-3-yl]methyl}-2-hydroxy-3-methoxyphenyl)-4-hydroxy-5-methoxyphenyl]methyl}oxolan-2-one

Traditional Name

(3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-{[3-(5-{[(3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-2-oxooxolan-3-yl]methyl}-2-hydroxy-3-methoxyphenyl)-4-hydroxy-5-methoxyphenyl]methyl}oxolan-2-one

CAS Registry Number

160433-41-0

SMILES

COC1=CC(C[C@@H]2[C@@H](CC3=CC(OC)=C(OC)C=C3)COC2=O)=CC(=C1O)C1=C(O)C(OC)=CC(C[C@@H]2[C@@H](CC3=CC(OC)=C(OC)C=C3)COC2=O)=C1

InChI Identifier

InChI=1S/C42H46O12/c1-47-33-9-7-23(17-35(33)49-3)11-27-21-53-41(45)29(27)13-25-15-31(39(43)37(19-25)51-5)32-16-26(20-38(52-6)40(32)44)14-30-28(22-54-42(30)46)12-24-8-10-34(48-2)36(18-24)50-4/h7-10,15-20,27-30,43-44H,11-14,21-22H2,1-6H3/t27-,28-,29+,30+/m0/s1

InChI Key

XYMRYKOVQDOJFH-VZNYXHRGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

Dibenzylbutyrolactone lignans

Alternative Parents

Substituents

Dibenzylbutyrolactone
Lignan lactone
Linear 1,7-diphenylheptane skeleton
Biphenyl
Methoxyphenol
Dimethoxybenzene
O-dimethoxybenzene
Anisole
Phenoxy compound
Methoxybenzene
Phenol ether
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Gamma butyrolactone
Dicarboxylic acid or derivatives
Tetrahydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Ether
Organoheterocyclic compound
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302059)

Food

Vegetable

Root vegetable

Burdock (FooDB: FOOD00017)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00094 g/L	ALOGPS
logP	5.75	ALOGPS
logP	6.55	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	9.17	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	148.44 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	199.31 m³·mol⁻¹	ChemAxon
Polarizability	77.77 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0302059

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001807

KNApSAcK ID

Not Available

Chemspider ID

17343375

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16215736

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Diarctigenin (CFc000281575)

MOL for CFc000281575 (Diarctigenin)

3D MOL for CFc000281575 (Diarctigenin)

3D SDF for CFc000281575 (Diarctigenin)

3D-SDF for CFc000281575 (Diarctigenin)

PDB for CFc000281575 (Diarctigenin)

3D PDB for CFc000281575 (Diarctigenin)

SMILES for CFc000281575 (Diarctigenin)

INCHI for CFc000281575 (Diarctigenin)

Structure for CFc000281575 (Diarctigenin)

3D Structure for CFc000281575 (Diarctigenin)