ChemFOnt: Showing chemical card for Secoisolariciresinol-sesquilignan (CFc000281254)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:27 UTC

Chemfont ID

CFc000281254

Molecule Identification

Common Name

Secoisolariciresinol-sesquilignan

Definition

Secoisolariciresinol-sesquilignan is a member of the class of compounds known as dibenzylbutanediol lignans. Dibenzylbutanediol lignans are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety. Secoisolariciresinol-sesquilignan is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Secoisolariciresinol-sesquilignan can be found in sesame, which makes secoisolariciresinol-sesquilignan a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₃₀H₃₈O₁₀

Average Molecular Weight

558.6167

Monoisotopic Molecular Weight

558.246497436

IUPAC Name

2-[(4-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3-methoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol

Traditional Name

2-[(4-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3-methoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol

CAS Registry Number

None

SMILES

COC1=CC(CC(CO)C(CO)CC2=CC=C(OC(CO)C(O)C3=CC=C(O)C(OC)=C3)C(OC)=C2)=CC=C1O

InChI Identifier

InChI=1S/C30H38O10/c1-37-26-12-18(4-7-23(26)34)10-21(15-31)22(16-32)11-19-5-9-25(28(13-19)39-3)40-29(17-33)30(36)20-6-8-24(35)27(14-20)38-2/h4-9,12-14,21-22,29-36H,10-11,15-17H2,1-3H3

InChI Key

XPALWKWOFOYYIV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutanediol lignans. These are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Dibenzylbutane lignans

Sub Class

Dibenzylbutanediol lignans

Direct Parent

Dibenzylbutanediol lignans

Alternative Parents

Substituents

Dibenzylbutanediol
Methoxyphenol
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Ether
Aromatic alcohol
Primary alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301738)

Food

Herb and spice

Oilseed crop

Sesame (FooDB: FOOD00170)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0076 g/L	ALOGPS
logP	2.65	ALOGPS
logP	2.48	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	9.75	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	158.3 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	148.75 m³·mol⁻¹	ChemAxon
Polarizability	59.04 Å³	ChemAxon
Number of Rings	3	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

HMDB0301738

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000327

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

59728532

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Secoisolariciresinol-sesquilignan (CFc000281254)

MOL for CFc000281254 (Secoisolariciresinol-sesquilignan)

3D MOL for CFc000281254 (Secoisolariciresinol-sesquilignan)

3D SDF for CFc000281254 (Secoisolariciresinol-sesquilignan)

3D-SDF for CFc000281254 (Secoisolariciresinol-sesquilignan)

PDB for CFc000281254 (Secoisolariciresinol-sesquilignan)

3D PDB for CFc000281254 (Secoisolariciresinol-sesquilignan)

SMILES for CFc000281254 (Secoisolariciresinol-sesquilignan)

INCHI for CFc000281254 (Secoisolariciresinol-sesquilignan)

Structure for CFc000281254 (Secoisolariciresinol-sesquilignan)

3D Structure for CFc000281254 (Secoisolariciresinol-sesquilignan)