ChemFOnt: Showing chemical card for Cyclolariciresinol (CFc000281255)

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

CFc000281255

Molecule Identification

Common Name

Cyclolariciresinol

Definition

Cyclolariciresinol is a member of the class of compounds known as 9,9p-dihydroxyaryltetralin lignans. 9,9p-dihydroxyaryltetralin lignans are lignans with a structure based on the 1-phenyltetralin skeleton carrying a hydroxyl group at the 9- and the 9'- position. Cyclolariciresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cyclolariciresinol can be found in sesame, which makes cyclolariciresinol a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2,3,4-Tetrahydro-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-6-methoxy-2,3-naphthalenedimethanol	ChEBI
(+)-Cyclolariciresinol	PhytoBank
(+)-Isolariciresinol	PhytoBank
Cyclolariciresinol	PhytoBank
alpha-Conidendryl alcohol	PhytoBank
α-Conidendryl alcohol	PhytoBank

Chemical Formula

C₂₀H₂₄O₆

Average Molecular Weight

360.401

Monoisotopic Molecular Weight

360.1572885

IUPAC Name

(6R,7R,8S)-8-(4-hydroxy-3-methoxyphenyl)-6,7-bis(hydroxymethyl)-3-methoxy-5,6,7,8-tetrahydronaphthalen-2-ol

Traditional Name

(6R,7R,8S)-8-(4-hydroxy-3-methoxyphenyl)-6,7-bis(hydroxymethyl)-3-methoxy-5,6,7,8-tetrahydronaphthalen-2-ol

CAS Registry Number

None

SMILES

COC1=C(O)C=C2[C@@H]([C@@H](CO)[C@H](CO)CC2=C1)C1=CC(OC)=C(O)C=C1

InChI Identifier

InChI=1S/C20H24O6/c1-25-18-6-11(3-4-16(18)23)20-14-8-17(24)19(26-2)7-12(14)5-13(9-21)15(20)10-22/h3-4,6-8,13,15,20-24H,5,9-10H2,1-2H3/t13-,15-,20-/m0/s1

InChI Key

OGFXBIXJCWAUCH-KPHUOKFYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 9,9p-dihydroxyaryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton carrying a hydroxyl group at the 9- and the 9'- position.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Aryltetralin lignans

Sub Class

9,9p-dihydroxyaryltetralin lignans

Direct Parent

9,9p-dihydroxyaryltetralin lignans

Alternative Parents

Substituents

9,9p-dihydroxyaryltetralin lignan
Methoxyphenol
Tetralin
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Ether
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Primary alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

polyphenol (CHEBI:69542 )
primary alcohol (CHEBI:69542 )
monomethoxybenzene (CHEBI:69542 )
lignan (CHEBI:69542 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301739)

Food

Herb and spice

Oilseed crop

Sesame (FooDB: FOOD00170)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.027 g/L	ALOGPS
logP	1.79	ALOGPS
logP	1.78	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.84	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	97.87 m³·mol⁻¹	ChemAxon
Polarizability	38.1 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0301739

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000328

KNApSAcK ID

C00007204

Chemspider ID

141054

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

69542

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Cyclolariciresinol (CFc000281255)

MOL for CFc000281255 (Cyclolariciresinol)

3D MOL for CFc000281255 (Cyclolariciresinol)

3D SDF for CFc000281255 (Cyclolariciresinol)

3D-SDF for CFc000281255 (Cyclolariciresinol)

PDB for CFc000281255 (Cyclolariciresinol)

3D PDB for CFc000281255 (Cyclolariciresinol)

SMILES for CFc000281255 (Cyclolariciresinol)

INCHI for CFc000281255 (Cyclolariciresinol)

Structure for CFc000281255 (Cyclolariciresinol)

3D Structure for CFc000281255 (Cyclolariciresinol)