ChemFOnt: Showing chemical card for Linonin (CFc000282054)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:02 UTC

Chemfont ID

CFc000282054

Molecule Identification

Common Name

Linonin

Definition

Linonin, also known as 7,16-dioxo-7,16-dideoxylimondiol or evodin, is a member of the class of compounds known as limonoids. Limonoids are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. Linonin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Linonin can be found in lemon, which makes linonin a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
7,16-Dioxo-7,16-dideoxylimondiol	ChEBI
Citrolimonin	ChEBI
Dictamnolactone	ChEBI
Evodia fruit	ChEBI
Evodin	ChEBI
Limonoate D-ring-lactone	ChEBI
Limonoic acid 3,19:16,17-dilactone	ChEBI
Limonoic acid, di-delta-lactone	ChEBI
Obaculactone	ChEBI
Limonoic acid D-ring-lactone	Generator
Limonoate 3,19:16,17-dilactone	Generator
Limonoate, di-delta-lactone	Generator
Limonoate, di-δ-lactone	Generator
Limonoic acid, di-δ-lactone	Generator

Chemical Formula

C₂₆H₃₀O₈

Average Molecular Weight

470.518

Monoisotopic Molecular Weight

470.194067926

IUPAC Name

(1R,2R,7S,10R,13R,14R,16S,19R,20S)-19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione

Traditional Name

limonin

CAS Registry Number

1180-71-8

SMILES

CC1(C)O[C@H]2CC(=O)OC[C@@]22[C@H]1CC(=O)[C@]1(C)[C@@H]2CC[C@@]2(C)[C@@H](OC(=O)[C@H]3O[C@@]123)C1=COC=C1

InChI Identifier

InChI=1S/C26H30O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-15,17,19-20H,5,7,9-10,12H2,1-4H3/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1

InChI Key

KBDSLGBFQAGHBE-MSGMIQHVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Steroid lactone
11-oxosteroid
Oxosteroid
2-oxosteroid
Steroid
Naphthopyran
Naphthalene
Delta valerolactone
Dioxepane
1,4-dioxepane
Delta_valerolactone
Pyran
Oxane
Dicarboxylic acid or derivatives
Tetrahydrofuran
Heteroaromatic compound
Furan
Carboxylic acid ester
Lactone
Ketone
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Oxirane
Ether
Organooxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

epoxide (CHEBI:16226 )
organic heterohexacyclic compound (CHEBI:16226 )
furans (CHEBI:16226 )
lactone (CHEBI:16226 )
limonoid (CHEBI:16226 )
hexacyclic triterpenoid (CHEBI:16226 )
Limonoids (C03514 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302538)

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.08 g/L	ALOGPS
logP	3.47	ALOGPS
logP	2.46	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	17.61	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	104.57 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	114.72 m³·mol⁻¹	ChemAxon
Polarizability	47.81 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon