ChemFOnt: Showing chemical card for Limonoate a-ring-lactone (CFc000282053)

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

CFc000282053

Molecule Identification

Common Name

Limonoate a-ring-lactone

Definition

Limonoate a-ring-lactone 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. Limonoate a-ring-lactone is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Limonoate a-ring-lactone can be found in lemon and sweet orange, which makes limonoate a-ring-lactone a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Limonoic acid a-ring-lactone	Generator

Chemical Formula

C₂₆H₃₂O₉

Average Molecular Weight

488.533

Monoisotopic Molecular Weight

488.20463261

IUPAC Name

(1'R,2R,2'R,3S,5'S,7'R,10'R,13'S)-5'-[(R)-(furan-3-yl)(hydroxy)methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadecane]-3-carboxylic acid

Traditional Name

limonoate A-ring-lactone

CAS Registry Number

None

SMILES

[H][C@](O)(C1=COC=C1)[C@]1(C)CC[C@]2([H])[C@@]34COC(=O)C[C@]3([H])OC(C)(C)[C@]4([H])CC(=O)[C@@]2(C)[C@]11O[C@]1([H])C(O)=O

InChI Identifier

InChI=1S/C26H32O9/c1-22(2)15-9-16(27)24(4)14(25(15)12-33-18(28)10-17(25)34-22)5-7-23(3,19(29)13-6-8-32-11-13)26(24)20(35-26)21(30)31/h6,8,11,14-15,17,19-20,29H,5,7,9-10,12H2,1-4H3,(H,30,31)/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1

InChI Key

JQTDUZWQZNXSOU-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
Delta valerolactone
Delta_valerolactone
Dicarboxylic acid or derivatives
Oxane
Oxirane carboxylic acid
Oxirane carboxylic acid or derivatives
Furan
Heteroaromatic compound
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid
Organoheterocyclic compound
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Aromatic alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

limonoid (CHEBI:80679 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302537)

Food

Fruit

Citrus

Lemon (FooDB: FOOD00054)
Sweet orange (FooDB: FOOD00057)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.37	ALOGPS
logP	1.79	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.07	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	135.8 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	118.21 m³·mol⁻¹	ChemAxon
Polarizability	49.21 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0302537

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005048

KNApSAcK ID

Not Available

Chemspider ID

30791758

KEGG Compound ID

C16718

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46173816

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Limonoate a-ring-lactone (CFc000282053)

MOL for CFc000282053 (Limonoate a-ring-lactone)

3D MOL for CFc000282053 (Limonoate a-ring-lactone)

3D SDF for CFc000282053 (Limonoate a-ring-lactone)

3D-SDF for CFc000282053 (Limonoate a-ring-lactone)

PDB for CFc000282053 (Limonoate a-ring-lactone)

3D PDB for CFc000282053 (Limonoate a-ring-lactone)

SMILES for CFc000282053 (Limonoate a-ring-lactone)

INCHI for CFc000282053 (Limonoate a-ring-lactone)

Structure for CFc000282053 (Limonoate a-ring-lactone)

3D Structure for CFc000282053 (Limonoate a-ring-lactone)