ChemFOnt: Showing chemical card for Isolimonic acid (CFc000019075)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:09:53 UTC

Chemfont ID

CFc000019075

Molecule Identification

Common Name

Isolimonic acid

Definition

Isolimonic acid is found in citrus. Isolimonic acid is a constituent of Citrus species.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Isolimonate	Generator
(3's,5AR,6R,7S,9BR)-9b-(2-carboxy-1-hydroxyethyl)-7-[(R)-(furan-3-yl)(hydroxy)methyl]-3,3,5a,7-tetramethyl-5-oxo-decahydro-1H-spiro[naphtho[1,2-c]furan-6,2'-oxirane]-3'-carboxylate	HMDB

Chemical Formula

C₂₆H₃₄O₁₀

Average Molecular Weight

506.5422

Monoisotopic Molecular Weight

506.215197308

IUPAC Name

(3'S,5aR,6R,7S,9bR)-9b-(2-carboxy-1-hydroxyethyl)-7-[(R)-furan-3-yl(hydroxy)methyl]-3,3,5a,7-tetramethyl-5-oxo-decahydro-1H-spiro[naphtho[1,2-c]furan-6,2'-oxirane]-3'-carboxylic acid

Traditional Name

(3'S,5aR,6R,7S,9bR)-9b-(2-carboxy-1-hydroxyethyl)-7-[(R)-furan-3-yl(hydroxy)methyl]-3,3,5a,7-tetramethyl-5-oxo-hexahydrospiro[naphtho[1,2-c]furan-6,2'-oxirane]-3'-carboxylic acid

CAS Registry Number

None

SMILES

CC1(C)OC[C@]2(C(O)CC(O)=O)C1CC(=O)[C@]1(C)C2CC[C@@](C)([C@@H](O)C2=COC=C2)[C@@]11O[C@@H]1C(O)=O

InChI Identifier

InChI=1S/C26H34O10/c1-22(2)15-9-16(27)24(4)14(25(15,12-35-22)17(28)10-18(29)30)5-7-23(3,19(31)13-6-8-34-11-13)26(24)20(36-26)21(32)33/h6,8,11,14-15,17,19-20,28,31H,5,7,9-10,12H2,1-4H3,(H,29,30)(H,32,33)/t14?,15?,17?,19-,20+,23-,24-,25+,26+/m0/s1

InChI Key

JSDNZHXBKWCZDG-RWQHKGFASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Carbocyclic fatty acid
Beta-hydroxy acid
Hydroxy fatty acid
Dicarboxylic acid or derivatives
Fatty acyl
Hydroxy acid
Oxirane carboxylic acid or derivatives
Oxirane carboxylic acid
Heteroaromatic compound
Furan
Tetrahydrofuran
Secondary alcohol
Ketone
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Aromatic alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0038170)
Cytoplasm (HMDB: HMDB0038170)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038170)

Source

Exogenous

Exogenous (HMDB: HMDB0038170)

Food

Food (HMDB: HMDB0038170)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0038170)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Emulsifier (HMDB: HMDB0038170)

Biological role

Nutrient (HMDB: HMDB0038170)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.3 g/L	ALOGPS
logP	1.79	ALOGPS
logP	1.13	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.73	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	167.03 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	121.7 m³·mol⁻¹	ChemAxon
Polarizability	50.86 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0038170

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB017401

KNApSAcK ID

Not Available

Chemspider ID

35014526

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752314

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Isolimonic acid (CFc000019075)

MOL for CFc000019075 (Isolimonic acid)

3D MOL for CFc000019075 (Isolimonic acid)

3D SDF for CFc000019075 (Isolimonic acid)

3D-SDF for CFc000019075 (Isolimonic acid)

PDB for CFc000019075 (Isolimonic acid)

3D PDB for CFc000019075 (Isolimonic acid)

SMILES for CFc000019075 (Isolimonic acid)

INCHI for CFc000019075 (Isolimonic acid)

Structure for CFc000019075 (Isolimonic acid)

3D Structure for CFc000019075 (Isolimonic acid)