Limoni (CED0016406)

Record Information
Version1.0
Creation Date2016-05-22 05:26:50 UTC
Update Date2026-04-03 01:46:10 UTC
Accession NumberCHEM018681
Identification
Common NameLimoni
ClassSmall Molecule
Description
Limoni is an organic compound with the chemical formula C26H30O8 and an average molecular weight of 470.52 g/mol. Limoni belongs to the triterpenoids, a subclass of prenol lipids within the organic compounds. This substance has been identified in or released from 11 recorded sources across several diverse categories. Within electrical and electronic equipment, it is associated with magnets, television systems, discharge lamps, and line transmission systems. In the context of food, food processing and cookware, it is linked to the preparation of malt, vinegar, and wine or sparkling wine. Additionally, limoni is found in household cleaning and consumer products, specifically regarding pipe accessories, other smoking requisites, and non-electric simulated smoking devices. It has also been recorded in building and construction materials, specifically ladders.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
7,16-Dioxo-7,16-dideoxylimondiolChEBI
CitrolimoninChEBI
DictamnolactoneChEBI
Evodia fruitChEBI
EvodinChEBI
Limonoate D-ring-lactoneChEBI
Limonoic acid 3,19:16,17-dilactoneChEBI
Limonoic acid, di-delta-lactoneChEBI
ObaculactoneChEBI
Limonoic acid D-ring-lactoneGenerator
Limonoate 3,19:16,17-dilactoneGenerator
Limonoate, di-delta-lactoneGenerator
Limonoate, di-δ-lactoneGenerator
Limonoic acid, di-δ-lactoneGenerator
Chemical FormulaC26H30O8
Average Molecular Mass470.518 g/mol
Monoisotopic Mass470.194 g/mol
CAS Registry Number1180-71-8
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 Namelimonin
SMILESCC1(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 IdentifierInChI=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 KeyKBDSLGBFQAGHBE-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentLimonoids
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.08 g/LALOGPS
logP3.47ALOGPS
logP2.46ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)17.61ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area104.57 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity114.72 m³·mol⁻¹ChemAxon
Polarizability47.81 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fk9-0000900000-14a8d5118cba8888143eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0imr-0012900000-e15742fc2818641d4e3cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-9451200000-62846b9bdf53b1e33f3bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00or-0000900000-bca1445462cc35111c20Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0gdi-1001900000-9172a8bb0d53d923c572Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0005-6009200000-2032a143d36c06bf2404Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0000900000-b8ab25ad98350c2823caNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00fr-0010900000-f78ec9bfcbf614a341cbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03gi-1460900000-329d430a9185fb234de4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0000900000-d297686d7426b68c96ceNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0000900000-ff496abcb051f215a95eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0001900000-52252c8a0c93946623bbNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
35.0Log mg/kg[20:63]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
498LaddersBuilding & ConstructionNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
652RopesTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
661UmbrellasTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Kappa-type opioid receptor structureClick to view 3D structureKappa-type opioid receptorP41145HumansPredicted (SEA)1956.27
Click to view 3D structureDelta-type opioid receptorP32300Mus musculusPredicted (SEA)915.118
Mu-type opioid receptor structureClick to view 3D structureMu-type opioid receptorP35372HumansPredicted (SEA)3906.71
Delta-type opioid receptor structureClick to view 3D structureDelta-type opioid receptorP41143HumansPredicted (SEA)3229.34
Click to view 3D structureMu-type opioid receptorP33535Rattus norvegicusPredicted (SEA)1709.96
Click to view 3D structureKappa-type opioid receptorP33534Mus musculusPredicted (SEA)900.248
Click to view 3D structureMacrophage migration inhibitory factor homologueQ8I5C5Plasmodium falciparum (isolate 3D7)Predicted (SEA)6.92858
E3 ubiquitin-protein ligase ZFP91 structureClick to view 3D structureE3 ubiquitin-protein ligase ZFP91Q96JP5HumansPredicted (SEA)26.0016
Click to view 3D structureKappa-type opioid receptorP34975Rattus norvegicusPredicted (SEA)1464.5
Click to view 3D structureKappa-type opioid receptorP41144Cavia porcellusPredicted (SEA)3577.95
Androgen receptor structureClick to view 3D structureAndrogen receptorP10275HumansPredicted (SEA)4999.09
Click to view 3D structureSerine/threonine-protein phosphatase 2A 65 kDa regulatory subunit A alpha isoformQ76MZ3Mus musculusPredicted (SEA)3.65891
Solute carrier organic anion transporter family member 1B1 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B1Q9Y6L6HumansPredicted (SEA)3692.62
Click to view 3D structureNucleoside diphosphate phosphatase ENTPD5O75356HumansPredicted (SEA)50.3684
Tyrosine-protein phosphatase non-receptor type 1 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 1P18031HumansPredicted (SEA)4757.05
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)6033.24
Glucocorticoid receptor structureClick to view 3D structureGlucocorticoid receptorP04150HumansPredicted (SEA)5598.06
Solute carrier organic anion transporter family member 1B3 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B3Q9NPD5HumansPredicted (SEA)2552.6
Orexin/Hypocretin receptor type 1 structureClick to view 3D structureOrexin/Hypocretin receptor type 1O43613HumansPredicted (SEA)5432.63
Progesterone receptor structureClick to view 3D structureProgesterone receptorP06401HumansPredicted (SEA)5864.85
Click to view 3D structureMu-type opioid receptorP42866Mus musculusPredicted (SEA)3577.17
Click to view 3D structureAndrogen receptorP15207Rattus norvegicusPredicted (SEA)2040.74
Click to view 3D structureProgesterone receptorQ690N0Bos taurusPredicted (SEA)491.073
Mineralocorticoid receptor structureClick to view 3D structureMineralocorticoid receptorP08235HumansPredicted (SEA)4976.82
Tyrosine-protein phosphatase non-receptor type 2 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 2P17706HumansPredicted (SEA)3830.57
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0302538
FooDB IDFDB005049
Phenol Explorer IDNot Available
KNApSAcK IDC00003719
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkLimonin
Chemspider ID156367
ChEBI ID16226
PubChem Compound IDNot Available
Kegg Compound IDC03514
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19782062
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21338095
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22907263
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22999474
5.