Limoni (CHEM018681)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:26:50 UTC
Update Date2016-11-09 01:15:51 UTC
Accession NumberCHEM018681
Identification
Common NameLimoni
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0000900000-14a8d5118cba8888143eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0imr-0012900000-e15742fc2818641d4e3cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9451200000-62846b9bdf53b1e33f3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00or-0000900000-bca1445462cc35111c20Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gdi-1001900000-9172a8bb0d53d923c572Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-6009200000-2032a143d36c06bf2404Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000900000-b8ab25ad98350c2823caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fr-0010900000-f78ec9bfcbf614a341cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03gi-1460900000-329d430a9185fb234de4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-d297686d7426b68c96ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000900000-ff496abcb051f215a95eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0001900000-52252c8a0c93946623bbSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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.