Limonoate a-ring-lactone (CHEM025769)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:35:47 UTC
Update Date2016-11-09 01:18:09 UTC
Accession NumberCHEM025769
Identification
Common NameLimonoate a-ring-lactone
ClassSmall Molecule
DescriptionNot Available
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Limonoic acid a-ring-lactoneGenerator
Chemical FormulaC26H32O9
Average Molecular Mass488.533 g/mol
Monoisotopic Mass488.205 g/mol
CAS Registry NumberNot Available
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 Namelimonoate A-ring-lactone
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 IdentifierInChI=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 KeyJQTDUZWQZNXSOU-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
  • 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 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 Solubility0.14 g/LALOGPS
logP2.37ALOGPS
logP1.79ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)4.07ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area135.8 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity118.21 m³·mol⁻¹ChemAxon
Polarizability49.21 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0000900000-a3680d5235fe0ad5f318Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f9t-1001900000-2438f13484188b290659Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9320300000-1e0bd597df24e45d2e41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000f-1001900000-dea7c894ea587259dc79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-7002900000-f20d095a3f47b21a47ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kb-7009500000-635ea44aea3ef97a263aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000900000-5c6216b9495013570caaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-0001900000-cb1e7e24868183bd4793Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-008c-1221900000-8c1eb424e2dd5425d4a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-0000900000-0e0464a50762289508f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1000900000-6b86d141d742aa21720bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02t9-9001600000-032a69bda51a3fb1a5b1Spectrum
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 IDHMDB0302537
FooDB IDFDB005048
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30791758
ChEBI IDNot Available
PubChem Compound ID46173816
Kegg Compound IDC16718
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available