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Showing Compound Limonoate a-ring-lactone (FDB005048)

Record Information
Version1.0
Creation date2010-04-08 22:06:30 UTC
Update date2019-11-26 03:00:20 UTC
Primary IDFDB005048
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLimonoate a-ring-lactone
DescriptionLimonoate 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.
CAS NumberNot Available
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC26H32O9
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
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
Isomeric 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
Average Molecular Weight488.533
Monoisotopic Molecular Weight488.20463261
Classification
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0000900000-a3680d5235fe0ad5f3182016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f9t-1001900000-2438f13484188b2906592016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9320300000-1e0bd597df24e45d2e412016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000f-1001900000-dea7c894ea587259dc792016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-7002900000-f20d095a3f47b21a47ec2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kb-7009500000-635ea44aea3ef97a263a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000900000-5c6216b9495013570caa2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-0001900000-cb1e7e24868183bd47932021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-008c-1221900000-8c1eb424e2dd5425d4a82021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-0000900000-0e0464a50762289508f72021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1000900000-6b86d141d742aa21720b2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02t9-9001600000-032a69bda51a3fb1a5b12021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDLIMONOATE-A-RING-LACTONE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).