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Showing Compound Obacunone (FDB014637)

Record Information
Version1.0
Creation date2010-04-08 22:11:23 UTC
Update date2019-11-26 03:10:31 UTC
Primary IDFDB014637
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameObacunone
DescriptionObacunone, also known as casimirolide or tricoccin S3, 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. Obacunone is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number751-03-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
CasimirolideHMDB
Obacunoic acid, eta-lactoneHMDB
Tricoccin S3HMDB
Obacunonedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.024 g/LALOGPS
logP3.76ALOGPS
logP3.88ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)17.92ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area95.34 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity116.19 m³·mol⁻¹ChemAxon
Polarizability47.09 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC26H30O7
IUPAC name7-(furan-3-yl)-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-ene-5,15,20-trione
InChI IdentifierInChI=1S/C26H30O7/c1-22(2)16-12-17(27)25(5)15(23(16,3)9-7-18(28)32-22)6-10-24(4)19(14-8-11-30-13-14)31-21(29)20-26(24,25)33-20/h7-9,11,13,15-16,19-20H,6,10,12H2,1-5H3
InChI KeyMAYJEFRPIKEYBL-UHFFFAOYSA-N
Isomeric SMILESCC12CCC3C4(C)C=CC(=O)OC(C)(C)C4CC(=O)C3(C)C11OC1C(=O)OC2C1=COC=C1
Average Molecular Weight454.5122
Monoisotopic Molecular Weight454.199153314
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
  • Naphthopyran
  • Naphthalene
  • 1,4-dioxepane
  • Delta valerolactone
  • Dioxepane
  • Delta_valerolactone
  • Dicarboxylic acid or derivatives
  • Pyran
  • Oxane
  • Heteroaromatic compound
  • Furan
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 68.71%; H 6.65%; O 24.64%DFC
Melting PointMp 229-230°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -50 (CHCl3)DFC
Spectroscopic UV Data[neutral] lmax 288 (e 1360) (MeOH) (Derep)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSObacunone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03g3-4763900000-f92282a5dc1cc0f37780Spectrum
Predicted GC-MSObacunone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-0001900000-91f82701dfbe9c1b89372016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pbi-0002900000-67e1b74e789b5b5f69bf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016s-9006000000-9e9ffb6bdd1b887e94522016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ufr-0000900000-2a1dbb5cddee36a5b4092021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0000900000-f1afb1f1fe1011d9791e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kk9-1023900000-aeeeda4f35507c3c79e62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0002900000-e1ec4288c41df91d3ba32016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0025900000-6a379fce8acd6dafc36d2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6t-9324100000-2e07d772eab4f19d665e2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000900000-edd8aed905ca850e4d7a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0044900000-ce3894bf62d35dff6da52021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xu-2952200000-55cb094ddec8d0b8027d2021-09-23View Spectrum
NMRNot Available
ChemSpider ID437433
ChEMBL IDNot Available
KEGG Compound IDC08775
Pubchem Compound ID500031
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35858
CRC / DFC (Dictionary of Food Compounds) IDJWX03-E:JTF28-I
EAFUS IDNot Available
Dr. Duke IDOBACUNONE
BIGG IDNot Available
KNApSAcK IDC00003723
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
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti cataleptic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti feedantDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
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).