Record Information
Version1.0
Creation date2010-04-08 22:11:28 UTC
Update date2019-11-26 03:10:45 UTC
Primary IDFDB014790
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameZapoterin
DescriptionZapoterin 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. Zapoterin is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number35796-71-5
Structure
Thumb
Synonyms
SynonymSource
Zapoterindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.063 g/LALOGPS
logP2.53ALOGPS
logP2.57ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)14.85ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area115.57 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity117.78 m³·mol⁻¹ChemAxon
Polarizability48.06 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC26H30O8
IUPAC name7-(furan-3-yl)-10-hydroxy-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/C26H30O8/c1-22(2)15-10-16(28)25(5)18(23(15,3)8-6-17(29)33-22)14(27)11-24(4)19(13-7-9-31-12-13)32-21(30)20-26(24,25)34-20/h6-9,12,14-15,18-20,27H,10-11H2,1-5H3
InChI KeyOZGKITZRRFNYRV-UHFFFAOYSA-N
Isomeric SMILESCC12CC(O)C3C4(C)C=CC(=O)OC(C)(C)C4CC(=O)C3(C)C11OC1C(=O)OC2C1=COC=C1
Average Molecular Weight470.5116
Monoisotopic Molecular Weight470.194067936
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
  • Cyclic alcohol
  • Heteroaromatic compound
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Furan
  • Carboxylic acid ester
  • Secondary alcohol
  • Ketone
  • Lactone
  • Ether
  • Oxirane
  • Organoheterocyclic compound
  • Oxacycle
  • Dialkyl ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Carbonyl group
  • 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 - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 66.37%; H 6.43%; O 27.20%DFC
Melting PointMp 257-259°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -51 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-2940600000-bea5563117b9b750e651JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004l-7716390000-7e216cb7159042ed2569JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0000900000-4cde74236abc79abcaa1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0002900000-44b148a8c069fe339c2cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0012-9316200000-3ddc75aa649d56e95bd5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00or-0000900000-aa9d019b2cd90495cd51JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0v00-0001900000-2e6ef8e31a6bd3dc3b49JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014j-9005100000-b243bcfc26af56f060a2JSpectraViewer
ChemSpider ID3680180
ChEMBL IDNot Available
KEGG Compound IDC08788
Pubchem Compound ID4482275
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35984
CRC / DFC (Dictionary of Food Compounds) IDJWX03-E:JVW83-Q
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00003736
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 / 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