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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:02:42 UTC
Update Date2022-03-07 02:54:43 UTC
HMDB IDHMDB0035984
Secondary Accession Numbers
  • HMDB35984
Metabolite Identification
Common 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).
Structure
Data?1563862803
SynonymsNot Available
Chemical FormulaC26H30O8
Average Molecular Weight470.5116
Monoisotopic Molecular Weight470.194067936
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
Traditional 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
CAS Registry Number35796-71-5
SMILES
CC12CC(O)C3C4(C)C=CC(=O)OC(C)(C)C4CC(=O)C3(C)C11OC1C(=O)OC2C1=COC=C1
InChI Identifier
InChI=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
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
  • 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
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point257 - 259 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+207.92631661259
DarkChem[M-H]-196.56231661259
DeepCCS[M-2H]-237.23430932474
DeepCCS[M+Na]+212.65830932474
AllCCS[M+H]+208.932859911
AllCCS[M+H-H2O]+206.932859911
AllCCS[M+NH4]+210.832859911
AllCCS[M+Na]+211.432859911
AllCCS[M-H]-214.432859911
AllCCS[M+Na-2H]-215.432859911
AllCCS[M+HCOO]-216.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ZapoterinCC12CC(O)C3C4(C)C=CC(=O)OC(C)(C)C4CC(=O)C3(C)C11OC1C(=O)OC2C1=COC=C14283.1Standard polar33892256
ZapoterinCC12CC(O)C3C4(C)C=CC(=O)OC(C)(C)C4CC(=O)C3(C)C11OC1C(=O)OC2C1=COC=C13087.2Standard non polar33892256
ZapoterinCC12CC(O)C3C4(C)C=CC(=O)OC(C)(C)C4CC(=O)C3(C)C11OC1C(=O)OC2C1=COC=C14005.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Zapoterin,1TMS,isomer #1CC1(C)OC(=O)C=CC2(C)C1CC(=O)C1(C)C2C(O[Si](C)(C)C)CC2(C)C(C3=COC=C3)OC(=O)C3OC3213734.4Semi standard non polar33892256
Zapoterin,1TMS,isomer #2CC1(C)OC(=O)C=CC2(C)C1C=C(O[Si](C)(C)C)C1(C)C2C(O)CC2(C)C(C3=COC=C3)OC(=O)C3OC3213707.9Semi standard non polar33892256
Zapoterin,2TMS,isomer #1CC1(C)OC(=O)C=CC2(C)C1C=C(O[Si](C)(C)C)C1(C)C2C(O[Si](C)(C)C)CC2(C)C(C3=COC=C3)OC(=O)C3OC3213627.0Semi standard non polar33892256
Zapoterin,2TMS,isomer #1CC1(C)OC(=O)C=CC2(C)C1C=C(O[Si](C)(C)C)C1(C)C2C(O[Si](C)(C)C)CC2(C)C(C3=COC=C3)OC(=O)C3OC3213223.2Standard non polar33892256
Zapoterin,1TBDMS,isomer #1CC1(C)OC(=O)C=CC2(C)C1CC(=O)C1(C)C2C(O[Si](C)(C)C(C)(C)C)CC2(C)C(C3=COC=C3)OC(=O)C3OC3213991.3Semi standard non polar33892256
Zapoterin,1TBDMS,isomer #2CC1(C)OC(=O)C=CC2(C)C1C=C(O[Si](C)(C)C(C)(C)C)C1(C)C2C(O)CC2(C)C(C3=COC=C3)OC(=O)C3OC3213964.5Semi standard non polar33892256
Zapoterin,2TBDMS,isomer #1CC1(C)OC(=O)C=CC2(C)C1C=C(O[Si](C)(C)C(C)(C)C)C1(C)C2C(O[Si](C)(C)C(C)(C)C)CC2(C)C(C3=COC=C3)OC(=O)C3OC3214082.3Semi standard non polar33892256
Zapoterin,2TBDMS,isomer #1CC1(C)OC(=O)C=CC2(C)C1C=C(O[Si](C)(C)C(C)(C)C)C1(C)C2C(O[Si](C)(C)C(C)(C)C)CC2(C)C(C3=COC=C3)OC(=O)C3OC3213642.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Zapoterin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-2940600000-bea5563117b9b750e6512017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zapoterin GC-MS (1 TMS) - 70eV, Positivesplash10-004l-7716390000-7e216cb7159042ed25692017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zapoterin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zapoterin 10V, Positive-QTOFsplash10-0uk9-0000900000-4cde74236abc79abcaa12015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zapoterin 20V, Positive-QTOFsplash10-0udr-0002900000-44b148a8c069fe339c2c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zapoterin 40V, Positive-QTOFsplash10-0012-9316200000-3ddc75aa649d56e95bd52015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zapoterin 10V, Negative-QTOFsplash10-00or-0000900000-aa9d019b2cd90495cd512015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zapoterin 20V, Negative-QTOFsplash10-0v00-0001900000-2e6ef8e31a6bd3dc3b492015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zapoterin 40V, Negative-QTOFsplash10-014j-9005100000-b243bcfc26af56f060a22015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zapoterin 10V, Positive-QTOFsplash10-00di-0000900000-4a4297bf0283c5dc27942021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zapoterin 20V, Positive-QTOFsplash10-0fki-0051900000-989cc41e7465d5a165162021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zapoterin 40V, Positive-QTOFsplash10-003f-3571900000-7ccb0375f22da397c51f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zapoterin 10V, Negative-QTOFsplash10-014i-0000900000-3ea147f9e912d29f22fb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zapoterin 20V, Negative-QTOFsplash10-014i-0001900000-029a95cbe20e4011a4f82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zapoterin 40V, Negative-QTOFsplash10-000i-0092300000-e0c35ece0c03bb5d591e2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014790
KNApSAcK IDC00003736
Chemspider ID3680180
KEGG Compound IDC08788
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4482275
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.