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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:40:50 UTC
Update Date2022-03-07 02:52:49 UTC
HMDB IDHMDB0031079
Secondary Accession Numbers
  • HMDB31079
Metabolite Identification
Common Name12-Ketoporrigenin
Description12-Ketoporrigenin belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 12-Ketoporrigenin is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862079
SynonymsNot Available
Chemical FormulaC27H42O5
Average Molecular Weight446.6194
Monoisotopic Molecular Weight446.303224454
IUPAC Name16',19'-dihydroxy-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10'-one
Traditional Name16',19'-dihydroxy-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10'-one
CAS Registry Number189014-45-7
SMILES
CC1C2C(CC3C4CC(O)C5CC(O)CCC5(C)C4CC(=O)C23C)OC11CCC(C)CO1
InChI Identifier
InChI=1S/C27H42O5/c1-14-5-8-27(31-13-14)15(2)24-22(32-27)11-19-17-10-21(29)20-9-16(28)6-7-25(20,3)18(17)12-23(30)26(19,24)4/h14-22,24,28-29H,5-13H2,1-4H3
InChI KeyAEDBOXCTQDATMF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0059 g/LALOGPS
logP2.23ALOGPS
logP3.36ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)14.75ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity121.7 m³·mol⁻¹ChemAxon
Polarizability51.17 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+203.50431661259
DarkChem[M-H]-196.85731661259
DeepCCS[M-2H]-245.01930932474
DeepCCS[M+Na]+220.64230932474
AllCCS[M+H]+212.532859911
AllCCS[M+H-H2O]+210.532859911
AllCCS[M+NH4]+214.232859911
AllCCS[M+Na]+214.732859911
AllCCS[M-H]-210.132859911
AllCCS[M+Na-2H]-211.832859911
AllCCS[M+HCOO]-213.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
12-KetoporrigeninCC1C2C(CC3C4CC(O)C5CC(O)CCC5(C)C4CC(=O)C23C)OC11CCC(C)CO13009.0Standard polar33892256
12-KetoporrigeninCC1C2C(CC3C4CC(O)C5CC(O)CCC5(C)C4CC(=O)C23C)OC11CCC(C)CO13345.9Standard non polar33892256
12-KetoporrigeninCC1C2C(CC3C4CC(O)C5CC(O)CCC5(C)C4CC(=O)C23C)OC11CCC(C)CO13739.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
12-Ketoporrigenin,1TMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C)C5CC(O)CCC5(C)C4CC(=O)C3(C)C1C2C3601.3Semi standard non polar33892256
12-Ketoporrigenin,1TMS,isomer #2CC1CCC2(OC1)OC1CC3C4CC(O)C5CC(O[Si](C)(C)C)CCC5(C)C4CC(=O)C3(C)C1C2C3649.0Semi standard non polar33892256
12-Ketoporrigenin,1TMS,isomer #3CC1CCC2(OC1)OC1CC3C4CC(O)C5CC(O)CCC5(C)C4C=C(O[Si](C)(C)C)C3(C)C1C2C3642.5Semi standard non polar33892256
12-Ketoporrigenin,2TMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C)C5CC(O[Si](C)(C)C)CCC5(C)C4CC(=O)C3(C)C1C2C3576.5Semi standard non polar33892256
12-Ketoporrigenin,2TMS,isomer #2CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C)C5CC(O)CCC5(C)C4C=C(O[Si](C)(C)C)C3(C)C1C2C3559.9Semi standard non polar33892256
12-Ketoporrigenin,2TMS,isomer #3CC1CCC2(OC1)OC1CC3C4CC(O)C5CC(O[Si](C)(C)C)CCC5(C)C4C=C(O[Si](C)(C)C)C3(C)C1C2C3618.5Semi standard non polar33892256
12-Ketoporrigenin,3TMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C)C5CC(O[Si](C)(C)C)CCC5(C)C4C=C(O[Si](C)(C)C)C3(C)C1C2C3535.7Semi standard non polar33892256
12-Ketoporrigenin,3TMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C)C5CC(O[Si](C)(C)C)CCC5(C)C4C=C(O[Si](C)(C)C)C3(C)C1C2C3246.3Standard non polar33892256
12-Ketoporrigenin,1TBDMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C(C)(C)C)C5CC(O)CCC5(C)C4CC(=O)C3(C)C1C2C3827.3Semi standard non polar33892256
12-Ketoporrigenin,1TBDMS,isomer #2CC1CCC2(OC1)OC1CC3C4CC(O)C5CC(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CC(=O)C3(C)C1C2C3878.6Semi standard non polar33892256
12-Ketoporrigenin,1TBDMS,isomer #3CC1CCC2(OC1)OC1CC3C4CC(O)C5CC(O)CCC5(C)C4C=C(O[Si](C)(C)C(C)(C)C)C3(C)C1C2C3880.7Semi standard non polar33892256
12-Ketoporrigenin,2TBDMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C(C)(C)C)C5CC(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CC(=O)C3(C)C1C2C4060.5Semi standard non polar33892256
12-Ketoporrigenin,2TBDMS,isomer #2CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C(C)(C)C)C5CC(O)CCC5(C)C4C=C(O[Si](C)(C)C(C)(C)C)C3(C)C1C2C4037.5Semi standard non polar33892256
12-Ketoporrigenin,2TBDMS,isomer #3CC1CCC2(OC1)OC1CC3C4CC(O)C5CC(O[Si](C)(C)C(C)(C)C)CCC5(C)C4C=C(O[Si](C)(C)C(C)(C)C)C3(C)C1C2C4093.6Semi standard non polar33892256
12-Ketoporrigenin,3TBDMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C(C)(C)C)C5CC(O[Si](C)(C)C(C)(C)C)CCC5(C)C4C=C(O[Si](C)(C)C(C)(C)C)C3(C)C1C2C4231.8Semi standard non polar33892256
12-Ketoporrigenin,3TBDMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C(C)(C)C)C5CC(O[Si](C)(C)C(C)(C)C)CCC5(C)C4C=C(O[Si](C)(C)C(C)(C)C)C3(C)C1C2C3831.4Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 12-Ketoporrigenin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f89-2616900000-c1e11f76f15b4eb47f9b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12-Ketoporrigenin GC-MS (2 TMS) - 70eV, Positivesplash10-004i-4531390000-9e146f722db065503c382017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12-Ketoporrigenin 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 - 12-Ketoporrigenin 10V, Positive-QTOFsplash10-01t9-3002900000-58ab776900859ce1f1b92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Ketoporrigenin 20V, Positive-QTOFsplash10-01p9-7098700000-d689d9d0c53adbdcdff32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Ketoporrigenin 40V, Positive-QTOFsplash10-014i-9115000000-e4f3266379cc8c5fcae92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Ketoporrigenin 10V, Negative-QTOFsplash10-00kb-3001900000-f1e46fa15e5a0654ccbe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Ketoporrigenin 20V, Negative-QTOFsplash10-00mk-2008900000-a11ac13511227fa0adb32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Ketoporrigenin 40V, Negative-QTOFsplash10-014i-9005100000-e7155e557fcf0170160c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Ketoporrigenin 10V, Negative-QTOFsplash10-0002-0000900000-cab8b24b67725b2134432021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Ketoporrigenin 20V, Negative-QTOFsplash10-0002-0000900000-c0525ec1278f13669bd22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Ketoporrigenin 40V, Negative-QTOFsplash10-00n4-0403900000-17f43fdaba343a17829e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Ketoporrigenin 10V, Positive-QTOFsplash10-002b-0000900000-2c7ea1884b7662df6b152021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Ketoporrigenin 20V, Positive-QTOFsplash10-01r2-0104900000-1af5d957ed43a30e25222021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Ketoporrigenin 40V, Positive-QTOFsplash10-016r-3943000000-95e2a272e4415380b1242021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 IDFDB003083
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound73313119
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.