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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:19:41 UTC
Update Date2022-03-07 02:53:47 UTC
HMDB IDHMDB0033583
Secondary Accession Numbers
  • HMDB33583
Metabolite Identification
Common NameLeontogenin
DescriptionLeontogenin belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals. Leontogenin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, leontogenin has been detected, but not quantified in, root vegetables. This could make leontogenin a potential biomarker for the consumption of these foods.
Structure
Data?1563862428
Synonyms
ValueSource
6b-Formyl-b-nor-5b,25R-spirostane-3b,25-diolHMDB
Chemical FormulaC27H42O5
Average Molecular Weight446.6194
Monoisotopic Molecular Weight446.303224454
IUPAC Name16',18'-dihydroxy-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.7.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]nonadecane]-19'-carbaldehyde
Traditional Name16',18'-dihydroxy-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.7.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]nonadecane]-19'-carbaldehyde
CAS Registry NumberNot Available
SMILES
CC1C2C(CC3C4C(CCC23C)C2(C)CCC(O)CC2(O)C4C=O)OC11CCC(C)CO1
InChI Identifier
InChI=1S/C27H42O5/c1-15-5-10-27(31-14-15)16(2)23-21(32-27)11-19-22-18(7-8-24(19,23)3)25(4)9-6-17(29)12-26(25,30)20(22)13-28/h13,15-23,29-30H,5-12,14H2,1-4H3
InChI KeyGKGKOBNJESCNOE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassEthers
Direct ParentKetals
Alternative Parents
Substituents
  • Ketal
  • Oxane
  • Tetrahydrofuran
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic heteropolycyclic compound
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 Solubility0.0035 g/LALOGPS
logP2.5ALOGPS
logP2.88ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)13.47ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity121.46 m³·mol⁻¹ChemAxon
Polarizability51.42 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]+198.8831661259
DarkChem[M-H]-193.16731661259
DeepCCS[M-2H]-241.05930932474
DeepCCS[M+Na]+217.05430932474
AllCCS[M+H]+210.732859911
AllCCS[M+H-H2O]+208.832859911
AllCCS[M+NH4]+212.532859911
AllCCS[M+Na]+213.032859911
AllCCS[M-H]-208.932859911
AllCCS[M+Na-2H]-210.532859911
AllCCS[M+HCOO]-212.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LeontogeninCC1C2C(CC3C4C(CCC23C)C2(C)CCC(O)CC2(O)C4C=O)OC11CCC(C)CO13049.0Standard polar33892256
LeontogeninCC1C2C(CC3C4C(CCC23C)C2(C)CCC(O)CC2(O)C4C=O)OC11CCC(C)CO13211.1Standard non polar33892256
LeontogeninCC1C2C(CC3C4C(CCC23C)C2(C)CCC(O)CC2(O)C4C=O)OC11CCC(C)CO13545.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Leontogenin,1TMS,isomer #1CC1CCC2(OC1)OC1CC3C4C(CCC3(C)C1C2C)C1(C)CCC(O[Si](C)(C)C)CC1(O)C4C=O3588.2Semi standard non polar33892256
Leontogenin,1TMS,isomer #2CC1CCC2(OC1)OC1CC3C4C(CCC3(C)C1C2C)C1(C)CCC(O)CC1(O[Si](C)(C)C)C4C=O3524.6Semi standard non polar33892256
Leontogenin,1TMS,isomer #3CC1CCC2(OC1)OC1CC3C4C(=CO[Si](C)(C)C)C5(O)CC(O)CCC5(C)C4CCC3(C)C1C2C3500.4Semi standard non polar33892256
Leontogenin,2TMS,isomer #1CC1CCC2(OC1)OC1CC3C4C(CCC3(C)C1C2C)C1(C)CCC(O[Si](C)(C)C)CC1(O[Si](C)(C)C)C4C=O3469.2Semi standard non polar33892256
Leontogenin,2TMS,isomer #2CC1CCC2(OC1)OC1CC3C4C(=CO[Si](C)(C)C)C5(O)CC(O[Si](C)(C)C)CCC5(C)C4CCC3(C)C1C2C3447.1Semi standard non polar33892256
Leontogenin,2TMS,isomer #3CC1CCC2(OC1)OC1CC3C4C(=CO[Si](C)(C)C)C5(O[Si](C)(C)C)CC(O)CCC5(C)C4CCC3(C)C1C2C3429.8Semi standard non polar33892256
Leontogenin,3TMS,isomer #1CC1CCC2(OC1)OC1CC3C4C(=CO[Si](C)(C)C)C5(O[Si](C)(C)C)CC(O[Si](C)(C)C)CCC5(C)C4CCC3(C)C1C2C3400.2Semi standard non polar33892256
Leontogenin,3TMS,isomer #1CC1CCC2(OC1)OC1CC3C4C(=CO[Si](C)(C)C)C5(O[Si](C)(C)C)CC(O[Si](C)(C)C)CCC5(C)C4CCC3(C)C1C2C3340.1Standard non polar33892256
Leontogenin,1TBDMS,isomer #1CC1CCC2(OC1)OC1CC3C4C(CCC3(C)C1C2C)C1(C)CCC(O[Si](C)(C)C(C)(C)C)CC1(O)C4C=O3834.8Semi standard non polar33892256
Leontogenin,1TBDMS,isomer #2CC1CCC2(OC1)OC1CC3C4C(CCC3(C)C1C2C)C1(C)CCC(O)CC1(O[Si](C)(C)C(C)(C)C)C4C=O3760.3Semi standard non polar33892256
Leontogenin,1TBDMS,isomer #3CC1CCC2(OC1)OC1CC3C4C(=CO[Si](C)(C)C(C)(C)C)C5(O)CC(O)CCC5(C)C4CCC3(C)C1C2C3738.3Semi standard non polar33892256
Leontogenin,2TBDMS,isomer #1CC1CCC2(OC1)OC1CC3C4C(CCC3(C)C1C2C)C1(C)CCC(O[Si](C)(C)C(C)(C)C)CC1(O[Si](C)(C)C(C)(C)C)C4C=O3938.9Semi standard non polar33892256
Leontogenin,2TBDMS,isomer #2CC1CCC2(OC1)OC1CC3C4C(=CO[Si](C)(C)C(C)(C)C)C5(O)CC(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CCC3(C)C1C2C3916.7Semi standard non polar33892256
Leontogenin,2TBDMS,isomer #3CC1CCC2(OC1)OC1CC3C4C(=CO[Si](C)(C)C(C)(C)C)C5(O[Si](C)(C)C(C)(C)C)CC(O)CCC5(C)C4CCC3(C)C1C2C3871.7Semi standard non polar33892256
Leontogenin,3TBDMS,isomer #1CC1CCC2(OC1)OC1CC3C4C(=CO[Si](C)(C)C(C)(C)C)C5(O[Si](C)(C)C(C)(C)C)CC(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CCC3(C)C1C2C4066.0Semi standard non polar33892256
Leontogenin,3TBDMS,isomer #1CC1CCC2(OC1)OC1CC3C4C(=CO[Si](C)(C)C(C)(C)C)C5(O[Si](C)(C)C(C)(C)C)CC(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CCC3(C)C1C2C3990.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Leontogenin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fl9-3228900000-ac5f7717d639b45408532017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Leontogenin GC-MS (2 TMS) - 70eV, Positivesplash10-004i-4120590000-11d201ebc8364ac9fbc12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Leontogenin 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 - Leontogenin 10V, Positive-QTOFsplash10-004j-3002900000-e22c71dbc47fae9cab532015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leontogenin 20V, Positive-QTOFsplash10-000i-8097800000-f01577111239aa8411c02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leontogenin 40V, Positive-QTOFsplash10-014i-9024000000-75ef5a7ddd09419298ea2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leontogenin 10V, Negative-QTOFsplash10-00kb-4001900000-49210b89875824eb49002015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leontogenin 20V, Negative-QTOFsplash10-004j-2008900000-159177dfc21d24a279322015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leontogenin 40V, Negative-QTOFsplash10-014i-9006100000-db7df0dbeaf03064e0282015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leontogenin 10V, Negative-QTOFsplash10-0002-0000900000-cab8b24b67725b2134432021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leontogenin 20V, Negative-QTOFsplash10-0002-0000900000-c7c8a8304fd4e650e2aa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leontogenin 40V, Negative-QTOFsplash10-0ug4-0003900000-9ade5e7e3837c2c0ef6b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leontogenin 10V, Positive-QTOFsplash10-002b-0000900000-1583edd7914d8391dad22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leontogenin 20V, Positive-QTOFsplash10-0f92-0013900000-884f9cd24cf06b8894802021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leontogenin 40V, Positive-QTOFsplash10-0fy5-4796300000-03771b51accde3cf38c32021-09-23Wishart 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 IDFDB011659
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14702651
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.