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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:16:11 UTC
Update Date2022-03-07 02:54:06 UTC
HMDB IDHMDB0034424
Secondary Accession Numbers
  • HMDB34424
Metabolite Identification
Common NameSpirotaccagenin
DescriptionSpirotaccagenin belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Spirotaccagenin is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862561
SynonymsNot Available
Chemical FormulaC27H42O5
Average Molecular Weight446.6194
Monoisotopic Molecular Weight446.303224454
IUPAC Name5-(hydroxymethyl)-7',9',13'-trimethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-5,16'-diol
Traditional Name5-(hydroxymethyl)-7',9',13'-trimethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-5,16'-diol
CAS Registry NumberNot Available
SMILES
CC1C2C(CC3C4CC=C5CC(O)CCC5(C)C4CCC23C)OC11CCC(O)(CO)CO1
InChI Identifier
InChI=1S/C27H42O5/c1-16-23-22(32-27(16)11-10-26(30,14-28)15-31-27)13-21-19-5-4-17-12-18(29)6-8-24(17,2)20(19)7-9-25(21,23)3/h4,16,18-23,28-30H,5-15H2,1-3H3
InChI KeyLAJZFNUUUUJYJR-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
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point225 - 227 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.008 g/LALOGPS
logP2.37ALOGPS
logP2.72ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)13.22ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area79.15 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity123.34 m³·mol⁻¹ChemAxon
Polarizability51.88 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]+201.40331661259
DarkChem[M-H]-198.39131661259
DeepCCS[M-2H]-235.94430932474
DeepCCS[M+Na]+211.35730932474
AllCCS[M+H]+212.932859911
AllCCS[M+H-H2O]+211.032859911
AllCCS[M+NH4]+214.732859911
AllCCS[M+Na]+215.232859911
AllCCS[M-H]-209.332859911
AllCCS[M+Na-2H]-211.132859911
AllCCS[M+HCOO]-213.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SpirotaccageninCC1C2C(CC3C4CC=C5CC(O)CCC5(C)C4CCC23C)OC11CCC(O)(CO)CO13080.6Standard polar33892256
SpirotaccageninCC1C2C(CC3C4CC=C5CC(O)CCC5(C)C4CCC23C)OC11CCC(O)(CO)CO13415.9Standard non polar33892256
SpirotaccageninCC1C2C(CC3C4CC=C5CC(O)CCC5(C)C4CCC23C)OC11CCC(O)(CO)CO13739.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Spirotaccagenin,1TMS,isomer #1CC1C2C(CC3C4CC=C5CC(O[Si](C)(C)C)CCC5(C)C4CCC32C)OC12CCC(O)(CO)CO23691.1Semi standard non polar33892256
Spirotaccagenin,1TMS,isomer #2CC1C2C(CC3C4CC=C5CC(O)CCC5(C)C4CCC32C)OC12CCC(CO)(O[Si](C)(C)C)CO23772.3Semi standard non polar33892256
Spirotaccagenin,1TMS,isomer #3CC1C2C(CC3C4CC=C5CC(O)CCC5(C)C4CCC32C)OC12CCC(O)(CO[Si](C)(C)C)CO23747.2Semi standard non polar33892256
Spirotaccagenin,2TMS,isomer #1CC1C2C(CC3C4CC=C5CC(O[Si](C)(C)C)CCC5(C)C4CCC32C)OC12CCC(CO)(O[Si](C)(C)C)CO23683.7Semi standard non polar33892256
Spirotaccagenin,2TMS,isomer #2CC1C2C(CC3C4CC=C5CC(O[Si](C)(C)C)CCC5(C)C4CCC32C)OC12CCC(O)(CO[Si](C)(C)C)CO23661.1Semi standard non polar33892256
Spirotaccagenin,2TMS,isomer #3CC1C2C(CC3C4CC=C5CC(O)CCC5(C)C4CCC32C)OC12CCC(CO[Si](C)(C)C)(O[Si](C)(C)C)CO23731.9Semi standard non polar33892256
Spirotaccagenin,3TMS,isomer #1CC1C2C(CC3C4CC=C5CC(O[Si](C)(C)C)CCC5(C)C4CCC32C)OC12CCC(CO[Si](C)(C)C)(O[Si](C)(C)C)CO23668.4Semi standard non polar33892256
Spirotaccagenin,1TBDMS,isomer #1CC1C2C(CC3C4CC=C5CC(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CCC32C)OC12CCC(O)(CO)CO23930.4Semi standard non polar33892256
Spirotaccagenin,1TBDMS,isomer #2CC1C2C(CC3C4CC=C5CC(O)CCC5(C)C4CCC32C)OC12CCC(CO)(O[Si](C)(C)C(C)(C)C)CO24003.4Semi standard non polar33892256
Spirotaccagenin,1TBDMS,isomer #3CC1C2C(CC3C4CC=C5CC(O)CCC5(C)C4CCC32C)OC12CCC(O)(CO[Si](C)(C)C(C)(C)C)CO23997.3Semi standard non polar33892256
Spirotaccagenin,2TBDMS,isomer #1CC1C2C(CC3C4CC=C5CC(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CCC32C)OC12CCC(CO)(O[Si](C)(C)C(C)(C)C)CO24163.7Semi standard non polar33892256
Spirotaccagenin,2TBDMS,isomer #2CC1C2C(CC3C4CC=C5CC(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CCC32C)OC12CCC(O)(CO[Si](C)(C)C(C)(C)C)CO24157.9Semi standard non polar33892256
Spirotaccagenin,2TBDMS,isomer #3CC1C2C(CC3C4CC=C5CC(O)CCC5(C)C4CCC32C)OC12CCC(CO[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)CO24225.6Semi standard non polar33892256
Spirotaccagenin,3TBDMS,isomer #1CC1C2C(CC3C4CC=C5CC(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CCC32C)OC12CCC(CO[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)CO24392.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Spirotaccagenin GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-3023900000-7572eb8be04f2dd680ff2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Spirotaccagenin GC-MS (3 TMS) - 70eV, Positivesplash10-0002-1114029000-f3fcf849201b2013d79a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Spirotaccagenin 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 - Spirotaccagenin 10V, Positive-QTOFsplash10-004j-0031900000-d7998a024e9eb3cc486f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spirotaccagenin 20V, Positive-QTOFsplash10-0wba-2193500000-ede15712fc805102d6fe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spirotaccagenin 40V, Positive-QTOFsplash10-001j-1093200000-df6fbf0c73d046c1fc822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spirotaccagenin 10V, Negative-QTOFsplash10-0002-0110900000-e0e37b85db541e0ea46a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spirotaccagenin 20V, Negative-QTOFsplash10-000b-6128900000-17ca956f08bebf69993b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spirotaccagenin 40V, Negative-QTOFsplash10-0002-9066000000-9ffb072b07866d0756b02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spirotaccagenin 10V, Negative-QTOFsplash10-0002-0000900000-cab8b24b67725b2134432021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spirotaccagenin 20V, Negative-QTOFsplash10-0002-0000900000-f10b2587c6aff59f71102021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spirotaccagenin 40V, Negative-QTOFsplash10-0002-0002900000-617b57bf69557b0e61092021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spirotaccagenin 10V, Positive-QTOFsplash10-002b-0000900000-23a3082c6e2cf4d099282021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spirotaccagenin 20V, Positive-QTOFsplash10-0gxt-0036900000-716d8dc31d026c94fa412021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spirotaccagenin 40V, Positive-QTOFsplash10-05fs-3933000000-80a6a38253bdebedf54e2021-09-23Wishart 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 IDFDB012822
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14539254
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.