Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:05:56 UTC
Update Date2022-03-07 02:54:03 UTC
HMDB IDHMDB0034293
Secondary Accession Numbers
  • HMDB34293
Metabolite Identification
Common NameAsperagenin
DescriptionAsperagenin belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Asperagenin is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862541
SynonymsNot Available
Chemical FormulaC27H44O5
Average Molecular Weight448.6353
Monoisotopic Molecular Weight448.318874518
IUPAC Name5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-5,16',19'-triol
Traditional Name5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-5,16',19'-triol
CAS Registry Number17305-15-6
SMILES
CC1C2C(CC3C4CC(O)C5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)(O)CO1
InChI Identifier
InChI=1S/C27H44O5/c1-15-23-22(32-27(15)10-9-24(2,30)14-31-27)13-19-17-12-21(29)20-11-16(28)5-7-25(20,3)18(17)6-8-26(19,23)4/h15-23,28-30H,5-14H2,1-4H3
InChI KeyILVZNZHXRYGRGV-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 Point265 - 268 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP2.04ALOGPS
logP2.86ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)14.15ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area79.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity122.54 m³·mol⁻¹ChemAxon
Polarizability52.38 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]+203.91431661259
DarkChem[M-H]-200.76331661259
DeepCCS[M-2H]-241.71930932474
DeepCCS[M+Na]+217.01330932474
AllCCS[M+H]+213.532859911
AllCCS[M+H-H2O]+211.632859911
AllCCS[M+NH4]+215.232859911
AllCCS[M+Na]+215.732859911
AllCCS[M-H]-209.732859911
AllCCS[M+Na-2H]-211.632859911
AllCCS[M+HCOO]-213.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AsperageninCC1C2C(CC3C4CC(O)C5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)(O)CO12999.3Standard polar33892256
AsperageninCC1C2C(CC3C4CC(O)C5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)(O)CO13282.1Standard non polar33892256
AsperageninCC1C2C(CC3C4CC(O)C5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)(O)CO13689.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Asperagenin,1TMS,isomer #1CC1C2C(CC3C4CC(O[Si](C)(C)C)C5CC(O)CCC5(C)C4CCC32C)OC12CCC(C)(O)CO23590.5Semi standard non polar33892256
Asperagenin,1TMS,isomer #2CC1C2C(CC3C4CC(O)C5CC(O[Si](C)(C)C)CCC5(C)C4CCC32C)OC12CCC(C)(O)CO23657.4Semi standard non polar33892256
Asperagenin,1TMS,isomer #3CC1C2C(CC3C4CC(O)C5CC(O)CCC5(C)C4CCC32C)OC12CCC(C)(O[Si](C)(C)C)CO23706.3Semi standard non polar33892256
Asperagenin,2TMS,isomer #1CC1C2C(CC3C4CC(O[Si](C)(C)C)C5CC(O[Si](C)(C)C)CCC5(C)C4CCC32C)OC12CCC(C)(O)CO23575.5Semi standard non polar33892256
Asperagenin,2TMS,isomer #2CC1C2C(CC3C4CC(O[Si](C)(C)C)C5CC(O)CCC5(C)C4CCC32C)OC12CCC(C)(O[Si](C)(C)C)CO23626.5Semi standard non polar33892256
Asperagenin,2TMS,isomer #3CC1C2C(CC3C4CC(O)C5CC(O[Si](C)(C)C)CCC5(C)C4CCC32C)OC12CCC(C)(O[Si](C)(C)C)CO23688.8Semi standard non polar33892256
Asperagenin,3TMS,isomer #1CC1C2C(CC3C4CC(O[Si](C)(C)C)C5CC(O[Si](C)(C)C)CCC5(C)C4CCC32C)OC12CCC(C)(O[Si](C)(C)C)CO23622.0Semi standard non polar33892256
Asperagenin,1TBDMS,isomer #1CC1C2C(CC3C4CC(O[Si](C)(C)C(C)(C)C)C5CC(O)CCC5(C)C4CCC32C)OC12CCC(C)(O)CO23814.6Semi standard non polar33892256
Asperagenin,1TBDMS,isomer #2CC1C2C(CC3C4CC(O)C5CC(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CCC32C)OC12CCC(C)(O)CO23884.4Semi standard non polar33892256
Asperagenin,1TBDMS,isomer #3CC1C2C(CC3C4CC(O)C5CC(O)CCC5(C)C4CCC32C)OC12CCC(C)(O[Si](C)(C)C(C)(C)C)CO23924.4Semi standard non polar33892256
Asperagenin,2TBDMS,isomer #1CC1C2C(CC3C4CC(O[Si](C)(C)C(C)(C)C)C5CC(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CCC32C)OC12CCC(C)(O)CO24034.7Semi standard non polar33892256
Asperagenin,2TBDMS,isomer #2CC1C2C(CC3C4CC(O[Si](C)(C)C(C)(C)C)C5CC(O)CCC5(C)C4CCC32C)OC12CCC(C)(O[Si](C)(C)C(C)(C)C)CO24074.4Semi standard non polar33892256
Asperagenin,2TBDMS,isomer #3CC1C2C(CC3C4CC(O)C5CC(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CCC32C)OC12CCC(C)(O[Si](C)(C)C(C)(C)C)CO24141.8Semi standard non polar33892256
Asperagenin,3TBDMS,isomer #1CC1C2C(CC3C4CC(O[Si](C)(C)C(C)(C)C)C5CC(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CCC32C)OC12CCC(C)(O[Si](C)(C)C(C)(C)C)CO24297.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Asperagenin GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1326900000-7e54d7f81733f31caa992017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Asperagenin GC-MS (3 TMS) - 70eV, Positivesplash10-0f6t-2211339000-d04a499a36fba0dca9082017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Asperagenin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Asperagenin 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 - Asperagenin 10V, Positive-QTOFsplash10-01qa-0011900000-b0f5c2b665fa1b2d4e592016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asperagenin 20V, Positive-QTOFsplash10-0231-1092700000-fa255546e7a98fbbace22016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asperagenin 40V, Positive-QTOFsplash10-0uxr-2198400000-fe82e47737ae2ad17c082016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asperagenin 10V, Negative-QTOFsplash10-0002-1001900000-a9da86f5cef94c4a77df2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asperagenin 20V, Negative-QTOFsplash10-00ba-5008900000-03ec27f622ca25f02cd52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asperagenin 40V, Negative-QTOFsplash10-014i-9006000000-7f15e6f76065fef2aa8d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asperagenin 10V, Negative-QTOFsplash10-0002-0000900000-c59d57b3407a520888652021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asperagenin 20V, Negative-QTOFsplash10-0002-0000900000-bb76c2e4725eb3fc7f242021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asperagenin 40V, Negative-QTOFsplash10-0002-0001900000-465f97dc576823fb24682021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asperagenin 10V, Positive-QTOFsplash10-001j-0000900000-2f27af50eb9007a1d0362021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asperagenin 20V, Positive-QTOFsplash10-001a-0173900000-424b2c8b6f06be9df3972021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Asperagenin 40V, Positive-QTOFsplash10-014j-6922000000-4738757f17630635f6122021-09-24Wishart 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 IDFDB012632
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71435521
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.