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 22:07:46 UTC
Update Date2022-03-07 02:55:07 UTC
HMDB IDHMDB0036940
Secondary Accession Numbers
  • HMDB36940
Metabolite Identification
Common NameSpirostane-3,6-dione
DescriptionSpirostane-3,6-dione, also known as chlorogenone, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Spirostane-3,6-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862953
Synonyms
ValueSource
ChlorogenoneHMDB
Chemical FormulaC27H40O4
Average Molecular Weight428.6041
Monoisotopic Molecular Weight428.292659768
IUPAC Name5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-16',19'-dione
Traditional Name5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-16',19'-dione
CAS Registry Number3514-59-8
SMILES
CC1C2C(CC3C4CC(=O)C5CC(=O)CCC5(C)C4CCC23C)OC11CCC(C)CO1
InChI Identifier
InChI=1S/C27H40O4/c1-15-5-10-27(30-14-15)16(2)24-23(31-27)13-20-18-12-22(29)21-11-17(28)6-8-25(21,3)19(18)7-9-26(20,24)4/h15-16,18-21,23-24H,5-14H2,1-4H3
InChI KeyCGXQJOWMWZPOPV-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 Point243.5 - 244.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00064 g/LALOGPS
logP3.41ALOGPS
logP4.62ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)17.77ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity119.06 m³·mol⁻¹ChemAxon
Polarizability50.51 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]+199.09831661259
DarkChem[M-H]-195.40331661259
DeepCCS[M-2H]-238.31230932474
DeepCCS[M+Na]+213.5430932474
AllCCS[M+H]+208.632859911
AllCCS[M+H-H2O]+206.532859911
AllCCS[M+NH4]+210.532859911
AllCCS[M+Na]+211.032859911
AllCCS[M-H]-208.532859911
AllCCS[M+Na-2H]-210.032859911
AllCCS[M+HCOO]-211.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Spirostane-3,6-dioneCC1C2C(CC3C4CC(=O)C5CC(=O)CCC5(C)C4CCC23C)OC11CCC(C)CO13673.7Standard polar33892256
Spirostane-3,6-dioneCC1C2C(CC3C4CC(=O)C5CC(=O)CCC5(C)C4CCC23C)OC11CCC(C)CO13203.2Standard non polar33892256
Spirostane-3,6-dioneCC1C2C(CC3C4CC(=O)C5CC(=O)CCC5(C)C4CCC23C)OC11CCC(C)CO13586.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Spirostane-3,6-dione,1TMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C)=C5CC(=O)CCC5(C)C4CCC3(C)C1C2C3367.5Semi standard non polar33892256
Spirostane-3,6-dione,1TMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C)=C5CC(=O)CCC5(C)C4CCC3(C)C1C2C3401.6Standard non polar33892256
Spirostane-3,6-dione,1TMS,isomer #2CC1CCC2(OC1)OC1CC3C4C=C(O[Si](C)(C)C)C5CC(=O)CCC5(C)C4CCC3(C)C1C2C3438.2Semi standard non polar33892256
Spirostane-3,6-dione,1TMS,isomer #2CC1CCC2(OC1)OC1CC3C4C=C(O[Si](C)(C)C)C5CC(=O)CCC5(C)C4CCC3(C)C1C2C3287.2Standard non polar33892256
Spirostane-3,6-dione,1TMS,isomer #3CC1CCC2(OC1)OC1CC3C4CC(=O)C5CC(O[Si](C)(C)C)=CCC5(C)C4CCC3(C)C1C2C3489.6Semi standard non polar33892256
Spirostane-3,6-dione,1TMS,isomer #3CC1CCC2(OC1)OC1CC3C4CC(=O)C5CC(O[Si](C)(C)C)=CCC5(C)C4CCC3(C)C1C2C3364.8Standard non polar33892256
Spirostane-3,6-dione,1TMS,isomer #4CC1CCC2(OC1)OC1CC3C4CC(=O)C5C=C(O[Si](C)(C)C)CCC5(C)C4CCC3(C)C1C2C3424.6Semi standard non polar33892256
Spirostane-3,6-dione,1TMS,isomer #4CC1CCC2(OC1)OC1CC3C4CC(=O)C5C=C(O[Si](C)(C)C)CCC5(C)C4CCC3(C)C1C2C3370.9Standard non polar33892256
Spirostane-3,6-dione,2TMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C)=C5CC(O[Si](C)(C)C)=CCC5(C)C4CCC3(C)C1C2C3336.1Semi standard non polar33892256
Spirostane-3,6-dione,2TMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C)=C5CC(O[Si](C)(C)C)=CCC5(C)C4CCC3(C)C1C2C3392.9Standard non polar33892256
Spirostane-3,6-dione,2TMS,isomer #2CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C)=C5C=C(O[Si](C)(C)C)CCC5(C)C4CCC3(C)C1C2C3454.7Semi standard non polar33892256
Spirostane-3,6-dione,2TMS,isomer #2CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C)=C5C=C(O[Si](C)(C)C)CCC5(C)C4CCC3(C)C1C2C3412.0Standard non polar33892256
Spirostane-3,6-dione,2TMS,isomer #3CC1CCC2(OC1)OC1CC3C4C=C(O[Si](C)(C)C)C5CC(O[Si](C)(C)C)=CCC5(C)C4CCC3(C)C1C2C3421.4Semi standard non polar33892256
Spirostane-3,6-dione,2TMS,isomer #3CC1CCC2(OC1)OC1CC3C4C=C(O[Si](C)(C)C)C5CC(O[Si](C)(C)C)=CCC5(C)C4CCC3(C)C1C2C3300.4Standard non polar33892256
Spirostane-3,6-dione,2TMS,isomer #4CC1CCC2(OC1)OC1CC3C4C=C(O[Si](C)(C)C)C5C=C(O[Si](C)(C)C)CCC5(C)C4CCC3(C)C1C2C3384.4Semi standard non polar33892256
Spirostane-3,6-dione,2TMS,isomer #4CC1CCC2(OC1)OC1CC3C4C=C(O[Si](C)(C)C)C5C=C(O[Si](C)(C)C)CCC5(C)C4CCC3(C)C1C2C3283.2Standard non polar33892256
Spirostane-3,6-dione,1TBDMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C(C)(C)C)=C5CC(=O)CCC5(C)C4CCC3(C)C1C2C3612.3Semi standard non polar33892256
Spirostane-3,6-dione,1TBDMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C(C)(C)C)=C5CC(=O)CCC5(C)C4CCC3(C)C1C2C3654.6Standard non polar33892256
Spirostane-3,6-dione,1TBDMS,isomer #2CC1CCC2(OC1)OC1CC3C4C=C(O[Si](C)(C)C(C)(C)C)C5CC(=O)CCC5(C)C4CCC3(C)C1C2C3668.5Semi standard non polar33892256
Spirostane-3,6-dione,1TBDMS,isomer #2CC1CCC2(OC1)OC1CC3C4C=C(O[Si](C)(C)C(C)(C)C)C5CC(=O)CCC5(C)C4CCC3(C)C1C2C3484.6Standard non polar33892256
Spirostane-3,6-dione,1TBDMS,isomer #3CC1CCC2(OC1)OC1CC3C4CC(=O)C5CC(O[Si](C)(C)C(C)(C)C)=CCC5(C)C4CCC3(C)C1C2C3738.0Semi standard non polar33892256
Spirostane-3,6-dione,1TBDMS,isomer #3CC1CCC2(OC1)OC1CC3C4CC(=O)C5CC(O[Si](C)(C)C(C)(C)C)=CCC5(C)C4CCC3(C)C1C2C3588.2Standard non polar33892256
Spirostane-3,6-dione,1TBDMS,isomer #4CC1CCC2(OC1)OC1CC3C4CC(=O)C5C=C(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CCC3(C)C1C2C3675.3Semi standard non polar33892256
Spirostane-3,6-dione,1TBDMS,isomer #4CC1CCC2(OC1)OC1CC3C4CC(=O)C5C=C(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CCC3(C)C1C2C3601.5Standard non polar33892256
Spirostane-3,6-dione,2TBDMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C(C)(C)C)=C5CC(O[Si](C)(C)C(C)(C)C)=CCC5(C)C4CCC3(C)C1C2C3778.5Semi standard non polar33892256
Spirostane-3,6-dione,2TBDMS,isomer #1CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C(C)(C)C)=C5CC(O[Si](C)(C)C(C)(C)C)=CCC5(C)C4CCC3(C)C1C2C3798.9Standard non polar33892256
Spirostane-3,6-dione,2TBDMS,isomer #2CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C(C)(C)C)=C5C=C(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CCC3(C)C1C2C3885.3Semi standard non polar33892256
Spirostane-3,6-dione,2TBDMS,isomer #2CC1CCC2(OC1)OC1CC3C4CC(O[Si](C)(C)C(C)(C)C)=C5C=C(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CCC3(C)C1C2C3790.2Standard non polar33892256
Spirostane-3,6-dione,2TBDMS,isomer #3CC1CCC2(OC1)OC1CC3C4C=C(O[Si](C)(C)C(C)(C)C)C5CC(O[Si](C)(C)C(C)(C)C)=CCC5(C)C4CCC3(C)C1C2C3857.8Semi standard non polar33892256
Spirostane-3,6-dione,2TBDMS,isomer #3CC1CCC2(OC1)OC1CC3C4C=C(O[Si](C)(C)C(C)(C)C)C5CC(O[Si](C)(C)C(C)(C)C)=CCC5(C)C4CCC3(C)C1C2C3629.7Standard non polar33892256
Spirostane-3,6-dione,2TBDMS,isomer #4CC1CCC2(OC1)OC1CC3C4C=C(O[Si](C)(C)C(C)(C)C)C5C=C(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CCC3(C)C1C2C3830.9Semi standard non polar33892256
Spirostane-3,6-dione,2TBDMS,isomer #4CC1CCC2(OC1)OC1CC3C4C=C(O[Si](C)(C)C(C)(C)C)C5C=C(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CCC3(C)C1C2C3632.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Spirostane-3,6-dione GC-MS (Non-derivatized) - 70eV, Positivesplash10-0nms-3379300000-b4c4e8c6429902ac84432017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Spirostane-3,6-dione GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Spirostane-3,6-dione 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 - Spirostane-3,6-dione 10V, Positive-QTOFsplash10-02di-6025900000-0c08379bc7e6c51a9ba22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spirostane-3,6-dione 20V, Positive-QTOFsplash10-02g9-8097300000-cda89a5e3dc0473b14f22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spirostane-3,6-dione 40V, Positive-QTOFsplash10-0gb9-9055000000-38a044e04d27068783cd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spirostane-3,6-dione 10V, Negative-QTOFsplash10-004i-4002900000-bd6400c880e5a484d56a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spirostane-3,6-dione 20V, Negative-QTOFsplash10-06vi-2009400000-ba081cf37ae2bcdf19962016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spirostane-3,6-dione 40V, Negative-QTOFsplash10-07vi-9005000000-05809f672fa682eee3992016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spirostane-3,6-dione 10V, Positive-QTOFsplash10-004i-0000900000-37f7822c437e446b17f22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spirostane-3,6-dione 20V, Positive-QTOFsplash10-02dr-1378900000-84b811d286dbae89406a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spirostane-3,6-dione 40V, Positive-QTOFsplash10-000l-3983000000-ce8f66a2af1e1e817c282021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spirostane-3,6-dione 10V, Negative-QTOFsplash10-004i-0000900000-f80757ff7e5e5a34875b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spirostane-3,6-dione 20V, Negative-QTOFsplash10-004i-0000900000-238ca72386b2dfe89acb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Spirostane-3,6-dione 40V, Negative-QTOFsplash10-01t9-1108900000-490ef84ef80d9e6ab4622021-09-23Wishart 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 IDFDB015909
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13889197
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.