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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:55:07 UTC
Update Date2022-03-07 02:54:18 UTC
HMDB IDHMDB0034983
Secondary Accession Numbers
  • HMDB34983
Metabolite Identification
Common NameCynaratriol
DescriptionCynaratriol belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Based on a literature review a small amount of articles have been published on Cynaratriol.
Structure
Data?1563862646
Synonyms
ValueSource
3,11,13-Trihydroxy-10(14)-guaien-12,6-olideHMDB
TipropidilHMDB
Chemical FormulaC15H22O5
Average Molecular Weight282.3322
Monoisotopic Molecular Weight282.146723814
IUPAC Name3,8-dihydroxy-3-(hydroxymethyl)-9-methyl-6-methylidene-dodecahydroazuleno[4,5-b]furan-2-one
Traditional Name3,8-dihydroxy-3-(hydroxymethyl)-9-methyl-6-methylidene-octahydro-3aH-azuleno[4,5-b]furan-2-one
CAS Registry Number70894-20-1
SMILES
CC1C(O)CC2C1C1OC(=O)C(O)(CO)C1CCC2=C
InChI Identifier
InChI=1S/C15H22O5/c1-7-3-4-10-13(20-14(18)15(10,19)6-16)12-8(2)11(17)5-9(7)12/h8-13,16-17,19H,1,3-6H2,2H3
InChI KeyOHBHGGYGWZIWCX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentGuaianolides and derivatives
Alternative Parents
Substituents
  • Guaianolide-skeleton
  • Guaiane sesquiterpenoid
  • Sesquiterpenoid
  • Gamma butyrolactone
  • Cyclic alcohol
  • Tertiary alcohol
  • Tetrahydrofuran
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Primary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point178 - 179 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility6738 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility17.1 g/LALOGPS
logP0.24ALOGPS
logP-0.014ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)11.36ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.06 m³·mol⁻¹ChemAxon
Polarizability29.54 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+165.44231661259
DarkChem[M-H]-160.87831661259
DeepCCS[M+H]+163.38430932474
DeepCCS[M-H]-161.02630932474
DeepCCS[M-2H]-193.91230932474
DeepCCS[M+Na]+169.47730932474
AllCCS[M+H]+166.432859911
AllCCS[M+H-H2O]+163.032859911
AllCCS[M+NH4]+169.532859911
AllCCS[M+Na]+170.432859911
AllCCS[M-H]-168.832859911
AllCCS[M+Na-2H]-168.732859911
AllCCS[M+HCOO]-168.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CynaratriolCC1C(O)CC2C1C1OC(=O)C(O)(CO)C1CCC2=C3335.7Standard polar33892256
CynaratriolCC1C(O)CC2C1C1OC(=O)C(O)(CO)C1CCC2=C2504.1Standard non polar33892256
CynaratriolCC1C(O)CC2C1C1OC(=O)C(O)(CO)C1CCC2=C2501.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cynaratriol,1TMS,isomer #1C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(O[Si](C)(C)C)C2C2306.1Semi standard non polar33892256
Cynaratriol,1TMS,isomer #2C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C)C2C1CC(O)C2C2364.4Semi standard non polar33892256
Cynaratriol,1TMS,isomer #3C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C)C2C1CC(O)C2C2329.6Semi standard non polar33892256
Cynaratriol,2TMS,isomer #1C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C)C2C1CC(O[Si](C)(C)C)C2C2415.2Semi standard non polar33892256
Cynaratriol,2TMS,isomer #2C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C)C2C1CC(O[Si](C)(C)C)C2C2367.6Semi standard non polar33892256
Cynaratriol,2TMS,isomer #3C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C)O[Si](C)(C)C)C2C1CC(O)C2C2412.9Semi standard non polar33892256
Cynaratriol,3TMS,isomer #1C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C)O[Si](C)(C)C)C2C1CC(O[Si](C)(C)C)C2C2447.1Semi standard non polar33892256
Cynaratriol,1TBDMS,isomer #1C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(O[Si](C)(C)C(C)(C)C)C2C2559.2Semi standard non polar33892256
Cynaratriol,1TBDMS,isomer #2C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C(C)(C)C)C2C1CC(O)C2C2608.8Semi standard non polar33892256
Cynaratriol,1TBDMS,isomer #3C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C(C)(C)C)C2C1CC(O)C2C2573.6Semi standard non polar33892256
Cynaratriol,2TBDMS,isomer #1C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C(C)(C)C)C2C1CC(O[Si](C)(C)C(C)(C)C)C2C2881.6Semi standard non polar33892256
Cynaratriol,2TBDMS,isomer #2C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C(C)(C)C)C2C1CC(O[Si](C)(C)C(C)(C)C)C2C2845.3Semi standard non polar33892256
Cynaratriol,2TBDMS,isomer #3C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C2C1CC(O)C2C2882.7Semi standard non polar33892256
Cynaratriol,3TBDMS,isomer #1C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C2C1CC(O[Si](C)(C)C(C)(C)C)C2C3123.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cynaratriol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pb9-5690000000-6f55598ba0e7bf3493c42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cynaratriol GC-MS (3 TMS) - 70eV, Positivesplash10-0fl9-2271900000-c1fb7b8c722a348b28282017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cynaratriol 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 - Cynaratriol 10V, Positive-QTOFsplash10-017i-0490000000-50b575204b51111c23e82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cynaratriol 20V, Positive-QTOFsplash10-014i-0290000000-c35f56ecb28e181873252016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cynaratriol 40V, Positive-QTOFsplash10-004i-3900000000-f7cf617a6e6923a2b99e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cynaratriol 10V, Negative-QTOFsplash10-001i-0090000000-1b8b21086edc314e30992016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cynaratriol 20V, Negative-QTOFsplash10-001i-0090000000-76fb16f22165e3a5ba8b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cynaratriol 40V, Negative-QTOFsplash10-002o-3900000000-bae847315dbfb2c725dc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cynaratriol 10V, Positive-QTOFsplash10-001i-0090000000-09add33fa558d15bac932021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cynaratriol 20V, Positive-QTOFsplash10-014i-1790000000-0673b4133fe07afc7fe72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cynaratriol 40V, Positive-QTOFsplash10-0avi-1900000000-12c50e985eef64ed99cc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cynaratriol 10V, Negative-QTOFsplash10-001i-0090000000-43f6dfe2305d9a856a612021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cynaratriol 20V, Negative-QTOFsplash10-001i-0090000000-49c3f45754d5c3d06bbe2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cynaratriol 40V, Negative-QTOFsplash10-01qj-0290000000-ca9c1792073d63766dc62021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart 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 IDFDB013584
KNApSAcK IDC00020855
Chemspider ID26503332
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14138149
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1846781
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.