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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:28:57 UTC
Update Date2022-03-07 02:55:40 UTC
HMDB IDHMDB0038202
Secondary Accession Numbers
  • HMDB38202
Metabolite Identification
Common NameZedoarol
DescriptionZedoarol belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively. Based on a literature review a small amount of articles have been published on Zedoarol.
Structure
Data?1563863156
SynonymsNot Available
Chemical FormulaC15H18O3
Average Molecular Weight246.3016
Monoisotopic Molecular Weight246.125594442
IUPAC Name4a-hydroxy-3,5-dimethyl-8-methylidene-4H,4aH,5H,6H,7H,7aH,8H,9H-azuleno[6,5-b]furan-4-one
Traditional Name4a-hydroxy-3,5-dimethyl-8-methylidene-5H,6H,7H,7aH,9H-azuleno[6,5-b]furan-4-one
CAS Registry Number103994-22-5
SMILES
CC1CCC2C(=C)CC3=C(C(C)=CO3)C(=O)C12O
InChI Identifier
InChI=1S/C15H18O3/c1-8-6-12-13(9(2)7-18-12)14(16)15(17)10(3)4-5-11(8)15/h7,10-11,17H,1,4-6H2,2-3H3
InChI KeyCKDRPCYJCDMPFO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentGuaianes
Alternative Parents
Substituents
  • Guaiane sesquiterpenoid
  • Cycloheptafuran
  • Aryl ketone
  • Aryl alkyl ketone
  • Cyclic alcohol
  • Furan
  • Tertiary alcohol
  • Heteroaromatic compound
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Alcohol
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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 Solubility146.8 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP2.06ALOGPS
logP2.43ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)12.46ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.44 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity68.71 m³·mol⁻¹ChemAxon
Polarizability26.76 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]+156.2231661259
DarkChem[M-H]-155.16131661259
DeepCCS[M-2H]-191.64630932474
DeepCCS[M+Na]+167.21130932474
AllCCS[M+H]+155.632859911
AllCCS[M+H-H2O]+151.832859911
AllCCS[M+NH4]+159.132859911
AllCCS[M+Na]+160.232859911
AllCCS[M-H]-161.832859911
AllCCS[M+Na-2H]-161.632859911
AllCCS[M+HCOO]-161.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ZedoarolCC1CCC2C(=C)CC3=C(C(C)=CO3)C(=O)C12O2796.7Standard polar33892256
ZedoarolCC1CCC2C(=C)CC3=C(C(C)=CO3)C(=O)C12O1920.1Standard non polar33892256
ZedoarolCC1CCC2C(=C)CC3=C(C(C)=CO3)C(=O)C12O1868.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Zedoarol,1TMS,isomer #1C=C1CC2=C(C(=O)C3(O[Si](C)(C)C)C(C)CCC13)C(C)=CO22052.1Semi standard non polar33892256
Zedoarol,1TBDMS,isomer #1C=C1CC2=C(C(=O)C3(O[Si](C)(C)C(C)(C)C)C(C)CCC13)C(C)=CO22261.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Zedoarol GC-MS (Non-derivatized) - 70eV, Positivesplash10-05u2-7920000000-59a04e3a2e4cb78c00ec2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zedoarol GC-MS (1 TMS) - 70eV, Positivesplash10-0fdn-9731000000-76a252b6f18f0a0eeabe2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zedoarol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zedoarol 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 - Zedoarol 10V, Positive-QTOFsplash10-0002-0090000000-d0ea8342b45d1cb88a332016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zedoarol 20V, Positive-QTOFsplash10-0f6t-7590000000-b4cdaf09957c845afbde2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zedoarol 40V, Positive-QTOFsplash10-0f6x-9120000000-3413747b5c83bd7adc472016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zedoarol 10V, Negative-QTOFsplash10-0002-0090000000-e10f3f664863537b9bdb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zedoarol 20V, Negative-QTOFsplash10-0002-0090000000-3ebcca8feb4b8610df2e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zedoarol 40V, Negative-QTOFsplash10-0037-9530000000-29e8ab0b9398bdc2b7522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zedoarol 10V, Positive-QTOFsplash10-0002-0090000000-db338c5d740c9ec522102021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zedoarol 20V, Positive-QTOFsplash10-00kb-3950000000-87bb791439f30710511c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zedoarol 40V, Positive-QTOFsplash10-0a7l-9680000000-dfda63175e95a2cc79222021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zedoarol 10V, Negative-QTOFsplash10-0002-0090000000-851e47b490f6973ef9e52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zedoarol 20V, Negative-QTOFsplash10-0002-0090000000-3df4d946ab283032c6b92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zedoarol 40V, Negative-QTOFsplash10-00bm-2790000000-d1a9e60deee5c4361c572021-09-25Wishart 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 IDFDB017441
KNApSAcK IDC00020430
Chemspider ID35014535
KEGG Compound IDC17490
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound75144776
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1866291
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.