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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:04:51 UTC
Update Date2022-03-07 02:54:22 UTC
HMDB IDHMDB0035137
Secondary Accession Numbers
  • HMDB35137
Metabolite Identification
Common NameHeliannuol D
DescriptionHeliannuol D belongs to the class of organic compounds known as benzoxepines. These are organic compounds containing a benzene ring fused to an oxepine ring (an unsaturated seven-membered heterocycle with one oxygen atom replacing a carbon atom). Heliannuol D has been detected, but not quantified in, fats and oils and sunflowers (Helianthus annuus). This could make heliannuol D a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Heliannuol D.
Structure
Data?1563862672
Synonyms
ValueSource
(+)-Heliannuol DHMDB
2'-DeoxytetrahydrouridineHMDB
3,4,5,6-TetrahydrodeoxyuridineHMDB
5,10-Epoxy-1,3,5-bisabolatriene-2,11-diolHMDB
tetrahydro-2'-DeoxyuridineHMDB
THDUHMDB
Heliannuol DMeSH
Chemical FormulaC15H22O3
Average Molecular Weight250.3334
Monoisotopic Molecular Weight250.15689457
IUPAC Name2-(2-hydroxypropan-2-yl)-5,8-dimethyl-2,3,4,5-tetrahydro-1-benzoxepin-7-ol
Traditional Name2-(2-hydroxypropan-2-yl)-5,8-dimethyl-2,3,4,5-tetrahydro-1-benzoxepin-7-ol
CAS Registry Number161730-09-2
SMILES
CC1CCC(OC2=C1C=C(O)C(C)=C2)C(C)(C)O
InChI Identifier
InChI=1S/C15H22O3/c1-9-5-6-14(15(3,4)17)18-13-7-10(2)12(16)8-11(9)13/h7-9,14,16-17H,5-6H2,1-4H3
InChI KeyBIIJJHXLFCDTIZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoxepines. These are organic compounds containing a benzene ring fused to an oxepine ring (an unsaturated seven-membered heterocycle with one oxygen atom replacing a carbon atom).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzoxepines
Sub ClassNot Available
Direct ParentBenzoxepines
Alternative Parents
Substituents
  • Benzoxepine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary alcohol
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point59 - 61 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility164.9 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.28 g/LALOGPS
logP3.1ALOGPS
logP3.31ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)10.34ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.62 m³·mol⁻¹ChemAxon
Polarizability28.35 ųChemAxon
Number of Rings2ChemAxon
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]+160.59331661259
DarkChem[M-H]-156.97531661259
DeepCCS[M+H]+165.70130932474
DeepCCS[M-H]-163.34330932474
DeepCCS[M-2H]-196.22830932474
DeepCCS[M+Na]+171.79430932474
AllCCS[M+H]+158.332859911
AllCCS[M+H-H2O]+154.432859911
AllCCS[M+NH4]+161.832859911
AllCCS[M+Na]+162.932859911
AllCCS[M-H]-165.932859911
AllCCS[M+Na-2H]-166.232859911
AllCCS[M+HCOO]-166.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Heliannuol DCC1CCC(OC2=C1C=C(O)C(C)=C2)C(C)(C)O3011.7Standard polar33892256
Heliannuol DCC1CCC(OC2=C1C=C(O)C(C)=C2)C(C)(C)O1940.5Standard non polar33892256
Heliannuol DCC1CCC(OC2=C1C=C(O)C(C)=C2)C(C)(C)O2054.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Heliannuol D,1TMS,isomer #1CC1=CC2=C(C=C1O[Si](C)(C)C)C(C)CCC(C(C)(C)O)O22098.4Semi standard non polar33892256
Heliannuol D,1TMS,isomer #2CC1=CC2=C(C=C1O)C(C)CCC(C(C)(C)O[Si](C)(C)C)O22103.0Semi standard non polar33892256
Heliannuol D,2TMS,isomer #1CC1=CC2=C(C=C1O[Si](C)(C)C)C(C)CCC(C(C)(C)O[Si](C)(C)C)O22123.1Semi standard non polar33892256
Heliannuol D,1TBDMS,isomer #1CC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C(C)CCC(C(C)(C)O)O22331.0Semi standard non polar33892256
Heliannuol D,1TBDMS,isomer #2CC1=CC2=C(C=C1O)C(C)CCC(C(C)(C)O[Si](C)(C)C(C)(C)C)O22329.0Semi standard non polar33892256
Heliannuol D,2TBDMS,isomer #1CC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C(C)CCC(C(C)(C)O[Si](C)(C)C(C)(C)C)O22568.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Heliannuol D GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9430000000-c15af6ea487892967c422017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heliannuol D GC-MS (2 TMS) - 70eV, Positivesplash10-003r-4819000000-e0d6ff3170a90bbd55cf2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Heliannuol D 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 - Heliannuol D 10V, Positive-QTOFsplash10-0ue9-0190000000-22940b2433c959e094aa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heliannuol D 20V, Positive-QTOFsplash10-0uyi-0890000000-a8f0be99aab549be4dc02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heliannuol D 40V, Positive-QTOFsplash10-05mk-4910000000-9710387b4c9a4fdd6bca2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heliannuol D 10V, Negative-QTOFsplash10-0002-0090000000-fe01d2b814324394b9f62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heliannuol D 20V, Negative-QTOFsplash10-000t-0390000000-3b0ec7b6d97bb52ba9132016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heliannuol D 40V, Negative-QTOFsplash10-00di-3910000000-35e74680c9c1b2c7d29b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heliannuol D 10V, Positive-QTOFsplash10-0udi-0390000000-d4861119f0d14d881e3e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heliannuol D 20V, Positive-QTOFsplash10-0uk9-4970000000-a22ab8d5b1feaba568232021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heliannuol D 40V, Positive-QTOFsplash10-0c03-5900000000-2e03514c7df437c961222021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heliannuol D 10V, Negative-QTOFsplash10-0002-0090000000-57a45c4032b87b6021b82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heliannuol D 20V, Negative-QTOFsplash10-0a4j-9170000000-6fb7db989aaf4b090c742021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heliannuol D 40V, Negative-QTOFsplash10-0596-7930000000-a109d21f0a27ee91a6262021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB013773
KNApSAcK IDC00037241
Chemspider ID9600106
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11425230
PDB IDNot Available
ChEBI ID174299
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1847921
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .