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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:55:34 UTC
Update Date2022-03-07 02:53:59 UTC
HMDB IDHMDB0034130
Secondary Accession Numbers
  • HMDB34130
Metabolite Identification
Common NameOsthenol
DescriptionOsthenol belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. Osthenol has been detected, but not quantified in, several different foods, such as angelicas (Angelica keiskei), fennels (Foeniculum vulgare), green vegetables, and wild celeries (Apium graveolens). This could make osthenol a potential biomarker for the consumption of these foods. Osthenol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Osthenol.
Structure
Data?1563862515
Synonyms
ValueSource
7-Hydroxy-8-(3-methyl-but-2-enyl)coumarinChEBI
7-Hydroxy-8-prenylcoumarinChEBI
8-(3-Methylbut-2-en-1-yl)umbelliferoneChEBI
8-PrenylumbelliferoneChEBI
7-Hydroxy-8-(3-methyl-2-butenyl)-2H-1-benzopyran-2-oneHMDB
7-Hydroxy-8-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one, 9ciHMDB
Chemical FormulaC14H14O3
Average Molecular Weight230.2592
Monoisotopic Molecular Weight230.094294314
IUPAC Name7-hydroxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one
Traditional Name7-hydroxy-8-(3-methylbut-2-en-1-yl)chromen-2-one
CAS Registry Number484-14-0
SMILES
CC(C)=CCC1=C(O)C=CC2=C1OC(=O)C=C2
InChI Identifier
InChI=1S/C14H14O3/c1-9(2)3-6-11-12(15)7-4-10-5-8-13(16)17-14(10)11/h3-5,7-8,15H,6H2,1-2H3
InChI KeyRAKJVIPCCGXHHS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassHydroxycoumarins
Direct Parent7-hydroxycoumarins
Alternative Parents
Substituents
  • 7-hydroxycoumarin
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point124 - 125 °CNot Available
Boiling Point422.00 to 423.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility148.1 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.342 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.054 g/LALOGPS
logP3.24ALOGPS
logP3.21ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)7.64ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity67.77 m³·mol⁻¹ChemAxon
Polarizability24.63 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]+156.18831661259
DarkChem[M-H]-150.831661259
DeepCCS[M+H]+153.35130932474
DeepCCS[M-H]-150.99330932474
DeepCCS[M-2H]-184.01530932474
DeepCCS[M+Na]+159.44430932474
AllCCS[M+H]+149.832859911
AllCCS[M+H-H2O]+145.732859911
AllCCS[M+NH4]+153.632859911
AllCCS[M+Na]+154.732859911
AllCCS[M-H]-152.832859911
AllCCS[M+Na-2H]-152.632859911
AllCCS[M+HCOO]-152.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
OsthenolCC(C)=CCC1=C(O)C=CC2=C1OC(=O)C=C23149.9Standard polar33892256
OsthenolCC(C)=CCC1=C(O)C=CC2=C1OC(=O)C=C22125.1Standard non polar33892256
OsthenolCC(C)=CCC1=C(O)C=CC2=C1OC(=O)C=C22170.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Osthenol,1TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C=CC2=C1OC(=O)C=C22121.8Semi standard non polar33892256
Osthenol,1TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OC(=O)C=C22392.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Osthenol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udu-3970000000-cbf063b17a9b1ff28fdf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Osthenol GC-MS (1 TMS) - 70eV, Positivesplash10-0abl-4090000000-75a6447476e3afd4a43f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Osthenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Osthenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Osthenol , positive-QTOFsplash10-004i-1900000000-13a982a68db0b067c3ad2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Osthenol 10V, Positive-QTOFsplash10-001i-0290000000-fe23cb680c0e7dd31c492016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Osthenol 20V, Positive-QTOFsplash10-00o0-3950000000-265a49635935bcc77eb52016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Osthenol 40V, Positive-QTOFsplash10-01e9-5900000000-3c86d1a1a031d6b9fd552016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Osthenol 10V, Negative-QTOFsplash10-004i-0290000000-0129cc47e1148c003a702016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Osthenol 20V, Negative-QTOFsplash10-004i-0690000000-5e2cd8fffc743828ac3a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Osthenol 40V, Negative-QTOFsplash10-014r-2910000000-24094198ef8b3c6f54f32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Osthenol 10V, Positive-QTOFsplash10-003r-0790000000-cecbb981baa3d40e1eba2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Osthenol 20V, Positive-QTOFsplash10-004i-0900000000-6945bc6ebaeea92789862021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Osthenol 40V, Positive-QTOFsplash10-001j-0900000000-736ee822dbb9d1410fd72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Osthenol 10V, Negative-QTOFsplash10-004i-0090000000-3b9ecf594e3ba8c418c22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Osthenol 20V, Negative-QTOFsplash10-004i-0290000000-6377690d47ed40e1bdf02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Osthenol 40V, Negative-QTOFsplash10-00lr-2900000000-3dda8af619d96c95b3982021-09-24Wishart 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 IDFDB012404
KNApSAcK IDC00030900
Chemspider ID4478430
KEGG Compound IDC18080
BioCyc IDCPD-9838
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5320318
PDB IDNot Available
ChEBI ID81485
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1050171
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.. .