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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:17:34 UTC
Update Date2022-03-07 02:56:42 UTC
HMDB IDHMDB0040716
Secondary Accession Numbers
  • HMDB40716
Metabolite Identification
Common NameIrenolone
DescriptionIrenolone belongs to the class of organic compounds known as phenylnaphthalenes. Phenylnaphthalenes are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group. Irenolone has been detected, but not quantified in, a few different foods, such as bananas (Musa acuminata), french plantains (Musa X paradisiaca), and fruits. This could make irenolone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Irenolone.
Structure
Data?1563863581
SynonymsNot Available
Chemical FormulaC19H12O3
Average Molecular Weight288.2968
Monoisotopic Molecular Weight288.07864425
IUPAC Name2-hydroxy-4-(4-hydroxyphenyl)-1H-phenalen-1-one
Traditional Name2-hydroxy-4-(4-hydroxyphenyl)phenalen-1-one
CAS Registry Number149184-19-0
SMILES
OC1=CC=C(C=C1)C1=C2C=C(O)C(=O)C3=CC=CC(C=C1)=C23
InChI Identifier
InChI=1S/C19H12O3/c20-13-7-4-11(5-8-13)14-9-6-12-2-1-3-15-18(12)16(14)10-17(21)19(15)22/h1-10,20-21H
InChI KeyUQMKPTIDKHEGFW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylnaphthalenes. Phenylnaphthalenes are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassPhenylnaphthalenes
Direct ParentPhenylnaphthalenes
Alternative Parents
Substituents
  • Phenylnaphthalene
  • Phenalen-1-one
  • Phenalen
  • Aryl ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Ketone
  • Enol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point285 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.48 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0063 g/LALOGPS
logP3.67ALOGPS
logP3.73ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)9.16ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity86.35 m³·mol⁻¹ChemAxon
Polarizability30.4 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-201.93330932474
DeepCCS[M+Na]+177.1630932474
AllCCS[M+H]+167.932859911
AllCCS[M+H-H2O]+164.232859911
AllCCS[M+NH4]+171.332859911
AllCCS[M+Na]+172.332859911
AllCCS[M-H]-170.632859911
AllCCS[M+Na-2H]-169.432859911
AllCCS[M+HCOO]-168.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IrenoloneOC1=CC=C(C=C1)C1=C2C=C(O)C(=O)C3=CC=CC(C=C1)=C234262.3Standard polar33892256
IrenoloneOC1=CC=C(C=C1)C1=C2C=C(O)C(=O)C3=CC=CC(C=C1)=C232754.0Standard non polar33892256
IrenoloneOC1=CC=C(C=C1)C1=C2C=C(O)C(=O)C3=CC=CC(C=C1)=C233184.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Irenolone,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(C2=CC=C3C=CC=C4C(=O)C(O)=CC2=C43)C=C13195.2Semi standard non polar33892256
Irenolone,1TMS,isomer #2C[Si](C)(C)OC1=CC2=C3C(=CC=CC3=CC=C2C2=CC=C(O)C=C2)C1=O3233.0Semi standard non polar33892256
Irenolone,2TMS,isomer #1C[Si](C)(C)OC1=CC2=C3C(=CC=CC3=CC=C2C2=CC=C(O[Si](C)(C)C)C=C2)C1=O3194.1Semi standard non polar33892256
Irenolone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC=C3C=CC=C4C(=O)C(O)=CC2=C43)C=C13444.0Semi standard non polar33892256
Irenolone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2=C3C(=CC=CC3=CC=C2C2=CC=C(O)C=C2)C1=O3472.5Semi standard non polar33892256
Irenolone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C3C(=CC=CC3=CC=C2C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C1=O3662.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Irenolone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bu0-0090000000-3bc82c31952bf2ce22ac2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Irenolone GC-MS (2 TMS) - 70eV, Positivesplash10-00xr-9008600000-53c05c277181d05a22662017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Irenolone 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 - Irenolone 10V, Positive-QTOFsplash10-000i-0090000000-418fac8b530b8c6ab5822015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Irenolone 20V, Positive-QTOFsplash10-000i-0190000000-8c41e7434cef043fbdcd2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Irenolone 40V, Positive-QTOFsplash10-0kmj-0190000000-b82626098c30f1b83d1d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Irenolone 10V, Negative-QTOFsplash10-000i-0090000000-8e165b5e31ea35c989a82015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Irenolone 20V, Negative-QTOFsplash10-000i-0090000000-96d79177be0638f922712015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Irenolone 40V, Negative-QTOFsplash10-0apu-1090000000-1923029a02fe63ae8a222015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Irenolone 10V, Negative-QTOFsplash10-000i-0090000000-ad76c01409fa18536a262021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Irenolone 20V, Negative-QTOFsplash10-000i-0090000000-775291b18c312826c59b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Irenolone 40V, Negative-QTOFsplash10-0a5i-0090000000-851d3b930599d858ab032021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Irenolone 10V, Positive-QTOFsplash10-000i-0090000000-9b8c528cd946b073787c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Irenolone 20V, Positive-QTOFsplash10-000i-0090000000-9b8c528cd946b073787c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Irenolone 40V, Positive-QTOFsplash10-053r-0090000000-b06b840bb662e372fdf42021-09-25Wishart 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 IDFDB020523
KNApSAcK IDC00037306
Chemspider ID2035535
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound2754650
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1885781
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.. .