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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:15:12 UTC
Update Date2022-03-07 02:53:44 UTC
HMDB IDHMDB0033515
Secondary Accession Numbers
  • HMDB33515
Metabolite Identification
Common NameCitreovirenone
DescriptionCitreovirenone belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Based on a literature review very few articles have been published on Citreovirenone.
Structure
Data?1563862418
SynonymsNot Available
Chemical FormulaC14H16O4
Average Molecular Weight248.2744
Monoisotopic Molecular Weight248.104859
IUPAC Name6-[(3-hydroxy-5-methoxyphenyl)methyl]-2-methyl-3,4-dihydro-2H-pyran-4-one
Traditional Name2-[(3-hydroxy-5-methoxyphenyl)methyl]-6-methyl-5,6-dihydropyran-4-one
CAS Registry Number103955-68-6
SMILES
COC1=CC(CC2=CC(=O)CC(C)O2)=CC(O)=C1
InChI Identifier
InChI=1S/C14H16O4/c1-9-3-11(15)8-14(18-9)6-10-4-12(16)7-13(5-10)17-2/h4-5,7-9,16H,3,6H2,1-2H3
InChI KeyWMCPLZDBHVOXCJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Dihydropyranone
  • Monocyclic benzene moiety
  • Vinylogous ester
  • Ketone
  • Cyclic ketone
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility3091 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.24 g/LALOGPS
logP2.4ALOGPS
logP2.01ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.4ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity69.01 m³·mol⁻¹ChemAxon
Polarizability25.84 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]+159.34231661259
DarkChem[M-H]-162.17931661259
DeepCCS[M+H]+165.34830932474
DeepCCS[M-H]-162.9930932474
DeepCCS[M-2H]-195.87730932474
DeepCCS[M+Na]+171.44230932474
AllCCS[M+H]+157.732859911
AllCCS[M+H-H2O]+153.732859911
AllCCS[M+NH4]+161.532859911
AllCCS[M+Na]+162.632859911
AllCCS[M-H]-160.632859911
AllCCS[M+Na-2H]-160.732859911
AllCCS[M+HCOO]-160.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CitreovirenoneCOC1=CC(CC2=CC(=O)CC(C)O2)=CC(O)=C13358.9Standard polar33892256
CitreovirenoneCOC1=CC(CC2=CC(=O)CC(C)O2)=CC(O)=C12180.7Standard non polar33892256
CitreovirenoneCOC1=CC(CC2=CC(=O)CC(C)O2)=CC(O)=C12338.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Citreovirenone,1TMS,isomer #1COC1=CC(CC2=CC(=O)CC(C)O2)=CC(O[Si](C)(C)C)=C12268.0Semi standard non polar33892256
Citreovirenone,1TMS,isomer #2COC1=CC(O)=CC(CC2=CC(O[Si](C)(C)C)=CC(C)O2)=C12223.4Semi standard non polar33892256
Citreovirenone,2TMS,isomer #1COC1=CC(CC2=CC(O[Si](C)(C)C)=CC(C)O2)=CC(O[Si](C)(C)C)=C12251.3Semi standard non polar33892256
Citreovirenone,2TMS,isomer #1COC1=CC(CC2=CC(O[Si](C)(C)C)=CC(C)O2)=CC(O[Si](C)(C)C)=C12290.5Standard non polar33892256
Citreovirenone,1TBDMS,isomer #1COC1=CC(CC2=CC(=O)CC(C)O2)=CC(O[Si](C)(C)C(C)(C)C)=C12521.2Semi standard non polar33892256
Citreovirenone,1TBDMS,isomer #2COC1=CC(O)=CC(CC2=CC(O[Si](C)(C)C(C)(C)C)=CC(C)O2)=C12507.6Semi standard non polar33892256
Citreovirenone,2TBDMS,isomer #1COC1=CC(CC2=CC(O[Si](C)(C)C(C)(C)C)=CC(C)O2)=CC(O[Si](C)(C)C(C)(C)C)=C12727.1Semi standard non polar33892256
Citreovirenone,2TBDMS,isomer #1COC1=CC(CC2=CC(O[Si](C)(C)C(C)(C)C)=CC(C)O2)=CC(O[Si](C)(C)C(C)(C)C)=C12705.8Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Citreovirenone GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-5960000000-ab51728ea87161d891d42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citreovirenone GC-MS (1 TMS) - 70eV, Positivesplash10-0c03-5192000000-d718708a04526b734f492017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citreovirenone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citreovirenone 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 - Citreovirenone 10V, Positive-QTOFsplash10-0002-0190000000-cac62387d88dc62f899f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citreovirenone 20V, Positive-QTOFsplash10-0002-8970000000-a73791477d8271986a132015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citreovirenone 40V, Positive-QTOFsplash10-00kf-9810000000-c877424da9df433c82142015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citreovirenone 10V, Negative-QTOFsplash10-0002-0090000000-f5a401a1366b05ecbd482015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citreovirenone 20V, Negative-QTOFsplash10-0002-2390000000-714ccf78a03070a5e6992015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citreovirenone 40V, Negative-QTOFsplash10-0543-9410000000-7a428ee4efa7429c1d1a2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citreovirenone 10V, Positive-QTOFsplash10-000b-0790000000-b81ab49381e8f49186c62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citreovirenone 20V, Positive-QTOFsplash10-053j-4930000000-69e480cdea1d45901b312021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citreovirenone 40V, Positive-QTOFsplash10-0a4s-5910000000-81477cfb09dbe01cc92a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citreovirenone 10V, Negative-QTOFsplash10-0002-0490000000-d0b16d17c36b9607d91d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citreovirenone 20V, Negative-QTOFsplash10-007a-5950000000-c5042f4390a0270862032021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citreovirenone 40V, Negative-QTOFsplash10-000e-3920000000-efc0126c898b32ac98db2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB011570
KNApSAcK IDC00055273
Chemspider ID35013619
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751444
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1836321
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.. .