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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:15:15 UTC
Update Date2022-03-07 02:53:44 UTC
HMDB IDHMDB0033516
Secondary Accession Numbers
  • HMDB33516
Metabolite Identification
Common NameCitreovirone
DescriptionCitreovirone 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 Citreovirone.
Structure
Data?1563862418
Synonyms
ValueSource
5,5-dichloro-4-Hydroxy-1-(3-hydroxy-5-methoxyphenyl)-2-pentanone, 9ciHMDB
Chemical FormulaC12H14Cl2O4
Average Molecular Weight293.143
Monoisotopic Molecular Weight292.02691435
IUPAC Name5,5-dichloro-4-hydroxy-1-(3-hydroxy-5-methoxyphenyl)pentan-2-one
Traditional Name5,5-dichloro-4-hydroxy-1-(3-hydroxy-5-methoxyphenyl)pentan-2-one
CAS Registry Number103955-67-5
SMILES
COC1=CC(CC(=O)CC(O)C(Cl)Cl)=CC(O)=C1
InChI Identifier
InChI=1S/C12H14Cl2O4/c1-18-10-4-7(2-8(15)5-10)3-9(16)6-11(17)12(13)14/h2,4-5,11-12,15,17H,3,6H2,1H3
InChI KeyASUNQAFARHTUFP-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
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Beta-hydroxy ketone
  • Secondary alcohol
  • Chlorohydrin
  • Ketone
  • Halohydrin
  • Ether
  • Hydrocarbon derivative
  • Organohalogen compound
  • Organochloride
  • Carbonyl group
  • Organooxygen compound
  • Alkyl chloride
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Alkyl halide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.34 g/LALOGPS
logP2.11ALOGPS
logP2.29ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)9.4ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity69.83 m³·mol⁻¹ChemAxon
Polarizability27.77 ųChemAxon
Number of Rings1ChemAxon
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+H]+166.16630932474
DeepCCS[M-H]-163.80830932474
DeepCCS[M-2H]-196.69430932474
DeepCCS[M+Na]+172.25930932474
AllCCS[M+H]+162.532859911
AllCCS[M+H-H2O]+159.232859911
AllCCS[M+NH4]+165.632859911
AllCCS[M+Na]+166.532859911
AllCCS[M-H]-162.132859911
AllCCS[M+Na-2H]-162.532859911
AllCCS[M+HCOO]-163.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CitreovironeCOC1=CC(CC(=O)CC(O)C(Cl)Cl)=CC(O)=C13867.5Standard polar33892256
CitreovironeCOC1=CC(CC(=O)CC(O)C(Cl)Cl)=CC(O)=C12230.3Standard non polar33892256
CitreovironeCOC1=CC(CC(=O)CC(O)C(Cl)Cl)=CC(O)=C12423.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Citreovirone,1TMS,isomer #1COC1=CC(O)=CC(CC(=O)CC(O[Si](C)(C)C)C(Cl)Cl)=C12330.8Semi standard non polar33892256
Citreovirone,1TMS,isomer #2COC1=CC(CC(=O)CC(O)C(Cl)Cl)=CC(O[Si](C)(C)C)=C12330.6Semi standard non polar33892256
Citreovirone,1TMS,isomer #3COC1=CC(O)=CC(CC(=CC(O)C(Cl)Cl)O[Si](C)(C)C)=C12449.6Semi standard non polar33892256
Citreovirone,1TMS,isomer #4COC1=CC(O)=CC(C=C(CC(O)C(Cl)Cl)O[Si](C)(C)C)=C12472.2Semi standard non polar33892256
Citreovirone,2TMS,isomer #1COC1=CC(CC(=O)CC(O[Si](C)(C)C)C(Cl)Cl)=CC(O[Si](C)(C)C)=C12348.4Semi standard non polar33892256
Citreovirone,2TMS,isomer #2COC1=CC(O)=CC(CC(=CC(O[Si](C)(C)C)C(Cl)Cl)O[Si](C)(C)C)=C12455.9Semi standard non polar33892256
Citreovirone,2TMS,isomer #3COC1=CC(O)=CC(C=C(CC(O[Si](C)(C)C)C(Cl)Cl)O[Si](C)(C)C)=C12432.4Semi standard non polar33892256
Citreovirone,2TMS,isomer #4COC1=CC(CC(=CC(O)C(Cl)Cl)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C12436.2Semi standard non polar33892256
Citreovirone,2TMS,isomer #5COC1=CC(C=C(CC(O)C(Cl)Cl)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C12448.9Semi standard non polar33892256
Citreovirone,3TMS,isomer #1COC1=CC(CC(=CC(O[Si](C)(C)C)C(Cl)Cl)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C12440.0Semi standard non polar33892256
Citreovirone,3TMS,isomer #1COC1=CC(CC(=CC(O[Si](C)(C)C)C(Cl)Cl)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C12264.5Standard non polar33892256
Citreovirone,3TMS,isomer #2COC1=CC(C=C(CC(O[Si](C)(C)C)C(Cl)Cl)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C12425.5Semi standard non polar33892256
Citreovirone,3TMS,isomer #2COC1=CC(C=C(CC(O[Si](C)(C)C)C(Cl)Cl)O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C12371.6Standard non polar33892256
Citreovirone,1TBDMS,isomer #1COC1=CC(O)=CC(CC(=O)CC(O[Si](C)(C)C(C)(C)C)C(Cl)Cl)=C12586.4Semi standard non polar33892256
Citreovirone,1TBDMS,isomer #2COC1=CC(CC(=O)CC(O)C(Cl)Cl)=CC(O[Si](C)(C)C(C)(C)C)=C12577.2Semi standard non polar33892256
Citreovirone,1TBDMS,isomer #3COC1=CC(O)=CC(CC(=CC(O)C(Cl)Cl)O[Si](C)(C)C(C)(C)C)=C12672.7Semi standard non polar33892256
Citreovirone,1TBDMS,isomer #4COC1=CC(O)=CC(C=C(CC(O)C(Cl)Cl)O[Si](C)(C)C(C)(C)C)=C12697.9Semi standard non polar33892256
Citreovirone,2TBDMS,isomer #1COC1=CC(CC(=O)CC(O[Si](C)(C)C(C)(C)C)C(Cl)Cl)=CC(O[Si](C)(C)C(C)(C)C)=C12809.2Semi standard non polar33892256
Citreovirone,2TBDMS,isomer #2COC1=CC(O)=CC(CC(=CC(O[Si](C)(C)C(C)(C)C)C(Cl)Cl)O[Si](C)(C)C(C)(C)C)=C12909.4Semi standard non polar33892256
Citreovirone,2TBDMS,isomer #3COC1=CC(O)=CC(C=C(CC(O[Si](C)(C)C(C)(C)C)C(Cl)Cl)O[Si](C)(C)C(C)(C)C)=C12873.8Semi standard non polar33892256
Citreovirone,2TBDMS,isomer #4COC1=CC(CC(=CC(O)C(Cl)Cl)O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C12878.6Semi standard non polar33892256
Citreovirone,2TBDMS,isomer #5COC1=CC(C=C(CC(O)C(Cl)Cl)O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C12870.9Semi standard non polar33892256
Citreovirone,3TBDMS,isomer #1COC1=CC(CC(=CC(O[Si](C)(C)C(C)(C)C)C(Cl)Cl)O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C13138.3Semi standard non polar33892256
Citreovirone,3TBDMS,isomer #1COC1=CC(CC(=CC(O[Si](C)(C)C(C)(C)C)C(Cl)Cl)O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C12838.6Standard non polar33892256
Citreovirone,3TBDMS,isomer #2COC1=CC(C=C(CC(O[Si](C)(C)C(C)(C)C)C(Cl)Cl)O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C13096.6Semi standard non polar33892256
Citreovirone,3TBDMS,isomer #2COC1=CC(C=C(CC(O[Si](C)(C)C(C)(C)C)C(Cl)Cl)O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C13013.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Citreovirone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ll-7920000000-9d32481b8e90d21016312017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citreovirone GC-MS (2 TMS) - 70eV, Positivesplash10-00dr-9222100000-ff1d67cd45750a32a44f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citreovirone 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 - Citreovirone 10V, Positive-QTOFsplash10-004l-0290000000-9ce95f3e076bacea4f1e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citreovirone 20V, Positive-QTOFsplash10-014i-0930000000-b9cd6f93428f0ea4906c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citreovirone 40V, Positive-QTOFsplash10-03di-0910000000-e0c00e5d4b24ab01cb772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citreovirone 10V, Negative-QTOFsplash10-002f-0790000000-c0bda84e06f686b542932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citreovirone 20V, Negative-QTOFsplash10-0c2c-0790000000-a03e883c8bf1233c44b52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citreovirone 40V, Negative-QTOFsplash10-05ic-2920000000-083fd83365c98944ba0f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citreovirone 10V, Negative-QTOFsplash10-000i-0960000000-a91e987a3a06a257920f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citreovirone 20V, Negative-QTOFsplash10-000i-3900000000-b9f7110002d5664304e42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citreovirone 40V, Negative-QTOFsplash10-00dr-3900000000-70c24cd23b12ee9a9bf02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citreovirone 10V, Positive-QTOFsplash10-0006-0090000000-033cac2014bed53416512021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citreovirone 20V, Positive-QTOFsplash10-000i-0590000000-0eb58989bb5505afe1ae2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citreovirone 40V, Positive-QTOFsplash10-059i-4900000000-fac642c742aba91266362021-09-22Wishart 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 IDFDB011571
KNApSAcK IDC00055274
Chemspider ID35013620
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound102115407
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.. .