Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:40:19 UTC
Update Date2022-03-07 02:55:19 UTC
HMDB IDHMDB0037424
Secondary Accession Numbers
  • HMDB37424
Metabolite Identification
Common NameCitrusinol
DescriptionCitrusinol belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton. Thus, citrusinol is considered to be a flavonoid lipid molecule. Citrusinol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Citrusinol has been detected, but not quantified in, citrus. This could make citrusinol a potential biomarker for the consumption of these foods.
Structure
Data?1563863028
Synonyms
ValueSource
3,5-Dihydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one, 9ciHMDB
Chemical FormulaC20H16O6
Average Molecular Weight352.3374
Monoisotopic Molecular Weight352.094688244
IUPAC Name3,5-dihydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-4H,8H-pyrano[2,3-f]chromen-4-one
Traditional Namecitrusinol
CAS Registry Number112516-43-5
SMILES
CC1(C)OC2=CC(O)=C3C(=O)C(O)=C(OC3=C2C=C1)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C20H16O6/c1-20(2)8-7-12-14(26-20)9-13(22)15-16(23)17(24)18(25-19(12)15)10-3-5-11(21)6-4-10/h3-9,21-22,24H,1-2H3
InChI KeyOKQQXHUICMLKQI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassPyranoflavonoids
Direct ParentPyranoflavonoids
Alternative Parents
Substituents
  • Pyranoflavonoid
  • 3-hydroxyflavone
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Pyranochromene
  • 2,2-dimethyl-1-benzopyran
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • 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 Point252 - 254 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.025 g/LALOGPS
logP3.48ALOGPS
logP3.66ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)8.18ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity97.29 m³·mol⁻¹ChemAxon
Polarizability36.28 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+H]+186.37330932474
DeepCCS[M-H]-184.01530932474
DeepCCS[M-2H]-218.15530932474
DeepCCS[M+Na]+193.38430932474
AllCCS[M+H]+184.232859911
AllCCS[M+H-H2O]+180.832859911
AllCCS[M+NH4]+187.332859911
AllCCS[M+Na]+188.232859911
AllCCS[M-H]-183.232859911
AllCCS[M+Na-2H]-182.532859911
AllCCS[M+HCOO]-182.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CitrusinolCC1(C)OC2=CC(O)=C3C(=O)C(O)=C(OC3=C2C=C1)C1=CC=C(O)C=C14338.5Standard polar33892256
CitrusinolCC1(C)OC2=CC(O)=C3C(=O)C(O)=C(OC3=C2C=C1)C1=CC=C(O)C=C13197.9Standard non polar33892256
CitrusinolCC1(C)OC2=CC(O)=C3C(=O)C(O)=C(OC3=C2C=C1)C1=CC=C(O)C=C13468.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Citrusinol,1TMS,isomer #1CC1(C)C=CC2=C(C=C(O[Si](C)(C)C)C3=C2OC(C2=CC=C(O)C=C2)=C(O)C3=O)O13390.3Semi standard non polar33892256
Citrusinol,1TMS,isomer #2CC1(C)C=CC2=C(C=C(O)C3=C2OC(C2=CC=C(O)C=C2)=C(O[Si](C)(C)C)C3=O)O13318.6Semi standard non polar33892256
Citrusinol,1TMS,isomer #3CC1(C)C=CC2=C(C=C(O)C3=C2OC(C2=CC=C(O[Si](C)(C)C)C=C2)=C(O)C3=O)O13385.6Semi standard non polar33892256
Citrusinol,2TMS,isomer #1CC1(C)C=CC2=C(C=C(O[Si](C)(C)C)C3=C2OC(C2=CC=C(O)C=C2)=C(O[Si](C)(C)C)C3=O)O13257.2Semi standard non polar33892256
Citrusinol,2TMS,isomer #2CC1(C)C=CC2=C(C=C(O[Si](C)(C)C)C3=C2OC(C2=CC=C(O[Si](C)(C)C)C=C2)=C(O)C3=O)O13344.0Semi standard non polar33892256
Citrusinol,2TMS,isomer #3CC1(C)C=CC2=C(C=C(O)C3=C2OC(C2=CC=C(O[Si](C)(C)C)C=C2)=C(O[Si](C)(C)C)C3=O)O13215.5Semi standard non polar33892256
Citrusinol,3TMS,isomer #1CC1(C)C=CC2=C(C=C(O[Si](C)(C)C)C3=C2OC(C2=CC=C(O[Si](C)(C)C)C=C2)=C(O[Si](C)(C)C)C3=O)O13245.3Semi standard non polar33892256
Citrusinol,1TBDMS,isomer #1CC1(C)C=CC2=C(C=C(O[Si](C)(C)C(C)(C)C)C3=C2OC(C2=CC=C(O)C=C2)=C(O)C3=O)O13635.4Semi standard non polar33892256
Citrusinol,1TBDMS,isomer #2CC1(C)C=CC2=C(C=C(O)C3=C2OC(C2=CC=C(O)C=C2)=C(O[Si](C)(C)C(C)(C)C)C3=O)O13572.5Semi standard non polar33892256
Citrusinol,1TBDMS,isomer #3CC1(C)C=CC2=C(C=C(O)C3=C2OC(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C(O)C3=O)O13619.9Semi standard non polar33892256
Citrusinol,2TBDMS,isomer #1CC1(C)C=CC2=C(C=C(O[Si](C)(C)C(C)(C)C)C3=C2OC(C2=CC=C(O)C=C2)=C(O[Si](C)(C)C(C)(C)C)C3=O)O13781.2Semi standard non polar33892256
Citrusinol,2TBDMS,isomer #2CC1(C)C=CC2=C(C=C(O[Si](C)(C)C(C)(C)C)C3=C2OC(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C(O)C3=O)O13874.7Semi standard non polar33892256
Citrusinol,2TBDMS,isomer #3CC1(C)C=CC2=C(C=C(O)C3=C2OC(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C(O[Si](C)(C)C(C)(C)C)C3=O)O13763.3Semi standard non polar33892256
Citrusinol,3TBDMS,isomer #1CC1(C)C=CC2=C(C=C(O[Si](C)(C)C(C)(C)C)C3=C2OC(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C(O[Si](C)(C)C(C)(C)C)C3=O)O13984.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Citrusinol GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0359000000-3b303a6db852fa4910112017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citrusinol GC-MS (3 TMS) - 70eV, Positivesplash10-0ufv-2370970000-01e0aa43d08cc24571cb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citrusinol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citrusinol 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 - Citrusinol 10V, Positive-QTOFsplash10-0udi-0019000000-a75d185b8170caae15a22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrusinol 20V, Positive-QTOFsplash10-0udi-1039000000-d08aaa3a0718be1eb0ed2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrusinol 40V, Positive-QTOFsplash10-014j-5490000000-9da76c4acd5a5d826cb82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrusinol 10V, Negative-QTOFsplash10-0udi-0009000000-76e922ed8787cdc2a2e92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrusinol 20V, Negative-QTOFsplash10-0udi-0039000000-2c5fecbc31b4246a6af12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrusinol 40V, Negative-QTOFsplash10-00lr-0791000000-61e2eb4c21b7824f6e772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrusinol 10V, Negative-QTOFsplash10-0udi-0009000000-4d16a6676fb6a009705b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrusinol 20V, Negative-QTOFsplash10-0udi-0049000000-8937570b885d0085f32c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrusinol 40V, Negative-QTOFsplash10-0gi3-4794000000-deabc5d2a258c26baf442021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrusinol 10V, Positive-QTOFsplash10-0udi-0009000000-2baef9d2edd9c62c0a8d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrusinol 20V, Positive-QTOFsplash10-0udi-0009000000-9faf695343b343b32b172021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrusinol 40V, Positive-QTOFsplash10-014i-2094000000-798a386c3586548112682021-09-22Wishart 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 IDFDB016472
KNApSAcK IDC00005077
Chemspider ID24691934
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44259051
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.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Citrusinol → 6-(4-{3,5-dihydroxy-8,8-dimethyl-4-oxo-4H,8H-pyrano[2,3-f]chromen-2-yl}phenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Citrusinol → 3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-4-oxo-4H,8H-pyrano[2,3-f]chromen-3-yl]oxy}oxane-2-carboxylic aciddetails
Citrusinol → 3,4,5-trihydroxy-6-{[3-hydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-4-oxo-4H,8H-pyrano[2,3-f]chromen-5-yl]oxy}oxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Citrusinol → (4-{3,5-dihydroxy-8,8-dimethyl-4-oxo-4H,8H-pyrano[2,3-f]chromen-2-yl}phenyl)oxidanesulfonic aciddetails