Record Information
Version1.0
Creation date2010-04-08 22:10:53 UTC
Update date2019-11-26 03:09:01 UTC
Primary IDFDB013764
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCitrunobin
DescriptionCitrunobin belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, citrunobin is considered to be a flavonoid. Citrunobin has been detected, but not quantified in, citrus and sweet oranges (Citrus sinensis). This could make citrunobin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Citrunobin.
CAS Number126026-23-1
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.0065 g/LALOGPS
logP4.13ALOGPS
logP4.68ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)8.31ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity101.7 m³·mol⁻¹ChemAxon
Polarizability37.71 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H20O5
IUPAC name(2E)-1-(7-hydroxy-5-methoxy-2,2-dimethyl-2H-chromen-8-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
InChI IdentifierInChI=1S/C21H20O5/c1-21(2)11-10-15-18(25-3)12-17(24)19(20(15)26-21)16(23)9-6-13-4-7-14(22)8-5-13/h4-12,22,24H,1-3H3/b9-6+
InChI KeyRPGWAGOTDRYEAD-RMKNXTFCSA-N
Isomeric SMILESCOC1=C2C=CC(C)(C)OC2=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=C1
Average Molecular Weight352.3805
Monoisotopic Molecular Weight352.13107375
Classification
Description Belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids
Sub ClassChalcones and dihydrochalcones
Direct Parent2'-Hydroxychalcones
Alternative Parents
Substituents
  • 2'-hydroxychalcone
  • Hydroxycinnamic acid or derivatives
  • 2,2-dimethyl-1-benzopyran
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Styrene
  • Aryl ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Acryloyl-group
  • Enone
  • Vinylogous acid
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCitrunobin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0019-0539000000-45344f3e26c3f27f28c8Spectrum
Predicted GC-MSCitrunobin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00si-2124900000-09a322a5816f54cca540Spectrum
Predicted GC-MSCitrunobin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0019000000-54df904dd8b0ba4436832016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uej-1489000000-8fb8ff7727320f1d04c62016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-4940000000-442c7d5abd3c42a889512016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0139000000-c3a80286a0b15246e6e02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-0696000000-182e0e99aa4a744795312016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-015i-0971000000-dd9b4aa1cd57c31d90802016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-aef0c8bb9eddc1b1db0d2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-100r-0139000000-e1b5ffeeb29c4274b3962021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3924000000-3c40558166dfabe3a86a2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-5b03a45bfabd225b6c202021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0191000000-ebc78f4955c7965feae12021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ou-3962000000-05c300f2c9eadd69f5e92021-09-25View Spectrum
NMRNot Available
ChemSpider ID24846002
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID14542258
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35129
CRC / DFC (Dictionary of Food Compounds) IDJGW63-J:JGW63-J
EAFUS IDNot Available
Dr. Duke IDCITRUNOBIN
BIGG IDNot Available
KNApSAcK IDC00007098
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.