Record Information
Version1.0
Creation date2010-04-08 22:05:17 UTC
Update date2020-02-24 19:10:27 UTC
Primary IDFDB002224
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCitracridone I
DescriptionCitracridone I, also known as citra-i, belongs to the class of organic compounds known as acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety. Citracridone I is found, on average, in the highest concentration within sweet oranges (Citrus sinensis). Citracridone I has also been detected, but not quantified in, citrus. This could make citracridone I a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Citracridone I.
CAS Number81525-61-3
Structure
Thumb
Synonyms
SynonymSource
Citracridone-IMeSH
Citra-IMeSH
Citracridone Idb_source
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP3.45ALOGPS
logP3.91ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)8.46ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity98.78 m³·mol⁻¹ChemAxon
Polarizability37.16 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H19NO5
IUPAC name7,11-dihydroxy-6-methoxy-2,2,5-trimethyl-5,10-dihydro-2H-1-oxa-5-azatetraphen-10-one
InChI IdentifierInChI=1S/C20H19NO5/c1-20(2)8-7-10-14(26-20)9-13(23)15-16(10)21(3)17-11(18(15)24)5-6-12(22)19(17)25-4/h5-9,22-23H,1-4H3
InChI KeyDIDVBISMWJGFOF-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C=CC2=C1N(C)C1=C(C(O)=CC3=C1C=CC(C)(C)O3)C2=O
Average Molecular Weight353.3686
Monoisotopic Molecular Weight353.126322723
Classification
Description Belongs to the class of organic compounds known as acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassBenzoquinolines
Direct ParentAcridones
Alternative Parents
Substituents
  • Acridone
  • Chromenopyridine
  • 2,2-dimethyl-1-benzopyran
  • Dihydroquinolone
  • Benzopyran
  • Dihydroquinoline
  • 1-benzopyran
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous amide
  • Vinylogous acid
  • Oxacycle
  • Ether
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 67.98%; H 5.42%; N 3.96%; O 22.64%DFC
Melting PointMp 275-278°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCitracridone I, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-0219000000-6c399de0ce86fa413cacSpectrum
Predicted GC-MSCitracridone I, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0089-2021900000-b4f57a01190cdb7e1998Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-534fa837948715df3662Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0019000000-62a373cbae65fe1c839dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fxy-2192000000-64ce2048a3fd765ce09dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-8ba610247a34545ddcc1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0019000000-55fbe69d3cf4406910caSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uy1-1393000000-9476d50fc31eb9e4ff0cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-61079e99e3d4b21fcb24Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0009000000-61079e99e3d4b21fcb24Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01pt-0096000000-e78acc1b64019f1f157dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-f71db31d05be47dcf661Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0009000000-c4fed6c2a8ce555636feSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01po-0098000000-e1ffa3c14d4204cfab91Spectrum
NMRNot Available
ChemSpider ID4589440
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5487591
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30375
CRC / DFC (Dictionary of Food Compounds) IDLJB55-Y:CHB62-P
EAFUS IDNot Available
Dr. Duke IDCITRACRIDONE-I
BIGG IDNot Available
KNApSAcK IDC00024247
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
FoodReference
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).