Record Information
Version1.0
Creation date2010-04-08 22:05:17 UTC
Update date2020-02-24 19:10:27 UTC
Primary IDFDB002223
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCitrusinine I
DescriptionCitrusinine 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. Citrusinine I is an extremely weak basic (essentially neutral) compound (based on its pKa). Citrusinine I is found, on average, in the highest concentration in sweet oranges. Citrusinine I has also been detected, but not quantified in, citrus. This could make citrusinine I a potential biomarker for the consumption of these foods.
CAS Number86680-32-2
Structure
Thumb
Synonyms
SynonymSource
1,5-Dihydroxy-3,4-dimethoxy-10-methyl-9(10H)-acridinoneHMDB
1,5-Dihydroxy-3,4-dimethoxy-10-methylacridoneHMDB
Citrusinine-IHMDB
Citrusinine IMeSH
9(10H)-Acridinone, 1,5-dihydroxy-3,4-dimethoxy-10-methyl-biospider
Predicted Properties
PropertyValueSource
Water Solubility0.39 g/LALOGPS
logP2.49ALOGPS
logP2.85ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)9.13ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity80.85 m³·mol⁻¹ChemAxon
Polarizability30.23 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC16H15NO5
IUPAC name1,5-dihydroxy-3,4-dimethoxy-10-methyl-9,10-dihydroacridin-9-one
InChI IdentifierInChI=1S/C16H15NO5/c1-17-13-8(5-4-6-9(13)18)15(20)12-10(19)7-11(21-2)16(22-3)14(12)17/h4-7,18-19H,1-3H3
InChI KeyUTEAJHNFBCLZHN-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(OC)C2=C(C(O)=C1)C(=O)C1=C(N2C)C(O)=CC=C1
Average Molecular Weight301.294
Monoisotopic Molecular Weight301.095022595
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
  • Dihydroquinolone
  • 8-hydroxyquinoline
  • Dihydroquinoline
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Vinylogous amide
  • Ether
  • Azacycle
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen 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:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 63.78%; H 5.02%; N 4.65%; O 26.55%DFC
Melting PointMp 206-207°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data416 () (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-0190000000-7ce6d1e07e0a6620d786JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00e9-3026900000-4d76148c6845b2b1566bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-696e87361a1033f85460JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0049000000-92f91c6e9558ede613b5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ue9-1090000000-b9192551271f60bdf1f5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-be3182d1a976ceb1a6dfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0029000000-779c143ad834b42f2587JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0l0w-0190000000-6740b0cbf8270082bc87JSpectraViewer
ChemSpider ID4589521
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5487772
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30374
CRC / DFC (Dictionary of Food Compounds) IDCHB54-O:CHB58-S
EAFUS IDNot Available
Dr. Duke IDCITRUSININE-I
BIGG IDNot Available
KNApSAcK IDC00024249
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).