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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:07:26 UTC
Update Date2022-03-07 02:57:01 UTC
HMDB IDHMDB0041436
Secondary Accession Numbers
  • HMDB41436
Metabolite Identification
Common NameCitbismine E
DescriptionCitbismine E 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. Citbismine E has been detected, but not quantified in, citrus. This could make citbismine e a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Citbismine E.
Structure
Data?1563863663
SynonymsNot Available
Chemical FormulaC36H34N2O11
Average Molecular Weight670.662
Monoisotopic Molecular Weight670.21625994
IUPAC Name2-[5,9-dihydroxy-2-(2-hydroxypropan-2-yl)-10-methoxy-11-methyl-6-oxo-1H,2H,6H,11H-furo[2,3-c]acridin-1-yl]-1,6-dihydroxy-3,5-dimethoxy-10-methyl-9,10-dihydroacridin-9-one
Traditional Name2-[5,9-dihydroxy-2-(2-hydroxypropan-2-yl)-10-methoxy-11-methyl-6-oxo-1H,2H-furo[2,3-c]acridin-1-yl]-1,6-dihydroxy-3,5-dimethoxy-10-methylacridin-9-one
CAS Registry Number173429-82-8
SMILES
COC1=CC2=C(C(O)=C1C1C(OC3=C1C1=C(C(O)=C3)C(=O)C3=C(N1C)C(OC)=C(O)C=C3)C(C)(C)O)C(=O)C1=C(N2C)C(OC)=C(O)C=C1
InChI Identifier
InChI=1S/C36H34N2O11/c1-36(2,45)35-26(24-21(49-35)13-19(41)23-29(24)38(4)28-15(31(23)43)9-11-18(40)34(28)48-7)25-20(46-5)12-16-22(32(25)44)30(42)14-8-10-17(39)33(47-6)27(14)37(16)3/h8-13,26,35,39-41,44-45H,1-7H3
InChI KeyCWDCMHOLSPPPAS-UHFFFAOYSA-N
Chemical Taxonomy
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
  • Dihydroquinoline
  • Coumaran
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Tertiary alcohol
  • Vinylogous amide
  • Vinylogous acid
  • Ether
  • Oxacycle
  • Azacycle
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.1 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.088 g/LALOGPS
logP4.37ALOGPS
logP5.33ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)7.91ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area178.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity178.53 m³·mol⁻¹ChemAxon
Polarizability68.06 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+247.31331661259
DarkChem[M-H]-241.9131661259
DeepCCS[M+H]+254.20430932474
DeepCCS[M-H]-252.33930932474
DeepCCS[M-2H]-286.30330932474
DeepCCS[M+Na]+260.11830932474
AllCCS[M+H]+252.632859911
AllCCS[M+H-H2O]+251.432859911
AllCCS[M+NH4]+253.632859911
AllCCS[M+Na]+253.932859911
AllCCS[M-H]-252.532859911
AllCCS[M+Na-2H]-255.232859911
AllCCS[M+HCOO]-258.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Citbismine ECOC1=CC2=C(C(O)=C1C1C(OC3=C1C1=C(C(O)=C3)C(=O)C3=C(N1C)C(OC)=C(O)C=C3)C(C)(C)O)C(=O)C1=C(N2C)C(OC)=C(O)C=C16375.5Standard polar33892256
Citbismine ECOC1=CC2=C(C(O)=C1C1C(OC3=C1C1=C(C(O)=C3)C(=O)C3=C(N1C)C(OC)=C(O)C=C3)C(C)(C)O)C(=O)C1=C(N2C)C(OC)=C(O)C=C14388.4Standard non polar33892256
Citbismine ECOC1=CC2=C(C(O)=C1C1C(OC3=C1C1=C(C(O)=C3)C(=O)C3=C(N1C)C(OC)=C(O)C=C3)C(C)(C)O)C(=O)C1=C(N2C)C(OC)=C(O)C=C16066.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Citbismine E GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-3000019000-c4636b461d167531c52f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbismine E GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbismine E GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbismine E GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbismine E GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbismine E GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbismine E GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbismine E GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbismine E GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbismine E GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbismine E GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbismine E GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbismine E GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbismine E GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbismine E GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbismine E GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbismine E GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbismine E GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbismine E GC-MS (TMS_3_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbismine E GC-MS (TMS_3_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbismine E GC-MS (TMS_3_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbismine E GC-MS (TMS_3_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbismine E GC-MS (TMS_3_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbismine E GC-MS (TMS_3_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbismine E GC-MS (TMS_3_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citbismine E 10V, Positive-QTOFsplash10-0fk9-0000009000-931498aae16a66bbb4602017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citbismine E 20V, Positive-QTOFsplash10-0fki-0002009000-de442649724f0cc0711e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citbismine E 40V, Positive-QTOFsplash10-01u0-0032091000-9faff6797c41ead357d22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citbismine E 10V, Negative-QTOFsplash10-014i-0000009000-130868010b919f29c9f02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citbismine E 20V, Negative-QTOFsplash10-0udi-0013009000-d3e64137725e56303f5e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citbismine E 40V, Negative-QTOFsplash10-0umi-0019032000-45186c5cb8f4490440b62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citbismine E 10V, Negative-QTOFsplash10-014i-0000009000-57238830170a072c11d92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citbismine E 20V, Negative-QTOFsplash10-0gb9-0000019000-09563c520b884dbb9df72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citbismine E 40V, Negative-QTOFsplash10-0002-0000091000-1c76dca2fbac4ec2df9f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citbismine E 10V, Positive-QTOFsplash10-00di-0000009000-ed40e6efc0f814af9aa52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citbismine E 20V, Positive-QTOFsplash10-00di-0001019000-be4b359531da8d6b2c652021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citbismine E 40V, Positive-QTOFsplash10-0a4i-9010066000-994916c866cd2ddadfd52021-09-23Wishart 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 IDFDB021387
KNApSAcK IDC00052239
Chemspider ID35015188
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131753143
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1892441
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.. .