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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:03:28 UTC
Update Date2022-03-07 02:55:31 UTC
HMDB IDHMDB0037797
Secondary Accession Numbers
  • HMDB37797
Metabolite Identification
Common NameCitbrasine
DescriptionCitbrasine 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. Citbrasine has been detected, but not quantified in, citrus. This could make citbrasine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Citbrasine.
Structure
Data?1563863089
Synonyms
ValueSource
1,5-Dihydroxy-2,3,4-trimethoxy-10-methylacridoneHMDB
Chemical FormulaC17H17NO6
Average Molecular Weight331.32
Monoisotopic Molecular Weight331.105587281
IUPAC Name1,5-dihydroxy-2,3,4-trimethoxy-10-methyl-9,10-dihydroacridin-9-one
Traditional Name1,5-dihydroxy-2,3,4-trimethoxy-10-methylacridin-9-one
CAS Registry Number86680-34-4
SMILES
COC1=C(O)C2=C(N(C)C3=C(C=CC=C3O)C2=O)C(OC)=C1OC
InChI Identifier
InChI=1S/C17H17NO6/c1-18-11-8(6-5-7-9(11)19)13(20)10-12(18)15(22-2)17(24-4)16(23-3)14(10)21/h5-7,19,21H,1-4H3
InChI KeyQYPQTPVQPNLXHV-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
  • 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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point154 - 156 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility95.59 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.45 g/LALOGPS
logP2.58ALOGPS
logP2.69ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)9.14ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area88.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity87.31 m³·mol⁻¹ChemAxon
Polarizability33.18 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+179.031661259
DarkChem[M-H]-175.91831661259
DeepCCS[M+H]+181.2530932474
DeepCCS[M-H]-178.89230932474
DeepCCS[M-2H]-213.12630932474
DeepCCS[M+Na]+188.35230932474
AllCCS[M+H]+174.732859911
AllCCS[M+H-H2O]+171.432859911
AllCCS[M+NH4]+177.832859911
AllCCS[M+Na]+178.732859911
AllCCS[M-H]-180.232859911
AllCCS[M+Na-2H]-179.832859911
AllCCS[M+HCOO]-179.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CitbrasineCOC1=C(O)C2=C(N(C)C3=C(C=CC=C3O)C2=O)C(OC)=C1OC3953.3Standard polar33892256
CitbrasineCOC1=C(O)C2=C(N(C)C3=C(C=CC=C3O)C2=O)C(OC)=C1OC2613.5Standard non polar33892256
CitbrasineCOC1=C(O)C2=C(N(C)C3=C(C=CC=C3O)C2=O)C(OC)=C1OC2919.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Citbrasine,1TMS,isomer #1COC1=C(OC)C(OC)=C2C(=C1O[Si](C)(C)C)C(=O)C1=CC=CC(O)=C1N2C2946.6Semi standard non polar33892256
Citbrasine,1TMS,isomer #2COC1=C(OC)C(OC)=C2C(=C1O)C(=O)C1=CC=CC(O[Si](C)(C)C)=C1N2C3016.8Semi standard non polar33892256
Citbrasine,2TMS,isomer #1COC1=C(OC)C(OC)=C2C(=C1O[Si](C)(C)C)C(=O)C1=CC=CC(O[Si](C)(C)C)=C1N2C2948.7Semi standard non polar33892256
Citbrasine,1TBDMS,isomer #1COC1=C(OC)C(OC)=C2C(=C1O[Si](C)(C)C(C)(C)C)C(=O)C1=CC=CC(O)=C1N2C3155.0Semi standard non polar33892256
Citbrasine,1TBDMS,isomer #2COC1=C(OC)C(OC)=C2C(=C1O)C(=O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1N2C3219.9Semi standard non polar33892256
Citbrasine,2TBDMS,isomer #1COC1=C(OC)C(OC)=C2C(=C1O[Si](C)(C)C(C)(C)C)C(=O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1N2C3331.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Citbrasine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uxr-0149000000-bd904c95cdff252a88ff2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbrasine GC-MS (2 TMS) - 70eV, Positivesplash10-03k9-2002900000-45862c1cd6c0bce2e0f52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citbrasine 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 - Citbrasine 10V, Positive-QTOFsplash10-001i-0009000000-12b035fa4955ec37e9682016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citbrasine 20V, Positive-QTOFsplash10-001i-0009000000-ccef8b6c1cbd6e4ad9dd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citbrasine 40V, Positive-QTOFsplash10-0079-1192000000-a728ce85cc548950baac2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citbrasine 10V, Negative-QTOFsplash10-001i-0009000000-df70469d3177d074be8c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citbrasine 20V, Negative-QTOFsplash10-001i-0019000000-91749809556780cea0be2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citbrasine 40V, Negative-QTOFsplash10-06vi-2192000000-1b14d996cf58b0fcd7582016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citbrasine 10V, Positive-QTOFsplash10-001i-0009000000-48f8fe2f6719b88bf13f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citbrasine 20V, Positive-QTOFsplash10-001i-0009000000-48f8fe2f6719b88bf13f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citbrasine 40V, Positive-QTOFsplash10-00di-0693000000-577168d8ebe51cac453a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citbrasine 10V, Negative-QTOFsplash10-001i-0009000000-d3fb9309a8d4ddce4b2a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citbrasine 20V, Negative-QTOFsplash10-001i-0009000000-976de9f58b2f2879521d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citbrasine 40V, Negative-QTOFsplash10-001u-1190000000-9623cfe10a610a3706ea2021-09-24Wishart 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 IDFDB016941
KNApSAcK IDC00055490
Chemspider ID14332664
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound19093029
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1863661
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.. .