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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:32:54 UTC
Update Date2022-03-07 02:52:18 UTC
HMDB IDHMDB0029827
Secondary Accession Numbers
  • HMDB29827
Metabolite Identification
Common NameJunosidine
DescriptionJunosidine is a member of the class of compounds known as acridones. Acridones are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety. Junosidine is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Junosidine is an alkaloid that has been found in the root bark of Citrus junos (yuzu).
Structure
Data?1601220880
Synonyms
ValueSource
2,11-Dihydro-5-hydroxy-10-methoxy-2,2,11-trimethyl-6H-pyrano[3,2-b]acridin-6-one, 9ciHMDB
Chemical FormulaC20H19NO4
Average Molecular Weight337.3692
Monoisotopic Molecular Weight337.131408101
IUPAC Name5-hydroxy-10-methoxy-2,2,11-trimethyl-6,11-dihydro-2H-1-oxa-11-azatetracen-6-one
Traditional Name5-hydroxy-10-methoxy-2,2,11-trimethyl-1-oxa-11-azatetracen-6-one
CAS Registry Number110883-39-1
SMILES
COC1=C2N(C)C3=C(C(O)=C4C=CC(C)(C)OC4=C3)C(=O)C2=CC=C1
InChI Identifier
InChI=1S/C20H19NO4/c1-20(2)9-8-11-15(25-20)10-13-16(18(11)22)19(23)12-6-5-7-14(24-4)17(12)21(13)3/h5-10,22H,1-4H3
InChI KeyAUWXWUDANKEVNS-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
  • Chromenopyridine
  • 2,2-dimethyl-1-benzopyran
  • Dihydroquinolone
  • Benzopyran
  • Dihydroquinoline
  • 1-benzopyran
  • Anisole
  • 1-hydroxy-4-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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point188 - 189 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.26 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP3.64ALOGPS
logP4.21ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)8.7ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity96.8 m³·mol⁻¹ChemAxon
Polarizability36.45 ųChemAxon
Number of Rings4ChemAxon
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]+177.3131661259
DarkChem[M-H]-179.37631661259
DeepCCS[M+H]+187.12130932474
DeepCCS[M-H]-184.76330932474
DeepCCS[M-2H]-218.59830932474
DeepCCS[M+Na]+193.82630932474
AllCCS[M+H]+178.932859911
AllCCS[M+H-H2O]+175.532859911
AllCCS[M+NH4]+182.032859911
AllCCS[M+Na]+182.932859911
AllCCS[M-H]-185.732859911
AllCCS[M+Na-2H]-185.032859911
AllCCS[M+HCOO]-184.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
JunosidineCOC1=C2N(C)C3=C(C(O)=C4C=CC(C)(C)OC4=C3)C(=O)C2=CC=C13836.2Standard polar33892256
JunosidineCOC1=C2N(C)C3=C(C(O)=C4C=CC(C)(C)OC4=C3)C(=O)C2=CC=C12795.1Standard non polar33892256
JunosidineCOC1=C2N(C)C3=C(C(O)=C4C=CC(C)(C)OC4=C3)C(=O)C2=CC=C13225.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Junosidine,1TMS,isomer #1COC1=CC=CC2=C1N(C)C1=CC3=C(C=CC(C)(C)O3)C(O[Si](C)(C)C)=C1C2=O3099.6Semi standard non polar33892256
Junosidine,1TBDMS,isomer #1COC1=CC=CC2=C1N(C)C1=CC3=C(C=CC(C)(C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O3265.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Junosidine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-0398000000-3c3bcb80f1c56d17a48a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Junosidine GC-MS (1 TMS) - 70eV, Positivesplash10-0076-2309000000-dff359af08c4f68adad02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Junosidine 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 - Junosidine 10V, Positive-QTOFsplash10-000i-0009000000-2c671cf08f3b57803e8f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Junosidine 20V, Positive-QTOFsplash10-000i-1049000000-ab2783a781d97e9ef8bc2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Junosidine 40V, Positive-QTOFsplash10-0gbd-4090000000-0f4524e0ba280ce7eace2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Junosidine 10V, Negative-QTOFsplash10-000i-0009000000-c75feaf8a50830d59bb92015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Junosidine 20V, Negative-QTOFsplash10-000i-0019000000-90b655a01cc13ef81a7a2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Junosidine 40V, Negative-QTOFsplash10-0udi-0090000000-cc38342ab6abc20a5c8d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Junosidine 10V, Positive-QTOFsplash10-000i-0009000000-195152c9499dc2b0f3dd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Junosidine 20V, Positive-QTOFsplash10-000i-0009000000-ead8640ecca32d9c48442021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Junosidine 40V, Positive-QTOFsplash10-05ar-0392000000-6766aa3fd524e4d5073c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Junosidine 10V, Negative-QTOFsplash10-000i-0009000000-e425d548b88b813581922021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Junosidine 20V, Negative-QTOFsplash10-000i-0009000000-ce9daf74b975234280052021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Junosidine 40V, Negative-QTOFsplash10-0006-0092000000-df927ad89fa7c72377832021-09-24Wishart 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 IDFDB001039
KNApSAcK IDC00052330
Chemspider ID9834814
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11660079
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1811581
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.. .