Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:11:20 UTC
Update Date2022-03-07 02:54:04 UTC
HMDB IDHMDB0034364
Secondary Accession Numbers
  • HMDB34364
Metabolite Identification
Common NameCepharadione A
DescriptionCepharadione A belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Cepharadione A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, cepharadione a has been detected, but not quantified in, herbs and spices. This could make cepharadione a a potential biomarker for the consumption of these foods.
Structure
Data?1563862552
Synonyms
ValueSource
7-Methyl-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline-5,6(7H)-dione, 9ciHMDB
Cepharadione aMeSH
Chemical FormulaC18H11NO4
Average Molecular Weight305.2842
Monoisotopic Molecular Weight305.068807845
IUPAC Name11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14,16,18-heptaene-9,10-dione
Traditional Name11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14,16,18-heptaene-9,10-dione
CAS Registry Number55610-01-0
SMILES
CN1C(=O)C(=O)C2=CC3=C(OCO3)C3=C2C1=CC1=CC=CC=C31
InChI Identifier
InChI=1S/C18H11NO4/c1-19-12-6-9-4-2-3-5-10(9)15-14(12)11(16(20)18(19)21)7-13-17(15)23-8-22-13/h2-7H,8H2,1H3
InChI KeyRZIGKFTVXWUUCX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassAporphines
Sub ClassNot Available
Direct ParentAporphines
Alternative Parents
Substituents
  • Aporphine
  • Benzoquinoline
  • Phenanthrene
  • Dihydroquinolone
  • Isoquinolone
  • Dihydroquinoline
  • Isoquinoline
  • Naphthalene
  • Quinoline
  • Benzodioxole
  • Pyridinone
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Lactam
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Acetal
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen 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 Point340 - 342 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.038 g/LALOGPS
logP2.73ALOGPS
logP2.42ChemAxon
logS-3.9ALOGPS
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area55.84 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity82.26 m³·mol⁻¹ChemAxon
Polarizability30.99 ųChemAxon
Number of Rings5ChemAxon
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]+169.47331661259
DarkChem[M-H]-167.55331661259
DeepCCS[M-2H]-198.04630932474
DeepCCS[M+Na]+173.23130932474
AllCCS[M+H]+168.732859911
AllCCS[M+H-H2O]+165.232859911
AllCCS[M+NH4]+172.132859911
AllCCS[M+Na]+173.032859911
AllCCS[M-H]-174.632859911
AllCCS[M+Na-2H]-173.532859911
AllCCS[M+HCOO]-172.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cepharadione ACN1C(=O)C(=O)C2=CC3=C(OCO3)C3=C2C1=CC1=CC=CC=C314337.6Standard polar33892256
Cepharadione ACN1C(=O)C(=O)C2=CC3=C(OCO3)C3=C2C1=CC1=CC=CC=C312776.2Standard non polar33892256
Cepharadione ACN1C(=O)C(=O)C2=CC3=C(OCO3)C3=C2C1=CC1=CC=CC=C313307.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cepharadione A GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-0092000000-77a5097731b3c195875e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cepharadione A 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 - Cepharadione A 10V, Positive-QTOFsplash10-0a4i-0009000000-eba3560d3db4d6b503eb2016-06-20Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cepharadione A 20V, Positive-QTOFsplash10-0a4i-0039000000-19c01a15c26b3c1c139f2016-06-20Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cepharadione A 40V, Positive-QTOFsplash10-0w90-1090000000-1402a0296675eaece20b2016-06-20Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cepharadione A 10V, Negative-QTOFsplash10-0udi-0009000000-e2636b9737b16ab74ef62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cepharadione A 20V, Negative-QTOFsplash10-0udi-2039000000-1ee3542a3f3724d8731b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cepharadione A 40V, Negative-QTOFsplash10-0kvk-4090000000-3864de5d2d7f290820752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cepharadione A 10V, Negative-QTOFsplash10-0udi-0009000000-4d7aa01ab3f7fcfbea792021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cepharadione A 20V, Negative-QTOFsplash10-0udi-0009000000-4d7aa01ab3f7fcfbea792021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cepharadione A 40V, Negative-QTOFsplash10-0ufr-1095000000-bee69bfa99d0ba2ad6bc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cepharadione A 10V, Positive-QTOFsplash10-0a4i-0009000000-fa89142e4337defa1ebe2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cepharadione A 20V, Positive-QTOFsplash10-0a4i-0019000000-c65c30077384b45f2a182021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cepharadione A 40V, Positive-QTOFsplash10-0kdi-0093000000-f0d3b800456e6c93e3f42021-09-25Wishart 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 IDFDB012737
KNApSAcK IDC00025787
Chemspider ID85344
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound94577
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.. .