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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:29:47 UTC
Update Date2022-03-07 02:53:50 UTC
HMDB IDHMDB0033737
Secondary Accession Numbers
  • HMDB33737
Metabolite Identification
Common NameDehydronuciferine
DescriptionDehydronuciferine 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. Dehydronuciferine has been detected, but not quantified in, a few different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make dehydronuciferine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dehydronuciferine.
Structure
Data?1563862452
Synonyms
ValueSource
L-cis-4-(Hydroxymethyl)-2-pyrrolidinecarboxylateHMDB
Chemical FormulaC19H19NO2
Average Molecular Weight293.3597
Monoisotopic Molecular Weight293.141578857
IUPAC Name15,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,8,13,15-heptaene
Traditional Name15,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,8,13,15-heptaene
CAS Registry Number7630-74-2
SMILES
COC1=C(OC)C2=C3C(CCN(C)C3=CC3=CC=CC=C23)=C1
InChI Identifier
InChI=1S/C19H19NO2/c1-20-9-8-13-11-16(21-2)19(22-3)18-14-7-5-4-6-12(14)10-15(20)17(13)18/h4-7,10-11H,8-9H2,1-3H3
InChI KeyJBGSWIBJAGBGOP-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
  • Naphthalene
  • Quinoline
  • Dialkylarylamine
  • Tertiary aliphatic/aromatic amine
  • Anisole
  • Aralkylamine
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary amine
  • Organoheterocyclic compound
  • Azacycle
  • Ether
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Amine
  • 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 Point130 - 131 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0069 g/LALOGPS
logP4.46ALOGPS
logP3.78ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)4.72ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area21.7 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity89.62 m³·mol⁻¹ChemAxon
Polarizability33.11 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+168.77231661259
DarkChem[M-H]-170.82731661259
DeepCCS[M-2H]-211.49730932474
DeepCCS[M+Na]+186.80530932474
AllCCS[M+H]+167.732859911
AllCCS[M+H-H2O]+164.132859911
AllCCS[M+NH4]+171.132859911
AllCCS[M+Na]+172.132859911
AllCCS[M-H]-177.432859911
AllCCS[M+Na-2H]-176.532859911
AllCCS[M+HCOO]-175.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DehydronuciferineCOC1=C(OC)C2=C3C(CCN(C)C3=CC3=CC=CC=C23)=C13612.0Standard polar33892256
DehydronuciferineCOC1=C(OC)C2=C3C(CCN(C)C3=CC3=CC=CC=C23)=C12494.8Standard non polar33892256
DehydronuciferineCOC1=C(OC)C2=C3C(CCN(C)C3=CC3=CC=CC=C23)=C12891.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dehydronuciferine GC-MS (Non-derivatized) - 70eV, Positivesplash10-01t9-0090000000-35c7edbe7dcecd1623442017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dehydronuciferine 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 - Dehydronuciferine 10V, Positive-QTOFsplash10-0006-0090000000-5ebb5916438c9c9865602016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydronuciferine 20V, Positive-QTOFsplash10-0006-0090000000-b6f04fb9d782244350be2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydronuciferine 40V, Positive-QTOFsplash10-0f7t-1090000000-6543a5568d03cfb9345b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydronuciferine 10V, Negative-QTOFsplash10-0006-0090000000-bf367de881fc92b532302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydronuciferine 20V, Negative-QTOFsplash10-0006-0090000000-f166a65b4c14d01610182016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydronuciferine 40V, Negative-QTOFsplash10-002b-0090000000-7c8a7419b5b1b8ad9ab92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydronuciferine 10V, Negative-QTOFsplash10-0006-0090000000-80f6742b4f6b5e8352cf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydronuciferine 20V, Negative-QTOFsplash10-0006-0090000000-393f18b89c0bd9306fa72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydronuciferine 40V, Negative-QTOFsplash10-0002-0090000000-37a1306bec044b0365802021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydronuciferine 10V, Positive-QTOFsplash10-0006-0090000000-c0ae6c1ee6eacc17ae1d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydronuciferine 20V, Positive-QTOFsplash10-0006-0090000000-c0ae6c1ee6eacc17ae1d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydronuciferine 40V, Positive-QTOFsplash10-0006-0190000000-cbc3b05b54cfc87b730c2021-09-24Wishart 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 IDFDB011863
KNApSAcK IDC00054276
Chemspider ID717588
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5318294
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.. .