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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:53:38 UTC
Update Date2022-03-07 02:53:35 UTC
HMDB IDHMDB0033084
Secondary Accession Numbers
  • HMDB33084
Metabolite Identification
Common Name7-Hydroxydehydroglaucine
Description7-Hydroxydehydroglaucine 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. 7-Hydroxydehydroglaucine is a strong basic compound (based on its pKa). Outside of the human body, 7-hydroxydehydroglaucine has been detected, but not quantified in, beverages and fruits. This could make 7-hydroxydehydroglaucine a potential biomarker for the consumption of these foods.
Structure
Data?1563862350
Synonyms
ValueSource
7-Hydroxy-dehydroglaucineHMDB
Chemical FormulaC21H23NO5
Average Molecular Weight369.411
Monoisotopic Molecular Weight369.157622851
IUPAC Name4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,8,13,15-heptaen-8-ol
Traditional Name4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,8,13,15-heptaen-8-ol
CAS Registry NumberNot Available
SMILES
COC1=C(OC)C=C2C(=C1)C(O)=C1N(C)CCC3=CC(OC)=C(OC)C2=C13
InChI Identifier
InChI=1S/C21H23NO5/c1-22-7-6-11-8-16(26-4)21(27-5)18-12-9-14(24-2)15(25-3)10-13(12)20(23)19(22)17(11)18/h8-10,23H,6-7H2,1-5H3
InChI KeyXTYGTYHSWAJTPX-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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point242 - 243 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.05 g/LALOGPS
logP3.76ALOGPS
logP3.17ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)9.63ChemAxon
pKa (Strongest Basic)3.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area60.39 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity104.53 m³·mol⁻¹ChemAxon
Polarizability40.1 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]+185.00231661259
DarkChem[M-H]-183.14931661259
DeepCCS[M-2H]-218.5530932474
DeepCCS[M+Na]+193.77730932474
AllCCS[M+H]+186.832859911
AllCCS[M+H-H2O]+183.932859911
AllCCS[M+NH4]+189.632859911
AllCCS[M+Na]+190.432859911
AllCCS[M-H]-195.332859911
AllCCS[M+Na-2H]-195.032859911
AllCCS[M+HCOO]-194.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
7-HydroxydehydroglaucineCOC1=C(OC)C=C2C(=C1)C(O)=C1N(C)CCC3=CC(OC)=C(OC)C2=C134023.2Standard polar33892256
7-HydroxydehydroglaucineCOC1=C(OC)C=C2C(=C1)C(O)=C1N(C)CCC3=CC(OC)=C(OC)C2=C133068.9Standard non polar33892256
7-HydroxydehydroglaucineCOC1=C(OC)C=C2C(=C1)C(O)=C1N(C)CCC3=CC(OC)=C(OC)C2=C133443.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
7-Hydroxydehydroglaucine,1TMS,isomer #1COC1=CC2=C(O[Si](C)(C)C)C3=C4C(=CC(OC)=C(OC)C4=C2C=C1OC)CCN3C3250.7Semi standard non polar33892256
7-Hydroxydehydroglaucine,1TBDMS,isomer #1COC1=CC2=C(O[Si](C)(C)C(C)(C)C)C3=C4C(=CC(OC)=C(OC)C4=C2C=C1OC)CCN3C3399.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 7-Hydroxydehydroglaucine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ug3-0009000000-2ca4e88b3b383b7873192017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7-Hydroxydehydroglaucine GC-MS (1 TMS) - 70eV, Positivesplash10-004j-1019800000-d69962c9f4c6f0ee12a22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7-Hydroxydehydroglaucine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7-Hydroxydehydroglaucine 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 - 7-Hydroxydehydroglaucine 10V, Positive-QTOFsplash10-00di-0009000000-5fe118d7938f477e82d02016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Hydroxydehydroglaucine 20V, Positive-QTOFsplash10-00di-0009000000-b0dba01c5b5ca17e94c12016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Hydroxydehydroglaucine 40V, Positive-QTOFsplash10-05gi-1019000000-6f867413d6738f34579e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Hydroxydehydroglaucine 10V, Negative-QTOFsplash10-014i-0009000000-33fc0e4d6ee1174e10ba2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Hydroxydehydroglaucine 20V, Negative-QTOFsplash10-0gb9-0009000000-b371d7ad0abb382745852016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Hydroxydehydroglaucine 40V, Negative-QTOFsplash10-00dj-1079000000-43fc35035c2a6dc358d52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Hydroxydehydroglaucine 10V, Positive-QTOFsplash10-00di-0009000000-ad1696003a3beba4181b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Hydroxydehydroglaucine 20V, Positive-QTOFsplash10-00di-0009000000-ad1696003a3beba4181b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Hydroxydehydroglaucine 40V, Positive-QTOFsplash10-0g59-0059000000-d300df86626ad2df364b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Hydroxydehydroglaucine 10V, Negative-QTOFsplash10-014i-0009000000-c0b0af865b3879fc49f62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Hydroxydehydroglaucine 20V, Negative-QTOFsplash10-014i-0009000000-8ffa0fa72a62326dfc732021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Hydroxydehydroglaucine 40V, Negative-QTOFsplash10-00xr-0019000000-2aacff4c5971f262e6e22021-09-25Wishart 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 IDFDB011079
KNApSAcK IDNot Available
Chemspider ID8492467
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10317002
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.. .