Record Information
Version1.0
Creation date2010-04-08 22:04:59 UTC
Update date2019-11-26 02:56:32 UTC
Primary IDFDB001502
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGlaucine
DescriptionGlaucine is a member of the class of compounds known as aporphines. Aporphines are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Glaucine is practically insoluble (in water) and a very strong basic compound (based on its pKa). Glaucine can be found in barley and custard apple, which makes glaucine a potential biomarker for the consumption of these food products. Glaucine has bronchodilator and antiinflammatory effects, acting as a PDE4 inhibitor and calcium channel blocker, and is used medically as an antitussive in some countries. Glaucine may produce side effects such as sedation, fatigue, and a hallucinogenic effect characterised by colourful visual images, and has been detected as a novel psychoactive drug .
CAS Number475-81-0
Structure
Thumb
Synonyms
SynonymSource
(+)-glaucinebiospider
1,2,9,10-Tetramethoxy-6a-alpha-aporphinebiospider
6a-alpha-Aporphine, 1,2,9,10-tetramethoxy-biospider
6aα-Aporphine, 1,2,9,10-tetramethoxy-biospider
6aalpha-Aporphine, 1,2,9,10-tetramethoxy-biospider
6aalpha-Aporphine, 1,2,9,10-tetramethoxy- (8CI)biospider
Boldine dimethyl etherbiospider
Bromcholitinbiospider
D-glaucinebiospider
Glaucine fumaratebiospider
Glaucine, (s)-isomerbiospider
Glaucine,(d)biospider
Glauventbiospider
O,O-Dimethylisoboldinebiospider
S-(+)-Glaucinebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.022 g/LALOGPS
logP3.08ALOGPS
logP3.07ChemAxon
logS-4.2ALOGPS
pKa (Strongest Basic)7.1ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.16 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity101.88 m³·mol⁻¹ChemAxon
Polarizability40.02 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H25NO4
IUPAC name4,5,15,16-tetramethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene
InChI IdentifierInChI=1S/C21H25NO4/c1-22-7-6-12-9-18(25-4)21(26-5)20-14-11-17(24-3)16(23-2)10-13(14)8-15(22)19(12)20/h9-11,15H,6-8H2,1-5H3
InChI KeyRUZIUYOSRDWYQF-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC2=C(C=C1OC)C1=C(OC)C(OC)=CC3=C1C(C2)N(C)CC3
Average Molecular Weight355.4275
Monoisotopic Molecular Weight355.178358293
Classification
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
  • Tetrahydroisoquinoline
  • Anisole
  • Aralkylamine
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary aliphatic amine
  • 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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-6632e0ad89f01f0fd47cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0019000000-51d9a7922101a1ab3961Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dj-0096000000-89dc50b1f8df6eb0eac6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-27f65a2acb3d1c79a37bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0009000000-2d4b982102b784c3499dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-0096000000-2c5faf624d965714d5c0Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09446
Pubchem Compound ID16754
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke ID(+)-GLAUCINE
BIGG IDNot Available
KNApSAcK IDC00001861
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGlaucine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).