Record Information
Version1.0
Creation date2010-04-08 22:05:14 UTC
Update date2018-01-25 19:29:00 UTC
Primary IDFDB002096
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBoldine
Description(s)-boldine 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 (s)-boldine is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (s)-boldine can be found in sweet bay, which makes (s)-boldine a potential biomarker for the consumption of this food product.
CAS Number476-70-0
Structure
Thumb
Synonyms
SynonymSource
2,9-Dihydroxy-1,10-dimethoxyaporphinedb_source
5,6,6a,7-Tetrahydro-1,10-dimethoxy-6-methyl-4H-dibenzo[de,g]quinoline-2,9-diol, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.33 g/LALOGPS
logP2.33ALOGPS
logP2.78ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)6.67ChemAxon
pKa (Strongest Basic)12.35ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area62.16 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity92.91 m³·mol⁻¹ChemAxon
Polarizability35.35 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC19H21NO4
IUPAC name4,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaene-5,15-diol
InChI IdentifierInChI=1S/C19H21NO4/c1-20-5-4-10-7-15(22)19(24-3)18-12-9-16(23-2)14(21)8-11(12)6-13(20)17(10)18/h7-9,13,21-22H,4-6H2,1-3H3
InChI KeyLZJRNLRASBVRRX-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C=C2CC3N(C)CCC4=CC(O)=C(OC)C(C2=C1)=C34
Average Molecular Weight327.3743
Monoisotopic Molecular Weight327.147058165
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
  • 2-naphthol
  • Naphthalene
  • Quinoline
  • Tetrahydroisoquinoline
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Ether
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 69.71%; H 6.47%; N 4.28%; O 19.55%DFC
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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ea-0193000000-4e9d104f3b9f63ebca85View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0c29-1003900000-b3664d5a9866ae0e674eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00kr-0590000000-f0be973ef3df7bed676dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0009000000-d2ba02385b9592588b92View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0090000000-95c8c50b071b50db4c52View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0009000000-34786ce337d46ea704b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00kr-0590000000-f0be973ef3df7bed676dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0019000000-1bf91ce02169cdc4f51bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0097000000-f405b3e19193547c8a34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-017i-0090000000-a3de726762f74254538dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-740d8346fca3f39b7095View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0029000000-4fb006bf9d3d6f7f1138View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01qc-0091000000-090643282c4d4b487254View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCFH49-G:CFH49-G
EAFUS IDNot Available
Dr. Duke IDBOLDINE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
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
abortifacient50691 A chemical substance that interrupts pregnancy after implantation.DUKE
anti diabetic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti edemicDUKE
anti hepatotic62868 Any compound that is able to prevent damage to the liver.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti lithicDUKE
anti mutagenicDUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti prostaglandin49020 A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.DUKE
anti pyretic35493 A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.DUKE
anti radicularDUKE
beta-adrenergic receptor blocker37962 Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.DUKE
calcium channel blocker38215 One of a class of drugs that acts by selective inhibition of calcium influx through cell membranes or on the release and binding of calcium in intracellular pools.DUKE
chemopreventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cholereticDUKE
convulsantDUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
gastrostimulant55324 A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion.DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
hydrogen-peroxide inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
hypnoticDUKE
immunomodulator50846 Biologically active substance whose activity affects or plays a role in the functioning of the immune system.DUKE
myorelaxantDUKE
neurolepticDUKE
nitric-oxide inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
prostaglandin synthesis inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
teratogenic50905 A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.DUKE
uricosuricDUKE
vasoconstrictor50514 Drug used to cause constriction of the blood vessels.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— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).