Record Information
Version1.0
Creation date2010-04-08 22:05:14 UTC
Update date2019-11-26 02:56:59 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSBoldine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03ea-0193000000-4e9d104f3b9f63ebca85Spectrum
Predicted GC-MSBoldine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0c29-1003900000-b3664d5a9866ae0e674eSpectrum
Predicted GC-MSBoldine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBoldine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBoldine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBoldine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBoldine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBoldine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBoldine, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00kr-0590000000-f0be973ef3df7bed676d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0009000000-d2ba02385b9592588b922017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0090000000-95c8c50b071b50db4c522017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0009000000-34786ce337d46ea704b52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-00kr-0590000000-f0be973ef3df7bed676d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03dj-0097000000-67d87760a4caee6d56882021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0002-0090000000-e4cefc23c5dfb8ba6b982021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-002b-0960000000-fea69a015955b1a8c78a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Negativesplash10-03xr-0096000000-eef48b135c01a8bce6092021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03fr-0009000000-ca3e6fc8ef8b4652939a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03di-0009000000-de5317cf2fdab8ede5f22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00or-0093000000-9ed026ef6b3924c143612021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03dj-0189000000-74839a87c32b59674b9e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03xr-0096000000-7a5557a34d23c54350042021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0002-0090000000-e2bcbd9b1e8cfe4b5c972021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00or-0093000000-6425dc8e8623be8ff1552021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00kb-0090000000-0189a512fde7a38e75082021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00kb-0950000000-cfbc617d88a4d97d884b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-002b-0980000000-99aa3f6034bdf51f0c8f2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0019000000-1bf91ce02169cdc4f51b2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0097000000-f405b3e19193547c8a342015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-017i-0090000000-a3de726762f74254538d2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-740d8346fca3f39b70952015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0029000000-4fb006bf9d3d6f7f11382015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01qc-0091000000-090643282c4d4b4872542015-04-25View Spectrum
NMRNot Available
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
Food Biomarker OntologyNot Available
VMH 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 An agent that induces abortion, disrupting pregnancy by blocking progesterone or causing uterine contractions. Therapeutically, it's used to terminate early pregnancies, manage ectopic pregnancies, or treat miscarriages. Key medical uses include medical abortion, pregnancy termination, and menstrual regulation.DUKE
Anti-diabetic52217 An agent that regulates blood sugar levels, enhancing insulin sensitivity or secretion. Therapeutically, it's used to manage diabetes, reducing symptoms and complications, and commonly prescribed to treat type 1 and 2 diabetes, as well as gestational diabetes.DUKE
Anti-edemicAn agent that relieves or prevents edema, reducing abnormal fluid accumulation in tissues or the circulatory system, commonly used to treat conditions such as swelling, inflammation, and water retention.DUKE
Anti hepatotic62868 An agent that protects the liver from damage, reducing inflammation and promoting liver health. It is used therapeutically to manage liver diseases, such as hepatitis and cirrhosis, and to prevent liver damage from toxins and medications. Key medical uses include treating liver conditions, supporting liver function, and preventing liver failure.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti-lithicAn agent that prevents the formation of calculi (kidney stones) or promotes their dissolution, playing a key role in urology. Its therapeutic applications include managing kidney stone disease, nephrolithiasis, and urinary tract disorders, helping to alleviate pain and prevent complications.DUKE
Anti-mutagenicAn agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti prostaglandin49020 An agent that inhibits prostaglandin production, reducing inflammation and pain. Therapeutically, it's used to treat conditions like arthritis, menstrual cramps, and post-surgical pain, by blocking prostaglandin-mediated responses, providing relief from inflammation and discomfort.DUKE
Anti pyretic35493 An agent that reduces fever, commonly used to relieve headache, pain, and discomfort associated with elevated body temperature, and to manage fever in various medical conditions, such as infections and inflammatory diseases.DUKE
Anti radicularAn agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management.DUKE
Beta-adrenergic receptor blocker37962 An agent that blocks beta-adrenergic receptors, reducing heart rate and blood pressure. Therapeutically, it manages hypertension, angina, and certain arrhythmias, while also being used to treat conditions like glaucoma, migraine headaches, and performance anxiety.DUKE
Calcium channel blocker38215 An agent that blocks calcium ion influx, reducing muscle contraction and vascular resistance. Therapeutically, it lowers blood pressure, alleviates angina, and controls certain arrhythmias, commonly used in managing hypertension, coronary artery disease, and cardiac conditions.DUKE
Chemopreventive35610 An agent that prevents or delays the development of cancer, reducing the risk of tumor formation and progression. It plays a biological role in inhibiting carcinogenesis, and has therapeutic applications in cancer prevention, with key medical uses including reducing the risk of colorectal, breast, and prostate cancers.DUKE
CholereticAn agent that increases bile production and secretion from the liver, enhancing digestion and fat absorption. Therapeutically, it's used to treat gallstones, liver disease, and indigestion, promoting healthy bile flow and liver function.DUKE
ConvulsantAn agent that induces convulsions and/or epileptic seizures, acting as a stimulant at low doses. It has no therapeutic applications due to its high risk of causing seizures and excitotoxicity, and is the opposite of an anticonvulsant.DUKE
Diuretic35498 An agent that increases urine production, helping remove excess fluids and salts from the body. It plays a key biological role in regulating fluid balance and blood pressure. Therapeutically, diuretics are used to treat conditions such as hypertension, edema, and heart failure, helping reduce swelling and lower blood pressure.DUKE
Gastrostimulant55324 An agent that stimulates digestive motility, increasing gastrointestinal movement and secretion. It enhances gut function, relieving symptoms of gastroparesis, constipation, and other motility disorders, commonly used in managing conditions like diabetes-related gastroparesis and postoperative ileus.DUKE
Hepatoprotective62868 An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities.DUKE
Hydrogen-peroxide inhibitor35222 An agent that blocks the harmful effects of hydrogen peroxide, reducing oxidative stress and inflammation. Therapeutically, it is used to manage conditions like cancer, neurodegenerative diseases, and cardiovascular disorders, protecting cells from damage and promoting overall health.DUKE
HypnoticAn agent that induces sleep, used to treat insomnia and facilitate surgical anesthesia, playing a key role in regulating sleep patterns and providing therapeutic relief for sleep disorders.DUKE
Immunomodulator50846 An agent that regulates the immune system, modifying its response to maintain balance. Therapeutically, it's used to treat autoimmune diseases, prevent transplant rejection, and manage chronic inflammatory conditions, such as rheumatoid arthritis and multiple sclerosis.DUKE
MyorelaxantAn agent that reduces muscle contractility by blocking nerve impulses or decreasing motor end plate excitability, used therapeutically to relieve muscle spasms, tension, and pain, commonly in managing musculoskeletal disorders, anxiety, and insomnia.DUKE
NeurolepticAn agent that reduces nervous tension by depressing nerve functions, primarily used to treat psychiatric disorders such as schizophrenia, anxiety, and agitation, and also used in managing symptoms of Tourette's syndrome and other neurological conditions.DUKE
Nitric-oxide inhibitor35222 An agent that blocks the production of nitric oxide, reducing inflammation and vascular relaxation. Therapeutically, it's used to treat conditions like hypertension, angina, and septic shock, by constricting blood vessels and improving blood pressure. Key medical uses include cardiovascular and critical care applications.DUKE
Prostaglandin synthesis inhibitor35222 An agent that blocks the production of prostaglandins, reducing inflammation and pain. Therapeutically, it's used to treat conditions like arthritis, menstrual cramps, and fever, commonly found in nonsteroidal anti-inflammatory drugs (NSAIDs).DUKE
Teratogenic50905 An agent that causes abnormal fetal development, disrupting embryonic growth and leading to birth defects. Its biological role is associated with developmental toxicity, and it has no therapeutic applications. Key medical uses include serving as a warning for substances that pose risks during pregnancy, guiding prenatal care and medication management to prevent birth defects.DUKE
UricosuricA substance that increases uric acid excretion in the urine, reducing blood plasma concentration. It plays a biological role in preventing uric acid buildup. Therapeutically, it's used to treat gout and hyperuricemia, managing symptoms and preventing complications. Key medical uses include reducing uric acid levels and alleviating gout attacks.DUKE
Vasoconstrictor50514 An agent that narrows blood vessels, reducing blood flow. It plays a biological role in regulating blood pressure and is therapeutically used to treat conditions like hypotension, nasal congestion, and bleeding. Key medical uses include managing shock, reducing bleeding during surgery, and relieving migraine headaches.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).