Showing Compound Boldine (FDB002096)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:14 UTC

Update date

2019-11-26 02:56:59 UTC

Primary ID

FDB002096

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Boldine

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 Number

476-70-0

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
2,9-Dihydroxy-1,10-dimethoxyaporphine	db_source
5,6,6a,7-Tetrahydro-1,10-dimethoxy-6-methyl-4H-dibenzo[de,g]quinoline-2,9-diol, 9CI	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.33 g/L	ALOGPS
logP	2.33	ALOGPS
logP	2.78	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	6.67	ChemAxon
pKa (Strongest Basic)	12.35	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.16 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	92.91 m³·mol⁻¹	ChemAxon
Polarizability	35.35 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C19H21NO4

IUPAC name

4,16-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 Identifier

InChI=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 Key

LZJRNLRASBVRRX-UHFFFAOYSA-N

Isomeric SMILES

COC1=C(O)C=C2CC3N(C)CCC4=CC(O)=C(OC)C(C2=C1)=C34

Average Molecular Weight

327.3743

Monoisotopic Molecular Weight

327.147058165

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.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Not Available

Direct Parent

Aporphines

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Food and nutrition:

Flavoring agent

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 69.71%; H 6.47%; N 4.28%; O 19.55%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Boldine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03ea-0193000000-4e9d104f3b9f63ebca85	Spectrum
Predicted GC-MS	Boldine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0c29-1003900000-b3664d5a9866ae0e674e	Spectrum
Predicted GC-MS	Boldine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Boldine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Boldine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Boldine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Boldine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Boldine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Boldine, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-00kr-0590000000-f0be973ef3df7bed676d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-03di-0009000000-d2ba02385b9592588b92	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0002-0090000000-95c8c50b071b50db4c52	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-000i-0009000000-34786ce337d46ea704b5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-00kr-0590000000-f0be973ef3df7bed676d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-03dj-0097000000-67d87760a4caee6d5688	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0002-0090000000-e4cefc23c5dfb8ba6b98	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-002b-0960000000-fea69a015955b1a8c78a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Negative	splash10-03xr-0096000000-eef48b135c01a8bce609	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-03fr-0009000000-ca3e6fc8ef8b4652939a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-03di-0009000000-de5317cf2fdab8ede5f2	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00or-0093000000-9ed026ef6b3924c14361	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-03dj-0189000000-74839a87c32b59674b9e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-03xr-0096000000-7a5557a34d23c5435004	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0002-0090000000-e2bcbd9b1e8cfe4b5c97	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00or-0093000000-6425dc8e8623be8ff155	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00kb-0090000000-0189a512fde7a38e7508	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00kb-0950000000-cfbc617d88a4d97d884b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-002b-0980000000-99aa3f6034bdf51f0c8f	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0019000000-1bf91ce02169cdc4f51b	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004j-0097000000-f405b3e19193547c8a34	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-017i-0090000000-a3de726762f74254538d	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0009000000-740d8346fca3f39b7095	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0029000000-4fb006bf9d3d6f7f1138	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01qc-0091000000-090643282c4d4b487254	2015-04-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

CFH49-G:CFH49-G

EAFUS ID

Not Available

Dr. Duke ID

BOLDINE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
abortifacient	50691	A chemical substance that interrupts pregnancy after implantation.	DUKE
anti diabetic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti edemic			DUKE
anti hepatotic	62868	Any compound that is able to prevent damage to the liver.	DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti lithic			DUKE
anti mutagenic			DUKE
antioxidant	22586	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 prostaglandin	49020	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 pyretic	35493	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 radicular			DUKE
beta-adrenergic receptor blocker	37962	Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.	DUKE
calcium channel blocker	38215	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
chemopreventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
choleretic			DUKE
convulsant			DUKE
diuretic	35498	An agent that promotes the excretion of urine through its effects on kidney function.	DUKE
gastrostimulant	55324	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
hepatoprotective	62868	Any compound that is able to prevent damage to the liver.	DUKE
hydrogen-peroxide inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
hypnotic			DUKE
immunomodulator	50846	Biologically active substance whose activity affects or plays a role in the functioning of the immune system.	DUKE
myorelaxant			DUKE
neuroleptic			DUKE
nitric-oxide inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
prostaglandin synthesis inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
teratogenic	50905	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
uricosuric			DUKE
vasoconstrictor	50514	Drug used to cause constriction of the blood vessels.	DUKE