ContaminantDB: Sanguinarine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-08-29 04:49:20 UTC

Update Date

2026-04-03 05:05:40 UTC

Accession Number

CHEM002982

Identification

Common Name

Sanguinarine

Class

Small Molecule

Description

Sanguinarine is found in opium poppy. Consumption of Sanguinarine, present in poppy seeds and in the oil of Argemone mexicana which has been used as an adulterant for mustard oil in India, has been linked to development of glaucoma. Sanguinarine is banned by FDA. Sanguinarine is a quaternary ammonium salt from the group of benzylisoquinoline alkaloids. It is extracted from some plants, including bloodroot (Sanguinaria canadensis), Mexican prickly poppy Argemone mexicana, Chelidonium majus and Macleaya cordata. It is also found in the root, stem and leaves of the opium poppy but not in the capsule. Sanguinarine is a toxin that kills animal cells through its action on the Na+-K+-ATPase transmembrane protein. Epidemic dropsy is a disease that results from ingesting sanguinarine. Sanguinarine has been shown to exhibit antibiotic, anti-apoptotic, anti-fungal, anti-inflammatory and anti-angiogenic functions Sanguinarine belongs to the family of Benzoquinolines. These are organic compounds containing a benzene fused to a quinoline ring system. (2, 3, 2, 2, 2).

Contaminant Sources

FooDB Chemicals
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Food Toxin
Metabolite
Natural Compound
Organic Compound
Plant Toxin

Chemical Structure

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

Synonyms

Value	Source
13-Methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium	ChEBI
13-Methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium(1+), 9ci	HMDB
5-Methyl-2,3:7,8-bis(methylenedioxy)benzo[c]phenanthridinium(1+)	HMDB
Benzophenanthridine alkaloid	HMDB
Dimethylenedioxy benzphenanthridine	HMDB
Pseudochelerythrine	HMDB
Sanguinarin	HMDB
Sanguinarine chloride	HMDB
Sanguinarium	HMDB
Sanguiritrin	HMDB
Sangvinarin	HMDB
Veadent	HMDB
Viadent	HMDB
Y-chelerythrine	HMDB
Pseudo-chelerythrine	HMDB
Sanguinarine sulfate (2:1)	HMDB
Sanguinarine sulfate (1:1)	HMDB
Sanguinarine hydroxide	HMDB
Sanguinarine nitrate	HMDB

Chemical Formula

C₂₀H₁₄NO₄

Average Molecular Mass

332.330 g/mol

Monoisotopic Mass

332.092 g/mol

CAS Registry Number

2447-54-3

IUPAC Name

24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaen-24-ium

Traditional Name

sanguinarine

SMILES

C[N+]1=C2C3=CC4=C(OCO4)C=C3C=CC2=C2C=CC3=C(OCO3)C2=C1

InChI Identifier

InChI=1S/C20H14NO4/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21/h2-8H,9-10H2,1H3/q+1

InChI Key

INVGWHRKADIJHF-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as quaternary benzophenanthridine alkaloids. These are alkaloids containing a quaternary N-demethylbenzophenanthridine skeleton, where the nitrogen atom of the phenanthridine moiety is part of four bonds.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Benzophenanthridine alkaloids

Sub Class

Quaternary benzophenanthridine alkaloids

Direct Parent

Quaternary benzophenanthridine alkaloids

Alternative Parents

Substituents

Quaternary benzophenanthridine alkaloid skeleton
Benzoquinoline
Phenanthridine
Isoquinoline
Naphthalene
Quinoline
Benzodioxole
Pyridine
Benzenoid
Pyridinium
Heteroaromatic compound
Azacycle
Oxacycle
Acetal
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzophenanthridine alkaloid (CHEBI:17183 )
alkaloid antibiotic (CHEBI:17183 )
botanical anti-fungal agent (CHEBI:17183 )
Isoquinoline alkaloids (C06162 )
a small molecule (SANGUINARINE )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	266°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00019 g/L	ALOGPS
logP	-0.51	ALOGPS
logP	-0.94	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.8 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	90.82 m³·mol⁻¹	ChemAxon
Polarizability	35.62 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-0019000000-00748d09c91de933d22a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0fz9-0089000000-f8aef246d6f8f144f417	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-01ba-0093000000-8e78de64c96cdc678a00	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0009000000-136b5256b656b11c43ed	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0009000000-908c2e468892ac93bbe7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0049000000-b15f0155462f7f9e3ab5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-01ba-0092000000-d8d44b51327d3e8b0a71	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-0udi-0039000000-c85daa2f888c3a5c8e7f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00lr-0397000000-57df1e4d4f5d79d09336	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0009000000-2ad2cccd8ab76cdff89f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0009000000-463ec0488cc6bf1210ec	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0wt9-0079000000-e461a044f76d24fe94ca	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0009000000-156aaa823d56af69fe05	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0009000000-1affdcdb9daee140befd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-003r-2089000000-f131958bee2ac1fc2c87	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0009000000-135a15e661484c68a718	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0009000000-18ac2ce9064730020599	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0019000000-f7f1076878f20b9585fe	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Sanguinarine, at micromolar concentrations, imparts cell growth inhibitory response in human squamous carcinoma (1) cells via an induction of apoptosis. This is while sanguinarine treatment did not result in apoptosis of the normal human epidermal keratinocytes at similar dose. Sanguinarine [0.1 (M-2 (M)] treatment to HaCaT cells was found to inhibit in a dose-dependent manner the cell proliferation and induce apoptosis, as measured by 3-(4,5 dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay and ELISA, respectively. Sanguinarine treatment also resulted in a significant cleavage of poly(ADP-ribose) polymerase in HaCaT cells. Sanguinarine treatment to HaCaT cells resulted in a dose-dependent (a) increase in the level of Bax with a concomitant decrease in Bcl-2 levels and (b) increase in Bax/Bcl-2 ratio. Sanguinarine also resulted in significant increases in the proapoptotic members of Bcl-2 family proteins, i.e., Bak and Bid. This was accompanied by increase in (a) protein expression of cytochrome c and apoptotic protease-activating factor-1 and (b) activity and protein expression of caspase-3, caspase-7, caspase-8, and caspase-9. This indicates the involvement of mitochondrial pathway and Bcl-2 family proteins during sanguinarine-mediated apoptosis of immortalized keratinocytes. (4)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Sanguinarine is found in opium poppy. Consumption of Sanguinarine, present in poppy seeds and in the oil of Argemone mexicana which has been used as an adulterant for mustard oil in India, has been linked to development of glaucoma. It is also found in the root, stem and leaves of the opium poppy but not in the capsule. Sanguinarine is a toxin that kills animal cells through its action on the Na+-K+-ATPase transmembrane protein. These are organic compounds containing a benzene fused to a quinoline ring system.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID