Common Name |
Sanguinarine
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 adliterant 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 capslie.[citation needed]; Sanguinarine is a toxin that kills animal cells through its action on the Na+-K+-ATPase transmembrane protein. Epidemic dropsy is a disease that reslits from ingesting sanguinarine.Sanguinarine has been shown to exhibit antibiotic, anti-apoptotic, anti-fungal, anti-inflammatory and anti-angiogenic functions (PMID 15063803 , 11770015 , 15063803 , 15063803 , 15063803 ).Sanguinarine belongs to the family of Benzoquinolines. These are organic compounds containing a benzene fused to a quinoline ring system.
Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Structure for HMDB29367 (Sanguinarine)
Synonyms |
Value |
Source |
13-Methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridiniumChEBI
13-Methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium(1+), 9ciHMDB
5-Methyl-2,3:7,8-bis(methylenedioxy)benzo[c]phenanthridinium(1+)HMDB
Benzophenanthridine alkaloidHMDB
Dimethylenedioxy benzphenanthridineHMDB
PseudochelerythrineHMDB
SanguinarinHMDB
Sanguinarine chlorideHMDB
SanguinariumHMDB
SanguiritrinHMDB
SangvinarinHMDB
VeadentHMDB
ViadentHMDB
Y-chelerythrineHMDB
pseudo-ChelerythrineMeSH
Sanguinarine slifate (2:1)MeSH
Sanguinarine slifate (1:1)MeSH
Sanguinarine hydroxideMeSH
Sanguinarine nitrateMeSH
Chemical Formlia |
C20H14NO4
Average Molecliar Weight |
332.3295
Monoisotopic Molecliar Weight |
332.092282941
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
CAS Registry Number |
2447-54-3
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 |
This compound belongs to the class of chemical entities 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 |
Chemical entities
Super Class |
Organic compounds
Class |
Alkaloids and derivatives
Sub Class |
Benzophenanthridine alkaloids
Direct Parent |
Quaternary benzophenanthridine alkaloids
Alternative Parents |
Phenanthridines and derivatives
Naphthalenes
Isoquinolines and derivatives
Benzodioxoles
Pyridinium derivatives
Heteroaromatic compounds
Oxacyclic compounds
Azacyclic compounds
Acetals
Organopnictogen compounds
Organonitrogen compounds
Hydrocarbon derivatives
Organic cations
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
Molecliar 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 moleclie (SANGUINARINE )
Ontology |
Status |
Expected but not Quantified
Origin |
Endogenous
Food
Biofunction |
anti-angiogenic
anti-apoptotic
anti-fungal
anti-inflammatory
Application |
Toxic Substance
Cellliar locations |
Cytoplasm
Extracellliar
Physical Properties |
State |
Not Available
Experimental Properties |
Property |
Value |
Reference |
Melting Point266 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties |
Property |
Value |
Source |
Water Solubility0.000192 mg/mLALOGPS
logP-0.51ALOGPS
logP-0.94ChemAxon
logS-6.3ALOGPS
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.8 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity90.82 m3·mol-1ChemAxon
Polarizability35.62 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
Spectra |
Spectra |
Spectrum Type |
Description |
Splash Key |
|
LC-MS/MS |
LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0fz9-0089000000-f8aef246d6f8f144f417View in MoNA
LC-MS/MS |
LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-01ba-0093000000-8e78de64c96cdc678a00View in MoNA
LC-MS/MS |
LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-001i-0009000000-136b5256b656b11c43edView in MoNA
LC-MS/MS |
LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-001i-0009000000-908c2e468892ac93bbe7View in MoNA
LC-MS/MS |
LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-001i-0049000000-b15f0155462f7f9e3ab5View in MoNA
LC-MS/MS |
LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-01ba-0092000000-d8d44b51327d3e8b0a71View in MoNA
LC-MS/MS |
LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0udi-0039000000-c85daa2f888c3a5c8e7fView in MoNA
LC-MS/MS |
LC-MS/MS Spectrum – , positivesplash10-00lr-0397000000-57df1e4d4f5d79d09336View in MoNA
Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
Biological Properties |
Cellliar Locations |
Cytoplasm
Extracellliar
Biofluid Locations |
Not Available
Tissue Location |
Not Available
Pathways |
Not Available
Normal Concentrations |
Not Available |
Abnormal Concentrations |
|
Not Available
Associated Disorders and Diseases |
Disease References |
None
Associated OMIM IDs |
None
External Links |
DrugBank ID |
Not Available
DrugBank Metabolite ID |
Not Available
Phenol Explorer Compound ID |
Not Available
Phenol Explorer Metabolite ID |
Not Available
FoodDB ID |
FDB000436
KNApSAcK ID |
C00024663
Chemspider ID |
4970
KEGG Compound ID |
C06162
BioCyc ID |
Not Available
BiGG ID |
Not Available
Wikipedia Link |
Sanguinarine
NuGOwiki Link |
HMDB29367
Metagene Link |
HMDB29367
METLIN ID |
Not Available
PubChem Compound |
5154
PDB ID |
SAU
ChEBI ID |
17183
Product: MNS
References |
Synthesis Reference |
Not Available |
Material Safety Data Sheet (MSDS) |
Not Available |
General References |
- Eun JP, Koh GY: Suppression of angiogenesis by the plant alkaloid, sanguinarine. Biochem Biophys Res Commun. 2004 Apr 30;317(2):618-24. [PubMed:15063803 ]
- Weerasinghe P, Hallock S, Tang SC, Liepins A: Sanguinarine induces bimodal cell death in K562 but not in high Bcl-2-expressing JM1 cells. Pathol Res Pract. 2001;197(11):717-26. [PubMed:11770015 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
|
PMID: 20217056