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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:00 UTC
Update Date2020-05-12 18:33:31 UTC
HMDB IDHMDB0029367
Secondary Accession Numbers
  • HMDB29367
Metabolite Identification
Common NameSanguinarine
DescriptionSanguinarine 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.[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 results from ingesting sanguinarine
Structure
Data?1589308411
Synonyms
ValueSource
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-chelerythrineHMDB
Sanguinarine sulfate (2:1)HMDB
Sanguinarine sulfate (1:1)HMDB
Sanguinarine hydroxideHMDB
Sanguinarine nitrateHMDB
Chemical FormulaC20H14NO4
Average Molecular Weight332.3295
Monoisotopic Molecular Weight332.092282941
IUPAC Name24-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 Namesanguinarine
CAS Registry Number2447-54-3
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 KeyINVGWHRKADIJHF-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.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassBenzophenanthridine alkaloids
Sub ClassQuaternary benzophenanthridine alkaloids
Direct ParentQuaternary 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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point266 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00019 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity90.82 m³·mol⁻¹ChemAxon
Polarizability35.62 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-0019000000-00748d09c91de933d22a2017-09-01View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0fz9-0089000000-f8aef246d6f8f144f4172017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01ba-0093000000-8e78de64c96cdc678a002017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0009000000-136b5256b656b11c43ed2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0009000000-908c2e468892ac93bbe72017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0049000000-b15f0155462f7f9e3ab52017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01ba-0092000000-d8d44b51327d3e8b0a712017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0udi-0039000000-c85daa2f888c3a5c8e7f2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00lr-0397000000-57df1e4d4f5d79d093362017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-2ad2cccd8ab76cdff89f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0009000000-463ec0488cc6bf1210ec2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0wt9-0079000000-e461a044f76d24fe94ca2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-156aaa823d56af69fe052016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-1affdcdb9daee140befd2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-2089000000-f131958bee2ac1fc2c872016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-135a15e661484c68a7182021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0009000000-18ac2ce90647300205992021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0019000000-f7f1076878f20b9585fe2021-09-07View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000436
KNApSAcK IDC00001917
Chemspider ID4970
KEGG Compound IDC06162
BioCyc IDSANGUINARINE
BiGG IDNot Available
Wikipedia LinkSanguinarine
METLIN IDNot Available
PubChem Compound5154
PDB IDSAU
ChEBI ID17183
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .