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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:00 UTC
Update Date2022-03-07 02:52:08 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
Thumb
Synonyms
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point266 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.32 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.653 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
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
Good Scents IDrw1665421
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.. .