Sanguinarine

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
    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.. .

    PMID: 20217056

    Sanguinarine

    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
    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.. .

    PMID: 20217056