24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(13),2,4(8),9,11,14(22),15,17(21),23-nonaen-24-ium chloride

• ChemBase ID: 134057
• Molecular Formular: C20H14ClNO4
• Molecular Mass: 367.78246
• Monoisotopic Mass: 367.06113561
• SMILES: C[n+]1cc2c(ccc3c2OCO3)c2c1c1cc3c(cc1cc2)OCO3.[Cl-]
• Canonical SMILES: C[n+]1cc2c3OCOc3ccc2c2c1c1cc3OCOc3cc1cc2.[Cl-]
• InChI: InChI=1S/C20H14NO4.ClH/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;1H/q+1;/p-1
• InChIKey: GIZKAXHWLRYMLE-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^2,^1^0.0^4,^8.0^1^4,^2^2.0^1^7,^2^1]tetracosa-1(13),2,4(8),9,11,14(22),15,17(21),23-nonaen-24-ium chloride; 24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^2,^1^0.0^4,^8.0^1^4,^2^2.0^1^7,^2^1]tetracosa-1(13),2,4(8),9,11,14,16,21,23-nonaen-24-ium chloride
• IUPAC Traditional name: 24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^2,^1^0.0^4,^8.0^1^4,^2^2.0^1^7,^2^1]tetracosa-1(13),2,4(8),9,11,14(22),15,17(21),23-nonaen-24-ium chloride; sanguinarine chloride
• Synonyms: Sanguinarine chloride hydrate; Sanguinarine chloride; 13-Methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium Chloride; Sanguinarine Hydrochloride; Sanguinarium Chloride

Database IDs

• CAS Number: 5578-73-4; 5578-73-4(anhydrous)
• MDL Number: MFCD00012126
• Beilstein Number: 3832138
• PubChem SID: 24278199; 162228334
• PubChem CID: 68635

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -0.94349664
• LogD (pH = 7.4): -0.94349664
• Log P: -0.94349664
• Molar Refractivity: 90.8184 cm^3
• Polarizability: 38.960384 Å^3
• Polar Surface Area: 40.8 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: slightly soluble <0.3 mg/mL; methanol: soluble20 mg/mL, clear, orange; methanol: soluble3.8 mg/mL

Safety Information

• RTECS: VP5220000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 26; 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98% (HPLC); ≥98.0% (HPLC)
• Biological Source: (Macleaya cordata and microcarpa)
• Empirical Formula (Hill Notation): C20H14ClNO4

DETAILS

Sigma Aldrich - S5890

Biochem/physiol Actions
A natural product with antimicrobial, anti-inflammatory, and anti-oxidant properties. Has antiproliferative, pro-apoptosis effects in some cancer cell lines.

Toronto Research Chemicals - S112500

Sanguinarium Chloride is a natural product with antimicrobial, anti-inflammatory, and anti-oxidant properties. Sanguinarium Chloride has antiproliferative, pro-apoptosis effects in some cancer cell lines.

REFERENCES

• Ahmad, N., et al.: Clin. Cancer Res., 6, 1524 (2000)
• Adhami, V., et al.: Mol. Cancer Ther., 3, 933 (2000)