24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1,3,8,10,12,14(22),15,17(21)-octaene

• ChemBase ID: 127040
• Molecular Formular: C20H15NO4
• Molecular Mass: 333.3374
• Monoisotopic Mass: 333.10010797
• SMILES: CN1Cc2c(ccc3c2OCO3)c2c1c1cc3c(cc1cc2)OCO3
• Canonical SMILES: CN1Cc2c3OCOc3ccc2c2c1c1cc3OCOc3cc1cc2
• InChI: InChI=1S/C20H15NO4/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/h2-7H,8-10H2,1H3
• InChIKey: CIUHLXZTZWTVFL-UHFFFAOYSA-N

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-1,3,8,10,12,14(22),15,17(21)-octaene; 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)-octaene
• 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-1,3,8,10,12,14(22),15,17(21)-octaene; dihydrosanguinarine
• Synonyms: Dihydrosanguinarine; 13,14-Dihydro-13-methyl-[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridine; 13,14-Dihydrosanguinarine; Hydrosanguinarine; Dihydro Sanguinarine

Database IDs

• CAS Number: 3606-45-9
• PubChem SID: 162221363
• PubChem CID: 124069
• Wikipedia Title: Dihydrosanguinarine

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 3.715453
• LogD (pH = 7.4): 3.715683
• Log P: 3.715686
• Molar Refractivity: 92.1614 cm^3
• Polarizability: 37.802025 Å^3
• Polar Surface Area: 40.16 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D454155

Dihydrosanguinarine (DHSG) is a metabolite of Sanguinarine (SG) (S112500) with antifungal activity.

REFERENCES

• Wink, M., et al.: Curr. Drug Metab., 9, 996 (2008)
• Vrba, J., et al.: Toxicol. Vitro, 23, 580 (2008)