5,7,17,19-tetraoxa-13-azahexacyclo[11.11.0.02,10.04,8.015,23.016,20]tetracosa-2,4(8),9,15(23),16(20),21-hexaene

• ChemBase ID: 177888
• Molecular Formular: C19H17NO4
• Molecular Mass: 323.34258
• Monoisotopic Mass: 323.11575803
• SMILES: c12c(cc3c(c1)C1N(CC3)Cc3c(C1)ccc1c3OCO1)OCO2
• Canonical SMILES: C1Oc2c(O1)cc1c(c2)CCN2C1Cc1ccc3c(c1C2)OCO3
• InChI: InChI=1S/C19H17NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,6-7,15H,3-5,8-10H2
• InChIKey: UXYJCYXWJGAKQY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,7,17,19-tetraoxa-13-azahexacyclo[11.11.0.0^2,^1^0.0^4,^8.0^1^5,^2^3.0^1^6,^2^0]tetracosa-2,4(8),9,15(23),16(20),21-hexaene
• IUPAC Traditional name: 5,7,17,19-tetraoxa-13-azahexacyclo[11.11.0.0^2,^1^0.0^4,^8.0^1^5,^2^3.0^1^6,^2^0]tetracosa-2,4(8),9,15(23),16(20),21-hexaene
• Synonyms: 6,7,12b,13-Tetrahydro-4H-bis[1,3]benzodioxolo[5,6-a:4',5'-g]quinolizine; (±)- 2,3:9,10-Bis(methylenedioxy)berbine; (±)-Stylopine; (±)-Tetrahydrocoptisine; 2,3:9,10-Bis(methylenedioxy)berbine; Chelidamine; NSC 110382; NSC 404529; Tetrahydrocoptisine; dl-Stylopine; dl-Tetrahydrocoptisine; (R,S)-Stylopine

Database IDs

• CAS Number: 4312-32-7
• PubChem SID: 164233798
• PubChem CID: 6770

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 2.7562387
• LogD (pH = 7.4): 3.0204632
• Log P: 3.0251267
• Molar Refractivity: 87.0365 cm^3
• Polarizability: 33.968124 Å^3
• Polar Surface Area: 40.16 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S687740

dl-Stylopineis is an isoquinoline alkaloid isolated from the whole plant of Argemone mexicana. (S)-Stylopine is an important intermediate in the biosynthesis of benzophenanthridine alkaloids, such as Sanguinarine.

REFERENCES

• Kutchan, T; J Biol Chem 1995, 270, 24475,,,Nelson, D; Plant Physiol 2004, 135, 756,,,