(1R,2R,4R,8S)-4-methoxy-14-oxa-7-azatetracyclo[6.6.1.01,11.02,7]pentadeca-9,11-dien-13-one

• ChemBase ID: 176709
• Molecular Formular: C14H17NO3
• Molecular Mass: 247.28968
• Monoisotopic Mass: 247.12084341
• SMILES: C1[C@H](C[C@H]2[C@@]34C[C@@H](C=CC3=CC(=O)O4)N2C1)OC
• Canonical SMILES: CO[C@@H]1CCN2[C@@H](C1)[C@@]13OC(=O)C=C3C=C[C@@H]2C1
• InChI: InChI=1S/C14H17NO3/c1-17-11-4-5-15-10-3-2-9-6-13(16)18-14(9,8-10)12(15)7-11/h2-3,6,10-12H,4-5,7-8H2,1H3/t10-,11-,12-,14-/m1/s1
• InChIKey: YKLWRYOORWTCQQ-HKUMRIAESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,4R,8S)-4-methoxy-14-oxa-7-azatetracyclo[6.6.1.0^1,^1^1.0^2,^7]pentadeca-9,11-dien-13-one
• IUPAC Traditional name: (1R,2R,4R,8S)-4-methoxy-14-oxa-7-azatetracyclo[6.6.1.0^1,^1^1.0^2,^7]pentadeca-9,11-dien-13-one
• Synonyms: (6S,10R,11aR,11bS)-9,10,11,11a-Tetrahydro-10-methoxy-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one; (4β)-4-Methoxysecurinan-11-one; (-)-Phyllanthine; 4-Methoxysecurinine; 4β-Methoxysecurinine; Phyllanthine

Database IDs

• CAS Number: 20072-02-0
• PubChem SID: 164232619
• PubChem CID: 71751660

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -2.7683113
• LogD (pH = 7.4): -1.2724133
• Log P: 0.51633376
• Molar Refractivity: 67.6526 cm^3
• Polarizability: 26.112606 Å^3
• Polar Surface Area: 38.77 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P397800

A new alkaloid from Phyllanthus niruri. These alkaloids have found a sporadic use clinically for such diseases as poliomyelitis, ALS (amyotrophic lateral sclerosis) and chronic aplastic anemia.

REFERENCES

• Horii, Z., et al.: Chem. Pharm. Bull., 20, 1768 (1972)
• Rognan, D., et al.: J. Med. Chem., 35, 1969 (1972)
• Weenen, H., et al.: Planta Med., 56, 371 (1972)