(1S,3R,6S,10S,11R)-3,12-dimethyl-7-methylidene-2,9-dioxatetracyclo[9.3.0.01,3.06,10]tetradec-12-en-8-one

• ChemBase ID: 179765
• Molecular Formular: C15H18O3
• Molecular Mass: 246.30162
• Monoisotopic Mass: 246.12559444
• SMILES: [C@@]123O[C@@]1(CC[C@@H]1[C@@H]([C@H]2C(=CC3)C)OC(=O)C1=C)C
• Canonical SMILES: CC1=CC[C@@]23[C@H]1[C@H]1OC(=O)C(=C)[C@@H]1CC[C@]3(O2)C
• InChI: InChI=1S/C15H18O3/c1-8-4-7-15-11(8)12-10(9(2)13(16)17-12)5-6-14(15,3)18-15/h4,10-12H,2,5-7H2,1,3H3/t10-,11+,12-,14+,15-/m0/s1
• InChIKey: UVJYAKBJSGRTHA-OEMOEHNSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3R,6S,10S,11R)-3,12-dimethyl-7-methylidene-2,9-dioxatetracyclo[9.3.0.0^1,^3.0^6,^1^0]tetradec-12-en-8-one
• IUPAC Traditional name: (1S,3R,6S,10S,11R)-3,12-dimethyl-7-methylidene-2,9-dioxatetracyclo[9.3.0.0^1,^3.0^6,^1^0]tetradec-12-en-8-one
• Synonyms: Arglabin

Database IDs

• CAS Number: 84692-91-1
• PubChem SID: 164235675
• PubChem CID: 10131102

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.1716745
• LogD (pH = 7.4): 2.1716745
• Log P: 2.1716745
• Molar Refractivity: 66.7907 cm^3
• Polarizability: 26.421297 Å^3
• Polar Surface Area: 38.83 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Farnesyl transferase inhibitor

Product Information

• Biological Source: Constit. of Artemisia glabella, Artemisia myriantha and Artemisia mexicana
• Application(s): Antineoplastic agent

REFERENCES

• Adekenov, S.M. et al., Khim. Prir. Soedin., 1982, 18, 655; Chem. Nat. Compd. (Engl. Transl.), 1982, 18, 623, (isol, ir, uv, ms, arglabin)
• Zdero, C. et al., Phytochemistry, 1990, 29, 189, (isol, pmr, arglabin)
• Appendino, G. et al., Fitoterapia, 1991, 62, 275, (struct)
• Adekenov, S.M. et al., Fitoterapia, 1995, 66, 142, (isol, pmr, cryst struct)
• Pat. Coop. Treaty (WIPO), 1998, 98 048 789; CA, 130, 480j, (arglabin, activity)
• Fazylova, A.S. et al., Khim. Prir. Soedin., 1999, 35, 305, (Arglabin)