(1R,2R,4S,7R,8S,12R,13R)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15,20-trioxo-3,6,16-trioxapentacyclo[9.9.0.0?,?.0?,?.0??,??]icosan-13-yl acetate

• ChemBase ID: 105694
• Molecular Formular: C28H34O9
• Molecular Mass: 514.56416
• Monoisotopic Mass: 514.22028267
• SMILES: CC(=O)O[C@@H]1CC(=O)OC(C)(C)C2CC(=O)[C@]3(C)C(CC[C@@]4(C)[C@H](c5ccoc5)OC(=O)[C@@H]5[C@]34O5)[C@@]12C
• Canonical SMILES: CC(=O)O[C@@H]1CC(=O)OC(C2[C@@]1(C)C1CC[C@@]3([C@]4([C@@]1(C(=O)C2)C)O[C@@H]4C(=O)O[C@H]3c1ccoc1)C)(C)C
• InChI: InChI=1S/C28H34O9/c1-14(29)34-19-12-20(31)36-24(2,3)17-11-18(30)27(6)16(26(17,19)5)7-9-25(4)21(15-8-10-33-13-15)35-23(32)22-28(25,27)37-22/h8,10,13,16-17,19,21-22H,7,9,11-12H2,1-6H3/t16?,17?,19-,21+,22-,25+,26-,27+,28-/m1/s1
• InChIKey: KPDOJFFZKAUIOE-ZUDUQEJMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,4S,7R,8S,12R,13R)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15,20-trioxo-3,6,16-trioxapentacyclo[9.9.0.0?,?.0?,?.0??,??]icosan-13-yl acetate
• IUPAC Traditional name: (1R,2R,4S,7R,8S,12R,13R)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15,20-trioxo-3,6,16-trioxapentacyclo[9.9.0.0?,?.0?,?.0??,??]icosan-13-yl acetate
• Synonyms: NOMILIN

Database IDs

• CAS Number: 1063-77-0
• PubChem SID: 162092662
• PubChem CID: 6710776

CALCULATED PROPERTIES

• Acid pKa: 17.842342
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 3.017384
• LogD (pH = 7.4): 3.017384
• Log P: 3.017384
• Molar Refractivity: 125.6061 cm^3
• Polarizability: 50.950157 Å^3
• Polar Surface Area: 121.64 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 278-279°C

Safety Information

• Storage Condition: Room Temperature (15-30°C)

DETAILS

MP Biomedicals - 02193771

From Citrus Seeds
A natural extract from grapefruit and other citrus seeds which induces Phase II detoxifying enzymes. It also inhibits chemically induced carcinogenesis.

REFERENCES

• Miller, E.G., et al., Carcinogenesis , 10 : 1535-37 (1989).