(1'S,2R,2'R,3'S,7'R,9'R,10'R,11'S)-3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-4'-oxo-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.02,7]dodecan]-5'-en-11'-yl acetate

• ChemBase ID: 169525
• Molecular Formular: C17H22O8
• Molecular Mass: 354.35178
• Monoisotopic Mass: 354.13146766
• SMILES: O1[C@H]2[C@@]3([C@@]([C@@]4([C@@H]1C=C(C(=O)[C@H]4O)C)CO)([C@@H]([C@H]2O)OC(=O)C)C)CO3
• Canonical SMILES: OC[C@@]12[C@H](C=C(C(=O)[C@H]1O)C)O[C@H]1[C@]3([C@]2(C)[C@H](OC(=O)C)[C@H]1O)OC3
• InChI: InChI=1S/C17H22O8/c1-7-4-9-16(5-18,12(22)10(7)20)15(3)13(24-8(2)19)11(21)14(25-9)17(15)6-23-17/h4,9,11-14,18,21-22H,5-6H2,1-3H3/t9-,11-,12-,13-,14-,15-,16-,17-/m1/s1
• InChIKey: XGCUCFKWVIWWNW-UWKSZNKUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1'S,2R,2'R,3'S,7'R,9'R,10'R,11'S)-3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-4'-oxo-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^2,^7]dodecan]-5'-en-11'-yl acetate
• IUPAC Traditional name: (1'S,2R,2'R,3'S,7'R,9'R,10'R,11'S)-3',10'-dihydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-4'-oxo-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^2,^7]dodecan]-5'-en-11'-yl acetate
• Synonyms: (3α,4β,7α)-4-(Acetyloxy)-12,13-epoxy-3,7,15-trihydroxy-trichothec-9-en-8-one; 4β-Acetoxy-3α,7α,15-trihydroxy-12,13-epoxytrichothec-9-en-8-one; 3-Acetylnivalenol; 4-Acetylnivalenol; Nivalenol Monoacetate; Fusarenon X

Database IDs

• CAS Number: 23255-69-8
• PubChem SID: 162263657
• PubChem CID: 12309986

CALCULATED PROPERTIES

• Acid pKa: 12.491937
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -1.4465677
• LogD (pH = 7.4): -1.4465711
• Log P: -1.4465677
• Molar Refractivity: 81.9796 cm^3
• Polarizability: 33.186726 Å^3
• Polar Surface Area: 125.82 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F865300

A mycotoxin produced by Fusarium, having immunosuppressive and carcinogenic properties.

REFERENCES

• Alvarez, C., et al.: Int. J. Food Microbiol., 135, 131 (2009)
• Steinmetz, W., et al.: Eur. J. Med. Chem., 44, 4485 (2009)
• Tanaka, H., et al.: J. Health Sci., 56, 188 (2009)
• Monbaliu, S., et al.: J. Agric. Food Chem., 58, 66 (2009)