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

• ChemBase ID: 170016
• Molecular Formular: C22H32O8
• Molecular Mass: 424.48468
• Monoisotopic Mass: 424.20971798
• SMILES: C1(=C[C@@H]2[C@](C[C@@H]1OC(=O)CC(C)C)([C@@]1([C@]3([C@H](O2)[C@@H]([C@H]1O)O)OC3)C)COC(=O)C)C
• Canonical SMILES: CC(CC(=O)O[C@H]1C[C@@]2(COC(=O)C)[C@@H](C=C1C)O[C@H]1[C@]3([C@]2(C)[C@H](O)[C@H]1O)CO3)C
• InChI: InChI=1S/C22H32O8/c1-11(2)6-16(24)29-14-8-21(9-27-13(4)23)15(7-12(14)3)30-19-17(25)18(26)20(21,5)22(19)10-28-22/h7,11,14-15,17-19,25-26H,6,8-10H2,1-5H3/t14-,15+,17+,18+,19?,20+,21+,22-/m0/s1
• InChIKey: PNKLMTPXERFKEN-RCIJJMAMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1'S,2S,2'R,4'S,7'R,9'R,10'R,11'S)-2'-[(acetyloxy)methyl]-10',11'-dihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^2,^7]dodecan]-5'-en-4'-yl 3-methylbutanoate
• IUPAC Traditional name: (1'S,2S,2'R,4'S,7'R,9'R,10'R,11'S)-2'-[(acetyloxy)methyl]-10',11'-dihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0^2,^7]dodecan]-5'-en-4'-yl 3-methylbutanoate
• Synonyms: (3α,4β,8α)-12,13-Epoxytrichothec-9-ene-3,4,8,15-tetrol 8-(3-Methylbutanoate) 15-Acetate; 12,13-Epoxytrichothec-9-ene-3α,4β,8α,15-tetro 15-Acetate 8-Isovalerate; 3,4-Dihydroxy-15-acetoxy-8-(3-methylbutyryloxy)-12,13-epoxy-Δ9-trichothecene; Isovaleric Acid 8-Ester with 12,13-epoxytrichothec-9-ene-3α,4β,8α,15-tetrol 15-Acetate; HT 2; HT 2 Toxin; Mycotoxin HT 2; NSC 278571; Toxin HT 2; HT-2 Toxin

Database IDs

• CAS Number: 26934-87-2
• PubChem SID: 164225926
• PubChem CID: 10093830

CALCULATED PROPERTIES

• Acid pKa: 12.975641
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.57831216
• LogD (pH = 7.4): 0.57831097
• Log P: 0.57831216
• Molar Refractivity: 104.3917 cm^3
• Polarizability: 42.37075 Å^3
• Polar Surface Area: 114.82 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H671800

HT-2 Toxin is a trichothecene group mycotoxin. HT-2 Toxin is the 4-hydroxy analogue of T-2 Toxin (T002980) which has been shown to induce DNA damage and cell death on prolonged administration.

REFERENCES

• Weidner, M. et al.: J. Agric. Food Chem., 60, 5676 (2012)
• Choi, H. et al.: Toxicol. Appl. Pharmacol., 240, 46 (2012)
• Amuzie, C. et al.: Toxicol. Sci., 113, 412 (2012)