(1R,3'R,6R,7R,11Z)-7-hydroxy-3',6,7,14-tetramethylspiro[2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-4,2'-oxirane]-3,8,17-trione
Petasitenine (Fukinotoxin) · C10359 · PETASITINENE · Petasitenine · Fukinotoxin【neutral】 · Petasitenine【neutral】 · (15R,20R)-15,20-Epoxy-15,20-dihydro-12-hydroxy-4-methyl-4,8-secosenecionan-8,11,16-trione · Spiro[2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-4,2'-oxirane]-3,8,17-trione, 7-hydroxy-3',6,7,14-tetramethyl-, (1R,2'R,3'R,6R,7R)-
![(1R,3'R,6R,7R,11Z)-7-hydroxy-3',6,7,14-tetramethylspiro[2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-4,2'-oxirane]-3,8,17-trione molecular structure](/img/chemical/5284440.png)
Identifiers & Physical Properties
| CAS No. | 60102-37-6 |
|---|---|
| Molecular formula | C19H27NO7 |
| Average molar mass | 381.4 g/mol |
| Monoisotopic mass | 381.1787522 g/mol |
| SMILES | C[C@@H]1CC2(O[C@@H]2C)C(=O)O[C@@H]2CCN(C)C/C=C(/COC(=O)[C@]1(C)O)C2=O |
| InChIKey | CZQLULNMKQAIQL-FOUXODHOSA-N |
| PubChem CID | 5284440 |
| DTXSID | DTXSID6021115 |
Chemical & Physical Properties
| XLogP | 0.6 |
|---|---|
| Topological polar surface area | 106 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 8 |
| Rotatable bonds | 0 |
| Heavy atoms | 27 |
| Formal charge | 0 |
| Complexity | 690 |
| Melting point | 129.5°C |
| Boiling point | 508.82°C (rough estimate) |
| Density | 1.2977 (rough estimate) |
| Refractive index | 1.5180 (estimate) |
| pKa (acidity coefficient) | 12.75±0.60(Predicted) |
| Color | Crystals from C6H6/hexane or Me2CO |
| EWG's Food Scores | 1 |
| FDA UNII | 737TK4X375 |
| IARC | 3 (Vol. 31, Sup 7) 1987 |
| UN transport number | 1544 |
| Hazard class | 6.1(b) |
| Packing group | III |
| Toxicity | mma-sat 1 mg/plate MUREAV 68,211,79 |
Safety & Regulations
| UN transport number | 1544 |
|---|---|
| Toxicity | mma-sat 1 mg/plate MUREAV 68,211,79 |
| Hazard class | 6.1(b) |
| Packing group | III |
Applications & Uses
Description
A pyrrolizidine alkaloid, petasitenine occurs, together with neopetasitenine (q.v.) in Petasites japonicus Maxim. Like the accompanying base, it possesses strong hepatotoxic properties.
Uses
Petasitenine (Fukinotoxin) is a pyrrolizidine alkaloid that can be found in the plant Petasites japonicus, which is a carcinogenic metabolite of neopetasitenine. Petasitenine causes lactate dehydrogenase leakage, and exhibits hepatotoxicity[1].