Basic information
- CAS
60102-37-6- Standard 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- Molecular formula
- C19H27NO7
- Average molar mass
- 381.4 g/mol
- Monoisotopic mass
- 381.1787522
Names & identifiers
- Preferred name
- (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
- IUPAC
- (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
- English name
- Petasitenine
- Molecular formula
- C19H27NO7
- Molecular weight
- 381.42
Names & synonyms
(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(1R,3'R,6R,7R,11Z)-7-hydroxy-3',6,7,14-tetramethyl-8H,17H-spiro[2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-4,2'-oxirane]-3,8,17-trionePetasitenine (Fukinotoxin)C10359PETASITINENEPetasitenineFukinotoxin【neutral】Petasitenine【neutral】(15R,20R)-15,20-Epoxy-15,20-dihydro-12-hydroxy-4-methyl-4,8-secosenecionan-8,11,16-trioneSpiro[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)-
Database identifiers
- CAS
60102-37-6- PubChem CID
- 5284440
- DTXSID
DTXSID6021115
Properties
Computed structural properties
- XLogP
- 0.6
- Topological polar surface area
- 106 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 0
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 690
Physicochemical properties
- Melting point
- 129.5 °C · 129.5°C
- Boiling point
- 508.82 °C · 508.82°C (rough estimate)
- Density
- 1.2977 · 1.2977 (rough estimate)
- refractive index
- 1.518 · 1.5180 (estimate)
- pka
- 12.75 · 12.75±0.60(Predicted)
- color
- 6 H6/hexane · Crystals from C6H6/hexane or Me2CO
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 737 TK4X375 · 737TK4X375
- IARC
- 3 · 3 (Vol. 31, Sup 7) 1987
- RIDADR
- 1544 · 1544
- HazardClass
- 6.1 · 6.1(b)
- PackingGroup
- III
- Toxicity
- 1 mg/plate · mma-sat 1 mg/plate MUREAV 68,211,79
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- ridadr
- 1544
- Toxicity
- mma-sat 1 mg/plate MUREAV 68,211,79
- hazard_class
- 6.1(b)
- packing_group
- III
Chemistry & industry
Applications
DescriptionA pyrrolizidine alkaloid, petasitenine occurs, together with neopetasitenine (q.v.) in Petasites japonicus Maxim. Like the accompanying base, it possesses strong hepatotoxic properties.
UsesPetasitenine (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].
Suppliers7 total
武汉众志诚生物技术有限公司13628624121 13628604890 · [email protected]
佛山宝诺生物科技有限公司0757-85921206 18520245316 · [email protected]
四川省维克奇生物科技有限公司028-81700200 18116577057 · [email protected]
EMMX Biotechnology LLC888-539-0666 · [email protected]
湖北扬信医药科技有限公司07143299675 13092790750 · [email protected]
上海贝万塔生物科技有限公司021-67187366 19901745723 · [email protected]
上海甄准生物科技有限公司18019219489 18901678489 · [email protected]
Additional notes
DefinitionChEBI: Petasitenine is a spiro-epoxide.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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