Lup-20(29)-en-3-one
Basic information
- CAS
1617-70-5- Standard SMILES
C=C(C)C1CCC2(C)CCC3(C)C(CCC4C5(C)CCC(=O)C(C)(C)C5CCC43C)C12- InChIKey
GRBHNQFQFHLCHO-UHFFFAOYSA-N- Molecular formula
- C30H48O
- Average molar mass
- 424.7 g/mol
- Monoisotopic mass
- 424.37051615
Overview
Lup-20(29)-en-3-one has been reported in Pongamia pinnata var. pinnata, Daphne aurantiaca, and other organisms with data available.
Names & identifiers
- Preferred name
- Lup-20(29)-en-3-one
- IUPAC
- 3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one
- English name
- Lupenone
- Molecular formula
- C30H48O
- Molecular weight
- 424.7
Names & synonyms
Lup-20(29)-en-3-oneDTXSID909365863a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta(a)chrysen-9-oneRefChem:351425DTXCID101365191Lup-20(30)-en-3-oneLupen-3-oneGRBHNQFQFHLCHO-UHFFFAOYSA-NNSC281807AKOS032948334NSC-281807
Show more names
Lupenone-en-3-oneAids082905Lup-20(29)Aids-082905LUPENONE(RG)18-LUPEN-3-ONELupa-20(30)-ene-3-oneLupa-20(29)-ene-3β-one
3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)octadecahydro-1H-cyclopenta[a]chrysen-9(5bH)-one [M+H]+
Database identifiers
Properties
Computed structural properties
- XLogP
- 9.6
- Topological polar surface area
- 17.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 1
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 807
Physicochemical properties
- Melting point
- 165 · 165-167°C
- Boiling point
- 485.7 · 485.7±14.0 °C(Predicted)
- Density
- 1.115 g/cm3 · 1.115 g/cm3(Temp: 18 °C)
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Solid
- color
- White
- LogP
- 10.4 · 10.400 (est)
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
- Hazard Codes
- Xi
- HS Code
- 29142990 · 29142990
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
- hs_code
- 29142990
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
UsesLupenone is a lupane triterpenoid with antioxidant and anticholinesterase activity. It also a potential protein tyrosine phosphatase 1B (PTP1B) inhibitor.
Additional notes
DefinitionChEBI: A natural product found in Cupania cinerea.
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Compound notes
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