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Protostemonine

CAT: 0931-T4S0083Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0931-T4S0083Size:10 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
27495-40-5
Target
Others
Related Pathways
Others
Bioactivity
1. Protostemonine has anti-inflammatory activity, it effectively attenuates LPS-induced inflammatory responses in vitro and in vivo; the beneficial effects are associated with the decreased phosphorylation of MAPK and AKT and the reduced expression of pro-inflammatory mediators, such as iNOS, NO and cytokines. 2. Protostemonine shows strong nematicidal activity against Panagrellus redivevus, with the IC50 value of 0.10 uM. 3. Protostemonine attenuates LPS/GalN-induced acute liver failure and upregulating HO-1 expression is implicated in its hepatoprotective activity. 4. Protostemonine shows significant antitussive activity in a citric acid-induced guinea pig cough model following peripheral administration.
Smiles
COC1=C(C)C(=O)OC\1=C1/O[C@@H]2CCCN3[C@@H](CC[C@H]3[C@H]2[C@@H]1C)[C@@H]1C[C@H](C)C(=O)O1
Molecular Formula
C23H31NO6
Molecular Weight
417.5
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

(5Z)-4-Methoxy-3-methyl-5-((3aR,10aS,10bR)-1-methyl-8-((2S,4S)-4-methyl-5-oxooxolan-2-yl)decahydro-2H-furo(3,2-c)pyrrolo(1,2-a)azepin-2-ylidene)furan-2(5H)-one

Protostemonine is a natural product found particularly in Stemona and Stemona. It has a role as a metabolite.

CAS Number27495-40-5
PubChem CID25256772
IUPAC Name(5Z)-4-methoxy-3-methyl-5-[(1S,2R,3S,6R,11S)-3-methyl-11-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-5-oxa-10-azatricyclo[8.3.0.02,6]tridecan-4-ylidene]furan-2-one
Molecular FormulaC23H31NO6
Molecular Weight417.5
XLogP3
Topological Polar Surface Area74.3
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count7
Rotatable Bond Count2
Heavy Atom Count30
Formal Charge0
Complexity832
SMILES
C[C@H]1C[C@H](OC1=O)[C@@H]2CC[C@@H]3N2CCC[C@@H]4[C@@H]3[C@@H](/C(=C/5\C(=C(C(=O)O5)C)OC)/O4)C
InChI
InChI=1S/C23H31NO6/c1-11-10-17(29-22(11)25)14-7-8-15-18-12(2)20(28-16(18)6-5-9-24(14)15)21-19(27-4)13(3)23(26)30-21/h11-12,14-18H,5-10H2,1-4H3/b21-20-/t11-,12-,14-,15-,16+,17-,18+/m0/s1
InChIKey
JDGNFRYDHRYXNL-ROHJGGRPSA-N
Chemical Structure
2D Structure
2D structure of (5Z)-4-Methoxy-3-methyl-5-((3aR,10aS,10bR)-1-methyl-8-((2S,4S)-4-methyl-5-oxooxolan-2-yl)decahydro-2H-furo(3,2-c)pyrrolo(1,2-a)azepin-2-ylidene)furan-2(5H)-one
CAS: 27495-40-5
CID: 25256772
Formula: C23H31NO6
MW: 417.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight417.5
XLogP33
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count7
Rotatable Bond Count2
Exact Mass417.21513771
Monoisotopic Mass417.21513771
Topological Polar Surface Area74.3 Ų
Heavy Atom Count30
Formal Charge0
Complexity832
Isotope Atom Count0
Defined Atom Stereocenter Count7
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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