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Heliosupine (Standard)

CAT: 0804-HY-124140RSize: 1 EachDry Ice: NoHazardous: No
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Description
Heliosupine (Standard) is the analytical standard of Heliosupine. This product is intended for research and analytical applications. Heliosupine is a pyrrolizidine alkaloid. Heliosupine is an acetylcholinesterase (AChE) inhibitor, with an IC50 0.57 mM. Heliosupine exhibits deterrent effects against generalist herbivores[1][2].
CAS Number
32728-78-2
UNSPSC
12352005
Target
Cholinesterase (ChE) ; Reference Standards
Type
Reference Standards
Related Pathways
Neuronal Signaling; Others
Field of Research
Others
Assay Protocol
https://www.medchemexpress.com/heliosupine-standard.html
Smiles
CC(C)(O)[C@]([C@@H](O)C)(O)C(OCC1=CCN2[C@@]1([H])[C@@H](OC(/C(C)=C\C)=O)CC2)=O
Molecular Formula
C20H31NO7
Molecular Weight
397.46
References & Citations
[1]Benamar H, et, al. Pyrrolizidine alkaloids from Solenanthus lanatus DC. with acetylcholinesterase inhibitory activity. Nat Prod Res. 2016 Nov;30 (22) :2567-2574.|[2]Dam NM, et, al. The "Raison D'être" of pyrrolizidine alkaloids in Cynoglossum officinale: Deterrent effects against generalist herbivores. J Chem Ecol. 1995 May;21 (5) :507-23.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards

Chemical Information

Heliosupine

Heliosupine is an azabicycloalkane compound having angelyloxy and echimidinyloxymethyl substituents attached to the ring system. It is a 2-methylbut-2-enoic acid, an azabicycloalkane and a diester. It is functionally related to an isocrotonic acid and an angelic acid.

CAS Number32728-78-2
PubChem CID5281732
IUPAC Name[(7S,8R)-7-[(Z)-2-methylbut-2-enoyl]oxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2,3-dihydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate
Molecular FormulaC20H31NO7
Molecular Weight397.5
XLogP-0.1
Topological Polar Surface Area117
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count8
Rotatable Bond Count9
Heavy Atom Count28
Formal Charge0
Complexity684
SMILES
C/C=C(/C)\C(=O)O[C@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@]([C@H](C)O)(C(C)(C)O)O
InChI
InChI=1S/C20H31NO7/c1-6-12(2)17(23)28-15-8-10-21-9-7-14(16(15)21)11-27-18(24)20(26,13(3)22)19(4,5)25/h6-7,13,15-16,22,25-26H,8-11H2,1-5H3/b12-6-/t13-,15-,16+,20+/m0/s1
InChIKey
HRSGCYGUWHGOPY-UKLMUADPSA-N
Chemical Structure
2D Structure
2D structure of Heliosupine
CAS: 32728-78-2
CID: 5281732
Formula: C20H31NO7
MW: 397.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight397.5
XLogP3-0.1
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count8
Rotatable Bond Count9
Exact Mass397.21005233
Monoisotopic Mass397.21005233
Topological Polar Surface Area117 Ų
Heavy Atom Count28
Formal Charge0
Complexity684
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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