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Heliosupine N-oxide

CAT: 0804-HY-131574Size: 1 EachDry Ice: NoHazardous: No
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Description
Heliosupine N-oxide, Heliosupin metabolite, inhibits muscarinic acetylcholine receptor (mAChR) with the IC50 of 350 μM. Heliosupine N-oxide is a pyrrolizidine alkaloid (PA) [1].
CAS Number
31701-88-9
UNSPSC
12352005
Target
MAChR
Type
Natural Products
Related Pathways
GPCR/G Protein; Neuronal Signaling
Applications
Neuroscience-Neuromodulation
Field of Research
Neurological Disease
Assay Protocol
https://www.medchemexpress.com/heliosupine-n-oxide.html
Solubility
10 mM in DMSO
Smiles
[O-][N+]12[C@]([C@H](CC2)OC(/C(C)=C\C)=O)([H])C(COC([C@@]([C@@H](O)C)(O)C(C)(O)C)=O)=CC1
Molecular Formula
C20H31NO8
Molecular Weight
413.46
References & Citations
[1]T. Schmeller, et al. Allelochemical Activities of Pyrrolizidine Alkaloids: Interactions with Neuroreceptors and Acetylcholine Related Enzymes.Journal of Chemical Ecology volume 23, pages399–416 (1997) .
Shipping Conditions
Room temperature
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

CID 163196230

Heliosupine N-oxide is a citraconoyl group.

CAS Number31701-88-9
PubChem CID163196230
IUPAC Name[(7S,8R)-7-[(Z)-2-methylbut-2-enoyl]oxy-4-oxido-5,6,7,8-tetrahydro-3H-pyrrolizin-4-ium-1-yl]methyl (2S)-2,3-dihydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate
Molecular FormulaC20H31NO8
Molecular Weight413.5
XLogP-0.6
Topological Polar Surface Area131
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count8
Rotatable Bond Count9
Heavy Atom Count29
Formal Charge0
Complexity730
SMILES
C/C=C(/C)\C(=O)O[C@H]1CC[N+]2([C@@H]1C(=CC2)COC(=O)[C@]([C@H](C)O)(C(C)(C)O)O)[O-]
InChI
InChI=1S/C20H31NO8/c1-6-12(2)17(23)29-15-8-10-21(27)9-7-14(16(15)21)11-28-18(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+,21?/m0/s1
InChIKey
KDJGEXAPDZNXSD-MIFYRBSSSA-N
Chemical Structure
2D Structure
2D structure of CID 163196230
CAS: 31701-88-9
CID: 163196230
Formula: C20H31NO8
MW: 413.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight413.5
XLogP3-0.6
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count8
Rotatable Bond Count9
Exact Mass413.20496695
Monoisotopic Mass413.20496695
Topological Polar Surface Area131 Ų
Heavy Atom Count29
Formal Charge0
Complexity730
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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