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Picrotin (Standard)

CAT: 0804-HY-107782RSize: 1 EachDry Ice: NoHazardous: No
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Description
Picrotin (Standard) is the analytical standard of Picrotin. This product is intended for research and analytical applications. Picrotin is an active compound, also is one of the composition of picrotoxin (an antagonist of GABAA receptors (GABAARs) and glycine receptors (GlyRs) ) . Picrotin has sensitivity for GlyRs with IC50 values range from 5.2 μM to 106 μM. Picrotin can be used for the research of neurotransmission[1][2].
CAS Number
21416-53-5
UNSPSC
12352005
Target
GABA Receptor; Reference Standards
Type
Reference Standards
Related Pathways
Membrane Transporter/Ion Channel; Neuronal Signaling; Others
Field of Research
Neurological Disease
Assay Protocol
https://www.medchemexpress.com/picrotin-standard.html
Smiles
C[C@]([C@@](C1)([C@]2([H])[C@@](C(O)(C)C)([H])[C@@]3([H])OC2=O)O)([C@]3([H])OC4=O)[C@@]54[C@@H]1O5
Molecular Formula
C15H18O7
Molecular Weight
310.30
References & Citations
[1]Yang Z, et al. A proposed structural basis for picrotoxinin and picrotin binding in the glycine receptor pore. J Neurochem. 2007 Oct;103 (2) :580-9.|[2]Dian-Shi Wang, et al. Mechanisms for picrotoxinin and picrotin blocks of alpha2 homomeric glycine receptors. J Biol Chem. 2007 Jun 1;282 (22) :16016-35.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards

Chemical Information

Picrotin

Picrotin is an organic heteropentacyclic compound that is picrotoxinin in which the olefinic double bond has undergone addition of water to give the corresponding tertiary alcohol. It is the less toxic component of picrotoxin, lacking GABA activity. It has a role as a plant metabolite. It is a picrotoxane sesquiterpenoid, a diol, a tertiary alcohol, an epoxide, a gamma-lactone and an organic heteropentacyclic compound. It is functionally related to a picrotoxinin.

CAS Number21416-53-5
PubChem CID442291
IUPAC Name(1R,3R,5S,8S,9R,12S,13R,14S)-1-hydroxy-14-(2-hydroxypropan-2-yl)-13-methyl-4,7,10-trioxapentacyclo[6.4.1.19,12.03,5.05,13]tetradecane-6,11-dione
Molecular FormulaC15H18O7
Molecular Weight310.30
XLogP-0.8
Topological Polar Surface Area106
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count1
Heavy Atom Count22
Formal Charge0
Complexity644
SMILES
C[C@@]12[C@H]3[C@H]4[C@H]([C@@H]([C@@]1(C[C@@H]5[C@]2(O5)C(=O)O3)O)C(=O)O4)C(C)(C)O
InChI
InChI=1S/C15H18O7/c1-12(2,18)6-7-10(16)20-8(6)9-13(3)14(7,19)4-5-15(13,22-5)11(17)21-9/h5-9,18-19H,4H2,1-3H3/t5-,6+,7-,8-,9-,13-,14-,15+/m1/s1
InChIKey
RYEFFICCPKWYML-QCGISDTRSA-N
Chemical Structure
2D Structure
2D structure of Picrotin
CAS: 21416-53-5
CID: 442291
Formula: C15H18O7
MW: 310.30
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight310.30
XLogP3-0.8
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count1
Exact Mass310.10525291
Monoisotopic Mass310.10525291
Topological Polar Surface Area106 Ų
Heavy Atom Count22
Formal Charge0
Complexity644
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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