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Picrinine

CAT: 0804-HY-N2074-02Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N2074-02Size:10 mg
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Description
Picrinine, an akuammiline alkaloid, is isolated from the leaves of Alstonia scholaris. Picrinine exhibits anti-inflammatory activity through inhibition of the 5-lipoxygenase enzyme[1].
CAS Number
4684-32-6
UNSPSC
12352005
Target
Lipoxygenase
Type
Natural Products
Related Pathways
Metabolic Enzyme/Protease
Applications
COVID-19-immunoregulation
Field of Research
Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/picrinine.html
Purity
99.33
Solubility
DMSO : 33.33 mg/mL (ultrasonic; warming; heat to 60°C)
Smiles
O=C([C@@]1([H])[C@@](C(C=CC=C2)=C2N3)(C[C@]4([H])O5)[C@@]35[C@]6([H])C[C@@]1([H])/C(CN64)=C\C)OC
Molecular Formula
C20H22N2O3
Molecular Weight
338.40
References & Citations
[1]Smith JM, et, al. Total synthesis of the akuammiline alkaloid picrinine. J Am Chem Soc. 2014 Mar 26;136 (12) :4504-7.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C (Powder, sealed storage, away from moisture and light)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
5-LOX

Chemical Information

Picrinine

Picrinine is a natural product with formula C20H22N2O3 that is the member of the akuammiline family of alkaloids, first isolated in 1965 from the leaves of Alstonia scholaris. It has a role as an analgesic, an antitussive, an anti-asthmatic agent, an anti-inflammatory agent and a plant metabolite. It is a methyl ester, a polycyclic ether, an organic heteropentacyclic compound, an alkaloid ester and an indole alkaloid.

CAS Number4684-32-6
PubChem CID46229104
IUPAC Namemethyl (1R,9R,11S,14E,15R,17S,19R)-14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.19,15.01,9.03,8.012,17]nonadeca-3,5,7-triene-19-carboxylate
Molecular FormulaC20H22N2O3
Molecular Weight338.4
XLogP2.1
Topological Polar Surface Area50.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Heavy Atom Count25
Formal Charge0
Complexity678
SMILES
C/C=C\1/CN2[C@H]3C[C@@H]1[C@H]([C@@]45[C@@]3(NC6=CC=CC=C64)O[C@H]2C5)C(=O)OC
InChI
InChI=1S/C20H22N2O3/c1-3-11-10-22-15-8-12(11)17(18(23)24-2)19-9-16(22)25-20(15,19)21-14-7-5-4-6-13(14)19/h3-7,12,15-17,21H,8-10H2,1-2H3/b11-3-/t12-,15-,16-,17-,19-,20-/m0/s1
InChIKey
BDXYPHKGNUGUFG-VETGLWQVSA-N
Chemical Structure
2D Structure
2D structure of Picrinine
CAS: 4684-32-6
CID: 46229104
Formula: C20H22N2O3
MW: 338.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight338.4
XLogP32.1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Exact Mass338.16304257
Monoisotopic Mass338.16304257
Topological Polar Surface Area50.8 Ų
Heavy Atom Count25
Formal Charge0
Complexity678
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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