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Jatrorrhizine (hydroxide)

CAT: 0804-HY-N0749A-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N0749A-01Size:5 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Jatrorrhizine hydroxide is an alkaloid isolated from Coptis chinensis with neuroprotective, antimicrobial, antiplasmodial and antioxidant activities[1]. Jatrorrhizine hydroxide is a potent and orally active inhibitor of AChE (IC50=872 nM) over >115-fold selectivity for BuChE[2]. Jatrorrhizine hydroxide reduces uptake of serotonin (5-HT) and norepinephrine (NE) via inhibition of uptake-2 transporters[3].
CAS Number
483-43-2
UNSPSC
12352005
Target
5-HT Receptor; Bacterial; Cholinesterase (ChE)
Type
Natural Products
Related Pathways
Anti-infection; GPCR/G Protein; Neuronal Signaling
Applications
COVID-19-immunoregulation
Field of Research
Inflammation/Immunology; Neurological Disease
Assay Protocol
https://www.medchemexpress.com/jatrorrhizine-hydroxide.html
Purity
98.06
Solubility
DMSO : 3.33 mg/mL (ultrasonic) |H2O : 2.5 mg/mL (ultrasonic)
Smiles
COC1=C(OC)C2=C[N+]3=C(C4=CC(OC)=C(O)C=C4CC3)C=C2C=C1.[OH-]
Molecular Formula
C20H21NO5
Molecular Weight
355.38
References & Citations
[1]Sun S, et al. Jatrorrhizine reduces 5-HT and NE uptake via inhibition of uptake-2 transporters and produces antidepressant-like action in mice. Xenobiotica. 2019 Oct;49 (10) :1237-1243.|[2]Xiaofei Jiang, et al. Synthesis and Biological Evaluation of Novel Jatrorrhizine Derivatives with Amino Groups Linked at the 3-Position as Inhibitors of Acetylcholinesterase. Research Article Volume 2017|[3]C W Wright, et al. In vitro antiplasmodial, antiamoebic, and cytotoxic activities of some monomeric isoquinoline alkaloids. J Nat Prod. 2000 Dec;63 (12) :1638-40.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
AChE

Chemical Information

Jatrorrhizine hydroxide
CAS Number483-43-2
PubChem CID12304700
IUPAC Name2,9,10-trimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-3-ol hydroxide
Molecular FormulaC20H21NO5
Molecular Weight355.4
Topological Polar Surface Area52.8
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Heavy Atom Count26
Formal Charge0
Complexity461
SMILES
COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)O)OC)OC.[OH-]
InChI
InChI=1S/C20H19NO4.H2O/c1-23-18-5-4-12-8-16-14-10-19(24-2)17(22)9-13(14)6-7-21(16)11-15(12)20(18)25-3;/h4-5,8-11H,6-7H2,1-3H3;1H2
InChIKey
FLLCSIZPVWDZQO-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Jatrorrhizine hydroxide
CAS: 483-43-2
CID: 12304700
Formula: C20H21NO5
MW: 355.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight355.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Exact Mass355.14197277
Monoisotopic Mass355.14197277
Topological Polar Surface Area52.8 Ų
Heavy Atom Count26
Formal Charge0
Complexity461
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes

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