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(S) - (-) -Tetrahydroberberine

CAT: 0804-HY-N1418-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N1418-01Size:1 mg
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Description
(S) - (-) -Tetrahydroberberine is an alkaloid and intermediate in the biosynthesis of berberine with insecticidal activity[1].
CAS Number
5096-57-1
Product Name Alternative
(-) -Canadine; (S) - (-) -Canadine
UNSPSC
12352005
Target
Others
Related Pathways
Others
Applications
COVID-19-immunoregulation
Field of Research
Inflammation/Immunology
Purity
98.0
Solubility
Acetone : ≥ 12.5 mg/mL
Smiles
COC1=CC=C(C[C@]23[H])C(CN2CCC(C3=C4)=CC5=C4OCO5)=C1OC
Molecular Formula
C20H21NO4
Molecular Weight
339.39
References & Citations
[1]Galanie S, Smolke CD. Optimization of yeast-based production of medicinal protoberberine alkaloids. Microb Cell Fact. 2015 Sep 16;14:144.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

(S)-Canadine

(S)-canadine is the (S)-enantiomer of canadine. It has a role as a plant metabolite. It is an an (S)-7,8,13,14-tetrahydroprotoberberine and a canadine. It is functionally related to a (S)-nandinine. It is an enantiomer of a (R)-canadine.

CAS Number5096-57-1
PubChem CID21171
IUPAC Name(1S)-16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaene
Molecular FormulaC20H21NO4
Molecular Weight339.4
XLogP3.1
Topological Polar Surface Area40.2
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Heavy Atom Count25
Formal Charge0
Complexity488
SMILES
COC1=C(C2=C(C[C@H]3C4=CC5=C(C=C4CCN3C2)OCO5)C=C1)OC
InChI
InChI=1S/C20H21NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,8-9,16H,5-7,10-11H2,1-2H3/t16-/m0/s1
InChIKey
VZTUIEROBZXUFA-INIZCTEOSA-N
Chemical Structure
2D Structure
2D structure of (S)-Canadine
CAS: 5096-57-1
CID: 21171
Formula: C20H21NO4
MW: 339.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight339.4
XLogP33.1
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Exact Mass339.14705815
Monoisotopic Mass339.14705815
Topological Polar Surface Area40.2 Ų
Heavy Atom Count25
Formal Charge0
Complexity488
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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