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Demethyleneberberine

CAT: 0804-HY-N0592-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N0592-01Size:5 mg
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Description
Demethyleneberberine is a natural mitochondria-targeted antioxidant. Demethyleneberberine alleviates mice colitis and inhibits the inflammatory responses by inhibiting NF-κB pathway and regulating the balance of Th cells. Demethyleneberberine could serve as a AMPK activator for treating non-alcoholic fatty liver disease (NAFLD) [1][2][3].
CAS Number
25459-91-0
UNSPSC
12352005
Target
AMPK; NF-κB
Type
Natural Products
Related Pathways
Epigenetics; NF-κB; PI3K/Akt/mTOR
Applications
COVID-19-immunoregulation
Field of Research
Cancer; Infection; Metabolic Disease; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/demethyleneberberine.html
Purity
98.0
Solubility
DMSO : 10 mg/mL (ultrasonic; adjust pH to 8 with NaOH)
Smiles
COC1=C(OC)C2=C[N+]3=C(C4=CC(O)=C(O)C=C4CC3)C=C2C=C1
Molecular Formula
C19H18NO4+
Molecular Weight
324.35
References & Citations
[1]Zhang P, et al. Demethyleneberberine, a natural mitochondria-targeted antioxidant, inhibits mitochondrial dysfunction, oxidative stress, and steatosis in alcoholic liver disease mouse model. J Pharmacol Exp Ther. 2015 Jan;352 (1) :139-47.|[2]Chen YY, et al. Demethyleneberberine alleviates inflammatory bowel disease in mice through regulating NF-κB signaling and T-helper cell homeostasis. Inflamm Res. 2017 Feb;66 (2) :187-196.|[3]Qiang X, et al. Demethyleneberberine attenuates non-alcoholic fatty liver disease with activation of AMPK and inhibition of oxidative stress. Biochem Biophys Res Commun. 2016 Apr 15;472 (4) :603-9.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Demethyleneberberine

Demethyleneberberine is a member of isoquinolines.

CAS Number25459-91-0
PubChem CID363209
IUPAC Name9,10-dimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-2,3-diol
Molecular FormulaC19H18NO4+
Molecular Weight324.3
XLogP3.1
Topological Polar Surface Area62.8
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Heavy Atom Count24
Formal Charge1
Complexity447
SMILES
COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)O)O)OC
InChI
InChI=1S/C19H17NO4/c1-23-18-4-3-11-7-15-13-9-17(22)16(21)8-12(13)5-6-20(15)10-14(11)19(18)24-2/h3-4,7-10,22H,5-6H2,1-2H3/p+1
InChIKey
HVTCKKMWZDDWOY-UHFFFAOYSA-O
Chemical Structure
2D Structure
2D structure of Demethyleneberberine
CAS: 25459-91-0
CID: 363209
Formula: C19H18NO4+
MW: 324.3
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight324.3
XLogP33.1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Exact Mass324.12358306
Monoisotopic Mass324.12358306
Topological Polar Surface Area62.8 Ų
Heavy Atom Count24
Formal Charge1
Complexity447
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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