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Dihydrosanguinarine

CAS No.:
3606-45-9
Catalog Number:
AG00BZCD
Molecular Formula:
C20H15NO4
Molecular Weight:
333.3374
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
99%
1 week
United States
$432
- +
10mg
99%
1 week
United States
$737
- +
Product Description
Catalog Number:
AG00BZCD
Chemical Name:
Dihydrosanguinarine
CAS Number:
3606-45-9
Molecular Formula:
C20H15NO4
Molecular Weight:
333.3374
MDL Number:
MFCD00872066
IUPAC Name:
24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(13),2,4(8),9,11,14(22),15,17(21)-octaene
InChI:
InChI=1S/C20H15NO4/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21/h2-7H,8-10H2,1H3
InChI Key:
CIUHLXZTZWTVFL-UHFFFAOYSA-N
SMILES:
CN1Cc2c3OCOc3ccc2c2c1c1cc3OCOc3cc1cc2
UNII:
3H1ZKG80F7
Properties
Complexity:
530  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
333.1g/mol
Formal Charge:
0
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
333.343g/mol
Monoisotopic Mass:
333.1g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
40.2A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
4.1  
Literature
Title Journal
NQO1 involves in the imine bond reduction of sanguinarine and recombinant adeno-associated virus mediated NQO1 overexpression decreases sanguinarine-induced cytotoxicity in rat BRL cells. Toxicology letters 20140210
A new protoberberine alkaloid from Meconopsis simplicifolia (D. Don) Walpers with potent antimalarial activity against a multidrug resistant Plasmodium falciparum strain. Journal of ethnopharmacology 20131212
Anti-inflammatory effects of Hylomecon hylomeconoides in RAW 264.7 cells. European review for medical and pharmacological sciences 20120701
Antiparasitic efficacy of dihydrosanguinarine and dihydrochelerythrine from Macleaya microcarpa against Ichthyophthirius multifiliis in richadsin (Squaliobarbus curriculus). Veterinary parasitology 20111229
Alkaloids from Papaver coreanum. Natural product communications 20111101
Potent family-18 chitinase inhibitors: x-ray structures, affinities, and binding mechanisms. The Journal of biological chemistry 20110708
Inhibitory activity of dihydrosanguinarine and dihydrochelerythrine against phytopathogenic fungi. Natural product research 20110701
Phytochemical and antimicrobial characterization of Macleaya cordata herb. Fitoterapia 20101201
Fluorescence of sanguinarine: spectral changes on interaction with amino acids. Physical chemistry chemical physics : PCCP 20101007
In vitro leishmanicidal activity of benzophenanthridine alkaloids from Bocconia pearcei and related compounds. Chemical & pharmaceutical bulletin 20100801
Interaction of sanguinarine and its dihydroderivative with the Na+/K+-ATPase. Complex view on the old problem. Toxicology letters 20100616
Antibacterial activity of Hylomecon hylomeconoides against methicillin-resistant Staphylococcus aureus. Applied biochemistry and biotechnology 20100401
Integration of deep transcriptome and proteome analyses reveals the components of alkaloid metabolism in opium poppy cell cultures. BMC plant biology 20100101
Antifungal activity of the benzo[c]phenanthridine alkaloids from Chelidonium majus Linn against resistant clinical yeast isolates. Journal of ethnopharmacology 20090925
Fluorescence of sanguinarine: fundamental characteristics and analysis of interconversion between various forms. Analytical and bioanalytical chemistry 20090901
[Alkaloids from Macleaya cordata]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090701
Cytotoxic activity of sanguinarine and dihydrosanguinarine in human promyelocytic leukemia HL-60 cells. Toxicology in vitro : an international journal published in association with BIBRA 20090601
Analysis of alkaloids in Macleaya cordata (Willd.) R. Br. using high-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry. Journal of chromatography. A 20090313
The toxicity and pharmacokinetics of dihydrosanguinarine in rat: a pilot study. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20080701
Synergistic effects of sequential treatment with methyl jasmonate, salicylic acid and yeast extract on benzophenanthridine alkaloid accumulation and protein expression in Eschscholtzia californica suspension cultures. Journal of biotechnology 20080520
Differential induction of protein expression and benzophenanthridine alkaloid accumulation in Eschscholtzia californica suspension cultures by methyl jasmonate and yeast extract. Journal of microbiology and biotechnology 20080201
Quantitative 1H NMR metabolomics reveals extensive metabolic reprogramming of primary and secondary metabolism in elicitor-treated opium poppy cell cultures. BMC plant biology 20080101
[Alkaloid constituents of Corydalis adunca]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20071101
Disposition of sanguinarine in the rat. Xenobiotica; the fate of foreign compounds in biological systems 20070501
Gene transcript and metabolite profiling of elicitor-induced opium poppy cell cultures reveals the coordinate regulation of primary and secondary metabolism. Planta 20070401
Metabolism of sanguinarine: the facts and the myths. Current drug metabolism 20070201
Sanguinarine reductase, a key enzyme of benzophenanthridine detoxification. Plant, cell & environment 20060201
A liquid chromatographic-mass spectrometric evidence of dihydrosanguinarine as a first metabolite of sanguinarine transformation in rat. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20060102
[Studies on the alkaloids from the herb of Corydalis adunca]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20050201
Identification and quantification of isoquinoline alkaloids in the genus Sarcocapnos by GC-MS. Phytochemical analysis : PCA 20050101
Achiral and chiral determination of benzophenanthridine alkaloids from methanol extracts of Hylomecon species by high performance liquid chromatography. Archives of pharmacal research 20030201
Argemone oil induced cellular damage in the reproductive tissues of transgenic Drosophila melanogaster: protective role of 70 kDa heat shock protein. Journal of biochemical and molecular toxicology 20030101
Identification of benzophenanthridine alkaloids from Bocconia arborea by gas chromatography-mass spectrometry. Phytochemical analysis : PCA 20020101
Direct determination of alkaloid contents in Fumaria species by GC-MS. Phytochemical analysis : PCA 20020101
Two antimicrobial alkaloids from Bocconia arborea. Journal of ethnopharmacology 19990801
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