200,000+ products from a single source!

sales@angenechem.com

Home > Quinoline > 485-19-8

485-19-8

485-19-8 | (S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-ol

CAS No: 485-19-8 Catalog No: AG00DBDY MDL No:MFCD01716982

Product Description

Catalog Number:
AG00DBDY
Chemical Name:
(S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-ol
CAS Number:
485-19-8
MDL Number:
MFCD01716982
IUPAC Name:
(1S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol
InChI:
InChI=1S/C19H23NO4/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12/h4-5,9-11,15,21-22H,6-8H2,1-3H3/t15-/m0/s1
InChI Key:
BHLYRWXGMIUIHG-HNNXBMFYSA-N
EC Number:
207-611-3
UNII:
X35Z551WT4

Properties

Complexity:
407  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
0
Exact Mass:
329.163g/mol
Formal Charge:
0
Heavy Atom Count:
24  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
329.396g/mol
Monoisotopic Mass:
329.163g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
62.2A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3  

Literature

Title Journal
Structural and Functional Studies of Pavine N-Methyltransferase from Thalictrum flavum Reveal Novel Insights into Substrate Recognition and Catalytic Mechanism. The Journal of biological chemistry 20161104
Systematic silencing of benzylisoquinoline alkaloid biosynthetic genes reveals the major route to papaverine in opium poppy. The Plant journal : for cell and molecular biology 20121001
Isotope effects suggest a stepwise mechanism for berberine bridge enzyme. Biochemistry 20120918
Rat CYP2D2, not 2D1, is functionally conserved with human CYP2D6 in endogenous morphine formation. FEBS letters 20120621
Characterization of three O-methyltransferases involved in noscapine biosynthesis in opium poppy. Plant physiology 20120601
On the biosynthetic pathway of papaverine via (S)-reticuline theoretical vs. experimental study. Natural product communications 20120501
Systematic knockdown of morphine pathway enzymes in opium poppy using virus-induced gene silencing. The Plant journal : for cell and molecular biology 20120301
The sequential exposure to jasmonate, salicylic acid and yeast extract promotes sanguinarine accumulation in Argemone mexicana cell cultures. Biotechnology letters 20120201
The good, the bad and the twisted: a survey of ligand geometry in protein crystal structures. Journal of computer-aided molecular design 20120201
Biocatalytic organic synthesis of optically pure (S)-scoulerine and berbine and benzylisoquinoline alkaloids. The Journal of organic chemistry 20110819
Gender differences in the morphometric properties of muscle fibres and the innervation ratio of motor units in rat medial gastrocnemius muscle. Anatomia, histologia, embryologia 20110801
A bacterial platform for fermentative production of plant alkaloids. Nature communications 20110501
Lancifoliaine, a new bisbenzylisoquinoline from the bark of Litsea lancifolia. Molecules (Basel, Switzerland) 20110413
[Studies on anti-tumor metastatic constituents from Lindera glauca]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20110401
Characterization of two methylenedioxy bridge-forming cytochrome P450-dependent enzymes of alkaloid formation in the Mexican prickly poppy Argemone mexicana. Archives of biochemistry and biophysics 20110301
Celiac disease in type-I diabetes mellitus: coexisting phenomenon. Journal of research in medical sciences : the official journal of Isfahan University of Medical Sciences 20110301
Biocatalytic enantioselective oxidative C-C coupling by aerobic C-H activation. Angewandte Chemie (International ed. in English) 20110201
Squamocin modulates histone H3 phosphorylation levels and induces G1 phase arrest and apoptosis in cancer cells. BMC cancer 20110101
The prognostic value of p53 mutation in pediatric marrow hypoplasia. Diagnostic pathology 20110101
Evaluation of Behavioral and Pharmacological Effects of Hydroalcoholic Extract of Valeriana prionophylla Standl. from Guatemala. Evidence-based complementary and alternative medicine : eCAM 20110101
The draft genome and transcriptome of Cannabis sativa. Genome biology 20110101
The biosynthesis of papaverine proceeds via (S)-reticuline. Phytochemistry 20100801
Benzylisoquinoline alkaloids from the tubers of Corydalis ternata and their cytotoxicity. Bioorganic & medicinal chemistry letters 20100801
Molecular characterization of O-methyltransferases involved in isoquinoline alkaloid biosynthesis in Coptis japonica. Proceedings of the Japan Academy. Series B, Physical and biological sciences 20100721
Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Eschscholzia californica (Papaveraceae). Natural product communications 20100701
Chronic alcohol exposure increases ganglia endogenous morphine levels. Archives of medical science : AMS 20100630
Dioxygenases catalyze the O-demethylation steps of morphine biosynthesis in opium poppy. Nature chemical biology 20100401
Endogenous morphine levels are increased in sepsis: a partial implication of neutrophils. PloS one 20100101
Alkaloids from the genus Duguetia. The Alkaloids. Chemistry and biology 20100101
A transcriptomic approach highlights induction of secondary metabolism in citrus fruit in response to Penicillium digitatum infection. BMC plant biology 20100101
Integration of deep transcriptome and proteome analyses reveals the components of alkaloid metabolism in opium poppy cell cultures. BMC plant biology 20100101
Mammalian cytochrome P450 enzymes catalyze the phenol-coupling step in endogenous morphine biosynthesis. The Journal of biological chemistry 20090904
Structural and mechanistic studies reveal the functional role of bicovalent flavinylation in berberine bridge enzyme. The Journal of biological chemistry 20090724
Berberine bridge enzyme catalyzes the six electron oxidation of (S)-reticuline to dehydroscoulerine. Phytochemistry 20090601
[Simultaneous determination of four alkaloids in Lindera aggregate by high performance liquid chromatography]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090301
(S)-reticuline induces vasorelaxation through the blockade of L-type Ca(2+) channels. Naunyn-Schmiedeberg's archives of pharmacology 20090201
Alkaloids from Lindera aggregata. Natural product communications 20090101
Evolution of morphine biosynthesis in opium poppy. Phytochemistry 20090101
A concerted mechanism for berberine bridge enzyme. Nature chemical biology 20081201
Cyclization in concert. Nature chemical biology 20081201
Simultaneous determination of four alkaloids in Lindera aggregata by ultra-high-pressure liquid chromatography-tandem mass spectrometry. Journal of chromatography. A 20081128
[Five alkaloids from vine stems of Diploclisia affinis]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20081101
Production of benzylisoquinoline alkaloids in Saccharomyces cerevisiae. Nature chemical biology 20080901
Frequency of celiac disease is not increased among multiple sclerosis patients. Multiple sclerosis (Houndmills, Basingstoke, England) 20080601
Applicability of ultra-performance liquid chromatography-tandem mass spectrometry for heroin profiling. Journal of chromatography. A 20080425
Molecular cloning and characterization of CYP80G2, a cytochrome P450 that catalyzes an intramolecular C-C phenol coupling of (S)-reticuline in magnoflorine biosynthesis, from cultured Coptis japonica cells. The Journal of biological chemistry 20080404
Differentiation of opium and poppy straw using capillary electrophoresis and pattern recognition techniques. Analytica chimica acta 20071212
Enhanced benzophenanthridine alkaloid production and protein expression with combined elicitor in Eschscholtzia californica suspension cultures. Biotechnology letters 20071201
Biotransformation of phenolic 1-benzyl-N-methyltetrahydroisoquinolines in plant cell cultures followed by LC/NMR, LC/MS, and LC/CD. Journal of natural products 20071101
Two new alkaloids and active anti-hepatitis B virus constituents from Hypserpa nitida. Bioorganic & medicinal chemistry letters 20071001
Bioactive constituents of the roots of Polyalthia cerasoides. Journal of natural products 20070901
6-S-cysteinylation of bi-covalently attached FAD in berberine bridge enzyme tunes the redox potential for optimal activity. The Journal of biological chemistry 20070817
Metabolic engineering in isoquinoline alkaloid biosynthesis. Current pharmaceutical biotechnology 20070801
Knockdown of berberine bridge enzyme by RNAi accumulates (S)-reticuline and activates a silent pathway in cultured California poppy cells. Transgenic research 20070601
Gene expression profiles of O3-treated Arabidopsis plants. Plant, cell & environment 20060901
Biochemical evidence that berberine bridge enzyme belongs to a novel family of flavoproteins containing a bi-covalently attached FAD cofactor. The Journal of biological chemistry 20060728
Neutral heroin impurities from tetrahydrobenzylisoquinoline alkaloids. Journal of forensic sciences 20060301
Minor alkaloids from Guatteria dumetorum with antileishmanial activity. Planta medica 20060201
Synteny conservation between the Prunus genome and both the present and ancestral Arabidopsis genomes. BMC genomics 20060101
Contributions to the micro-anatomical evaluation of the ratio between the muscular tunic structures of the oesophagus. Biomechanical, anatomic and clinical implications. Romanian journal of morphology and embryology = Revue roumaine de morphologie et embryologie 20060101
Morpho-physiological aspects of rapports between bone and marrow bone. Romanian journal of morphology and embryology = Revue roumaine de morphologie et embryologie 20060101
Silencing nature's narcotics: metabolic engineering of the opium poppy. Trends in biotechnology 20050701
Sanguinarine biosynthesis is associated with the endoplasmic reticulum in cultured opium poppy cells after elicitor treatment. Plant physiology 20050501
In vivo and in vitro L-DOPA and reticuline exposure increases ganglionic morphine levels. Medical science monitor : international medical journal of experimental and clinical research 20050501
Mammalian morphine: de novo formation of morphine in human cells. Medical science monitor : international medical journal of experimental and clinical research 20050501
Analysis of benzylisoquinoline-type alkaloids by electrospray tandem mass spectrometry and atmospheric pressure photoionization. European journal of mass spectrometry (Chichester, England) 20050101
RNAi-mediated replacement of morphine with the nonnarcotic alkaloid reticuline in opium poppy. Nature biotechnology 20041201
Putting the opium in poppy to sleep. Nature biotechnology 20041201
Transformation of opium poppy (Papaver somniferum L.) with antisense berberine bridge enzyme gene (anti-bbe) via somatic embryogenesis results in an altered ratio of alkaloids in latex but not in roots. Transgenic research 20041201
Reticuline exposure to invertebrate ganglia increases endogenous morphine levels. Neuro endocrinology letters 20041001
Detection and determination of reticuline and N-methylcoculaurine in the Annonaceae family using liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20040625
The GC-MS detection and characterization of reticuline as a marker of opium use. Forensic science international 20040528
Cardiovascular effects induced by reticuline in normotensive rats. Planta medica 20040401
1,2-Dehydroreticuline synthase, the branch point enzyme opening the morphinan biosynthetic pathway. Phytochemistry 20040401
The GC-MS detection and characterization of reticuline as a marker of opium use. Forensic science international 20040310
Tobacco nectarin V is a flavin-containing berberine bridge enzyme-like protein with glucose oxidase activity. Plant physiology 20040101
(R,S)-Reticuline 7-O-methyltransferase and (R,S)-norcoclaurine 6-O-methyltransferase of Papaver somniferum - cDNA cloning and characterization of methyl transfer enzymes of alkaloid biosynthesis in opium poppy. The Plant journal : for cell and molecular biology 20031201
A tale of three cell types: alkaloid biosynthesis is localized to sieve elements in opium poppy. The Plant cell 20031101
Presence of reticuline in rat brain: a pathway for morphine biosynthesis. Brain research. Molecular brain research 20030910
Modulation of berberine bridge enzyme levels in transgenic root cultures of California poppy alters the accumulation of benzophenanthridine alkaloids. Plant molecular biology 20030101
Cytotoxic benzophenanthridine and benzylisoquinoline alkaloids from Argemone mexicana. Zeitschrift fur Naturforschung. C, Journal of biosciences 20030101
Immunocytological localization of two enzymes involved in berberine biosynthesis. Planta 20021101
Presence of isoquinoline alkaloids in molluscan ganglia. Neuro endocrinology letters 20020801
Antisense RNA-mediated suppression of benzophenanthridine alkaloid biosynthesis in transgenic cell cultures of California poppy. Plant physiology 20020201
Toxicity of Annonaceae for dopaminergic neurons: potential role in atypical parkinsonism in Guadeloupe. Movement disorders : official journal of the Movement Disorder Society 20020101
Berberine bridge enzyme, a key branch-point enzyme in benzylisoquinoline alkaloid biosynthesis, contains a vacuolar sorting determinant. Planta 20011001

Related Products

© 2019 Angene International Limited. All rights Reserved.