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6907-59-1 | 1-Benzylisoquinoline
CAS No: 6907-59-1 Catalog No: AG00FEI0 MDL No:
Product Description
Catalog Number:
AG00FEI0
Chemical Name:
1-Benzylisoquinoline
CAS Number:
6907-59-1
IUPAC Name:
1-benzylisoquinoline
InChI:
InChI=1S/C16H13N/c1-2-6-13(7-3-1)12-16-15-9-5-4-8-14(15)10-11-17-16/h1-11H,12H2
InChI Key:
IZTUINVRJSCOIR-UHFFFAOYSA-N
Properties
Complexity:
232
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
219.105g/mol
Formal Charge:
0
Heavy Atom Count:
17
Hydrogen Bond Acceptor Count:
1
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
219.287g/mol
Monoisotopic Mass:
219.105g/mol
Rotatable Bond Count:
2
Topological Polar Surface Area:
12.9A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
4.1
Literature
| Title | Journal |
|---|---|
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| Berberine inhibits human colon cancer cell migration via AMP-activated protein kinase-mediated downregulation of integrin β1 signaling. | Biochemical and biophysical research communications 20121005 |
| 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 |
| Biodegradation of drotaverine hydrochloride by free and immobilized cells of Rhodococcus rhodochrous IEGM 608. | World journal of microbiology & biotechnology 20121001 |
| Vasorelaxant effect of isoquinoline derivatives from two species of Popowia perakensis and Phaeanthus crassipetalus on rat aortic artery. | Journal of natural medicines 20120701 |
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| Characterization of three O-methyltransferases involved in noscapine biosynthesis in opium poppy. | Plant physiology 20120601 |
| Transcript and metabolite profiling in cell cultures of 18 plant species that produce benzylisoquinoline alkaloids. | Phytochemistry 20120501 |
| Molecular characterization, recombinant expression in Escherichia coli and biological activity of (S)-Tetrahydroberberine oxidase from Corydalis saxicola Bunt. | Molecular biology reports 20120301 |
| Bench-top fermentative production of plant benzylisoquinoline alkaloids using a bacterial platform. | Bioengineered bugs 20120101 |
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| Sensitivity to rocuronium-induced neuromuscular block and reversibility with sugammadex in a patient with myotonic dystrophy. | Case reports in anesthesiology 20120101 |
| Improvement of benzylisoquinoline alkaloid productivity by overexpression of 3'-hydroxy-N-methylcoclaurine 4'-O-methyltransferase in transgenic Coptis japonica plants. | Biological & pharmaceutical bulletin 20120101 |
| Biochemical genomics for gene discovery in benzylisoquinoline alkaloid biosynthesis in opium poppy and related species. | Methods in enzymology 20120101 |
| Novel carbon-carbon bond formations for biocatalysis. | Current opinion in biotechnology 20111201 |
| A case of anaphylactic shock attributed to latex allergy during gastric cancer surgery. | Journal of the Korean Surgical Society 20111201 |
| Benzylisoquinoline alkaloids from the papaveraceae: the heritage of Johannes Gadamer (1867-1928). | Journal of natural products 20111128 |
| Tyrosine aminotransferase contributes to benzylisoquinoline alkaloid biosynthesis in opium poppy. | Plant physiology 20111101 |
| Determination of noscapine's localization and interaction with the tubulin-α/β heterodimer. | Chemical biology & drug design 20111001 |
| [Screen for natural benzylisoquinoline alkaloids against tumor]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20111001 |
| Biocatalytic organic synthesis of optically pure (S)-scoulerine and berbine and benzylisoquinoline alkaloids. | The Journal of organic chemistry 20110819 |
| A bacterial platform for fermentative production of plant alkaloids. | Nature communications 20110501 |
| An (R)-specific N-methyltransferase involved in human morphine biosynthesis. | Archives of biochemistry and biophysics 20110201 |
| Cytotoxic effects of bangladeshi medicinal plant extracts. | Evidence-based complementary and alternative medicine : eCAM 20110101 |
| A synthetic library of RNA control modules for predictable tuning of gene expression in yeast. | Molecular systems biology 20110101 |
| Antitumor activity of Noscapine in combination with Doxorubicin in triple negative breast cancer. | PloS one 20110101 |
| Statistics-based model for prediction of chemical biosynthesis yield from Saccharomyces cerevisiae. | Microbial cell factories 20110101 |
| A retrosynthetic biology approach to metabolic pathway design for therapeutic production. | BMC systems biology 20110101 |
| Pronounced hypoxia in models of murine and human leukemia: high efficacy of hypoxia-activated prodrug PR-104. | PloS one 20110101 |
| Genome-wide analysis of WRKY gene family in Cucumis sativus. | BMC genomics 20110101 |
| Phytochemical investigation and diuretic activity of Cyclea peltata leaf extracts. | Journal of advanced pharmaceutical technology & research 20110101 |
| Development and validation of simultaneous spectrophotometric methods for drotaverine hydrochloride and aceclofenac from tablet dosage form. | Indian journal of pharmaceutical sciences 20110101 |
| Triterpenoid biosynthesis and engineering in plants. | Frontiers in plant science 20110101 |
| An Internet misadventure: bloodroot salve toxicity. | Journal of alternative and complementary medicine (New York, N.Y.) 20101001 |
| Norcoclaurine synthase is a member of the pathogenesis-related 10/Bet v1 protein family. | The Plant cell 20101001 |
| 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 |
| Catechol-O-methyltransferase: potential relationship to idiopathic hypertension. | Archives of medical science : AMS 20100630 |
| Metabolic diversification of benzylisoquinoline alkaloid biosynthesis through the introduction of a branch pathway in Eschscholzia californica. | Plant & cell physiology 20100601 |
| Noscapine, a benzylisoquinoline alkaloid, sensitizes leukemic cells to chemotherapeutic agents and cytokines by modulating the NF-kappaB signaling pathway. | Cancer research 20100415 |
| (6,7-Dimethoxy-4-methylisoquinolinyl)-(4'-methoxyphenyl)-methanone, a new benzylisoquinoline alkaloid from Beilschmiedia brevipes. | Molecules (Basel, Switzerland) 20100331 |
| Norcoclaurine synthase: mechanism of an enantioselective pictet-spengler catalyzing enzyme. | Molecules (Basel, Switzerland) 20100324 |
| Three new O-methyltransferases are sufficient for all O-methylation reactions of ipecac alkaloid biosynthesis in root culture of Psychotria ipecacuanha. | The Journal of biological chemistry 20100305 |
| A new benzylisoquinoline alkaloid from Argemone mexicana. | Natural product research 20100101 |
| Toward engineering synthetic microbial metabolism. | Journal of biomedicine & biotechnology 20100101 |
| BIAdb: a curated database of benzylisoquinoline alkaloids. | BMC pharmacology 20100101 |
| Engineering cofactor preference of ketone reducing biocatalysts: A mutagenesis study on a γ-diketone reductase from the yeast Saccharomyces cerevisiae serving as an example. | International journal of molecular sciences 20100101 |
| Prediction of cytochrome P450 isoform responsible for metabolizing a drug molecule. | BMC pharmacology 20100101 |
| Rhizoma Coptidis inhibits LPS-induced MCP-1/CCL2 production in murine macrophages via an AP-1 and NFkappaB-dependent pathway. | Mediators of inflammation 20100101 |
| Lotus leaf extract and L-carnitine influence different processes during the adipocyte life cycle. | Nutrition & metabolism 20100101 |
| Virus-induced gene silencing as a tool for comparative functional studies in Thalictrum. | PloS one 20100101 |
| Effect of nitrous oxide on cisatracurium infusion demands: a randomized controlled trial. | BMC anesthesiology 20100101 |
| A transcriptomic approach highlights induction of secondary metabolism in citrus fruit in response to Penicillium digitatum infection. | BMC plant biology 20100101 |
| Comparative transcriptomics among floral organs of the basal eudicot Eschscholzia californica as reference for floral evolutionary developmental studies. | Genome biology 20100101 |
| Biology by design: from top to bottom and back. | Journal of biomedicine & biotechnology 20100101 |
| Optimizing pentose utilization in yeast: the need for novel tools and approaches. | Biotechnology for biofuels 20100101 |
| Integration of deep transcriptome and proteome analyses reveals the components of alkaloid metabolism in opium poppy cell cultures. | BMC plant biology 20100101 |
| Recent N-atom containing compounds from indo-pacific invertebrates. | Marine drugs 20100101 |
| Sertraline-induced pseudocholinesterase enzyme deficiency. | International journal of general medicine 20100101 |
| Cisatracurium in different doses versus atracurium during general anesthesia for abdominal surgery. | Saudi journal of anaesthesia 20100101 |
| Biochemistry and occurrence of o-demethylation in plant metabolism. | Frontiers in physiology 20100101 |
| Medicinally important secondary metabolites in recombinant microorganisms or plants: progress in alkaloid biosynthesis. | Biotechnology journal 20091201 |
| Targeted metabolite and transcript profiling for elucidating enzyme function: isolation of novel N-methyltransferases from three benzylisoquinoline alkaloid-producing species. | The Plant journal : for cell and molecular biology 20091101 |
| Simultaneous characterization of quaternary alkaloids, 8-oxoprotoberberine alkaloids, and a steroid compound in Coscinium fenestratum by liquid chromatography hybrid ion trap time-of-flight mass spectrometry. | Journal of pharmaceutical and biomedical analysis 20091015 |
| Functional characterization of a novel benzylisoquinoline O-methyltransferase suggests its involvement in papaverine biosynthesis in opium poppy (Papaver somniferum L). | The Plant journal : for cell and molecular biology 20091001 |
| Quaternary alkaloid, pseudocoptisine isolated from tubers of Corydalis turtschaninovi inhibits LPS-induced nitric oxide, PGE(2), and pro-inflammatory cytokines production via the down-regulation of NF-kappaB in RAW 264.7 murine macrophage cells. | International immunopharmacology 20091001 |
| Antimalarial benzylisoquinoline alkaloid from the rainforest tree Doryphora sassafras. | Journal of natural products 20090801 |
| Clinical implications of sugammadex. | Anaesthesia 20090301 |
| Structural basis of enzymatic (S)-norcoclaurine biosynthesis. | The Journal of biological chemistry 20090109 |
| Plant defense responses in opium poppy cell cultures revealed by liquid chromatography-tandem mass spectrometry proteomics. | Molecular & cellular proteomics : MCP 20090101 |
| Metabolic engineering of microorganisms: general strategies and drug production. | Drug discovery today 20090101 |
| The effect of mimicking febrile temperature and drug stress on malarial development. | Annals of clinical microbiology and antimicrobials 20090101 |
| Exploring transcriptional signalling mediated by OsWRKY13, a potential regulator of multiple physiological processes in rice. | BMC plant biology 20090101 |
| An overview on benzylisoquinoline derivatives with dopaminergic and serotonergic activities. | Current medicinal chemistry 20090101 |
| Yeast artificial chromosomes employed for random assembly of biosynthetic pathways and production of diverse compounds in Saccharomyces cerevisiae. | Microbial cell factories 20090101 |
| Significant differences in alkaloid content of Coptis chinensis (Huanglian), from its related American species. | Chinese medicine 20090101 |
| Pseudocholinesterase enzyme deficiency: a case series and review of the literature. | Cases journal 20090101 |
| Purification, crystallization and X-ray diffraction analysis of pavine N-methyltransferase from Thalictrum flavum. | Acta crystallographica. Section F, Structural biology and crystallization communications 20081101 |
| Production of benzylisoquinoline alkaloids in Saccharomyces cerevisiae. | Nature chemical biology 20080901 |
| Quantitative 1H nuclear magnetic resonance metabolite profiling as a functional genomics platform to investigate alkaloid biosynthesis in opium poppy. | Plant physiology 20080801 |
| Conformation, catalytic site, and enzymatic mechanism of the PR10 allergen-related enzyme norcoclaurine synthase. | The Biochemical journal 20080715 |
| Opium poppy and Madagascar periwinkle: model non-model systems to investigate alkaloid biosynthesis in plants. | The Plant journal : for cell and molecular biology 20080501 |
| Cloning, expression, crystallization and preliminary X-ray data analysis of norcoclaurine synthase from Thalictrum flavum. | Acta crystallographica. Section F, Structural biology and crystallization communications 20080401 |
| Evolutionary and cellular webs in benzylisoquinoline alkaloid biosynthesis. | Current opinion in biotechnology 20080401 |
| Galactinol synthase gene of Coptis japonica is involved in berberine tolerance. | Bioscience, biotechnology, and biochemistry 20080201 |
| Anti-amnestic activity of pseudocoptisine from Corydalis Tuber. | Biological & pharmaceutical bulletin 20080101 |
| Quantitative 1H NMR metabolomics reveals extensive metabolic reprogramming of primary and secondary metabolism in elicitor-treated opium poppy cell cultures. | BMC plant biology 20080101 |
| Berberine induced down-regulation of matrix metalloproteinase-1, -2 and -9 in human gastric cancer cells (SNU-5) in vitro. | In vivo (Athens, Greece) 20080101 |
| Expression of Brugmansia candida Hyoscyamine 6beta-Hydroxylase gene in Saccharomyces cerevisiae and its potential use as biocatalyst. | Microbial cell factories 20080101 |
| Chemistry and bioactivity of Flos Magnoliae, a Chinese herb for rhinitis and sinusitis. | Current medicinal chemistry 20080101 |
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| Persistence of evolutionary memory: primordial six-transmembrane helical domain mu opiate receptors selectively linked to endogenous morphine signaling. | Medical science monitor : international medical journal of experimental and clinical research 20071201 |
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| Molecular cloning and characterization of tetrahydroprotoberberine cis-N-methyltransferase, an enzyme involved in alkaloid biosynthesis in opium poppy. | The Journal of biological chemistry 20070518 |
| Infusions of rocuronium and cisatracurium exert different effects on rat diaphragm function. | Intensive care medicine 20070501 |
| Molecular modeling and site-directed mutagenesis reveal the benzylisoquinoline binding site of the short-chain dehydrogenase/reductase salutaridine reductase. | Plant physiology 20070401 |
| [Characterization of polyphenoloxidase from the latex of greater celandine (Chelidonium majus L.)]. | Ceska a Slovenska farmacie : casopis Ceske farmaceuticke spolecnosti a Slovenske farmaceuticke spolecnosti 20070401 |
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| Overexpression of Coptis japonica norcoclaurine 6-O-methyltransferase overcomes the rate-limiting step in Benzylisoquinoline alkaloid biosynthesis in cultured Eschscholzia californica. | Plant & cell physiology 20070201 |
| Poppy alkaloid profiling by electrospray tandem mass spectrometry and electrospray FT-ICR mass spectrometry after [ring-13C6]-tyramine feeding. | Phytochemistry 20070101 |
| Identification of a WRKY protein as a transcriptional regulator of benzylisoquinoline alkaloid biosynthesis in Coptis japonica. | Plant & cell physiology 20070101 |
| Antiviral and antimicrobial profiles of selected isoquinoline alkaloids from Fumaria and Corydalis species. | Zeitschrift fur Naturforschung. C, Journal of biosciences 20070101 |
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| [Preliminary pharmaphylogenetic study on Ranunculaceae]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20060701 |
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| 1H and 13C NMR signal assignment of benzylisoquinoline alkaloids from Fumaria officinalis L. (Papaveraceae). | Magnetic resonance in chemistry : MRC 20041001 |
| Molecular cloning and characterization of norcoclaurine synthase, an enzyme catalyzing the first committed step in benzylisoquinoline alkaloid biosynthesis. | The Plant journal : for cell and molecular biology 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 |
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| Thalictrum minus cell cultures and ABC-like transporter. | Phytochemistry 20030201 |
| Cytotoxic benzophenanthridine and benzylisoquinoline alkaloids from Argemone mexicana. | Zeitschrift fur Naturforschung. C, Journal of biosciences 20030101 |
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| Characterization of berberine transport into Coptis japonica cells and the involvement of ABC protein. | Journal of experimental botany 20020901 |
| Cytotoxic constituents of the stem bark of Neolitsea acuminatissima. | Journal of natural products 20020301 |
| A benzylisoquinoline alkaloid from Doryphora sassafras. | Journal of natural products 20011201 |
| Simple isoquinoline and benzylisoquinoline alkaloids as potential antimicrobial, antimalarial, cytotoxic, and anti-HIV agents. | Bioorganic & medicinal chemistry 20011101 |
| Berberine bridge enzyme, a key branch-point enzyme in benzylisoquinoline alkaloid biosynthesis, contains a vacuolar sorting determinant. | Planta 20011001 |
| Isolation and partial characterization of norcoclaurine synthase, the first committed step in benzylisoquinoline alkaloid biosynthesis, from opium poppy. | Planta 20011001 |
| Inhibitory effects of ethaverine, a homologue of papaverine, on monoamine oxidase activity in mouse brain. | Biological & pharmaceutical bulletin 20010701 |
| Chemical ecological characteristics of herbivory of Siparuna guianensis seeds by buffy-headed marmosets (Callithrix flaviceps) in the Atlantic Forest of southeastern Brazil. | Journal of chemical ecology 20010101 |
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