2182-14-1 | Aspidospermidine-3-carboxylic acid,4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-, methylester, (2b,3b,4b,5a,12R,19a)-

Packsize	Purity	Availability	Price	Discounted Price
5mg	98%	in stock	$48.00	$34.00
20mg	98%	in stock	$58.00	$40.00
250mg	98%	in stock	$136.00	$95.00
1g	98%	in stock	$268.00	$187.00

Description

• Catalog Number: AI45094
• Chemical Name: Aspidospermidine-3-carboxylic acid,4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-, methylester, (2b,3b,4b,5a,12R,19a)-
• CAS Number: 2182-14-1
• Molecular Formula: C25H32N2O5
• Molecular Weight: 440.532
• MDL Number: MFCD27991347
• SMILES: COc1ccc2c(c1)N(C)[C@@H]1[C@@]32CCN2[C@H]3[C@]([C@H]([C@]1(O)C(=O)OC)C(=O)C)(CC)C=CC2
• NSC Number: 91994

Computed Properties

• Complexity: 864
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 6
• Heavy Atom Count: 33
• Hydrogen Bond Acceptor Count: 8
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 6
• XLogP3: 1.3

Literature

• Completion of the seven-step pathway from tabersonine to the anticancer drug precursor vindoline and its assembly in yeast.

  Proceedings of the National Academy of Sciences of the United States of America 20150512

• Increased availability of tryptophan in 5-methyltryptophan-tolerant shoots of Catharanthus roseus and their postharvest in vivo elicitation induces enhanced vindoline production.

  Applied biochemistry and biotechnology 20121001

• Negative-pressure cavitation extraction of four main vinca alkaloids from Catharanthus roseus leaves.

  Molecules (Basel, Switzerland) 20120725

• Modifications on the basic skeletons of vinblastine and vincristine.

  Molecules (Basel, Switzerland) 20120518

• The effect of vindoline C-16 substituents on the biomimetic coupling reaction: synthesis and cytotoxicity evaluation of the corresponding vinorelbine analogues.

  Bioorganic & medicinal chemistry letters 20120515

• [Effects of water stress and nitrogen nutrition on regulation of Catharanthus roseus alkaloids metabolism].

  Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20120501

• A virus-induced gene silencing approach to understanding alkaloid metabolism in Catharanthus roseus.

  Phytochemistry 20111101

• Simultaneous determination of vinblastine and its monomeric precursors vindoline and catharanthine in Catharanthus roseus by capillary electrophoresis-mass spectrometry.

  Journal of separation science 20111001

• A stereoselective hydroxylation step of alkaloid biosynthesis by a unique cytochrome P450 in Catharanthus roseus.

  The Journal of biological chemistry 20110513

• Spatial organization of the vindoline biosynthetic pathway in Catharanthus roseus.

  Journal of plant physiology 20110415

• Molecular docking and pharmacogenomics of vinca alkaloids and their monomeric precursors, vindoline and catharanthine.

  Biochemical pharmacology 20110315

• Synthesis and study of a molecularly imprinted polymer for the specific extraction of indole alkaloids from Catharanthus roseus extracts.

  Analytica chimica acta 20110110

• Enhancement of vindoline production in suspension culture of the Catharanthus roseus cell line C20hi by light and methyl jasmonate elicitation.

  Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20110101

• [Distribution and accumulation of vindoline, catharanthine and vinblastine in Catharanthus roseus cultivated in China].

  Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20101201

• Catharanthine C16 substituent effects on the biomimetic coupling with vindoline: preparation and evaluation of a key series of vinblastine analogues.

  Bioorganic & medicinal chemistry letters 20101115

• Asymmetric total synthesis of vindorosine, vindoline, and key vinblastine analogues.

  Journal of the American Chemical Society 20100929

• [The characterization on the site of vindoline binding to human serum albumin].

  Yao xue xue bao = Acta pharmaceutica Sinica 20100501

• [Monomeric indole alkaloids from the aerial parts of Catharanthus roseus].

  Yao xue xue bao = Acta pharmaceutica Sinica 20100401

• Asymmetric total synthesis of vindoline.

  Journal of the American Chemical Society 20100324

• Elaboration of simplified vinca alkaloids and phomopsin hybrids.

  Chemical biology & drug design 20100301

• Total synthesis of vinblastine, vincristine, related natural products, and key structural analogues.

  Journal of the American Chemical Society 20090408

• [Effects of NaCl on the growth and alkaloid content of Catharanthus roseus seedlings].

  Ying yong sheng tai xue bao = The journal of applied ecology 20081001

• Vindoline formation in shoot cultures of Catharanthus roseus is synchronously activated with morphogenesis through the last biosynthetic step.

  Annals of botany 20080901

• John Bryant takes a closer look at some of this month's Original Articles.

  Annals of botany 20080901

• Inhibitors of tubulin polymerization: synthesis and biological evaluation of hybrids of vindoline, anhydrovinblastine and vinorelbine with thiocolchicine, podophyllotoxin and baccatin III.

  Bioorganic & medicinal chemistry 20080601

• The leaf epidermome of Catharanthus roseus reveals its biochemical specialization.

  The Plant cell 20080301

• Direct coupling of catharanthine and vindoline to provide vinblastine: total synthesis of (+)- and ent-(-)-vinblastine.

  Journal of the American Chemical Society 20080116

• Optimisation of supercritical fluid extraction of indole alkaloids from Catharanthus roseus using experimental design methodology--comparison with other extraction techniques.

  Phytochemical analysis : PCA 20080101

• Application of carborundum abrasion for investigating the leaf epidermis: molecular cloning of Catharanthus roseus 16-hydroxytabersonine-16-O-methyltransferase.

  The Plant journal : for cell and molecular biology 20080101

• A simplified procedure for indole alkaloid extraction from Catharanthus roseus combined with a semi-synthetic production process for vinblastine.

  Molecules (Basel, Switzerland) 20070705

• [Simultaneous determination of vindoline, catharanthine and anhydrovinblastine in Catharanthus roseus by high performance liquid chromatography].

  Se pu = Chinese journal of chromatography 20070701

• The Suzuki-Miyaura reaction in the chemical transformations of vindoline.

  Acta biochimica Polonica 20070101

• Synthesis of C-15 vindoline analogues by palladium-catalyzed cross-coupling reactions.

  The Journal of organic chemistry 20060929

• Total synthesis of (-)- and ent-(+)-vindoline and related alkaloids.

  Journal of the American Chemical Society 20060816

• Identification of a low vindoline accumulating cultivar of Catharanthus roseus (L.) G. Don by alkaloid and enzymatic profiling.

  Phytochemistry 20060801

• Localization of tabersonine 16-hydroxylase and 16-OH tabersonine-16-O-methyltransferase to leaf epidermal cells defines them as a major site of precursor biosynthesis in the vindoline pathway in Catharanthus roseus.

  The Plant journal : for cell and molecular biology 20051101

• Simultaneous determination of vincristine, vinblastine, catharanthine, and vindoline in leaves of catharanthus roseus by high-performance liquid chromatography.

  Journal of chromatographic science 20051001

• Total synthesis of (-)- and ent-(+)-vindoline.

  Organic letters 20050929

• Intramolecular [3 + 2]-cycloaddition reaction of push-pull dipoles across heteroaromatic pi-systems.

  Organic letters 20040916

• Vindoline and 16-demethoxyvindoline: two catharanthus-derived alkaloids.

  Acta crystallographica. Section C, Crystal structure communications 20040501

• Vindoline synthesis in in vitro shoot cultures of Catharanthus roseus.

  Biotechnology letters 20040401

• Catharanthus roseus L. plants and explants infected with phytoplasmas: alkaloid production and structural observations.

  Protoplasma 20040301

• Alkaloid metabolism in wounded Catharanthus roseus seedlings.

  Plant physiology and biochemistry : PPB 20040101

• Novel bisindole derivatives of Catharanthus alkaloids with potential cytotoxic properties.

  Advances in experimental medicine and biology 20030101

• Vindoline biosynthesis is transcriptionally blocked in Catharanthus roseus cell suspension cultures.

  Molecular biotechnology 20020901

• Indole synthesis by radical cyclization of o-alkenylphenyl isocyanides and its application to the total synthesis of natural products.

  Chemical record (New York, N.Y.) 20020101

• Syntheses of 5a'-homo-vinblastine and congeners designed to establish structural determinants for isolation of atropisomers.

  The Journal of organic chemistry 20010810