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

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

CAS No.:
2182-14-1
Catalog Number:
AG00I48E
Molecular Formula:
C25H32N2O5
Molecular Weight:
440.5320
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
98%
In Stock USA
United States
$73
- +
10mg
98%
In Stock USA
United States
$122
- +
25mg
98%
In Stock USA
United States
$262
- +
50mg
98%
In Stock USA
United States
$450
- +
Product Description
Catalog Number:
AG00I48E
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:
440.5320
MDL Number:
MFCD27991347
IUPAC Name:
methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,13-tetraene-10-carboxylate
InChI:
InChI=1S/C25H32N2O6/c1-6-23-10-7-12-27-13-11-24(19(23)27)17-9-8-16(31-4)14-18(17)26(3)20(24)25(30,22(29)32-5)21(23)33-15(2)28/h7-10,14,19-21,30H,6,11-13H2,1-5H3/t19-,20+,21+,23+,24+,25-/m0/s1
InChI Key:
CXBGOBGJHGGWIE-ACSXSLCXSA-N
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
EC Number:
218-558-0
UNII:
571PJ1LW03
NSC Number:
91994
Properties
Complexity:
864  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
6  
Defined Bond Stereocenter Count:
0
Exact Mass:
456.226g/mol
Formal Charge:
0
Heavy Atom Count:
33  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
456.539g/mol
Monoisotopic Mass:
456.226g/mol
Rotatable Bond Count:
6  
Topological Polar Surface Area:
88.5A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.3  
Literature
Title Journal
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
Properties