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Narciclasine

CAS No.:
29477-83-6
Catalog Number:
AG002YIC
Molecular Formula:
C14H13NO7
Molecular Weight:
307.2555
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
99%
1 week
United States
$223
- +
5mg
99%
1 week
United States
$740
- +
10mg
99%
1 week
United States
$1190
- +
Product Description
Catalog Number:
AG002YIC
Chemical Name:
Narciclasine
CAS Number:
29477-83-6
Molecular Formula:
C14H13NO7
Molecular Weight:
307.2555
MDL Number:
MFCD01729949
IUPAC Name:
(2S,3R,4S,4aR)-2,3,4,7-tetrahydroxy-3,4,4a,5-tetrahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one
InChI:
InChI=1S/C14H13NO7/c16-6-1-5-4-2-7-13(22-3-21-7)11(18)8(4)14(20)15-9(5)12(19)10(6)17/h1-2,6,9-10,12,16-19H,3H2,(H,15,20)/t6-,9+,10+,12-/m0/s1
InChI Key:
LZAZURSABQIKGB-AEKGRLRDSA-N
SMILES:
O[C@H]1C=C2[C@H]([C@@H]([C@@H]1O)O)NC(=O)c1c2cc2OCOc2c1O
NSC Number:
266535
Properties
Complexity:
523  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
0
Exact Mass:
307.069g/mol
Formal Charge:
0
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
5  
Isotope Atom Count:
0
Molecular Weight:
307.258g/mol
Monoisotopic Mass:
307.069g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
129A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.2  
Literature
Title Journal
Simultaneous quantification of Amaryllidaceae alkaloids from Zephyranthes grandiflora by UPLC-DAD/ESI-MS/MS. Journal of pharmaceutical and biomedical analysis 20121201
Apoptosis-inducing effects of distichamine and narciprimine, rare alkaloids of the plant family Amaryllidaceae. Bioorganic & medicinal chemistry letters 20121001
Antineoplastic agents. 587. Isolation and structure of 3-epipancratistatin from Narcissus cv. Ice Follies. Journal of natural products 20120427
Oxidative stress and mitochondrial dysfunctions are early events in narciclasine-induced programmed cell death in tobacco Bright Yellow-2 cells. Physiologia plantarum 20120101
[Study on chemical constituents of the bulbs of Lycoris longituba]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20110901
Synthesis of C-1 homologues of pancratistatin and their preliminary biological evaluation. Bioorganic & medicinal chemistry letters 20110815
Alkaloid diversity in Galanthus elwesii and Galanthus nivalis. Chemistry & biodiversity 20110101
Concentration-dependent effects of narciclasine on cell cycle progression in Arabidopsis root tips. BMC plant biology 20110101
Targeting of eEF1A with Amaryllidaceae isocarbostyrils as a strategy to combat melanomas. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20101101
Investigations of fungal secondary metabolites with potential anticancer activity. Journal of natural products 20100528
Narciclasine, a plant growth modulator, activates Rho and stress fibers in glioblastoma cells. Molecular cancer therapeutics 20090701
Selective cytochrome P450 3A4 inhibitory activity of Amaryllidaceae alkaloids. Bioorganic & medicinal chemistry letters 20090615
Chemistry, biology, and medicinal potential of narciclasine and its congeners. Chemical reviews 20080601
Isolation and structural modification of 7-deoxynarciclasine and 7-deoxy-trans-dihydronarciclasine. Journal of natural products 20060101
Antineoplastic agents. 553. The Texas grasshopper Brachystola magna. Journal of natural products 20050801
Antineoplastic agents. 527. Synthesis of 7-deoxynarcistatin, 7-deoxy-trans-dihydronarcistatin, and trans-dihydronarcistatin 1(1). Journal of natural products 20050201
A short route to enantiomerically pure benzophenanthridinone skeleton: synthesis of lactone analogues of narciclasine and lycoricidine. The Journal of organic chemistry 20041001
Synthesis and biological activity of some structural modifications of pancratistatin. Bioorganic & medicinal chemistry letters 20040607
Daffodil flowers delay senescence in cut Iris flowers. Phytochemistry 20040301
Antineoplastic agents. 511. Direct phosphorylation of phenpanstatin and pancratistatin. Journal of natural products 20040301
Changes in some enzymes of microbodies and plastid development in excised radish cotyledons: effect of narciclasine. Journal of plant physiology 20030901
Antineoplastic agents 500. Narcistatin. Journal of natural products 20030101
Total synthesis and biological evaluation of Amaryllidaceae alkaloids: narciclasine, ent-7-deoxypancratistatin, regioisomer of 7-deoxypancratistatin, 10b-epi-deoxypancratistatin, and truncated derivatives. The Journal of organic chemistry 20021213
A short synthesis of (+)-narciclasine via a strategy derived from stereocontrolled epoxide formation and SnCl(4)-catalyzed arene-epoxide coupling. The Journal of organic chemistry 20021004
Antineoplastic agents. 450. Synthesis of (+)-pancratistatin from (+)-narciclasine as relay(1a). The Journal of organic chemistry 20010420
Identification of HIV-1 integrase inhibitors based on a four-point pharmacophore. Antiviral chemistry & chemotherapy 19981101
Antiviral (RNA) activity of selected Amaryllidaceae isoquinoline constituents and synthesis of related substances. Journal of natural products 19921101
Properties