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Merck
CN

N9789

Narciclasine

≥98% (HPLC)

Synonym(s):

(2S-(2-alpha,3-beta,4-beta,4a-beta))-3,4,4a,5-tetrahydro-2,3,4,7-tetrahydroxy-(1,3)Dioxolo(4,5-j)phenanthridin-6(2H)-one, 3,4,4a,5-Tetrahydro-2,3,4,7-tetrahydroxy-(1,3)dioxolo(4,5-j)phenanthridin-6(2H)-one, BRN 1087400, Lycoricidin-A, Lycoricidinol, NSC 266535

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About This Item

Empirical Formula (Hill Notation):
C14H13NO7
CAS Number:
29477-83-6
Molecular Weight:
307.26
UNSPSC Code:
12352200
PubChem Substance ID:
329818695
MDL number:
MFCD01729949

Key Documents

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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

SMILES string

O[C@H]1C=C2[C@@H](NC(=O)c3c(O)c4OCOc4cc23)[C@H](O)[C@@H]1O

InChI key

LZAZURSABQIKGB-AEKGRLRDSA-N

assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: ≥10 mg/mL

storage temp.

room temp

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Biochem/physiol Actions

Narciclasine is a Rho/Rho kinase/LIM kinase/cofilin signaling pathway activator. Also narciclasine is an actin stress fiber formation inducer; a plant growth modulator.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
072M4714V
010M4700

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Gwendoline Van Goietsenoven et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 24(11), 4575-4584 (2010-07-21)
Melanomas display poor response rates to adjuvant therapies because of their intrinsic resistance to proapoptotic stimuli. This study indicates that such resistance can be overcome, at least partly, through the targeting of eEF1A elongation factor with narciclasine, an Amaryllidaceae isocarbostyril
George R Pettit et al.
Journal of natural products, 68(8), 1256-1258 (2005-08-30)
Bioassay (P388 lymphocytic leukemia cell line and human cancer cell lines) guided separation of an extract prepared from the previously chemically uninvestigated Texas grasshopper Brachystola magna led to isolation of the cancer cell growth inhibitory pancratistatin (1), narciclasine (2), and
Xiaofan Na et al.
Journal of plant physiology, 168(11), 1149-1156 (2011-04-23)
Plant development displays an exceptional plasticity and adaptability that involves the dynamic, asymmetric distribution of the phytohormone auxin. Polar auxin flow, which requires transport facilitators of the PIN family, largely contributes to the establishment and maintenance of auxin gradients and
Chemistry, biology, and medicinal potential of narciclasine and its congeners.
Alexander Kornienko et al.
Chemical reviews, 108(6), 1982-2014 (2008-05-21)
George R Pettit et al.
Journal of natural products, 75(4), 771-773 (2012-03-15)
Bioassay-guided (cancer cell line) separation of an extract prepared from Narcissus cv. Ice Follies (from The Netherlands) led to the isolation of a new Amaryllidaceae isocarbostiryl, 3-epipancratistatin (1b), as well as narciclasine (2). This Narcissus cultivar was found to be
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