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Safety Information

N9789

Sigma-Aldrich

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
MDL number:
MFCD01729949
UNSPSC Code:
12352200
PubChem Substance ID:
329818695

Assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: ≥10 mg/mL

storage temp.

room temp

SMILES string

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

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

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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

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310 + P330

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

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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Chemistry, biology, and medicinal potential of narciclasine and its congeners.
Alexander Kornienko et al.
Chemical reviews, 108(6), 1982-2014 (2008-05-21)
Gwendoline Van Goietsenoven et al.
Medicinal research reviews, 33(2), 439-455 (2012-03-16)
The anticancer activity of Amaryllidaceae isocarbostyrils is well documented. At pharmacological concentrations, that is, approximately 1 μM in vitro and approximately 10 mg/kg in vivo, narciclasine displays marked proapoptotic and cytotoxic activity, as does pancratistatin, and significant in vivo anticancer
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
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
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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