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J4145

Sigma-Aldrich

Jervine

≥98% (HPLC), powder

Synonyma:

(3β, 23β)-17,23-Epoxy-3-hydroxyveratraman-11-one, 11-Ketocyclopamine

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About This Item

Empirický vzorec (Hillův zápis):
C27H39NO3
Číslo CAS:
469-59-0
Molekulová hmotnost:
425.60
EC Number:
207-417-9
MDL number:
MFCD01684066
UNSPSC Code:
51111800
PubChem Substance ID:
24896194
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

solubility

methanol: >2 mg/mL
H2O: insoluble

storage temp.

−20°C

SMILES string

[H][C@@]12C[C@H](C)CN[C@@]1([H])[C@@H](C)[C@@]3(CC[C@]4([H])C(=C3C)C(=O)[C@@]5([H])[C@@]4([H])CC=C6C[C@@H](O)CC[C@]56C)O2

InChI

1S/C27H39NO3/c1-14-11-21-24(28-13-14)16(3)27(31-21)10-8-19-20-6-5-17-12-18(29)7-9-26(17,4)23(20)25(30)22(19)15(27)2/h5,14,16,18-21,23-24,28-29H,6-13H2,1-4H3/t14-,16+,18-,19-,20-,21+,23+,24-,26-,27-/m0/s1

InChI key

CLEXYFLHGFJONT-DNMILWOZSA-N

Gene Information

human ... EBP(10682)

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General description

Jervine is a steroid alkaloid present in Veratrum californicum.

Biochem/physiol Actions

Jervine is a potent teratogenic agent. It can induce apoptosis in leukemia cells and MUTZ-1 cells. Jervine is an inhibitor of Hedgehog signaling. It exhibits anti-cancer effects on human prostate cancer. It also increases the chemosensitivity of breast cancer cells to doxorubicin treatment. Jervine may be used for treating hypertension and heart disease.
Jervine is a sonic hedgehog (Shh) pathway inhibitor.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Repr. 1B

Storage Class

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

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Vyberte jednu z posledních verzí:

Osvědčení o analýze (COA)

Lot/Batch Number
062M4709V
081M4727V
019K4707
057K4710
104K4703

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Stephen T Lee et al.
Journal of agricultural and food chemistry, 51(3), 582-586 (2003-01-23)
Veratrum californicum was responsible for large losses of sheep grazing high mountain ranges in central Idaho in the 1950s. Veratrum induces various birth defects including the cyclopic-type craniofacial defect (monkey-faced lambs) that is specifically induced in lambs after pregnant ewes
K A El Sayed et al.
Phytochemistry, 55(1), 19-22 (2000-10-06)
Preparative-scale fermentation of the known C-nor-D-homosteroidal jerveratrum alkaloid jervine with Cunninghamella elegans (ATCC 9245) has resulted in the isolation of (-)-jervinone as the major metabolite. In addition, C. elegans ATCC 9245 was able to epimerize C-3 of jervine, producing 3-epi-jervine.
F R Sim et al.
Teratogenesis, carcinogenesis, and mutagenesis, 3(2), 111-121 (1983-01-01)
The Veratrum-derived steroidal alkaloid, jervine, induces cyclopia and limb malformations in sheep, and various other craniofacial malformations in several other mammalian and avian species. In the present study, the question whether jervine acts directly or indirectly on mammalian embryos to
Carlos M Moran et al.
Developmental dynamics : an official publication of the American Association of Anatomists, 240(6), 1354-1364 (2011-03-09)
Signaling by the hedgehog (Hh) family of secreted growth factors is essential for development of embryonic blood vessels. Embryos lacking Hh function have abundant endothelial cells but fail to assemble vascular cords or lumenized endothelial tubes. However, the role of
Lamia Ghezali et al.
Experimental cell research, 319(7), 1043-1053 (2013-01-30)
Erythroleukemia is generally associated with a very poor response and survival to current available therapeutic agents. Cyclooxygenase-2 (COX-2) has been described to play a crucial role in the proliferation and differentiation of leukemia cells, this enzyme seems to play an
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