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J4145

Sigma-Aldrich

Jervine

≥98% (HPLC), powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C27H39NO3
CAS Number:
469-59-0
Molecular Weight:
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

Signal Word

Danger

Hazard Statements

H301,H360D

Hazard Classifications

Acute Tox. 3 Oral - Repr. 1B

Storage Class Code

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

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
Miki Nagase et al.
Microvascular research, 71(2), 85-90 (2006-01-18)
Hedgehog family was reported to be involved in murine yolk sac angiogenesis. However, it has not been clarified whether impaired angiogenesis under hedgehog signaling blockade is attributable to true defect in angiogenic process or just a sequel of earlier vasculogenic
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.
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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