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J4145

Sigma-Aldrich

Jervine

≥98% (HPLC), powder

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Synonym(s):
(3β, 23β)-17,23-Epoxy-3-hydroxyveratraman-11-one, 11-Ketocyclopamine
Empirical Formula (Hill Notation):
C27H39NO3
CAS Number:
Molecular Weight:
425.60
EC Number:
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Repr. 1B

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, 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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L K Bechtel et al.
Clinical toxicology (Philadelphia, Pa.), 48(5), 435-442 (2010-07-01)
We report a case of digoxin-like toxicity because of ingestion of foraged plants. This patient presented with nausea, vomiting, bradycardia, and hypotension after ingesting Veratrum viride (false hellebore). The patient's serum specimen demonstrated a positive digoxin level (0.38 ng/mL) measured
M Campbell et al.
Teratology, 36(2), 235-243 (1987-10-01)
Jervine and retinoic acid are both teratogenic to structures which are initially modelled in cartilage. Differences in periods of maximal sensitivity, as well as in certain aspects of the morphological manifestations of exposure, indicate that these two teratogens act via
H Li et al.
Acta pharmacologica Sinica, 21(1), 23-28 (2001-03-27)
To study the central hypotensive mechanism of Veratrum nigrum L var ussurience Nakai alkaloids (VnA) in renal hypertensive rats(RHR). The quantitative method of immunocytochemistry (ICC) was used to observe and detect the effect of VnA (30 micrograms.kg-1, i.v.) on activity
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

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