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J4145

Sigma-Aldrich

Jervine

≥98% (HPLC), powder

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C27H39NO3
Numéro CAS:
469-59-0
Poids moléculaire :
425.60
Numéro CE :
207-417-9
Numéro MDL:
MFCD01684066
Code UNSPSC :
51111800
ID de substance PubChem :
24896194
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Solubilité

methanol: >2 mg/mL
H2O: insoluble

Température de stockage

−20°C

Chaîne SMILES 

[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

Clé InChI

CLEXYFLHGFJONT-DNMILWOZSA-N

Informations sur le gène

human ... EBP(10682)

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Description générale

Jervine is a steroid alkaloid present in Veratrum californicum.

Actions biochimiques/physiologiques

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.

Pictogrammes

Skull and crossbonesHealth hazard
GHS06,GHS08

Mention d'avertissement

Danger

Mentions de danger

H301,H360D

Classification des risques

Acute Tox. 3 Oral - Repr. 1B

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
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
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
D L Young et al.
Critical reviews in oral biology and medicine : an official publication of the American Association of Oral Biologists, 11(3), 304-317 (2000-10-06)
Craniofacial malformations are the most common birth defects that occur in humans, with facial clefting representing the majority of these defects. Facial clefts can arise at any stage of development due to perturbations that alter the extracellular matrix as well
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