Jervine

Jervine
IUPAC name (2'R,3S,3'R,3'aS,6'S, 6aS,6bS,7'aR,11aS,11bR)- 2,3,3'a,4,4',5',6,6',6a, 6b,7,7',7'a,8,11a,11b- Hexadecahydro- 3-hydroxy- 3',6',10,11b- tetramethyl- spiro [9H-benzo [a] fluorene- 9,2'(3'H)- furo [3,2-b] pyridin]- 11(1H)- one
Other names (3β,23β)- 17,23- Epoxy- 3-hydroxyveratraman- 11-one
Identifiers
CAS number	469-59-0 Y
PubChem	10098
ChemSpider	9694 Y
ChEMBL	CHEMBL186779 N
Jmol-3D images	Image 1
SMILES O=C5/C3=C(/[C@@]1(O[C@@H]2C[C@@H](CN[C@H]2[C@H]1C)C)CC[C@H]3[C@@H]6C/C=C4/C[C@@H](O)CC[C@]4(C)[C@@H]56)C
InChI 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 Y Key: CLEXYFLHGFJONT-DNMILWOZSA-N Y InChI=1/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 Key: CLEXYFLHGFJONT-DNMILWOZBJ
Properties
Molecular formula	C27H39NO3
Molar mass	425.60 g/mol
Solubility	10 mg/mL in EtOH 6 mg/mL in DMF
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Jervine is a steroidal alkaloid with molecular formula C₂₇H₃₉NO₃ which is derived from the Veratrum plant genus. Similar to cyclopamine, which also occurs in the Veratrum genus, it is a teratogen implicated in birth defects when consumed by animals during a certain period of their gestation.

Physiological effects

Jervine is a potent teratogen causing birth defects in vertebrates. In severe cases it can cause cyclopia and holoprosencephaly.

Mechanism of action

Jervine's biological activity is mediated via its interaction with the 7 pass trans membrane protein smoothened. Jervine binds with and inhibits smoothened, which is an integral part of the hedgehog signaling pathways.^[1] With smoothened inhibited, the GLI1 transcription cannot be activated and hedgehog target genes cannot be transcribed.

References

1. ^ Chen, J; Taipale, J; Cooper, M. (2002). "Inhibition of Hedgehog Signaling by direct binding of Cyclopamine to Smoothened". Genes Dev. 16 (21): 2743–2748. doi:10.1101/gad.1025302. PMC 187469. PMID 12414725. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=187469. 

This article about an organic compound is a stub. You can help Wikipedia by expanding it.v · Categories: Teratogens Jervines Spiro compounds Alcohols Ketones Oxygen heterocycles Nitrogen heterocycles Organic compound stubs Wikimedia Foundation. 2010. Игры ⚽ Нужен реферат? John Ashburton Thompson Cedarvale Park (Toronto) Look at other dictionaries: Jervine — Jer vine, n. [Prob. fr. Sp. yerba herb, OSp., the poison of the veratrum.] (Chem.) A poisonous alkaloid resembling veratrine, and found with it in white hellebore ({Veratrum album}); called also {jervina}. [1913 Webster] …   The Collaborative International Dictionary of English jervine — [ʒɛʀvin] n. f. ÉTYM. 1898, Nouveau Larousse illustré; orig. inconnue. ❖ ♦ Chim., biol. Alcaloïde toxique contenu dans les tiges souterraines de certains ellébores …   Encyclopédie Universelle jervine — noun A steroidal alkaloid, obtained from plants of the genus Veratrum, that is teratogenic …   Wiktionary jervine — (jèr vi n ) s. f. Terme de chimie. Espèce d alcaloïde végétal trouvé dans le veratrum album, L …   Dictionnaire de la Langue Française d'Émile Littré jervine — jer·vine …   English syllables jervine — ˈjərˌvēn, və̇n noun ( s) Etymology: New Latin jervina, from Spanish yervina, perhaps from yervo vetch, chick pea (from Latin ervum) + ina ine : a crystalline alkaloid C26H39NO3 related in structure to the steroids and found in the rhizomes and… …   Useful english dictionary jervina — Jervine Jer vine, n. [Prob. fr. Sp. yerba herb, OSp., the poison of the veratrum.] (Chem.) A poisonous alkaloid resembling veratrine, and found with it in white hellebore ({Veratrum album}); called also {jervina}. [1913 Webster] …   The Collaborative International Dictionary of English Veratrum album — Jervine Jer vine, n. [Prob. fr. Sp. yerba herb, OSp., the poison of the veratrum.] (Chem.) A poisonous alkaloid resembling veratrine, and found with it in white hellebore ({Veratrum album}); called also {jervina}. [1913 Webster] …   The Collaborative International Dictionary of English pseudojervine — |sü(ˌ)dō+ noun Etymology: pseud + jervine : a crystalline alkaloid C29H43NO7 resembling jervine and occurring with it …   Useful english dictionary rubijervine — |rübə̇+ noun Etymology: ruby (I) + jervine : a nonpoisonous crystalline alkaloid C27H43NO2 found with jervine in green and white hellebore …   Useful english dictionary 18+ © Academic, 2000-2024 Contact us: Technical Support, Advertising Dictionaries export, created on PHP, Joomla, Drupal, WordPress, MODx. Mark and share Search through all dictionaries Translate… Search Internet Share the article and excerpts Direct link … Do a right-click on the link above and select “Copy Link”