Jervine

From Infogalactic: the planetary knowledge core
Jump to: navigation, search
Jervine
200px
Names
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
469-59-0 N
ChEMBL ChEMBL186779 YesY
ChemSpider 9694 YesY
Jmol 3D model Interactive image
PubChem 10098
  • 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 YesY
    Key: CLEXYFLHGFJONT-DNMILWOZSA-N YesY
  • 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
  • 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
Properties
C27H39NO3
Molar mass 425.60 g/mol
Solubility 10 mg/mL in EtOH
6 mg/mL in DMF
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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. Lua error in package.lua at line 80: module 'strict' not found.