Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H39NO3.C2H4O2 |
| Molecular Weight | 485.6554 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(O)=O.[H][C@@]12C[C@H](C)CN[C@@]1([H])[C@@H](C)[C@@]3(CC[C@]4([H])C(C(=O)[C@@]5([H])[C@@]4([H])CC=C6C[C@@H](O)CC[C@]56C)=C3C)O2
InChI
InChIKey=JEDVQALXWXZHFN-AVEQMEPMSA-N
InChI=1S/C27H39NO3.C2H4O2/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;1-2(3)4/h5,14,16,18-21,23-24,28-29H,6-13H2,1-4H3;1H3,(H,3,4)/t14-,16+,18-,19-,20-,21+,23+,24-,26-,27-;/m0./s1
| Molecular Formula | C2H4O2 |
| Molecular Weight | 60.052 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C27H39NO3 |
| Molecular Weight | 425.6035 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including:
https://en.wikipedia.org/wiki/Jervine | https://www.google.com/patents/US20150259313
Curator's Comment: description was created based on several sources, including:
https://en.wikipedia.org/wiki/Jervine | https://www.google.com/patents/US20150259313
Jervine (11-Ketocyclopamine) is a naturally occuring steroidal alkaloid is derived from the Veratrum plant species. Jervine is a teratogen implicated in birth defects when consumed by animals during a certain period of their gestation. Over the Hedgehog signaling pathway Jervine effectively inhibit the tumor growth using three human tumor xenograft models including lung cancer, pancreatic cancer and basal cell carcinoma. Jervine has the potential to advance to a treatment for different tumors.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Prx1 and Prx2 are upstream regulators of sonic hedgehog and control cell proliferation during mandibular arch morphogenesis. | 2001 Aug |
|
| Small-molecule modulators of Hedgehog signaling: identification and characterization of Smoothened agonists and antagonists. | 2002 Nov 6 |
|
| Roughing up Smoothened: chemical modulators of hedgehog signaling. | 2002 Nov 6 |
|
| Cyclopamine and jervine in embryonic rat tongue cultures demonstrate a role for Shh signaling in taste papilla development and patterning: fungiform papillae double in number and form in novel locations in dorsal lingual epithelium. | 2003 Feb 1 |
|
| Development of an enzyme-linked immunosorbent assay for the veratrum plant teratogens: cyclopamine and jervine. | 2003 Jan 29 |
|
| Sonic hedgehog exerts distinct, stage-specific effects on tongue and taste papilla development. | 2004 Dec 15 |
|
| Glycoalkaloids and metabolites inhibit the growth of human colon (HT29) and liver (HepG2) cancer cells. | 2004 May 19 |
|
| Critical time window of hedgehog-dependent angiogenesis in murine yolk sac. | 2006 Mar |
|
| Factors that regulate embryonic gustatory development. | 2007 Sep 18 |
|
| Antitumor activity of extracts and compounds from the rhizomes of Veratrum dahuricum. | 2008 Aug |
|
| [Determination of jervine and veratramine in Veratrum plants using high performance liquid chromatography coupled with evaporative light scattering detection]. | 2008 Jan |
|
| A study on the chemical constituents of Veratrum nigrum L. processed by rice vinegar. | 2008 Jul-Aug |
|
| Accidental intoxication with Veratrum album. | 2008 Nov-Dec |
|
| Smoothened adopts multiple active and inactive conformations capable of trafficking to the primary cilium. | 2009 |
|
| Synthesis of all diastereomers of the piperidine--alkaloid substructure of cyclopamine. | 2009 Dec 3 |
|
| Ingestion of false hellebore plants can cross-react with a digoxin clinical chemistry assay. | 2010 Jun |
|
| Antitumor and antiplatelet activity of alkaloids from veratrum dahuricum. | 2010 Jun |
|
| Hedgehog signaling is required at multiple stages of zebrafish tooth development. | 2010 Nov 30 |
|
| Characterization and identification of steroidal alkaloids in Fritillaria species using liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry. | 2010 Nov 5 |
Patents
Sample Use Guides
Oral: 40 or 60 or 80 mg/kg once every day (during 21 days).
Intravenous: 20 or 40 or 80 mg/kg once every day (during 21 days).
Route of Administration:
Other
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:47:05 GMT 2023
by
admin
on
Sat Dec 16 08:47:05 GMT 2023
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| Record UNII |
K01ZXO2SIH
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| Record Status |
Validated (UNII)
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| Record Version |
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