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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
Structure of JERVINE ACETATE

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

HIDE SMILES / InChI

Description
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

Targets

Targets

Primary TargetPharmacologyConditionPotency
50.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Critical time window of hedgehog-dependent angiogenesis in murine yolk sac.
2006 Mar
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
Isolation, purification, and full NMR assignments of cyclopamine from Veratrum californicum.
2008 Jun 24
Accidental intoxication with Veratrum album.
2008 Nov-Dec
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
Tongues treated with jervine at 10 μM exhibited a dorsal anterior tongue that was almost completely occupied by fungiform papillae.
Name Type Language
JERVINE ACETATE
Common Name English
VERATRAMAN-11-ONE, 17,23-EPOXY-3-HYDROXY-, (3.BETA.,23.BETA.)-, ACETATE (SALT)
Systematic Name English
Code System Code Type Description
PUBCHEM
91800144
Created by admin on Sat Dec 16 08:47:05 GMT 2023 , Edited by admin on Sat Dec 16 08:47:05 GMT 2023
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FDA UNII
K01ZXO2SIH
Created by admin on Sat Dec 16 08:47:05 GMT 2023 , Edited by admin on Sat Dec 16 08:47:05 GMT 2023
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CAS
64047-51-4
Created by admin on Sat Dec 16 08:47:05 GMT 2023 , Edited by admin on Sat Dec 16 08:47:05 GMT 2023
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EPA CompTox
DTXSID70982228
Created by admin on Sat Dec 16 08:47:05 GMT 2023 , Edited by admin on Sat Dec 16 08:47:05 GMT 2023
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