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Details

Stereochemistry ABSOLUTE
Molecular Formula C31H45NO5
Molecular Weight 511.6927
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYL JERVINE-N-PROPIONATE

SMILES

[H][C@@]12C[C@H](C)CN(CCC(=O)OC)[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=MXDPCHQGAQFRMD-YSKIUEDOSA-N
InChI=1S/C31H45NO5/c1-17-14-24-28(32(16-17)13-10-25(34)36-5)19(3)31(37-24)12-9-22-23-7-6-20-15-21(33)8-11-30(20,4)27(23)29(35)26(22)18(31)2/h6,17,19,21-24,27-28,33H,7-16H2,1-5H3/t17-,19+,21-,22-,23-,24+,27+,28-,30-,31-/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
Small-molecule modulators of Hedgehog signaling: identification and characterization of Smoothened agonists and antagonists.
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
Critical time window of hedgehog-dependent angiogenesis in murine yolk sac.
2006 Mar
Smoothened adopts multiple active and inactive conformations capable of trafficking to the primary cilium.
2009
Antitumor and antiplatelet activity of alkaloids from veratrum dahuricum.
2010 Jun
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
METHYL JERVINE-N-PROPIONATE
Common Name English
VERATRAMAN-28-PROPANOIC ACID, 17,23-EPOXY-3-HYDROXY-11-OXO-, METHYL ESTER, (3.BETA.,23.BETA.)-
Systematic Name English
Code System Code Type Description
CAS
132943-48-7
Created by admin on Sat Dec 16 08:47:06 GMT 2023 , Edited by admin on Sat Dec 16 08:47:06 GMT 2023
PRIMARY
PUBCHEM
14804161
Created by admin on Sat Dec 16 08:47:06 GMT 2023 , Edited by admin on Sat Dec 16 08:47:06 GMT 2023
PRIMARY
FDA UNII
28779ZEX29
Created by admin on Sat Dec 16 08:47:06 GMT 2023 , Edited by admin on Sat Dec 16 08:47:06 GMT 2023
PRIMARY