JERVINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H39NO3
Molecular Weight	425.6035
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[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=CLEXYFLHGFJONT-DNMILWOZSA-N

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

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15137822
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Hedgehog signaling pathway 11 Target ID: map04340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12606278	Inhibitor 8297		50.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20013819 https://www.ncbi.nlm.nih.gov/pubmed/15137822	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Prx1 and Prx2 are upstream regulators of sonic hedgehog and control cell proliferation during mandibular arch morphogenesis.	2001 Aug	11532916
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	12606278
Factors that regulate embryonic gustatory development.	2007 Sep 18	17903280
Antitumor activity of extracts and compounds from the rhizomes of Veratrum dahuricum.	2008 Aug	18570211
[Determination of jervine and veratramine in Veratrum plants using high performance liquid chromatography coupled with evaporative light scattering detection].	2008 Jan	18438025
A study on the chemical constituents of Veratrum nigrum L. processed by rice vinegar.	2008 Jul-Aug	18636372
Isolation, purification, and full NMR assignments of cyclopamine from Veratrum californicum.	2008 Jun 24	18577213
Accidental intoxication with Veratrum album.	2008 Nov-Dec	19021933
Smoothened adopts multiple active and inactive conformations capable of trafficking to the primary cilium.	2009	19365551
Synthesis of all diastereomers of the piperidine--alkaloid substructure of cyclopamine.	2009 Dec 3	19883099
Ingestion of false hellebore plants can cross-react with a digoxin clinical chemistry assay.	2010 Jun	20586573
Antitumor and antiplatelet activity of alkaloids from veratrum dahuricum.	2010 Jun	20013819
Hedgehog signaling is required at multiple stages of zebrafish tooth development.	2010 Nov 30	21118524
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	20926090

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

Tongues treated with jervine at 10 μM exhibited a dorsal anterior tongue that was almost completely occupied by fungiform papillae.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:58:12 UTC 2023` Edited by `admin` on `Fri Dec 15 17:58:12 UTC 2023`
Record UNII	19V3ECX465
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

JERVINE

Common Name

English

JERVINE [HSDB]

Common Name

English

NSC-23898

Code

English

NSC-7520

Code

English

VERATRAMAN-11-ONE, 17,23-EPOXY-3-HYDROXY-, (3.BETA.,23.BETA.)-

Common Name

English

SPIRO(9H-BENZO(A)FLUORENE-9,2'(3'H)-FURO(3,2-B)PYRIDIN)-11(1H)-ONE, 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-, (2'R,3S,3'R,3'AS,6'S,6AS,6BS,7'AR,11AS,11BR)-

Systematic Name

English

JERVIN

Common Name

English

JERVINE [MI]

Common Name

English

Code System Code Type Description

PUBCHEM

10098