JERVINE TANNATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C76H52O46.C27H39NO3
Molecular Weight	2126.8019
Optical Activity	UNSPECIFIED
Defined Stereocenters	15 / 15
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.OC7=CC(=CC(O)=C7O)C(=O)OC8=CC(=CC(O)=C8O)C(=O)OC[C@H]9O[C@@H](OC(=O)C%10=CC(O)=C(O)C(OC(=O)C%11=CC(O)=C(O)C(O)=C%11)=C%10)[C@H](OC(=O)C%12=CC(O)=C(O)C(OC(=O)C%13=CC(O)=C(O)C(O)=C%13)=C%12)[C@@H](OC(=O)C%14=CC(O)=C(O)C(OC(=O)C%15=CC(O)=C(O)C(O)=C%15)=C%14)[C@@H]9OC(=O)C%16=CC(O)=C(O)C(OC(=O)C%17=CC(O)=C(O)C(O)=C%17)=C%16

InChI

InChIKey=ILZNSORIOPBINX-BMBUXRDQSA-N

InChI=1S/C76H52O46.C27H39NO3/c77-32-1-22(2-33(78)53(32)92)67(103)113-47-16-27(11-42(87)58(47)97)66(102)112-21-52-63(119-72(108)28-12-43(88)59(98)48(17-28)114-68(104)23-3-34(79)54(93)35(80)4-23)64(120-73(109)29-13-44(89)60(99)49(18-29)115-69(105)24-5-36(81)55(94)37(82)6-24)65(121-74(110)30-14-45(90)61(100)50(19-30)116-70(106)25-7-38(83)56(95)39(84)8-25)76(118-52)122-75(111)31-15-46(91)62(101)51(20-31)117-71(107)26-9-40(85)57(96)41(86)10-26;1-14-11-21-24(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/h1-20,52,63-65,76-101H,21H2;5,14,16,18-21,23-24,28-29H,6-13H2,1-4H3/t52-,63-,64+,65-,76+;14-,16+,18-,19-,20-,21+,23+,24-,26-,27-/m10/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

Molecular Formula	C76H52O46
Molecular Weight	1701.1985
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
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
Roughing up Smoothened: chemical modulators of hedgehog signaling.	2002 Nov 6	12437769
Development of an enzyme-linked immunosorbent assay for the veratrum plant teratogens: cyclopamine and jervine.	2003 Jan 29	12537426
Sonic hedgehog exerts distinct, stage-specific effects on tongue and taste papilla development.	2004 Dec 15	15581865
Glycoalkaloids and metabolites inhibit the growth of human colon (HT29) and liver (HepG2) cancer cells.	2004 May 19	15137822
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
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

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 `Sat Dec 16 01:03:34 GMT 2023` Edited by `admin` on `Sat Dec 16 01:03:34 GMT 2023`
Record UNII	4L3IA7D34B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

JERVINE TANNATE

Common Name

English

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

Common Name

English

Code System Code Type Description

PUBCHEM

165411851

Created by admin on Sat Dec 16 01:03:34 GMT 2023 , Edited by admin on Sat Dec 16 01:03:34 GMT 2023

PRIMARY

FDA UNII

4L3IA7D34B

Created by admin on Sat Dec 16 01:03:34 GMT 2023 , Edited by admin on Sat Dec 16 01:03:34 GMT 2023

PRIMARY

Related Record Type Details


					19V3ECX465

JERVINE

ACTIVE MOIETY

Amount: