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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

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

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
Prx1 and Prx2 are upstream regulators of sonic hedgehog and control cell proliferation during mandibular arch morphogenesis.
2001 Aug
Antitumor activity of extracts and compounds from the rhizomes of Veratrum dahuricum.
2008 Aug
Isolation, purification, and full NMR assignments of cyclopamine from Veratrum californicum.
2008 Jun 24
Accidental intoxication with Veratrum album.
2008 Nov-Dec
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
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 08:47:05 GMT 2023
Edited
by admin
on Sat Dec 16 08:47:05 GMT 2023
Record UNII
K01ZXO2SIH
Record Status Validated (UNII)
Record Version
  • Download
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
Related Record Type Details
ACTIVE MOIETY