Jervine

Modify Date: 2025-08-20 18:29:11

Jervine Structure
Jervine structure
 Common Name Jervine
CAS Number 469-59-0 Molecular Weight 425.603
Density 1.2±0.1 g/cm3 Boiling Point 592.0±50.0 °C at 760 mmHg
Molecular Formula C27H39NO3 Melting Point 242- 244ºC
MSDS Chinese USA Flash Point 311.8±30.1 °C
Symbol GHS06
GHS06		 Signal Word Danger

 Use of Jervine


Jervine(11-Ketocyclopamine) is a naturally occuring steroidal alkaloid that causes cyclopia by blocking sonic hedgehog(Shh) signaling; Jervine is an inhibitor of Smo.IC50 value:Target: sonic hedgehog is derived from the Veratrum plant species. It is a close structural analog of cyclopamine which specifically inhibits the hedgehog (Hh) pathway by interaction with the hedgehog signaling protein Smo. Jervine can be used to induce abnormal morphogenesis in a number of experimental models. Jervine is an inhibitor of Smo.

 Names

Name jervine
Synonym More Synonyms

 Jervine Biological Activity

Description Jervine(11-Ketocyclopamine) is a naturally occuring steroidal alkaloid that causes cyclopia by blocking sonic hedgehog(Shh) signaling; Jervine is an inhibitor of Smo.IC50 value:Target: sonic hedgehog is derived from the Veratrum plant species. It is a close structural analog of cyclopamine which specifically inhibits the hedgehog (Hh) pathway by interaction with the hedgehog signaling protein Smo. Jervine can be used to induce abnormal morphogenesis in a number of experimental models. Jervine is an inhibitor of Smo.
Related Catalog
References

[1]. Incardona JP, et al. Cyclopamine inhibition of Sonic hedgehog signal transduction is not mediated through effects on cholesterol transport. Dev Biol. 2000 Aug 15;224(2):440-52.

[2]. Chen JK, et al. Small molecule modulation of Smoothened activity. Proc Natl Acad Sci U S A. 2002 Oct 29;99(22):14071-6.

[3]. Mistretta CM, et al. 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. D

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Boiling Point 592.0±50.0 °C at 760 mmHg
Melting Point 242- 244ºC
Molecular Formula C27H39NO3
Molecular Weight 425.603
Flash Point 311.8±30.1 °C
Exact Mass 425.292999
PSA 58.56000
LogP 3.46
Vapour Pressure 0.0±3.8 mmHg at 25°C
Index of Refraction 1.591

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
WG9700000
CHEMICAL NAME :
Spiro(9H-benzo(a)fluorene-9,2'(3'H)-furo(3,2-b)-pyrid in)-11(1H)-one, 2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11a,11b-hexadec ahydro-3-hydroxy- 3',6',10,11b-tetramethyl-
CAS REGISTRY NUMBER :
469-59-0
BEILSTEIN REFERENCE NO. :
0059109
LAST UPDATED :
199709
DATA ITEMS CITED :
14
MOLECULAR FORMULA :
C27-H39-N-O3
MOLECULAR WEIGHT :
425.67
WISWESSER LINE NOTATION :
L D6 B566 CV FX DU LUTJ A1 E1 OQ F-& CT56 BOX FMTJ D1 H1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
240 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 149,302,1975
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
260 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 42,105,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
15 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DIPHAH Dissertationes Pharmaceuticae. (Warsaw, Poland) V.1-17, 1949-65. For publisher information, see PJPPAA. Volume(issue)/page/year: 8,9,1956
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
29 mg/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 113,89,1955
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - hamster
DOSE/DURATION :
80 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 17,327,1978 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
400 mg/kg
SEX/DURATION :
female 8-12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 149,302,1975
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
150 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 42,105,1990
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
66700 ug/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 136,1174,1971
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
55500 ug/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 136,1174,1971
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
127 mg/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Specific Developmental Abnormalities - eye/ear
REFERENCE :
41CIAR "Effects of Poisonous Plants on Livestock, Proceedings of a Joint U.S.-Australian Symposium on Poisonous Plants, Logan, UT, 1977," Keeler, R.F., et al. eds., New York, Academic Press, Inc., 1978 Volume(issue)/page/year: -,409,1978
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
170 mg/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
REFERENCE :
PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 149,302,1975
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
80 mg/kg
SEX/DURATION :
female 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 17,327,1978 *** REVIEWS *** TOXICOLOGY REVIEW LYPHAD Lyon Pharmaceutique. (Medipharly, 12, rue de la Barre, 69002 Lyons, France) V.1- 1950- Volume(issue)/page/year: 26,5,1975 TOXICOLOGY REVIEW AEMBAP Advances in Experimental Medicine and Biology. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) V.1- 1967- Volume(issue)/page/year: 27,107,1972

 Safety Information

Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301
Precautionary Statements P301 + P310
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Faceshields;Gloves
Hazard Codes Xn: Harmful;
Risk Phrases R22
RIDADR UN 2811 6.1/PG 3
WGK Germany 3
RTECS WG9700000

 Synthetic Route

 Articles20

More Articles
Development of an enzyme-linked immunosorbent assay for the veratrum plant teratogens: cyclopamine and jervine.

J. Agric. Food Chem. 51(3) , 582-6, (2003)

Veratrum californicum was responsible for large losses of sheep grazing high mountain ranges in central Idaho in the 1950s. Veratrum induces various birth defects including the cyclopic-type craniofac...

Cyclopamine and jervine induce COX-2 overexpression in human erythroleukemia cells but only cyclopamine has a pro-apoptotic effect.

Exp. Cell Res. 319(7) , 1043-53, (2013)

Erythroleukemia is generally associated with a very poor response and survival to current available therapeutic agents. Cyclooxygenase-2 (COX-2) has been described to play a crucial role in the prolif...

Effects of Veratrum nigrum alkaloids on central catecholaminergic neurons of renal hypertensive rats.

Acta Pharmacol. Sin. 21(1) , 23-8, (2000)

To study the central hypotensive mechanism of Veratrum nigrum L var ussurience Nakai alkaloids (VnA) in renal hypertensive rats(RHR).The quantitative method of immunocytochemistry (ICC) was used to ob...

 Synonyms

17,23β-Epoxy-3β-hydroxyveratraman-11-one
(3β, 23β)-17,23-Epoxy-3-hydroxyveratraman-11-one
(3β,22S,23R)-3-Hydroxy-17,23-epoxyveratraman-11-one
Veratraman-11-one, 17,23-epoxy-3-hydroxy-, (3-β,23-β)- (9CI)
DL-ISOLEUCINE GRADE II
(3b,23b)-17,23-Epoxy-3-hydroxyveratraman-11-one
4-27-00-03590 (Beilstein Handbook Reference)
(3β,23β)-17,23-Epoxy-3-hydroxyveratraman-11-one
Veratraman-11-one, 17,23-epoxy-3-hydroxy-, (3β,23β)-
11-KETOCYCLOPAMINE
Iervin
Veratraman-11-one, 17,23-epoxy-3-hydroxy-, (3β,23β)- (9CI)
jerwiny
Jervin-11-one
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-, (3S,3'R,3a'S,6'S,6aS,6bS,7a'R,9R,11aS,11bR)-
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Related Compounds: More...
O-Acetyljervine
14788-78-4
Jervine,acetate
64047-51-4
N-Formyljervine
66409-98-1
JERVINE,TETRAHYDRO
7595-52-0
N,O-diacetyl-jervine
7622-06-2
(5α,12α,13αH)-tetrahydro-jervine
24508-94-9
1-{[1-(2,3-dihydro-1,4-benzodioxine-5-carbonyl)azetidin-3-yl]methyl}-4-methyl-1H-pyrazole
2548985-59-5
1-{4-[(5-methoxypyrimidin-2-yl)oxy]piperidin-1-yl}-2-(1H-1,2,4-triazol-1-yl)ethan-1-one
2549045-85-2
3-[2-Oxo-2-(4-{[5-(pyridin-4-yl)pyrimidin-2-yl]oxy}piperidin-1-yl)ethyl]-1,3-oxazolidin-2-one
2549056-78-0
N-[(4-hydroxy-4,5,6,7-tetrahydro-1-benzothiophen-4-yl)methyl]-1-methanesulfonylpiperidine-4-carboxamide
2548988-90-3
2-(2-bromo-4-fluorophenyl)-1-{3-[(4-methyl-1H-pyrazol-1-yl)methyl]azetidin-1-yl}ethan-1-one
2548989-31-5
1-[5-(Pyridin-2-yl)-octahydropyrrolo[3,4-b]pyrrol-1-yl]-2-[3-(trifluoromethyl)phenyl]ethan-1-one
2549054-52-4
N-(2-chlorophenyl)-5-(pyridin-2-yl)-octahydropyrrolo[3,4-b]pyrrole-1-carboxamide
2549062-64-6
N-(4-fluorophenyl)-3-[(4-methyl-1H-pyrazol-1-yl)methyl]azetidine-1-carboxamide
2549010-58-2
1,3,5-trimethyl-4-({3-[(4-methyl-1H-pyrazol-1-yl)methyl]azetidin-1-yl}sulfonyl)-1H-pyrazole
2549021-87-4
4-methyl-1-({1-[4-(propan-2-yloxy)benzoyl]azetidin-3-yl}methyl)-1H-pyrazole
2549010-85-5
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