CAS 469-59-0|Jervine
| 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 | ChineseUSA | Flash Point | 311.8±30.1 °C |
| Symbol | GHS06 | Signal Word | Danger |
Names
| Name | jervine |
|---|---|
| Synonym | More Synonyms |
Jervine BiologicalActivity
| 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 | Signaling Pathways >>Stem Cell/Wnt >>HedgehogSignaling Pathways >>Stem Cell/Wnt >>SmoNatural Products >>AlkaloidResearch Areas >>Cancer |
| 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 |
| InChIKey | CLEXYFLHGFJONT-DNMILWOZSA-N |
| SMILES | CC1=C2C(=O)C3C(CC=C4CC(O)CCC43C)C2CCC12OC1CC(C)CNC1C2C |
Toxicological Information
CHEMICAL IDENTIFICATION |
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 |
|---|---|
| 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 |
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)- |
