CAS Number469-59-0
Synonyms17,23β-Epoxy-3β-hydroxyveratraman-11-one; (3β, 23β)-17,23-Epoxy-3-hydroxyveratraman-11-one; (3β,22S,23R)-3-Hydroxy-17,23-epoxyveratraman-11-one; 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; 11-KETOCYCLOPAMINE; Iervin; jerwiny; Jervin-11-one
Molecular FormulaC27H39NO3
Molecular Weight425.60
Purity≥98 (HPLC)%
Density1.2±0.1 g/cm3
Boiling Point592.0±50.0 °C at 760 mmHg
Melting Point242- 244ºC
Appearancepowder
EINECS207-417-9
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 469-59-0 |
| Catalog No. | 2A-9093125 |
| Chinese Name | 蒜藜芦碱 |
| 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; 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; 11-KETOCYCLOPAMINE; Iervin; jerwiny; Jervin-11-one |
| Molecular Formula | C27H39NO3 |
| Molecular Weight | 425.60 |
| Purity | ≥98 (HPLC) |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 592.0±50.0 °C at 760 mmHg |
| Melting Point | 242- 244ºC |
| Appearance | powder |
| Storage Condition | <0°C; avoid heating |
| Application | Jervine (11-Ketocyclopamine) is a steroidal alkaloid that can block the sonic hedgehog (Shh) signaling pathway and inhibit Smo. |
| EINECS | 207-417-9 |
| PubChem ID | 24896194 |
| MDL Number | MFCD01684066 |
| SMILES | [H][C@@]12C[C@H](C)CN[C@@]1([H])[C@@H](C)[C@@]3(CC[C@]4([H])C(=C3C)C(=O)[C@@]5([H])[C@@]4([H])CC=C6C[C@@H](O)CC[C@]56C)O2 |
| 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 |
| InChI Key | CLEXYFLHGFJONT-DNMILWOZSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 51111800 |
| Hazard Symbols | transportation |
| MSDS | msds/93125_1_469_59_0.pdf |
| Bioactivity | 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 >> Hedgehog Signaling Pathways >> Stem Cell/Wnt >> Smo Natural Products >> Alkaloid Research 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 |
| Use of | 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. Properties Articles20 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 Signaling Pathways >> Stem Cell/Wnt >> Hedgehog Signaling Pathways >> Stem Cell/Wnt >> Smo Natural Products >> Alkaloid Research 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 Molecular Formula C27H39NO3 Exact Mass 425.292999 PSA 58.56000 Index of Refraction 1.591 InChIKey CLEXYFLHGFJONT-DNMILWOZSA-N |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Dangerous Regulations for land transport: 2811 International Dangerous Regulations for sea transport: 2811 International Dangerous Regulations for air transport: 2811 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: TOXIC SOLID, ORGANIC, N.O.S. (Jervine) IMDG: TOXIC SOLID, ORGANIC, N.O.S. (Jervine) International air transport hazard regulations: Toxic solid, organic, n.o.s. (Jervine) 14.3 Transport hazard categories European Land Transport Danger Regulations: 6.1 International Maritime Transport Danger Regulations: 6.1 International Air Transport Danger Regulations: 6.1 14.4 Package group European Land Transport Danger Regulations: III International Maritime Transport Danger Regulations: III International Air Transport Danger Regulations: III 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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