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| Activity Type | Activity Value -log(M) | Mechanism of Action | Activity Reference | Publications (PubMed IDs) |
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Basic Description
| Synonyms | JERVINE | 469-59-0 | Iervin | 11-Ketocyclopamine | Jerwiny | Jerwiny [Polish] | CHEBI:6088 | CHEMBL186779 | (3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethylspiro[1,2,3,4,6,6a,6b,7,8,11a-decahydrobenzo[a]fluorene-9,2'-3a,4,5,6,7,7a-hexahydro- |
|---|---|
| Specifications & Purity | 10mM in DMSO |
| Biochemical and Physiological Mechanisms | Smoothened inhibitor (IC 50 = 500-700 nM). Steroidal alkaloid. Prevents hedgehog signaling and therefore Gli1 transcription. |
| Storage Temp | Store at -80°C |
| Shipped In | Ice chest + Ice pads |
| Product Description | Jervine (11-Ketocyclopamine) is a Hedgehog signaling (IC50=500-700 nM) inhibitor that inhibits the sonic hedgehog (shh) pathway by interacting with smoothened. |
Associated Targets(Human)
SHH Tchem Sonic hedgehog protein (1 Activities)
ACHE Tclin Acetylcholinesterase (18204 Activities)
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EBP Tchem 3-beta-hydroxysteroid-delta(8),delta(7)-isomerase (102 Activities)
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A498 (42825 Activities)
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ACHN (49357 Activities)
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CAKI-1 (44928 Activities)
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CCRF-CEM (65223 Activities)
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COLO 205 (50209 Activities)
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DLD-1 (17511 Activities)
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DMS-273 (14108 Activities)
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DU-145 (51482 Activities)
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HL-60 (67320 Activities)
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HT-29 (80576 Activities)
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K562 (73714 Activities)
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KM12 (47707 Activities)
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M14 (47487 Activities)
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MCF7 (126967 Activities)
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MOLT-4 (49676 Activities)
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OVCAR-3 (48710 Activities)
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OVCAR-4 (44535 Activities)
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OVCAR-5 (45555 Activities)
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OVCAR-8 (47708 Activities)
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PC-3 (62116 Activities)
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RPMI-8226 (44974 Activities)
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RXF 393 (41971 Activities)
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RXF 631 (11415 Activities)
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SF-295 (48000 Activities)
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SK-MEL-2 (46422 Activities)
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SK-MEL-28 (48833 Activities)
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SK-MEL-5 (47095 Activities)
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SK-OV-3 (52876 Activities)
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SN12C (47755 Activities)
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SNB-19 (46794 Activities)
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SNB-78 (14240 Activities)
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TK-10 (45540 Activities)
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U-251 (51189 Activities)
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UACC-257 (46019 Activities)
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UACC-62 (47335 Activities)
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UO-31 (46270 Activities)
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786-0 (47912 Activities)
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A549 (127892 Activities)
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NCI/ADR-RES (33767 Activities)
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T47D (39041 Activities)
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EKVX (44102 Activities)
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NCI-H322M (45589 Activities)
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HCC 2998 (41480 Activities)
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HCT-116 (91556 Activities)
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HOP-18 (11577 Activities)
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HOP-92 (41141 Activities)
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Hs-578T (29457 Activities)
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NCI-H460 (60772 Activities)
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Associated Targets(non-human)
ERG2 C-8 sterol isomerase (237 Activities)
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Sigmar1 Sigma opioid receptor (160 Activities)
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Chlamydia pneumoniae (241 Activities)
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Shh Sonic hedgehog protein (356 Activities)
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Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Names and Identifiers
| IUPAC Name | (3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethylspiro[1,2,3,4,6,6a,6b,7,8,11a-decahydrobenzo[a]fluorene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-11-one |
|---|---|
| INCHI | 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 |
| Canonical SMILES | CC1CC2C(C(C3(O2)CCC4C5CC=C6CC(CCC6(C5C(=O)C4=C3C)C)O)C)NC1 |
| Isomeric SMILES | C[C@H]1C[C@@H]2[C@H]([C@H]([C@]3(O2)CC[C@H]4[C@@H]5CC=C6C[C@H](CC[C@@]6([C@H]5C(=O)C4=C3C)C)O)C)NC1 |
| WGK Germany | 3 |
| RTECS | WG9700000 |
| PubChem CID | 10098 |
| Molecular Weight | 425.6 |
Certificates
Certificate of Analysis(COA)
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Chemical and Physical Properties
| Sensitivity | Heat sensitive |
|---|---|
| Melt Point(°C) | 246 °C |
Safety and Hazards(GHS)
| Pictogram(s) | GHS06 |
|---|---|
| Signal | Danger |
| Hazard Statements | H301:Toxic if swallowed |
| Precautionary Statements | P301+P310:IF SWALLOWED: Immediately call a POISON CENTER/doctor/... |
| WGK Germany | 3 |
| RTECS | WG9700000 |
| Merck Index | 5264 |