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Basic Description
| Synonyms | (3beta,22S,23R)-17,23-epoxyveratraman-3-ol | A881419 | HMS3403D13 | GAMMA CYCLODEXTRIN [MART.] | BRD-K58938839-001-03-8 | CCG-208181 | Cyclopamine Tartrate | Jervine, 11-deoxo- | (E)-4,4'-(1,2-Ethenediyl)bisbenzenamine | 11-Deoxyjervine | CYCLOPAMINE [HSD |
|---|---|
| Specifications & Purity | Moligand™, ≥99% |
| Biochemical and Physiological Mechanisms | Cyclopamine is a teratogenic Smo inhibitor famous for inducing cyclopia in developing mammalian fetuses. Cyclopia arises from improper differentiation in the fetus, a process heavily regulated by the Hedgehog (Hh) signaling pathway. The proteins Smo and p |
| Storage Temp | Store at 2-8°C |
| Shipped In |
Wet ice This product requires cold chain shipping. Ground and other economy services are not available. |
| Grade | Moligand™ |
| Action Type | ANTAGONIST |
| Mechanism of action | Antagonist of SMO |
| Note | This product is supplied in one (or more) pack size which is freeze dried. Therefore the contents may not be readily visible, as they can coat the bottom or walls of the vial. Please see our FAQs and information page for more details on handling. Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details. |
| Product Description |
Cyclopamine is a specific Hedgehog (Hh) signaling pathway antagonist of Smoothened (Smo) with IC50 of 46 nM. |
Taxonomic Classification
Taxonomy Tree
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Kingdom
Organic compounds
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Superclass
Lipids and lipid-like molecules
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Class
Steroids and steroid derivatives
- Subclass Steroidal alkaloids
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Class
Steroids and steroid derivatives
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Superclass
Lipids and lipid-like molecules
| Kingdom | Organic compounds |
|---|---|
| Superclass | Lipids and lipid-like molecules |
| Class | Steroids and steroid derivatives |
| Subclass | Steroidal alkaloids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Jerveratrum-type alkaloids |
| Alternative Parents | Azasteroids and derivatives Alkaloids and derivatives Piperidines Tetrahydrofurans Secondary alcohols Cyclic alcohols and derivatives Oxacyclic compounds Dialkylamines Dialkyl ethers Azacyclic compounds Organopnictogen compounds Hydrocarbon derivatives |
| Molecular Framework | Aliphatic heteropolycyclic compounds |
| Substituents | Jerveratrum-type alkaloid - Azasteroid - Alkaloid or derivatives - Piperidine - Cyclic alcohol - Tetrahydrofuran - Secondary alcohol - Oxacycle - Dialkyl ether - Secondary aliphatic amine - Ether - Azacycle - Secondary amine - Organoheterocyclic compound - Organic oxygen compound - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Alcohol - Hydrocarbon derivative - Organopnictogen compound - Amine - Aliphatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as jerveratrum-type alkaloids. These are steroidal alkaloids with a structure that is based on the jervane ring system. Jerveratrum alkaloids have alkamines with 1-3 oxygen atoms, and occur as such or as monoglycosides. |
| External Descriptors | Steroidal alkaloids |
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Associated Targets(Human)
SMO
Tclin
Smoothened homolog (5 Activities)
| Activity Type | Activity Value -log(M) | Mechanism of Action | Activity Reference | Publications (PubMed IDs) |
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SHH
Tchem
Sonic hedgehog protein (1 Activities)
| Activity Type | Activity Value -log(M) | Mechanism of Action | Activity Reference | Publications (PubMed IDs) |
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ABL1
Tclin
Tyrosine-protein kinase ABL (18331 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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ADRB2
Tclin
Beta-2 adrenergic receptor (11824 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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ADRA2A
Tclin
Alpha-2a adrenergic receptor (9450 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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VDR
Tclin
Vitamin D receptor (26531 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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ACHE
Tclin
Acetylcholinesterase (18204 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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AVPR2
Tclin
Vasopressin V2 receptor (2912 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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AGTR1
Tclin
Type-1 angiotensin II receptor (5176 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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GSK3B
Tclin
Glycogen synthase kinase-3 beta (11785 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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CSNK1D
Tchem
Casein kinase I delta (4546 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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S1PR1
Tclin
Sphingosine 1-phosphate receptor Edg-1 (5806 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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CDK2
Tchem
Cyclin-dependent kinase 2 (9050 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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GLP1R
Tclin
Glucagon-like peptide 1 receptor (111429 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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C5AR1
Tclin
C5a anaphylatoxin chemotactic receptor (2677 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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AURKA
Tchem
Serine/threonine-protein kinase Aurora-A (10240 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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A498 (42825 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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BT-474 (2113 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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C8166 (1658 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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CA46 (271 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Calu-6 (398 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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CCRF-CEM (65223 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Daudi (625 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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DMS-79 (150 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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DU-145 (51482 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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EVSA-T (142 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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HL-60 (67320 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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HuTu80 (255 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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IM-9 (160 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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JAR (316 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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JIYOYE (162 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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K562 (73714 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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KM12 (47707 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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ML-2 (146 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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MOLT-4 (49676 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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NALM-6 (592 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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NCI-H128 (54 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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NCI-H345 (89 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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NTERA-2-cl-D1 (234 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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OVCAR-4 (44535 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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PSN1 (345 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Raji (5516 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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RKO (1376 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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RPMI-8226 (44974 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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RXF 393 (41971 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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SCC-15 (194 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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SF-126 (160 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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SK-MEL-1 (285 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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SK-MEL-2 (46422 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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SNU1 (253 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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SNU-16 (476 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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SNU-5 (270 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Associated Targets(non-human)
Aplnr
Apelin receptor (201 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Mapk1
MAP kinase ERK2 (650 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Fgfr3
Fibroblast growth factor receptor 3 (21 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
C3H 10T1/2 (488 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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MEF (1005 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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H4 (48 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Shh
Sonic hedgehog protein (356 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Gpr119
Glucose-dependent insulinotropic receptor (270 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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BCHE
Cholinesterase (8742 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Oryzias latipes (115 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Shh Light II (88 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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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',6',10,11b-tetramethylspiro[2,3,4,6,6a,6b,7,8,11,11a-decahydro-1H-benzo[a]fluorene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-3-ol |
|---|---|
| INCHI | InChI=1S/C27H41NO2/c1-15-11-24-25(28-14-15)17(3)27(30-24)10-8-20-21-6-5-18-12-19(29)7-9-26(18,4)23(21)13-22(20)16(27)2/h5,15,17,19-21,23-25,28-29H,6-14H2,1-4H3/t15-,17+,19-,20-,21-,23-,24+,25-,26-,27-/m0/s1 |
| InChIKey | QASFUMOKHFSJGL-LAFRSMQTSA-N |
| Smiles | CC1CC2C(C(C3(O2)CCC4C5CC=C6CC(CCC6(C5CC4=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]5CC4=C3C)C)O)C)NC1 |
| Alternate CAS | 4449-51-8 |
| NSC Number | 734950 |
| MeSH Entry Terms | cyclopamine |
| Molecular Weight | 411.62 |
| Reaxy-Rn | 1228666 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1228666&ln= |
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Date | Item |
|---|---|---|---|
 E1803071 |
Certificate of Analysis | Jul 09, 2025 | C125994 |
| E1803072 |
Certificate of Analysis | Jul 09, 2025 | C125994 |
| E1528101 |
Certificate of Analysis | Dec 08, 2022 | C125994 |
Chemical and Physical Properties
| Solubility | Soluble in ethanol (5 mg/ml warm), DMSO (4 mg/ml), DMF (10 mg/ml), methylene chloride, chloroform, methanol (7 mg/ml), and benzene |
|---|---|
| Molecular Weight | 411.600 g/mol |
| XLogP3 | 3.500 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 0 |
| Exact Mass | 411.314 Da |
| Monoisotopic Mass | 411.314 Da |
| Topological Polar Surface Area | 41.500 Ų |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Complexity | 801.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 10 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
Citations of This Product
| 1. Ju Li, Jinmei Zuo, Xiaoyan Lv, Jiahe Ma, Xiaohong Li, Simiao Fu, Jinsheng Sun. (2023) Hedgehog signaling is essential in the regulation of limb regeneration in the Chinese mitten crab, Eriocheir sinensis. FISH & SHELLFISH IMMUNOLOGY, 140 (108981). |
| 2. Zhao Ye, Wang Huiling, He Tianhua, Ma Bo, Chen Guoguang, Tzeng Chimeng. (2023) Knockdown of Yap attenuates TAA-induced hepatic fibrosis by interaction with hedgehog signals. Journal of Cell Communication and Signaling, (1-20). |
| 3. Tingting Lv, Lei Shen, Lei Yang, Wenxiu Diao, Zhenming Yang, Ying Zhang, Shijie Yu, Yanxia Li. (2018) Polydatin ameliorates dextran sulfate sodium-induced colitis by decreasing oxidative stress and apoptosis partially via Sonic hedgehog signaling pathway. INTERNATIONAL IMMUNOPHARMACOLOGY, 64 (256). |
| 4. Kuiyuan Song, Guanqun Zheng, Yue Zhao. (2018) Liver kinase B1 suppresses growth of lung cancer cells through sonic hedgehog signaling pathway. CELL BIOLOGY INTERNATIONAL, 42 (8): (994-1005). |
| 5. Sha Feng, Jue Liu, Biao Cheng, Aiping Deng, Hong Zhang. (2018) (-)-Epigallocatechin-3-gallate protects PC12 cells against corticosterone-induced neurotoxicity via the hedgehog signaling pathway. Experimental and Therapeutic Medicine, 15 (5): (4284-4290). |
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