Compound Detail

CHEMBL254129

CYCLOPAMINE

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CC1=C2C[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]2CC[C@]12O[C@@H]1C[C@H](C)CN[C@H]1[C@H]2C

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL254129
Name	CYCLOPAMINE
Phase	Preclinical
Structure Type	MOL
InChI Key	QASFUMOKHFSJGL-LAFRSMQTSA-N

Targets

394

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

411.6

MW (Da)

5.00

ALogP

HBA

HBD

41.5

PSA (Å²)

0.55

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C27H41NO2
MW	411.63
Aromatic Rings	0
Heavy Atoms	30
NP-Likeness	2.99

Activity Summary

IC50 381 meas. best 7.34

EC50 6 meas. best 6.77

Ki 5 meas. best 7.9

Kd 2 meas. best 7.91

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Protein smoothened CHEMBL5971	Kd	7.91	7.425	12.4	2
Protein smoothened CHEMBL5971	Ki	7.9	7.2733	12.7	3
Molecular identity unknown CHEMBL612546	IC50	7.34	6.6533	46.0	6
Protein smoothened CHEMBL5971	IC50	7.19	6.7533	64.0	3
NON-PROTEIN TARGET CHEMBL3879801	IC50	7.0	5.71	100.0	4
Unchecked CHEMBL612545	IC50	6.96	6.765	110.0	2
Molecular identity unknown CHEMBL612546	EC50	6.77	6.77	170.0	1
Sonic hedgehog protein CHEMBL5387	IC50	6.52	6.2067	300.0	3
Unchecked CHEMBL612545	EC50	6.52	6.52	300.0	2
Protein smoothened CHEMBL6080	IC50	6.32	5.945	484.0	4
Sonic hedgehog protein CHEMBL5387	EC50	6.3	6.3	500.0	1
Sigma intracellular receptor 2 CHEMBL4105907	Ki	6.22	6.22	598.7	1
Sonic hedgehog protein CHEMBL5602	IC50	6.22	6.22	600.0	1
C3H 10T1/2 CHEMBL614531	IC50	6.21	6.21	620.0	1
NON-PROTEIN TARGET CHEMBL3879801	EC50	6.0	5.435	1000.0	2
Sodium-dependent dopamine transporter CHEMBL238	Ki	5.46	5.46	3424.5	1
Zinc finger protein GLI1 CHEMBL5461	IC50	5.3	5.3	5000.0	1
OS-RC-2 CHEMBL2366188	IC50	5.23	5.23	5866.6	1
DOHH-2 CHEMBL2366181	IC50	5.03	5.03	9356.9	1
no-10 CHEMBL2366071	IC50	5.0	5.0	9903.9	1
LS-513 CHEMBL2366311	IC50	4.95	4.95	11354.7	1
ALL-PO CHEMBL2366294	IC50	4.93	4.93	11773.4	1
8-MG-BA CHEMBL2366115	IC50	4.88	4.88	13112.3	1
RPMI 8402 CHEMBL612517	IC50	4.8	4.8	15853.7	1
EOL1 CHEMBL614489	IC50	4.73	4.73	18594.8	1
NALM-6 CHEMBL614187	IC50	4.72	4.72	19016.7	1
DEL CHEMBL2366186	IC50	4.7	4.7	20147.1	1
SR CHEMBL614300	IC50	4.63	4.63	23671.5	1
697 CHEMBL2366253	IC50	4.58	4.58	26615.5	1
COLO-829 CHEMBL2366275	IC50	4.57	4.57	26848.3	1
EVSA-T CHEMBL614295	IC50	4.56	4.56	27556.1	1
ATN-1 CHEMBL2366277	IC50	4.5	4.5	31232.9	1
L-363 CHEMBL2366267	IC50	4.5	4.5	31746.1	1
LAMA-84 CHEMBL2366090	IC50	4.49	4.49	32521.1	1
NOS-1 CHEMBL2366141	IC50	4.46	4.46	34295.6	1
BB30-HNC CHEMBL2366271	IC50	4.46	4.46	34330.6	1
BC1 cell line CHEMBL614277	IC50	4.42	4.42	37974.6	1
IST-SL2 CHEMBL2366101	IC50	4.42	4.42	38224.0	1
D-392MG CHEMBL2366161	IC50	4.4	4.4	40221.5	1
no-11 CHEMBL2366326	IC50	4.39	4.39	40552.1	1
LC4-1 CHEMBL2366091	IC50	4.39	4.39	40871.6	1
A388 CHEMBL2366355	IC50	4.37	4.37	42584.8	1
NTERA-2-cl-D1 CHEMBL614206	IC50	4.37	4.37	42707.4	1
CESS CHEMBL2366361	IC50	4.35	4.35	44223.2	1
A549 CHEMBL392	IC50	4.31	4.31	49000.0	1
RS4-11 CHEMBL2366159	IC50	4.31	4.31	49093.8	1
CTV-1 CHEMBL2366360	IC50	4.29	4.29	51074.0	1
D-502MG CHEMBL2366343	IC50	4.29	4.29	51627.1	1
MS-1 CHEMBL2366125	IC50	4.29	4.29	50935.1	1
ML-2 CHEMBL614356	IC50	4.28	4.28	52919.5	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Protein smoothened	Kd	=	12.4	nM	7.91	Binding affinity to wild type Smo expressed in U2OS cells by scintillation count...	23063522
Protein smoothened	Ki	=	12.7	nM	7.9	Displacement of [3H]cyclopamine from wild type Smo expressed in U2OS cells after...	23063522
Molecular identity unknown	IC50	=	46.0	nM	7.34	Inhibition of Hedgehog signaling pathway in mouse TM3 cells bearing pTA-8xGli-Lu...	19091559
Protein smoothened	Ki	=	51.0	nM	7.29	Displacement of [3H]-cyclopamine from SMO V404M mutant in gefitinib resistant hu...	28787156
Protein smoothened	IC50	=	64.0	nM	7.19	Displacement of BODIPY-labelled cyclopamine from human Smo receptor expressed in...	22268551
Molecular identity unknown	IC50	=	74.1	nM	7.13	Inhibition of hedgehog signaling pathway in mouse Shh Light2 cells assessed as i...	27567371
NON-PROTEIN TARGET	IC50	=	100.0	nM	7.0	Antiproliferative activity against SAG-induced rat cerebellar granule cell precu...	22268551
Unchecked	IC50	=	110.0	nM	6.96	Inhibition of Shh-induced hedgehog signalling pathway in mouse MEF cells express...	37001245
Protein smoothened	Kd	=	116.0	nM	6.94	Binding affinity to Smo D473H mutant expressed in U2OS cells by scintillation co...	23063522
Molecular identity unknown	IC50	=	160.0	nM	6.8	Inhibition of Hedgehog signaling in human DaOY cells assessed as downregulation ...	24900716
Molecular identity unknown	EC50	=	170.0	nM	6.77	Inhibition of Hedgehog pathway-dependent oxysterol-induced mouse C3 H10T1/2 cell...	18842035
Protein smoothened	Ki	=	232.0	nM	6.63	Displacement of [3H]cyclopamine from Smo D473H mutant expressed in U2OS cells af...	23063522
Unchecked	IC50	=	270.0	nM	6.57	Inhibition of Shh-induced hedgehog signalling pathway in mouse NIH/3T3 cells exp...	37001245
Protein smoothened	IC50	=	280.0	nM	6.55	Antagonist activity at human Smo receptor expressed in CHO cells by [3H]Hh-Ag bi...	19091559
Unchecked	EC50	=	300.0	nM	6.52	Inhibition of hedgehog receptor mediated Gli transcription	20708941
Sonic hedgehog protein	IC50	=	300.0	nM	6.52	Inhibition of SHH pathway in mouse Shh Light2 cells after 40 hrs by Gli-dependen...	21592788
Unchecked	EC50	=	300.0	nM	6.52	Inhibition of hedgehog receptor mediated Ptch1 transcription	20708941
Protein smoothened	IC50	=	300.0	nM	6.52	Inhibition of Smo-mediated Hh signaling in human Shh-light2 cells by luciferase ...	22268551
NON-PROTEIN TARGET	IC50	=	414.0	nM	6.38	Antiproliferative activity against Shh-stimulated C57BL/6 mouse granule cell pre...	23063522
Molecular identity unknown	IC50	=	430.0	nM	6.37	Inhibition of Hedgehog signaling in mouse M210B4 cells assessed as downregulatio...	24900716

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL5724696	U2OS	24
-	10.6019/CHEMBL5724696	TERT-RPE1	24
18024584	10.1073/pnas.0709695104	H4	12
-	10.6019/CHEMBL4689842	Fibroblast	10
-	10.6019/CHEMBL4689842	HEK-293T	10
21592788	10.1016/j.bmcl.2011.04.103	Sonic hedgehog protein	7
-	10.6019/CHEMBL4689842	U2OS	7
23074541	10.1021/ml300172p	Protein smoothened	6
24900716	10.1021/ml400014t	Molecular identity unknown	6
33845416	10.1016/j.bmc.2021.116144	Unchecked	6
23063522	10.1016/j.bmc.2012.09.030	Protein smoothened	6
-	10.6019/CHEMBL5209801	Free fatty acid receptor 4	5
-	10.6019/CHEMBL5209801	Sphingosine 1-phosphate receptor 1	5
-	10.6019/CHEMBL5209801	Alpha-2A adrenergic receptor	5
-	10.6019/CHEMBL5209801	Glucagon-like peptide 1 receptor	5
-	10.6019/CHEMBL5209801	Apelin receptor	5
-	10.6019/CHEMBL5209801	CX3C chemokine receptor 1	5
-	10.6019/CHEMBL5209801	Type-1 angiotensin II receptor	5
-	10.6019/CHEMBL5209801	Adhesion G-protein coupled receptor F1	5
-	10.6019/CHEMBL5209801	Glucose-dependent insulinotropic receptor	5

Data from ChEMBL 36 via Core Engine