Compound Detail

CHEMBL428496

WORTMANNIN

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COC[C@H]1OC(=O)c2coc3c2[C@@]1(C)C1=C(C3=O)[C@@H]2CCC(=O)[C@@]2(C)C[C@H]1OC(C)=O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL428496
Name	WORTMANNIN
Phase	Preclinical
Structure Type	MOL
InChI Key	QDLHCMPXEPAAMD-QAIWCSMKSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

428.4

MW (Da)

2.54

ALogP

HBA

HBD

109.1

PSA (Å²)

0.68

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	C23H24O8
MW	428.44
Aromatic Rings	1
Heavy Atoms	31
NP-Likeness	2.59

Activity Summary

IC50 66 meas. best 9.1

Kd 5 meas. best 8.27

Ki 4 meas. best 8.38

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Unchecked CHEMBL612545	IC50	9.1	8.178	0.8	15
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform CHEMBL4005	IC50	9.0	8.2525	1.0	8
PI3-kinase p110-alpha/p85-alpha CHEMBL2111367	IC50	8.92	7.6575	1.2	4
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform CHEMBL3130	IC50	8.4	8.1667	4.0	3
Phosphatidylinositol 3-kinase catalytic subunit type 3 CHEMBL1075165	IC50	8.38	8.38	4.2	1
Unchecked CHEMBL612545	Ki	8.38	8.38	4.2	1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform CHEMBL3267	IC50	8.3	7.126	5.0	5
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform CHEMBL4005	Kd	8.27	8.27	5.4	1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform CHEMBL3130	Kd	8.26	8.26	5.5	1
Serine/threonine-protein kinase PLK1 CHEMBL3024	IC50	8.24	7.25	5.8	3
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform CHEMBL3145	Kd	8.12	8.12	7.6	1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform CHEMBL3145	IC50	8.0	7.89	10.0	3
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform CHEMBL3267	Kd	7.82	7.82	15.0	1
Neutrophil CHEMBL613710	IC50	7.72	7.72	19.0	1
Serine/threonine-protein kinase mTOR CHEMBL2842	IC50	7.4	7.4	40.0	1
Serine/threonine-protein kinase PLK3 CHEMBL4897	IC50	7.32	7.0967	48.0	3
Rattus norvegicus CHEMBL376	IC50	7.01	7.01	98.0	1
DNA-dependent protein kinase catalytic subunit CHEMBL3142	Ki	6.92	6.92	120.0	2
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform CHEMBL4005	Ki	6.92	6.92	120.0	1
Myosin light chain kinase, smooth muscle CHEMBL2428	IC50	6.77	5.93	170.0	3
Myosin light chain kinase, smooth muscle CHEMBL3062	IC50	6.58	6.58	260.0	1
Phosphatidylinositol 4-kinase alpha CHEMBL3667	IC50	6.55	6.55	280.0	1
Serine/threonine-protein kinase mTOR CHEMBL1075134	IC50	6.52	6.52	300.0	1
Phosphatidylinositol 4-kinase beta CHEMBL3268	IC50	6.36	6.36	440.0	1
Serine/threonine-protein kinase mTOR CHEMBL2842	Kd	5.04	5.04	9200.0	1
Plasmodium falciparum CHEMBL364	IC50	5.0	4.94	10000.0	5
A549 CHEMBL392	IC50	4.94	4.94	11400.0	1
Bile salt export pump CHEMBL6020	IC50	4.87	4.87	13600.0	2
ATP-binding cassette sub-family C member 2 CHEMBL5748	IC50	4.34	4.34	46100.0	1
ATP-binding cassette sub-family C member 4 CHEMBL1743128	IC50	4.2	4.2	63200.0	1
Measles morbillivirus CHEMBL613738	IC50	4.12	4.12	75000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
T1/2	57.83	hr	-
T1/2	0.025	hr	-
T1/2	0.3067	hr	-
T1/2	0.06833	hr	-
T1/2	0.0165	hr	-

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Unchecked	IC50	=	0.8	nM	9.1	Inhibition of PI3K (unknown origin)	27996267
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	IC50	=	1.0	nM	9.0	Inhibition of human PI3Kalpha	16789742
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	IC50	=	1.0	nM	9.0	Inhibition of PI3Kalpha	22924688
PI3-kinase p110-alpha/p85-alpha	IC50	=	1.2	nM	8.92	Inhibition of PI3 kinase p110alpha/p85-alpha complex	16464575
Unchecked	IC50	=	2.0	nM	8.7	Inhibition of PI3K	23040731
Unchecked	IC50	=	2.0	nM	8.7	Inhibition of calf thymus PI3 kinase using [gamma-32P]ATP by immunoprecipitate a...	36503229
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	IC50	=	2.4	nM	8.62	Inhibition of PI3Kalpha (unknown origin) using PIP2 as substrate preincubated fo...	24900173
Unchecked	IC50	=	3.0	nM	8.52	Inhibition of PIK3 (unknown origin)	38295689
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform	IC50	=	4.0	nM	8.4	Inhibition of human PI3K p110delta catalytic subunit by AlphaScreen assay	21169017
Unchecked	IC50	=	4.2	nM	8.38	Inhibition of Phosphatidylinositol 3-kinase	-
Unchecked	Ki	=	4.2	nM	8.38	Inhibition of GST-tagged PI3K gamma mutant (unknown origin) expressed in HEK293 ...	31188592
Phosphatidylinositol 3-kinase catalytic subunit type 3	IC50	=	4.2	nM	8.38	Inhibition of VPS34 (unknown origin)	36283182
Unchecked	IC50	=	4.2	nM	8.38	Inhibition of PI3K (unknown origin)	-
Unchecked	IC50	=	4.2	nM	8.38	Inhibition of bovine Phosphatidylinositol 3-kinase	-
Unchecked	IC50	=	4.2	nM	8.38	In vitro inhibitory activity against Phosphatidylinositol 3-Kinase	8676346
Unchecked	IC50	=	5.0	nM	8.3	Inhibition of phosphatidylinositol-3-kinase (P13-K)	12672248
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	IC50	=	5.0	nM	8.3	Inhibition of human PI3Kgamma	16789742
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	IC50	=	5.0	nM	8.3	Inhibition of PI3Kgamma	22924688
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	Kd	=	5.4	nM	8.27	Binding affinity to human PI3Kalpha after 1 hr by KINOMEscan assay	30380865
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform	Kd	=	5.5	nM	8.26	Binding affinity to human PI3Kdelta after 1 hr by KINOMEscan assay	30380865

Literature References

PubMed	DOI	Target Context	# Activities
8676346	10.1021/jm950619p	Homo sapiens	20
8676346	10.1021/jm950619p	Mus musculus	14
17135248	10.1074/jbc.m609603200	Serine/threonine-protein kinase PLK3	5
10998351	10.1042/0264-6021:3510095	Unchecked	5
19523825	10.1016/j.bmcl.2009.05.105	No relevant target	5
19734910	10.1038/nchembio.215	Plasmodium falciparum	5
29019677	10.1021/acs.jnatprod.7b00515	HEK293	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
29211480	10.1021/acs.jmedchem.7b01019	Unchecked	3
22906130	10.1111/j.1538-7836.2012.04898.x	Unchecked	3
12672248	10.1021/jm020427b	Unchecked	2
27487570	10.1016/j.ejmech.2016.07.042	Molecular identity unknown	2
17850214	10.1042/bj20070797	Unchecked	2
28462836	10.1016/j.bmcl.2017.03.093	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	2
30380865	10.1021/acs.jmedchem.8b00975	Epidermal growth factor receptor	2
27608432	10.1016/j.ejmech.2016.08.041	Unchecked	2
10998351	10.1042/0264-6021:3510095	Myosin light chain kinase, smooth muscle	2
18630894	10.1021/jm800374f	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	2
17850214	10.1042/bj20070797	Serine/threonine-protein kinase PLK1	2
16562855	10.1021/np050487v	Candida albicans	2

Data from ChEMBL 36 via Core Engine