Compound Detail

CHEMBL517449

LIMONIN

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CC1(C)O[C@H]2CC(=O)OC[C@]23[C@H]2CC[C@@]4(C)[C@H](c5ccoc5)OC(=O)[C@H]5O[C@]54[C@]2(C)C(=O)C[C@@H]13

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL517449
Name	LIMONIN
Phase	Preclinical
Structure Type	MOL
InChI Key	KBDSLGBFQAGHBE-MSGMIQHVSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

470.5

MW (Da)

3.14

ALogP

HBA

HBD

104.6

PSA (Å²)

0.46

QED

Ro5 Violations

Rot. Bonds

Natural Product First in Class Prodrug

IC50 6 meas. best 5.37

EC50 1 meas. best 7.75

Ki 1 meas. best 4.63

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
NON-PROTEIN TARGET CHEMBL3879801	EC50	7.75	7.75	18.0	1
MCF7 CHEMBL387	IC50	5.37	5.37	4300.0	1
ATP-dependent translocase ABCB1 CHEMBL4302	IC50	4.72	4.72	19140.0	1
Cytochrome P450 3A4 CHEMBL340	Ki	4.63	4.63	23200.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.58	4.58	26100.0	1
MDA-MB-435 CHEMBL614697	IC50	4.58	4.58	26000.0	1
Neutrophil CHEMBL613710	IC50	4.42	4.42	38200.0	1
Unchecked CHEMBL612545	IC50	4.38	4.38	42000.0	1

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
NON-PROTEIN TARGET	EC50	=	18.0	nM	7.75	Neuroprotective activity against rat cortical cells assessed as glutamate-induce...	18198838
MCF7	IC50	=	4300.0	nM	5.37	Antiproliferative activity against human MCF7 cells incubated for 48 hrs by [3H]...	33289552
ATP-dependent translocase ABCB1	IC50	=	19140.0	nM	4.72	Inhibition of P-gp in human Caco2 cells assessed as potentiation of doxorubicin-...	31103904
Cytochrome P450 3A4	Ki	=	23200.0	nM	4.63	Mechanism based inhibition of human cytochrome P450 3A4 measured by (14C)formald...	16248836
NON-PROTEIN TARGET	IC50	=	26100.0	nM	4.58	Immunomodulatory activity in whole blood assessed as inhibition of luminol-induc...	18950230
MDA-MB-435	IC50	=	26000.0	nM	4.58	Antiproliferative activity against human MDA-MB-435 cells incubated for 48 hrs b...	33289552
Neutrophil	IC50	=	38200.0	nM	4.42	Immunomodulatory activity in polymorphoneutrophils assessed as inhibition of lum...	18950230
Unchecked	IC50	=	42000.0	nM	4.38	Antiproliferative activity against human Panc-28 cells incubated for 72 hrs by M...	33289552

PubMed	DOI	Target Context	# Activities
33479680	10.1039/d0md00117a	Mus musculus	6
21334901	10.1016/j.bmc.2011.01.024	ADMET	4
24569111	10.1016/j.bmcl.2014.02.003	No relevant target	3
24569111	10.1016/j.bmcl.2014.02.003	Mus musculus	3
18950230	10.1021/np800276f	Neutrophil	3
21334901	10.1016/j.bmc.2011.01.024	Unchecked	3
37544186	10.1016/j.ejmech.2023.115704	Tobacco mosaic virus	3
21334901	10.1016/j.bmc.2011.01.024	Human T-cell leukemia virus type I	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
-	10.1016/S0367-326X(99)00155-0	Puccinia arachidis	2
16248836	10.2174/138920005774330639	Cytochrome P450 3A4	2
18198838	10.1021/np070588o	NON-PROTEIN TARGET	2
21334901	10.1016/j.bmc.2011.01.024	Human immunodeficiency virus 1	2
21334901	10.1016/j.bmc.2011.01.024	Human immunodeficiency virus type 1 reverse transcriptase	2
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
9134742	10.1021/np9605394	Plasmodium falciparum	2
21334901	10.1016/j.bmc.2011.01.024	PBMC	1
18950230	10.1021/np800276f	NON-PROTEIN TARGET	1
12405773	10.1021/jf020607u	Spodoptera frugiperda	1
14510598	10.1021/np030034v	Tyrosinase	1

Data from ChEMBL 36 via Core Engine