Compound Detail

CHEMBL837

7-ETHYL-10-HYDROXYCAMPTOTHECIN

🧪 Phase II

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🧪 Phase II

CCc1c2c(nc3ccc(O)cc13)-c1cc3c(c(=O)n1C2)COC(=O)[C@]3(O)CC

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL837
Name	7-ETHYL-10-HYDROXYCAMPTOTHECIN
Phase	Phase II
Structure Type	MOL
InChI Key	FJHBVJOVLFPMQE-QFIPXVFZSA-N

Known Names

7-ethyl-10-hydroxy-camptothecin 7-ethyl-10-hydroxycamptothecin Camptothecin, 7-ethyl-10-hydroxy- Irinotecan related compound b It-141 NK 012 NK-012 Nk012 SN 38 SN-38 SN38

Targets

135

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

392.4

MW (Da)

2.35

ALogP

HBA

HBD

101.7

PSA (Å²)

0.51

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula	C22H20N2O5
MW	392.41
Aromatic Rings	3
Heavy Atoms	29
NP-Likeness	1.20

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
DNA topoisomerase I inhibitor	INHIBITOR	DNA topoisomerase 1	✓	✓

Indications

Breast Neoplasms Colorectal Neoplasms Lung Neoplasms Small Cell Lung Carcinoma Neoplasms Neoplasms

Activity Summary

IC50 132 meas. best 10.0

EC50 2 meas. best 7.16

Ki 1 meas. best 4.58

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
MCF7 CHEMBL387	IC50	10.0	6.96	0.1	5
PC-6 CHEMBL614235	IC50	9.37	8.83	0.4	2
HCT-116 CHEMBL394	IC50	9.26	8.099	0.6	10
COLO 205 CHEMBL614561	IC50	9.12	7.89	0.8	2
A549 CHEMBL392	IC50	8.79	7.4918	1.6	17
HL-60 CHEMBL383	IC50	8.7	7.3467	2.0	3
PC-3 CHEMBL390	IC50	8.59	7.83	2.6	3
QG-56 CHEMBL612268	IC50	8.55	8.55	2.8	1
Unchecked CHEMBL612545	IC50	8.48	7.606	3.3	5
NCI-H460 CHEMBL396	IC50	8.48	7.162	3.3	10
DU-145 CHEMBL613508	IC50	8.4	7.6925	4.0	4
SK-BR-3 CHEMBL613834	IC50	8.4	8.4	4.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	8.4	7.6278	4.0	9
Raji CHEMBL614628	IC50	8.3	8.3	5.0	1
HT-29 CHEMBL384	IC50	8.23	6.9256	5.9	18
NCI-H128 CHEMBL614771	IC50	8.22	8.22	6.0	1
CAPAN-1 CHEMBL614536	IC50	8.1	8.1	8.0	1
MKN-45 CHEMBL614354	IC50	8.1	8.1	8.0	1
L1210 CHEMBL386	IC50	8.05	7.8333	8.9	3
A2780 CHEMBL614004	IC50	8.05	8.05	9.0	1
SK-OV-3 CHEMBL614925	IC50	7.96	7.05	11.0	2
Bel-7402 CHEMBL614279	IC50	7.89	6.695	13.0	2
MIA PaCa-2 CHEMBL614725	IC50	7.89	7.89	13.0	1
HEK-293T CHEMBL3706568	IC50	7.85	7.85	14.2	1
WiDr CHEMBL614647	IC50	7.85	7.85	14.0	1
L02 CHEMBL4296457	IC50	7.75	7.75	18.0	1
U-251 CHEMBL615022	IC50	7.68	7.68	21.0	1
HeLa CHEMBL399	IC50	7.66	6.7657	22.0	7
DNA topoisomerase 1 CHEMBL1781	EC50	7.16	6.83	70.0	2
Broad substrate specificity ATP-binding cassette transporter ABCG2 CHEMBL5393	IC50	6.75	6.75	176.0	1
MDA-MB-231 CHEMBL400	IC50	6.75	6.23	176.0	2
RPMI-7951 CHEMBL612447	IC50	6.58	6.58	260.0	1
16HBE14o- CHEMBL4296395	IC50	6.52	6.52	300.0	1
LoVo CHEMBL614721	IC50	6.52	6.52	301.0	1
SK-HEP1 CHEMBL614912	IC50	6.52	6.52	300.0	1
SiHa CHEMBL612542	IC50	6.52	6.52	300.0	1
HepG2 CHEMBL395	IC50	6.32	6.32	480.0	2
SK-MEL-24 CHEMBL2366314	IC50	6.32	6.32	480.0	1
NCI-H1975 CHEMBL614348	IC50	6.09	6.09	810.0	1
DNA topoisomerase 1 CHEMBL1781	IC50	6.0	5.63	1000.0	2
DNA topoisomerase 1 CHEMBL2814	IC50	5.4	5.4	4000.0	1
CCD-841CoN CHEMBL4296406	IC50	5.3	5.3	4980.0	1
MRC5 CHEMBL614181	IC50	4.82	4.82	15300.0	1
Cytochrome P450 3A4 CHEMBL340	Ki	4.58	4.58	26000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	410.0	ng.hr.mL-1	Canis lupus familiaris
CL	23.99	uL.min-1.(10^6cells)-1	Rattus norvegicus
CL	25.12	mL.min-1.g-1	Homo sapiens
Cmax	2505.03	nM	Canis lupus familiaris
MRT	10.0	hr	Homo sapiens
T1/2	0.3317	hr	-
T1/2	0.5833	hr	-
T1/2	0.5333	hr	Homo sapiens
T1/2	0.6017	hr	-
T1/2	0.3483	hr	-
T1/2	0.4067	hr	-
T1/2	0.3317	hr	Homo sapiens
T1/2	0.5833	hr	Homo sapiens
T1/2	0.5717	hr	Homo sapiens
T1/2	0.19	hr	-
T1/2	0.09	hr	-
T1/2	2.67	hr	Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
MCF7	IC50	=	0.1	nM	10.0	Cytotoxicity against human MCF7 cells assessed as reduction in cell growth measu...	38421819
PC-6	IC50	=	0.43	nM	9.37	Antiproliferative activity against human PC6 cells carrying pRC after 6 days	19254843
HCT-116	IC50	=	0.55	nM	9.26	Antiproliferative activity against human HCT116 cells after 3 days	19254843
HCT-116	IC50	=	0.55	nM	9.26	Cytotoxicity against human HCT-116 cells assessed as reduction in cell growth me...	38421819
COLO 205	IC50	=	0.75	nM	9.12	Cytotoxicity against human COLO 205 cells incubated for 48 hrs by SRB assay	37413981
HCT-116	IC50	=	0.78	nM	9.11	Antiproliferative activity against human HCT116 cells after 72 hrs by SRB assay	30115492
A549	IC50	=	1.62	nM	8.79	Cytotoxicity against human A549 cells assessed as reduction in cell growth measu...	38421819
A549	IC50	=	1.62	nM	8.79	Antiproliferative activity against human A549 cells after 72 hrs by SRB assay	30115492
HL-60	IC50	=	2.0	nM	8.7	Cytotoxicity against human HL-60 cells assessed as inhibition of cell growth mea...	34048881
PC-3	IC50	=	2.6	nM	8.59	Cytotoxicity against human PC3 cells expressing alpha5beta3 integrin assessed as...	22959246
A549	IC50	=	2.72	nM	8.56	Cytotoxicity against human A549 cells assessed as growth inhibition after 3 days...	24529870
QG-56	IC50	=	2.8	nM	8.55	Antiproliferative activity against human QG56 cells after 3 days	19254843
Unchecked	IC50	=	3.3	nM	8.48	In-vitro inhibitory concentration for human tumor HCT116 cell-line was determine...	15913996
NCI-H460	IC50	=	3.3	nM	8.48	Antiproliferative activity against human NCI-H460 cells after 3 days	19254843
A549	IC50	=	3.8	nM	8.42	Cytotoxicity against human A549 cells assessed as cell growth inhibition incubat...	34963283
NON-PROTEIN TARGET	IC50	=	4.0	nM	8.4	Cytotoxicity against human KB3-1 cells after 4 days by MTT method	19303306
DU-145	IC50	=	4.0	nM	8.4	Antiproliferative activity against human DU145 cells after 96 hrs	18276141
HCT-116	IC50	=	4.0	nM	8.4	Antiproliferative activity against human HCT116 cells assessed as reduction in c...	32352777
SK-BR-3	IC50	=	4.0	nM	8.4	In Vitro cytotoxicity against human breast cancer cell line (SK-BR-3)	11334569
NON-PROTEIN TARGET	IC50	=	4.28	nM	8.37	Cytotoxicity against human HCT116 cells after 72 hrs by sulforhodamine B assay	25835359

Literature References

PubMed	DOI	Target Context	# Activities
15689169	10.1021/jm049405a	NON-PROTEIN TARGET	21
8355258	10.1021/jm00069a020	Homo sapiens	10
32650182	10.1016/j.ejmech.2020.112528	HCT-116	8
11052802	10.1021/jm000144o	ADMET	8
-	10.6019/CHEMBL4495565	SARS-CoV-2	6
14977862	10.1124/dmd.32.3.291	Solute carrier organic anion transporter family member 1B1	5
15608127	10.1124/dmd.104.001909	Solute carrier organic anion transporter family member 1B1	5
8289200	10.1021/jm00027a005	Albumin	4
11334569	10.1021/jm0004751	Unchecked	4
21030469	10.1124/dmd.110.035030	UDP-glucuronosyltransferase 1A1	4
-	10.6019/CHEMBL3301361	ADMET	4
15454230	10.1016/j.bmcl.2004.08.010	DNA topoisomerase 1	4
15808456	10.1016/j.bmcl.2005.02.072	Mus musculus	3
28350997	10.1016/j.ejmech.2017.03.040	NCI-H460	3
19254843	10.1016/j.bmcl.2009.02.031	PC-6	3
20884089	10.1016/j.ejmech.2010.09.023	NON-PROTEIN TARGET	3
28740613	10.1021/acsmedchemlett.7b00189	HT-29	3
28350997	10.1016/j.ejmech.2017.03.040	HT-29	3
18424133	10.1016/j.bmcl.2008.03.074	HT-29	3
19303306	10.1016/j.bmc.2009.02.023	NON-PROTEIN TARGET	3

Data from ChEMBL 36 via Core Engine