Compound Detail

CHEMBL465843

PIPLARTINE

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COc1cc(/C=C/C(=O)N2CCC=CC2=O)cc(OC)c1OC

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL465843
Name	PIPLARTINE
Phase	Preclinical
Structure Type	MOL
InChI Key	VABYUUZNAVQNPG-BQYQJAHWSA-N

Targets

159

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

317.3

MW (Da)

2.04

ALogP

HBA

HBD

65.1

PSA (Å²)

0.78

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	C17H19NO5
MW	317.34
Aromatic Rings	1
Heavy Atoms	23
NP-Likeness	0.80

Activity Summary

IC50 147 meas. best 6.8

EC50 12 meas. best 6.27

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Unchecked CHEMBL612545	IC50	6.8	5.4844	160.0	18
MV4-11 CHEMBL613835	IC50	6.54	6.19	289.1	2
CMK CHEMBL2366177	IC50	6.38	5.965	421.8	4
HL-60 CHEMBL383	IC50	6.28	5.782	529.2	5
HT-29 CHEMBL384	EC50	6.27	6.27	540.0	1
HGC-27 CHEMBL1075463	IC50	6.12	5.4333	760.0	3
U-937 CHEMBL612794	IC50	6.12	5.8533	767.0	3
MOLM-13 CHEMBL3706572	IC50	6.03	5.885	934.5	2
OCI-AML-3 CHEMBL4296479	IC50	5.96	5.845	1109.0	2
MCF7 CHEMBL387	IC50	5.92	5.2017	1200.0	6
Jurkat CHEMBL397	IC50	5.85	5.4767	1400.0	3
HT-29 CHEMBL384	IC50	5.85	5.5675	1400.0	4
KB CHEMBL398	IC50	5.78	5.78	1670.0	1
MOLT-4 CHEMBL614177	IC50	5.77	5.77	1700.0	1
MDA-MB-231 CHEMBL400	IC50	5.76	5.3075	1720.0	4
Thioredoxin reductase 1, cytoplasmic CHEMBL1927	IC50	5.75	5.045	1800.0	2
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.7	5.2838	2000.0	8
HCT-8 CHEMBL613510	IC50	5.66	5.48	2200.0	3
MGC-803 CHEMBL3706566	IC50	5.64	5.64	2285.0	1
A-375 CHEMBL613859	IC50	5.6	5.6	2500.0	1
P388 CHEMBL389	IC50	5.55	5.55	2800.0	1
HaCaT CHEMBL614392	IC50	5.52	5.16	3030.0	2
RAW264.7 CHEMBL612557	IC50	5.52	5.52	3000.0	1
A549 CHEMBL392	IC50	5.5	5.04	3200.0	11
DU-145 CHEMBL613508	IC50	5.47	5.47	3400.0	1
SK-MEL-2 CHEMBL614917	EC50	5.36	5.36	4390.0	1
CCRF-CEM CHEMBL382	IC50	5.36	5.36	4400.0	1
HaCaT CHEMBL614392	EC50	5.35	5.35	4460.0	1
SW-620 CHEMBL612262	IC50	5.33	5.33	4620.0	1
PC-3 CHEMBL390	IC50	5.31	5.31	4900.0	1
T98G CHEMBL614775	IC50	5.31	5.31	4920.0	1
K562 CHEMBL385	IC50	5.3	5.2767	5050.0	3
HeLa CHEMBL399	IC50	5.29	5.04	5148.0	2
Bel-7402 CHEMBL614279	IC50	5.25	5.25	5600.0	2
SH-SY5Y CHEMBL614910	IC50	5.23	5.23	5940.0	1
HCT-116 CHEMBL394	IC50	5.22	5.0755	6040.0	11
A-375 CHEMBL613859	EC50	5.21	5.21	6170.0	1
Unchecked CHEMBL612545	EC50	5.19	5.19	6410.0	1
HepG2 CHEMBL395	IC50	5.17	5.1125	6800.0	4
Signal transducer and activator of transcription 3 CHEMBL4026	IC50	5.16	5.16	7000.0	1
U-87 MG CHEMBL614247	IC50	5.14	4.8967	7180.0	3
SAOS-2 CHEMBL614894	IC50	5.14	5.14	7310.0	1
WI-38 CHEMBL614391	EC50	5.1	4.895	8000.0	2
WI-38 CHEMBL614391	IC50	5.1	4.865	8000.0	4
Bel7402/5-FU CHEMBL4483230	IC50	5.08	5.08	8400.0	2
NSCLC CHEMBL612554	IC50	5.04	5.04	9200.0	1
U2OS CHEMBL615023	IC50	5.02	5.02	9490.0	1
LN-229 CHEMBL4296459	IC50	5.0	5.0	10000.0	1
8-MG-BA CHEMBL2366115	IC50	5.0	5.0	10000.0	1
NON-PROTEIN TARGET CHEMBL3879801	EC50	4.94	4.94	11500.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	273.0	ng.hr.mL-1	Rattus norvegicus
CL	0.001233	mL.min-1.kg-1	Rattus norvegicus
Cmax	1776.64	nM	Rattus norvegicus
T1/2	2.87	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Unchecked	IC50	=	160.0	nM	6.8	Inhibition of TrxR in human MDA-MB-231 cells	33930801
MV4-11	IC50	=	289.1	nM	6.54	Antiproliferative activity against human MV4-11 cells after 72 hrs in presence o...	27505848
Unchecked	IC50	=	400.0	nM	6.4	Antiproliferative activity against human NCI-H660 cells assessed as cell growth ...	33930801
CMK	IC50	=	421.8	nM	6.38	Antiproliferative activity against Ara-C resistant human CMK cells after 72 hrs ...	27505848
Unchecked	IC50	=	442.4	nM	6.35	Antiproliferative activity against human CMY cells after 72 hrs in presence of S...	27505848
HL-60	IC50	=	529.2	nM	6.28	Antiproliferative activity against human HL60 cells after 72 hrs in presence of ...	27505848
HT-29	EC50	=	540.0	nM	6.27	Anti-necroptosis activity against TNFalpha-induced human HT-29 cells assessed as...	38199165
CMK	IC50	=	612.7	nM	6.21	Antiproliferative activity against human CMK cells after 72 hrs in presence of S...	27505848
HGC-27	IC50	=	760.0	nM	6.12	Antiproliferative activity against human HGC-27 cells assessed as cell growth in...	33930801
U-937	IC50	=	767.0	nM	6.12	Antiproliferative activity against p53 null human U937 cells after 72 hrs in pre...	27505848
MOLM-13	IC50	=	934.5	nM	6.03	Antiproliferative activity against human MOLM13 cells harboring wild type p53/FL...	27505848
Unchecked	IC50	=	1037.0	nM	5.98	Antiproliferative activity against human CMS cells after 72 hrs in presence of S...	27505848
OCI-AML-3	IC50	=	1109.0	nM	5.96	Antiproliferative activity against human OCI-AML3 cells after 72 hrs in presence...	27505848
HL-60	IC50	=	1128.0	nM	5.95	Antiproliferative activity against Ara-C resistant human HL60 cells after 72 hrs...	27505848
MCF7	IC50	=	1200.0	nM	5.92	Antiproliferative activity in human MCF7 cells assessed as cell viability after ...	27689728
Jurkat	IC50	=	1400.0	nM	5.85	Antiproliferative activity in human Jurkat cells assessed as cell viability afte...	27689728
HT-29	IC50	=	1400.0	nM	5.85	Antiproliferative activity against human HT-29 cells assessed as cell growth inh...	33930801
MV4-11	IC50	=	1439.0	nM	5.84	Antiproliferative activity against human MV4-11 cells after 72 hrs by MTT assay	27505848
Unchecked	IC50	=	1520.0	nM	5.82	Inhibition of TrxR in human MDA-MB-231 cells measured after 72 hrs by colorimetr...	32736231
Unchecked	IC50	=	1620.0	nM	5.79	Antiproliferative activity against human CMY cells after 72 hrs by MTT assay	27505848

Literature References

PubMed	DOI	Target Context	# Activities
27505848	10.1021/acs.jmedchem.6b00772	U-937	24
27689728	10.1016/j.ejmech.2016.09.048	MCF7	18
29424539	10.1021/acs.jmedchem.7b01096	HCT-116	15
27689728	10.1016/j.ejmech.2016.09.048	Unchecked	9
32736231	10.1016/j.ejmech.2020.112610	MDA-MB-231	8
28434764	10.1016/j.bmcl.2017.04.035	SAOS-2	7
33930801	10.1016/j.ejmech.2021.113471	Unchecked	7
29807795	10.1016/j.bmcl.2018.05.025	Signal transducer and activator of transcription 3	7
31009908	10.1016/j.ejmech.2019.04.009	Platelet	7
27505848	10.1021/acs.jmedchem.6b00772	Unchecked	6
29807795	10.1016/j.bmcl.2018.05.025	DU-145	6
28434764	10.1016/j.bmcl.2017.04.035	HCT-116	6
27505848	10.1021/acs.jmedchem.6b00772	MOLM-13	6
29424539	10.1021/acs.jmedchem.7b01096	Rattus norvegicus	5
31009908	10.1016/j.ejmech.2019.04.009	Unchecked	5
25453809	10.1016/j.bmcl.2014.10.054	RAW264.7	5
25826398	10.1021/jm501846y	A549	5
27505848	10.1021/acs.jmedchem.6b00772	CMK	4
27505848	10.1021/acs.jmedchem.6b00772	HL-60	4
39045852	10.1021/acs.jnatprod.4c00084	A549	4

Data from ChEMBL 36 via Core Engine