Compound Detail

CHEMBL306946

TRYPTANTHRIN

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O=C1c2ccccc2-n2c1nc1ccccc1c2=O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL306946
Name	TRYPTANTHRIN
Phase	Preclinical
Structure Type	MOL
InChI Key	VQQVWGVXDIPORV-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

248.2

MW (Da)

1.93

ALogP

HBA

HBD

52.0

PSA (Å²)

0.48

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	C15H8N2O2
MW	248.24
Aromatic Rings	3
Heavy Atoms	19
NP-Likeness	0.03

Activity Summary

IC50 62 meas. best 7.52

Ki 5 meas. best 6.24

EC50 3 meas. best 6.67

Kd 3 meas. best 5.14

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
NCI/ADR-RES CHEMBL613829	IC50	7.52	5.77	30.0	2
Indoleamine 2,3-dioxygenase 1 CHEMBL4685	IC50	7.27	5.7075	53.7	4
Prostaglandin G/H synthase 2 CHEMBL230	IC50	7.19	7.19	64.0	3
Plasmodium falciparum CHEMBL364	IC50	6.94	6.74	114.0	2
Tryptophan 2,3-dioxygenase CHEMBL2140	IC50	6.85	6.255	140.0	4
Polyunsaturated fatty acid 5-lipoxygenase CHEMBL215	IC50	6.82	6.82	150.0	1
Unchecked CHEMBL612545	IC50	6.71	5.755	195.0	2
Plasmodium falciparum CHEMBL364	EC50	6.67	6.615	211.7	2
Plasmodium yoelii CHEMBL612889	IC50	6.65	6.65	225.1	1
MCF7 CHEMBL387	IC50	6.24	5.0767	580.0	3
Tryptophan 2,3-dioxygenase CHEMBL2140	Ki	6.24	6.24	581.0	1
Protein RecA CHEMBL1741171	EC50	6.19	6.19	643.0	1
WEHI3B CHEMBL614249	IC50	5.82	5.82	1500.0	1
HL-60 CHEMBL383	IC50	5.7	5.5	2000.0	2
Histone deacetylase 6 CHEMBL1865	IC50	5.48	5.48	3286.0	1
HEK293 CHEMBL614818	IC50	5.39	5.39	4110.0	1
Indoleamine 2,3-dioxygenase 1 CHEMBL4685	Ki	5.32	5.32	4810.0	2
K562 CHEMBL385	IC50	5.3	5.0133	5000.0	3
Indoleamine 2,3-dioxygenase 2 CHEMBL3627587	IC50	5.3	5.03	5000.0	4
DU-145 CHEMBL613508	IC50	5.21	5.21	6220.0	1
BDNF/NT-3 growth factors receptor CHEMBL4898	Kd	5.14	5.14	7200.0	1
MOLT-4 CHEMBL614177	IC50	5.1	5.05	8000.0	2
A549 CHEMBL392	IC50	5.08	4.4467	8250.0	3
HCT-15 CHEMBL612263	IC50	5.07	5.07	8490.0	1
NCI-H460 CHEMBL396	IC50	5.05	5.05	9000.0	1
A-431 CHEMBL614069	IC50	5.05	5.05	9000.0	1
High affinity nerve growth factor receptor CHEMBL2815	Kd	5.04	5.04	9200.0	1
HepG2 CHEMBL395	IC50	5.02	4.3667	9510.0	3
SK-N-DZ CHEMBL1075579	IC50	4.85	4.85	14000.0	1
PC-3 CHEMBL390	IC50	4.84	4.84	14520.0	1
T47D CHEMBL614361	IC50	4.84	4.84	14290.0	1
Indoleamine 2,3-dioxygenase 2 CHEMBL3627587	Ki	4.82	4.82	15180.0	2
HCT-116 CHEMBL394	IC50	4.76	4.76	17490.0	1
SH-SY5Y CHEMBL614910	IC50	4.66	4.66	22000.0	1
Mitogen-activated protein kinase 8 CHEMBL2276	Kd	4.64	4.64	23000.0	1
SF-268 CHEMBL613977	IC50	4.61	4.61	24400.0	1
Bel-7402 CHEMBL614279	IC50	4.38	4.38	41290.0	1
CCRF-CEM CHEMBL382	IC50	4.35	4.35	44360.0	1
MGC-803 CHEMBL3706566	IC50	4.15	4.15	70190.0	1
SK-OV-3 CHEMBL614925	IC50	4.07	4.07	85090.0	1
L02 CHEMBL4296457	IC50	4.04	4.04	90120.0	2

Pharmacokinetic Data

Parameter	Value	Units	Species
Cmax	7613599742.18	nM	Rattus norvegicus
Cmax	10554302288.11	nM	Rattus norvegicus
T1/2	4.35	hr	Rattus norvegicus
T1/2	5.6	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
NCI/ADR-RES	IC50	=	30.0	nM	7.52	Cytotoxicity against human MCF7/ADR cells after 72 hrs	28720329
Indoleamine 2,3-dioxygenase 1	IC50	=	53.7	nM	7.27	Inhibition of human IDO1 expressed in HEK293 cells assessed as kynurenine releas...	24099220
Prostaglandin G/H synthase 2	IC50	=	64.0	nM	7.19	Inhibition of COX2	16038536
Prostaglandin G/H synthase 2	IC50	=	64.0	nM	7.19	Inhibition of COX2	22819942
Prostaglandin G/H synthase 2	IC50	=	64.0	nM	7.19	Inhibition of COX2 in lipopolysaccharide-stimulated human MONO-MAC-6 cells	23146282
Plasmodium falciparum	IC50	=	114.0	nM	6.94	Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum DD2 ...	33823394
Tryptophan 2,3-dioxygenase	IC50	=	140.0	nM	6.85	Inhibition of TDO (unknown origin) expressed in HEK293 cells using L-Trp as subs...	30321802
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	150.0	nM	6.82	Inhibition of 5-lipoxygenase	22819942
Tryptophan 2,3-dioxygenase	IC50	=	194.0	nM	6.71	Inhibition of TDO in human U87 MG cells using L-Trp as substrate after 8 hrs	30321802
Unchecked	IC50	=	195.0	nM	6.71	PUBCHEM_BIOASSAY: High Throughput Screen to Identify Inhibitors of Mycobacterium...	-
Plasmodium falciparum	EC50	=	211.7	nM	6.67	NOVARTIS: Inhibition of Plasmodium falciparum 3D7 (drug-susceptible) proliferati...	18579783
Plasmodium yoelii	IC50	=	225.1	nM	6.65	NOVARTIS: Antimalarial liver stage activity measured as reduction in Plasmodium ...	22096101
Plasmodium falciparum	EC50	=	275.6	nM	6.56	NOVARTIS: Inhibition of Plasmodium falciparum W2 (drug-resistant) proliferation ...	18579783
Plasmodium falciparum	IC50	=	288.0	nM	6.54	Antiplasmodial activity against Plasmodium falciparum NF54 assessed as growth in...	33823394
MCF7	IC50	=	580.0	nM	6.24	Cytotoxicity against human wild-type MCF7 cells after 72 hrs	28720329
Tryptophan 2,3-dioxygenase	Ki	=	581.0	nM	6.24	Uncompetitive inhibition of recombinant full length C-terminal His-tagged human ...	30321802
Protein RecA	EC50	=	643.0	nM	6.19	PUBCHEM_BIOASSAY: Fluorescence Cell-Free Homogeneous Dose Retest to Identify Inh...	-
Tryptophan 2,3-dioxygenase	IC50	=	900.0	nM	6.05	Inhibition of TDO (unknown origin)	30773421
WEHI3B	IC50	=	1500.0	nM	5.82	Antiproliferative activity against mouse WEHI3B cells assessed as inhibition of ...	38665827
HL-60	IC50	=	2000.0	nM	5.7	Antiproliferative activity against human HL60 cells after 48 hrs	28720329

Literature References

PubMed	DOI	Target Context	# Activities
28720329	10.1016/j.bmc.2017.07.003	K562	6
24885014	10.1021/np500108r	Unchecked	6
27475108	10.1016/j.ejmech.2016.07.013	Indoleamine 2,3-dioxygenase 2	5
38665827	10.1039/d3md00698k	A549	5
-	10.6019/CHEMBL4808148	Histone deacetylase 6	4
23360475	10.1021/np3007167	No relevant target	4
33823394	10.1016/j.ejmech.2021.113400	Plasmodium falciparum	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
20485427	10.1038/nature09107	Plasmodium falciparum	4
28720329	10.1016/j.bmc.2017.07.003	Rattus norvegicus	4
28720329	10.1016/j.bmc.2017.07.003	Unchecked	4
23360475	10.1021/np3007167	Rattus norvegicus	4
30321802	10.1016/j.ejmech.2018.10.017	Tryptophan 2,3-dioxygenase	4
38665827	10.1039/d3md00698k	L02	3
24099220	10.1021/jm401195n	Indoleamine 2,3-dioxygenase 1	3
23360475	10.1021/np3007167	Caco-2	3
22096101	10.1126/science.1211936	Plasmodium yoelii	3
38665827	10.1039/d3md00698k	HepG2	3
23360475	10.1021/np3007167	Mycobacterium tuberculosis	3
28720329	10.1016/j.bmc.2017.07.003	MOLT-4	2

Data from ChEMBL 36 via Core Engine