Compound Detail

CHEMBL309490

GALANGIN

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O=c1c(O)c(-c2ccccc2)oc2cc(O)cc(O)c12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL309490
Name	GALANGIN
Phase	Preclinical
Structure Type	MOL
InChI Key	VCCRNZQBSJXYJD-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

270.2

MW (Da)

2.58

ALogP

HBA

HBD

90.9

PSA (Å²)

0.63

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	C15H10O5
MW	270.24
Aromatic Rings	3
Heavy Atoms	20
NP-Likeness	1.43

Activity Summary

IC50 29 meas. best 8.52

Ki 17 meas. best 7.61

EC50 8 meas. best 4.72

Kd 2 meas. best 5.23

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Cytochrome P450 1B1 CHEMBL4878	IC50	8.52	8.06	3.0	2
Acetylcholinesterase CHEMBL220	IC50	7.92	7.92	12.0	1
Carbonic anhydrase 7 CHEMBL2326	Ki	7.61	7.61	24.5	1
Cytochrome P450 1A2 CHEMBL3356	IC50	7.4	7.4	40.0	1
Carbonic anhydrase 12 CHEMBL3242	Ki	7.38	7.38	41.8	1
Cytochrome P450 1A1 CHEMBL2231	IC50	7.11	7.11	77.0	1
Amine oxidase [flavin-containing] A CHEMBL1951	IC50	6.89	6.89	130.0	1
Short transient receptor potential channel 5 CHEMBL1250411	IC50	6.35	6.35	450.0	1
Carbonic anhydrase 4 CHEMBL3729	Ki	6.25	6.25	568.3	1
Adenosine receptor A1 CHEMBL318	Ki	6.06	6.06	863.0	2
Adenosine A2 receptor CHEMBL2094117	Ki	6.01	6.01	966.0	1
Adenosine receptor A2a CHEMBL302	Ki	6.01	6.01	966.0	1
Unchecked CHEMBL612545	IC50	5.78	5.0133	1670.0	3
Xanthine dehydrogenase/oxidase CHEMBL1929	IC50	5.75	5.75	1800.0	1
Adenosine receptor A3 CHEMBL256	Ki	5.5	5.5	3150.0	2
Amine oxidase [flavin-containing] B CHEMBL2039	IC50	5.44	5.44	3650.0	1
Leishmania donovani CHEMBL367	IC50	5.26	5.26	5550.0	1
Peroxisome proliferator-activated receptor gamma CHEMBL235	Ki	5.25	5.25	5600.0	1
Protein disulfide-isomerase CHEMBL5422	Ki	5.23	5.23	5900.0	1
ATP-dependent translocase ABCB1 CHEMBL4302	Kd	5.23	5.23	5888.4	1
ATP-dependent translocase ABCB1 CHEMBL2573	Kd	5.23	5.23	5900.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.17	4.585	6740.0	2
Cholinesterase CHEMBL1914	Ki	5.16	5.16	6900.0	1
Mitochondrial import inner membrane translocase subunit TIM23 CHEMBL1741180	IC50	5.07	5.07	8560.0	1
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 CHEMBL4693	IC50	5.05	5.05	9000.0	1
Adenosine receptor A2a CHEMBL251	Ki	4.78	4.6667	16700.0	3
B16 CHEMBL381	IC50	4.77	4.77	17000.0	1
NON-PROTEIN TARGET CHEMBL3879801	EC50	4.72	4.645	19200.0	2
Human immunodeficiency virus 1 CHEMBL378	EC50	4.55	4.55	28000.0	1
HT-1080 CHEMBL614580	EC50	4.45	4.45	35700.0	1
Mitochondrial import inner membrane translocase subunit TIM10 CHEMBL1741194	IC50	4.45	4.45	35500.0	1
Plasmodium falciparum CHEMBL364	IC50	4.41	4.41	39400.0	1
L929 CHEMBL612267	EC50	4.4	4.35	40000.0	2
H9 CHEMBL614806	IC50	4.36	4.36	44000.0	1
Trypanosoma brucei rhodesiense CHEMBL612348	IC50	4.21	4.21	61060.0	1
Trypanosoma cruzi CHEMBL368	IC50	4.13	4.13	73270.0	1
HeLa CHEMBL399	EC50	4.1	4.1	79000.0	1
Acetylcholinesterase CHEMBL220	Ki	4.07	4.07	85600.0	1
A549 CHEMBL392	EC50	4.03	4.03	93600.0	1
Aromatase CHEMBL1978	Ki	4.0	4.0	100000.0	1
3-oxoacyl-acyl-carrier protein reductase CHEMBL4513	IC50	4.0	4.0	100000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Cytochrome P450 1B1	IC50	=	3.0	nM	8.52	Inhibition of human CYP1B1 expressed in Escherichia coli DH5alpha coexpressing h...	28458135
Acetylcholinesterase	IC50	=	12.0	nM	7.92	Inhibition of AChE (unknown origin)	-
Carbonic anhydrase 7	Ki	=	24.5	nM	7.61	Inhibition of human recombinant carbonic anhydrase 7 preincubated for 15 mins at...	26498393
Cytochrome P450 1B1	IC50	=	25.0	nM	7.6	Inhibition of human CYP1B1 by EROD assay	20696580
Cytochrome P450 1A2	IC50	=	40.0	nM	7.4	Inhibition of human CYP1A2 by EROD assay	20696580
Carbonic anhydrase 12	Ki	=	41.8	nM	7.38	Inhibition of human recombinant carbonic anhydrase 12 preincubated for 15 mins a...	26498393
Cytochrome P450 1A1	IC50	=	77.0	nM	7.11	Inhibition of human CYP1A1 by EROD assay	20696580
Amine oxidase [flavin-containing] A	IC50	=	130.0	nM	6.89	Inhibition of recombinant human MAO-A assessed as reduction in 4-hydroxyquinolin...	27754693
Short transient receptor potential channel 5	IC50	=	450.0	nM	6.35	Inhibition of human TRPC5 expressed in HEK293 cells assessed as reduction in gad...	30943030
Carbonic anhydrase 4	Ki	=	568.3	nM	6.25	Inhibition of human recombinant carbonic anhydrase 4 preincubated for 15 mins at...	26498393
Adenosine receptor A1	Ki	=	863.0	nM	6.06	Displacement of specific [3H]PIA binding from adenosine A1 receptor in rat brain...	8576921
Adenosine receptor A1	Ki	=	863.0	nM	6.06	Binding affinity at Adenosine A1 receptor in rat brain membranes by [3H]PIA disp...	8691424
Adenosine receptor A2a	Ki	=	966.0	nM	6.01	Affinity at Adenosine A2A receptor in rat striatal membranes by [3H]- CGS 21680 ...	8576921
Adenosine A2 receptor	Ki	=	966.0	nM	6.01	Binding affinity at Adenosine A2 receptor in rat striatal membranes by [3H]-CGS-...	8691424
Unchecked	IC50	=	1670.0	nM	5.78	Inhibition of beef heart mitochondrial NADH oxidase assessed per mg of protein	2959755
Xanthine dehydrogenase/oxidase	IC50	=	1800.0	nM	5.75	Inhibition of xanthine oxidase assessed as decrease in uric acid production by s...	9461655
Adenosine receptor A3	Ki	=	3150.0	nM	5.5	Displacement of [125I]AB-MECA binding to human Adenosine A3 receptor expressed i...	8576921
Adenosine receptor A3	Ki	=	3150.0	nM	5.5	Binding affinity against human adenosine A3 receptor in HEK293 cells using [125I...	8691424
Amine oxidase [flavin-containing] B	IC50	=	3650.0	nM	5.44	Inhibition of recombinant human MAO-B assessed as reduction in 4-hydroxyquinolin...	27754693
Leishmania donovani	IC50	=	5550.0	nM	5.26	Antileishmanial activity against Leishmania donovani MHOM/ET/67/L82 amastigotes ...	30145372

Literature References

PubMed	DOI	Target Context	# Activities
32912432	10.1016/j.bmc.2020.115663	Mus musculus	15
26517554	10.1021/acs.jnatprod.5b00075	ADMET	9
19615910	10.1016/j.bmc.2009.06.057	Unchecked	9
24727463	10.1016/j.ejmech.2014.04.002	Unchecked	7
19931462	10.1016/j.bmc.2009.10.063	Unchecked	6
31427220	10.1016/j.bmcl.2019.07.048	Nakaseomyces glabratus	6
32912432	10.1016/j.bmc.2020.115663	Unchecked	6
19615910	10.1016/j.bmc.2009.06.057	Tyrosinase	6
19615910	10.1016/j.bmc.2009.06.057	NON-PROTEIN TARGET	6
34922307	10.1016/j.bmc.2021.116564	Mesenchymal stem cells	6
31427220	10.1016/j.bmcl.2019.07.048	Candida albicans	5
9287415	10.1021/np960581z	L929	5
32912432	10.1016/j.bmc.2020.115663	NIH3T3	5
21824690	10.1016/j.ejmech.2011.07.031	HepG2	4
35471830	10.1021/acs.jnatprod.2c00080	Protein disulfide-isomerase	4
2959755	10.1021/np50051a014	Unchecked	4
-	10.1016/S0960-894X(01)80881-7	Escherichia coli	4
26517554	10.1021/acs.jnatprod.5b00075	Unchecked	4
1338212	10.1021/np50090a003	Human alphaherpesvirus 1	4
27720556	10.1016/j.bmc.2016.09.054	Mushroom tyrosinase	3

Data from ChEMBL 36 via Core Engine