Compound Detail

CHEMBL131921

BIOCHANIN

Enter ChEMBL ID:

Free Research Context This compound will appear in recent viewed items on the research home for this browser.

COc1ccc(-c2coc3cc(O)cc(O)c3c2=O)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL131921
Name	BIOCHANIN
Phase	Preclinical
Structure Type	MOL
InChI Key	WUADCCWRTIWANL-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

284.3

MW (Da)

2.88

ALogP

HBA

HBD

79.9

PSA (Å²)

0.76

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	C16H12O5
MW	284.27
Aromatic Rings	3
Heavy Atoms	21
NP-Likeness	1.12

Activity Summary

IC50 27 meas. best 7.99

Ki 8 meas. best 7.28

EC50 5 meas. best 6.68

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Aromatase CHEMBL1978	IC50	7.99	5.6433	10.2	3
Carbonic anhydrase 12 CHEMBL3242	Ki	7.28	7.28	52.5	1
MCF7 CHEMBL387	EC50	6.68	6.68	210.0	1
Unchecked CHEMBL612545	EC50	6.52	6.45	300.0	2
Carbonic anhydrase 7 CHEMBL2326	Ki	6.43	6.43	371.5	1
Monoamine oxidase CHEMBL2095205	IC50	6.4	6.4	400.0	1
Cytochrome P450 1B1 CHEMBL4878	Ki	5.72	5.72	1900.0	1
Carbonyl reductase [NADPH] 1 CHEMBL5586	Ki	5.69	5.69	2030.0	1
Lysine-specific histone demethylase 1A CHEMBL6136	IC50	5.53	5.53	2950.0	3
MGC-803 CHEMBL3706566	IC50	5.53	5.29	2950.0	3
Unchecked CHEMBL612545	IC50	5.42	5.42	3800.0	1
Carbonic anhydrase 4 CHEMBL3729	Ki	5.15	5.15	7078.5	1
Fatty acid synthase CHEMBL4512	IC50	5.1	5.1	8000.0	1
MCF7 CHEMBL387	IC50	5.0	5.0	10000.0	1
17-beta-hydroxysteroid dehydrogenase type 2 CHEMBL2789	IC50	5.0	5.0	9900.0	2
Aromatase CHEMBL1978	Ki	4.92	4.92	12000.0	3
Trypanosoma brucei brucei CHEMBL612851	IC50	4.91	4.91	12300.0	1
Carbonyl reductase [NADPH] 1 CHEMBL5586	IC50	4.9	4.9	12710.0	1
Plasmodium falciparum CHEMBL364	IC50	4.46	4.46	34300.0	1
Silene noctiflora CHEMBL2367198	EC50	4.45	4.45	35800.0	1
Aldo-keto reductase family 1 member B10 CHEMBL5983	IC50	4.44	4.44	36100.0	1
Nuclear factor NF-kappa-B complex CHEMBL2094258	EC50	4.25	4.25	55941.0	1
Leishmania donovani CHEMBL367	IC50	4.05	4.05	89900.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.01	4.01	98000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	99.0	nM hr ml	-
AUC	480.8	ng.hr.mL-1	Rattus norvegicus
AUC	220.29	ng.hr.mL-1	Rattus norvegicus
CL	261.67	mL.min-1.kg-1	Rattus norvegicus
Cmax	3904.74	nM	Rattus norvegicus
Cmax	117.74	nM	Rattus norvegicus
T1/2	1.0	hr	Rattus norvegicus
T1/2	13.73	hr	Rattus norvegicus
Tmax	1.0	hr	-
Tmax	0.42	hr	Rattus norvegicus
Vd	10.56	L.kg-1	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Aromatase	IC50	=	10.2	nM	7.99	Inhibition of human placental microsome CYP19	20413308
Carbonic anhydrase 12	Ki	=	52.5	nM	7.28	Inhibition of human recombinant carbonic anhydrase 12 preincubated for 15 mins a...	26498393
MCF7	EC50	=	210.0	nM	6.68	Antiproliferative activity against estrogen-deficient human MCF7 cells after 72 ...	22464681
Unchecked	EC50	=	300.0	nM	6.52	Estrogenic activity at estrogen receptor in human MCF7:D5L cells co-expressing E...	22464681
Carbonic anhydrase 7	Ki	=	371.5	nM	6.43	Inhibition of human recombinant carbonic anhydrase 7 preincubated for 15 mins at...	26498393
Monoamine oxidase	IC50	=	400.0	nM	6.4	Inhibition of Hamster Liver mitochondrial Monoamine oxidase.	11063613
Unchecked	EC50	=	420.0	nM	6.38	Estrogenic activity at estrogen receptor in human Ishikawa cells assessed as ind...	22464681
Cytochrome P450 1B1	Ki	=	1900.0	nM	5.72	Inhibition of CYP1B1 in human liver microsomes coexpressing recombinant human cy...	28458135
Carbonyl reductase [NADPH] 1	Ki	=	2030.0	nM	5.69	Binding affinity to human recombinant carbonyl reductase 1 expressed in Escheric...	19097799
Lysine-specific histone demethylase 1A	IC50	=	2950.0	nM	5.53	Inhibition of recombinant LSD1 (unknown origin) using H3K4me2 as a substrate mea...	33581557
Lysine-specific histone demethylase 1A	IC50	=	2950.0	nM	5.53	Inhibition of recombinant LSD1 (unknown origin) incubated for 1 hr	35820351
Lysine-specific histone demethylase 1A	IC50	=	2950.0	nM	5.53	Inhibition of recombinant KDM1A (unknown origin) using H3K4Me2 peptide as substr...	35101649
MGC-803	IC50	=	2950.0	nM	5.53	Antiproliferative activity against human MGC-803 cells assessed as reduction in ...	33619958
Unchecked	IC50	=	3800.0	nM	5.42	Inhibition of alpha-Glucosidase (unknown origin) using pNPG as substrate incubat...	32196343
MGC-803	IC50	=	6770.0	nM	5.17	Antiproliferative activity against human MGC-803 cells assessed as reduction in ...	33581557
MGC-803	IC50	=	6770.0	nM	5.17	Antiproliferative activity against human MGC-803 cells assessed as reduction in ...	33619958
Carbonic anhydrase 4	Ki	=	7078.5	nM	5.15	Inhibition of human recombinant carbonic anhydrase 4 preincubated for 15 mins at...	26498393
Fatty acid synthase	IC50	=	8000.0	nM	5.1	Inhibition of FabZ	16722653
MCF7	IC50	=	10000.0	nM	5.0	Antiproliferative activity against human MCF7 cells assessed as inhibition of ce...	33257172
17-beta-hydroxysteroid dehydrogenase type 2	IC50	=	9900.0	nM	5.0	Inhibition of human 17beta-HSD2 expressed in HEK293 cell lysates incubated for 1...	28319389

Literature References

PubMed	DOI	Target Context	# Activities
36181478	10.1021/acs.jnatprod.2c00457	A549	48
23030687	10.1021/jf3023589	Root	33
23030687	10.1021/jf3023589	Shoot	32
-	10.1007/s00044-010-9445-8	Rattus norvegicus	9
28964936	10.1016/j.ejmech.2017.09.014	Mycobacterium avium	8
-	10.6019/CHEMBL5303304	Fibroblast	7
22464681	10.1016/j.bmc.2012.03.012	Unchecked	6
-	10.6019/CHEMBL5303304	U2OS	6
30199256	10.1021/acs.jnatprod.8b00131	Progesterone receptor	6
19097799	10.1016/j.bmc.2008.11.076	Carbonyl reductase [NADPH] 1	6
11063613	10.1021/jm990614i	Monoamine oxidase	5
11063613	10.1021/jm990614i	Aldehyde dehydrogenase, mitochondrial	5
33359607	10.1016/j.bmcl.2020.127761	BV-2	4
22464681	10.1016/j.bmc.2012.03.012	MCF7	4
21493073	10.1016/j.bmc.2011.03.040	3T3-L1	4
19928832	10.1021/np900676y	T47D	4
19928832	10.1021/np900676y	MCF7	4
28964936	10.1016/j.ejmech.2017.09.014	Unchecked	4
3069957	10.1021/np50060a006	Salmonella typhimurium	3
15911319	10.1016/j.bmc.2005.03.050	Aromatase	3

Data from ChEMBL 36 via Core Engine