Compound Detail

CHEMBL266564

TILIROSIDE

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O=C(/C=C/c1ccc(O)cc1)OC[C@H]1O[C@@H](Oc2c(-c3ccc(O)cc3)oc3cc(O)cc(O)c3c2=O)[C@H](O)[C@@H](O)[C@@H]1O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL266564
Name	TILIROSIDE
Phase	Preclinical
Structure Type	MOL
InChI Key	DVGGLGXQSFURLP-VWMSDXGPSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

594.5

MW (Da)

1.73

ALogP

HBA

HBD

216.6

PSA (Å²)

0.12

QED

Ro5 Violations

Rot. Bonds

Natural Product First in Class Prodrug

IC50 5 meas. best 6.16

Ki 3 meas. best 8.34

EC50 1 meas. best 6.81

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Carbonic anhydrase 7 CHEMBL2326	Ki	8.34	8.34	4.6	1
Carbonic anhydrase 12 CHEMBL3242	Ki	6.87	6.87	134.3	1
HepG2 CHEMBL395	EC50	6.81	6.81	155.0	1
Cytochrome P450 3A4 CHEMBL340	IC50	6.16	6.16	700.0	1
Monocyte CHEMBL614076	IC50	5.28	5.28	5200.0	1
Carbonic anhydrase 4 CHEMBL3729	Ki	5.26	5.26	5468.7	1
Glyceraldehyde-3-phosphate dehydrogenase, glycosomal CHEMBL5926	IC50	4.34	4.34	46000.0	1
Ehrlich CHEMBL614641	IC50	4.16	4.16	69500.0	1
Tyrosinase CHEMBL1973	IC50	4.11	4.11	78530.0	1

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Carbonic anhydrase 7	Ki	=	4.6	nM	8.34	Inhibition of human recombinant carbonic anhydrase 7 preincubated for 15 mins at...	26498393
Carbonic anhydrase 12	Ki	=	134.3	nM	6.87	Inhibition of human recombinant carbonic anhydrase 12 preincubated for 15 mins a...	26498393
HepG2	EC50	=	155.0	nM	6.81	Increase in glucose consumption in insulin-resistant human HepG2 cells after 24 ...	21856048
Cytochrome P450 3A4	IC50	=	700.0	nM	6.16	Inhibition of human CYP3A4	15568772
Monocyte	IC50	=	5200.0	nM	5.28	Inhibition of procoagulant activity in monocyte from human blood assessed as cou...	8882428
Carbonic anhydrase 4	Ki	=	5468.7	nM	5.26	Inhibition of human recombinant carbonic anhydrase 4 preincubated for 15 mins at...	26498393
Glyceraldehyde-3-phosphate dehydrogenase, glycosomal	IC50	=	46000.0	nM	4.34	Inhibition of Trypanosoma cruzi recombinant glycosomal GAPDH expressed in Escher...	19254846
Ehrlich	IC50	=	69500.0	nM	4.16	Cytotoxicity against mouse Ehrlich carcinoma cells	19254846
Tyrosinase	IC50	=	78530.0	nM	4.11	Inhibition of tyrosinase (unknown origin)	35395370

PubMed	DOI	Target Context	# Activities
17400451	10.1016/j.bmcl.2007.03.051	Mus musculus	81
21719287	10.1016/j.bmcl.2011.05.087	Osteoblast	6
19596200	10.1016/j.bmc.2009.06.050	Unchecked	4
19596200	10.1016/j.bmc.2009.06.050	RBL-2H3	4
38896992	10.1016/j.ejmech.2024.116610	Isocitrate dehydrogenase [NADP] cytoplasmic	3
17287127	10.1016/j.bmc.2007.01.035	Tyrosinase	2
22901896	10.1016/j.bmcl.2012.07.089	Pyricularia grisea	2
22901896	10.1016/j.bmcl.2012.07.089	Thielaviopsis paradoxa	2
22901896	10.1016/j.bmcl.2012.07.089	Athelia rolfsii	2
22901896	10.1016/j.bmcl.2012.07.089	Alternaria mali	2
19254846	10.1016/j.bmc.2009.01.079	Glyceraldehyde-3-phosphate dehydrogenase, glycosomal	1
17400451	10.1016/j.bmcl.2007.03.051	Liver	1
1710653	10.1021/np50073a012	Human immunodeficiency virus type 1 reverse transcriptase	1
19596200	10.1016/j.bmc.2009.06.050	Radical scavenging activity	1
19254846	10.1016/j.bmc.2009.01.079	Trypanosoma cruzi	1
9461655	10.1021/np970237h	Xanthine dehydrogenase/oxidase	1
9917285	10.1021/np980179f	Micrococcus luteus	1
9917285	10.1021/np980179f	Staphylococcus aureus	1
9917285	10.1021/np980179f	Bacillus cereus	1
15568772	10.1021/np0400104	Cytochrome P450 3A4	1

Data from ChEMBL 36 via Core Engine