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Compound Detail

CHEMBL250450

ISOQUERCETIN
🧪 Phase II
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🧪 Phase II
O=c1c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c(-c2ccc(O)c(O)c2)oc2cc(O)cc(O)c12

Basic Information

ChEMBL ID CHEMBL250450
Name ISOQUERCETIN
Phase Phase II
Structure Type MOL
InChI Key OVSQVDMCBVZWGM-QSOFNFLRSA-N

Known Names

3-glucosylquercetin Contigoside b FEMA NO. 4225 Glucosyl-3-quercetin Hirsutrin Isoquercetin Isoquercetin, (-)- Isoquercitrin Isoquercitroside Isotrifoliin Isotrifolin NSC-115918 +10 more
27
Targets
61
Activities
3
Assay Types
0
PK Parameters
20
Publications
22
Known Names
5
Indications

Molecular Properties

464.4
MW (Da)
-0.54
ALogP
12
HBA
8
HBD
210.5
PSA (Ų)
0.23
QED
2
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula C21H20O12
MW 464.38
Aromatic Rings 3
Heavy Atoms 33
NP-Likeness 2.16

Indications

Anemia, Sickle Cell Renal Insufficiency, Chronic Severe Acute Respiratory Syndrome Carcinoma, Renal Cell Kidney Neoplasms

Activity Summary

IC50 41 meas. best 6.52
EC50 11 meas. best 8.87
Ki 9 meas. best 8.42

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Pyruvate kinase PKM
CHEMBL1075189
EC50 8.87 8.87 1.3 1
Carbonic anhydrase 7
CHEMBL2326
Ki 8.42 8.42 3.8 1
Carbonic anhydrase 12
CHEMBL3242
Ki 7.28 7.025 52.1 2
Carbonic anhydrase 4
CHEMBL3729
Ki 7.12 7.12 75.7 1
Unchecked
CHEMBL612545
IC50 6.52 4.96 300.0 7
Carbonic anhydrase 2
CHEMBL205
Ki 6.39 5.8 410.0 2
Lysine-specific histone demethylase 1A
CHEMBL6136
IC50 6.02 6.02 950.0 1
Lysine-specific histone demethylase 1A
CHEMBL6136
Ki 6.0 6.0 1000.0 1
Xanthine dehydrogenase/oxidase
CHEMBL1929
IC50 5.8 5.19 1600.0 2
Intestinal-type alkaline phosphatase
CHEMBL3151
IC50 5.78 5.78 1660.0 1
Arginase
CHEMBL3108635
IC50 5.7 5.7 2000.0 1
Plasmodium falciparum
CHEMBL364
IC50 5.39 5.325 4050.0 2
Aldo-keto reductase family 1 member B1
CHEMBL2622
IC50 5.36 5.36 4400.0 1
Aldo-keto reductase family 1 member B1
CHEMBL1900
IC50 5.35 5.35 4500.0 1
Intestinal-type alkaline phosphatase
CHEMBL5573
IC50 5.28 5.165 5250.0 2
Protein disulfide-isomerase
CHEMBL5422
IC50 5.15 5.15 7100.0 1
No relevant target
CHEMBL2362975
IC50 5.04 4.58 9200.0 2
Radical scavenging activity
CHEMBL613712
IC50 4.93 4.5975 11700.0 4
NON-PROTEIN TARGET
CHEMBL3879801
IC50 4.87 4.87 13390.0 1
Alkaline phosphatase, tissue-nonspecific isozyme
CHEMBL5979
IC50 4.85 4.85 14000.0 1
Solute carrier organic anion transporter family member 2B1
CHEMBL1743124
IC50 4.83 4.83 14791.1 2
Aldo-keto reductase family 1 member B1
CHEMBL4559
IC50 4.8 4.8 16000.0 1
Amine oxidase [flavin-containing] A
CHEMBL1951
IC50 4.72 4.72 19060.0 1
BV-2
CHEMBL614781
IC50 4.7 4.475 19800.0 2
Unchecked
CHEMBL612545
Ki 4.59 4.51 25900.0 2
Bifunctional epoxide hydrolase 2
CHEMBL2409
IC50 4.55 4.55 28430.0 1
RAW264.7
CHEMBL612557
IC50 4.21 4.165 61200.0 2
N9
CHEMBL613516
IC50 4.12 4.12 75200.0 1
Brain
CHEMBL613617
EC50 4.03 4.03 94000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Pyruvate kinase PKM EC50 = 1.34 nM 8.87 Activation of recombinant PKM2 (unknown origin) Glu397, Lys3I I, Asp354, Leu353,... 34726055
Carbonic anhydrase 7 Ki = 3.8 nM 8.42 Inhibition of human recombinant carbonic anhydrase 7 preincubated for 15 mins at... 26498393
Carbonic anhydrase 12 Ki = 52.1 nM 7.28 Inhibition of human recombinant carbonic anhydrase 12 preincubated for 15 mins a... 26498393
Carbonic anhydrase 4 Ki = 75.7 nM 7.12 Inhibition of human recombinant carbonic anhydrase 4 preincubated for 15 mins at... 26498393
Carbonic anhydrase 12 Ki = 170.0 nM 6.77 Inhibition of human recombinant carbonic anhydrase 12 26498393
Unchecked IC50 = 300.0 nM 6.52 Inhibition of Trichomonas vaginalis adenosine-guanosine preferring ribohydrolase... 26592812
Carbonic anhydrase 2 Ki = 410.0 nM 6.39 Inhibition of human recombinant carbonic anhydrase 2 26498393
Unchecked IC50 = 900.0 nM 6.05 Inhibition of Trichomonas vaginalis adenosine-guanosine preferring ribohydrolase... 26592812
Lysine-specific histone demethylase 1A IC50 = 950.0 nM 6.02 Inhibition of LSD1 (unknown origin) by fluorescence assay 30552007
Lysine-specific histone demethylase 1A Ki = 1000.0 nM 6.0 Competitive inhibition of LSD1 (unknown origin) using H3Kme2 as substrate by Lin... 30552007
Xanthine dehydrogenase/oxidase IC50 = 1600.0 nM 5.8 Inhibition of xanthine oxidase (unknown origin) using xanthine as substrate prei... 28511908
Intestinal-type alkaline phosphatase IC50 = 1660.0 nM 5.78 PUBCHEM_BIOASSAY: Dose Response confirmation of uHTS hits from a small molecule ... -
Arginase IC50 = 2000.0 nM 5.7 Inhibition of Leishmania amazonensis recombinant arginase expressed in Escherich... 24521209
Plasmodium falciparum IC50 = 4050.0 nM 5.39 Antiplasmodial activity against chloroquine-resistant blood stage Plasmodium fal... 24530004
Aldo-keto reductase family 1 member B1 IC50 = 4400.0 nM 5.36 Inhibition of Sprague-Dawley rat lens aldose reductase 22264115
Aldo-keto reductase family 1 member B1 IC50 = 4500.0 nM 5.35 Inhibition of human recombinant aldose reductase using D-glyceraldehyde as subst... 22261024
Intestinal-type alkaline phosphatase IC50 = 5250.0 nM 5.28 PUBCHEM_BIOASSAY: Dose Response confirmation of uHTS hits from a small molecule ... -
Plasmodium falciparum IC50 = 5540.0 nM 5.26 Antiplasmodial activity against chloroquine-sensitive blood stage Plasmodium fal... 24530004
Carbonic anhydrase 2 Ki = 6211.2 nM 5.21 Inhibition of human recombinant carbonic anhydrase 2 preincubated for 15 mins at... 26498393
Protein disulfide-isomerase IC50 = 7100.0 nM 5.15 Non-covalent inhibition of PDI (unknown origin) by GSSG fluorescence assay 38381886

Literature References

PubMed DOI Target Context # Activities
30552007 10.1016/j.bmc.2018.12.013 MDA-MB-231 24
25397870 10.1021/np500231g Danio rerio 8
24433966 10.1016/j.bmc.2013.12.062 B16-F10 7
24853321 10.1016/j.bmc.2014.04.053 B16-F0 7
24485782 10.1016/j.bmcl.2014.01.028 NON-PROTEIN TARGET 7
3430165 10.1021/np50052a017 Angiotensin-converting enzyme 7
25987378 10.1016/j.bmcl.2015.04.052 Unchecked 6
24679441 10.1016/j.bmcl.2014.03.014 RAW264.7 6
24433966 10.1016/j.bmc.2013.12.062 Tyrosinase 6
21353543 10.1016/j.bmcl.2011.01.066 RAW264.7 5
17190444 10.1021/np068016b Unchecked 5
30552007 10.1016/j.bmc.2018.12.013 Lysine-specific histone demethylase 1A 5
27623545 10.1016/j.bmcl.2016.08.094 NON-PROTEIN TARGET 5
34971873 10.1016/j.ejmech.2021.114068 Candida albicans 5
25987378 10.1016/j.bmcl.2015.04.052 ADMET 5
17997321 10.1016/j.bmc.2007.10.072 BGC-823 4
- 10.1007/s00044-013-0563-y Huh-7 4
25564380 10.1016/j.bmc.2014.12.015 Unchecked 4
10479312 10.1021/np9900674 Radical scavenging activity 4
24485782 10.1016/j.bmcl.2014.01.028 Tartrate-resistant acid phosphatase type 5 4

Data from ChEMBL 36 via Core Engine