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Compound Detail

CHEMBL73930

TANGERETIN
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COc1ccc(-c2cc(=O)c3c(OC)c(OC)c(OC)c(OC)c3o2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL73930
Name TANGERETIN
Phase Preclinical
Structure Type MOL
InChI Key ULSUXBXHSYSGDT-UHFFFAOYSA-N
10
Targets
16
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

372.4
MW (Da)
3.50
ALogP
7
HBA
0
HBD
76.4
PSA (Ų)
0.66
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C20H20O7
MW 372.37
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness 0.83

Activity Summary

IC50 14 meas. best 5.17
Ki 2 meas. best 5.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 5.17 4.79 6800.0 3
Delta-type opioid receptor
CHEMBL3222
 Ki 5.16 5.16 7000.0 1
P2Y purinoceptor 2
CHEMBL1075298
 IC50 4.92 4.92 12000.0 1
Mu-type opioid receptor
CHEMBL2858
 Ki 4.79 4.79 16300.0 1
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 IC50 4.77 4.745 17000.0 2
Monocyte
CHEMBL614076
 IC50 4.52 4.52 30000.0 1
ATP-dependent translocase ABCB1
CHEMBL4302
 IC50 4.41 4.41 39000.0 1
SH-SY5Y
CHEMBL614910
 IC50 4.38 4.38 41200.0 1
3T3-L1
CHEMBL614510
 IC50 4.32 4.32 48000.0 1
HT-29
CHEMBL384
 IC50 4.11 4.11 77000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 6800.0 nM 5.17 Inhibition of PMA-stimulated pro MMP9 production in human SRA 01/04 cells after ... 22047798
Delta-type opioid receptor Ki = 7000.0 nM 5.16 Displacement of [3H]DPDPE from delta opioid receptor in CD1 mouse whole brain mi... 25562563
P2Y purinoceptor 2 IC50 = 12000.0 nM 4.92 Antagonist activity at mouse P2Y2 27413802
Mu-type opioid receptor Ki = 16300.0 nM 4.79 Displacement of [3H]DAMGO from mu opioid receptor in CD1 mouse whole brain minus... 25562563
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 17000.0 nM 4.77 Inhibition of BCRP expressed in MCF-7 MX cells using Hoechst 33342 staining 21354800
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 19000.0 nM 4.72 Inhibition of BCRP expressed in MDCK cells using Hoechst 33342 staining 21354800
Unchecked IC50 = 19000.0 nM 4.72 Inhibition of P-gp expressed in A2780adr cells by calcein AM accumulation assay 21354800
Monocyte IC50 = 30000.0 nM 4.52 Inhibition of TNFalpha expression in LPS-stimulated human monocytes treated 30 m... 10096854
Unchecked IC50 = 33200.0 nM 4.48 Inhibition of TNFalpha-stimulated pro MMP9 production in human SRA 01/04 cells a... 22047798
ATP-dependent translocase ABCB1 IC50 = 39000.0 nM 4.41 Inhibition of MDR1 expressed in MDCK cells using rhodamine 123 staining by flow ... 21354800
SH-SY5Y IC50 = 41200.0 nM 4.38 Growth inhibition of human SHSY5Y cells assessed as viable cells after 48 hrs by... 18282757
3T3-L1 IC50 = 48000.0 nM 4.32 Anticorpulence activity against mouse 3T3L1 cells assessed as inhibition of lipi... 19054677
HT-29 IC50 = 77000.0 nM 4.11 Anticancer activity against human HT-29 cells after 72 hrs by MTT assay 19054677

Literature References

PubMed DOI Target Context # Activities
23137376 10.1021/np3003468 LoVo 13
23137376 10.1021/np3003468 Unchecked 9
- 10.1039/C4MD00196F Unchecked 4
- 10.1039/C4MD00196F Quinolone resistance protein NorA 3
3069957 10.1021/np50060a006 Salmonella typhimurium 3
23137376 10.1021/np3003468 ATP-dependent translocase ABCB1 3
- 10.1039/C4MD00196F Fluoroquinolone resistance protein 2
21354800 10.1016/j.bmc.2010.12.043 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
21354800 10.1016/j.bmc.2010.12.043 Unchecked 2
11982408 10.1021/jf011382a Citrus 2
11982408 10.1021/jf011382a Phytophthora citrophthora 2
22047798 10.1016/j.bmc.2011.10.001 Unchecked 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
469554 10.1021/np50001a002 Unchecked 2
15504753 10.1038/sj.bjp.0706008 ATP-dependent translocase ABCB1 2
10820110 10.1021/jf990282q Spodoptera litura 2
15640378 10.1124/dmd.104.002337 Solute carrier organic anion transporter family member 2B1 2
- 10.1039/C4MD00196F ATP-dependent translocase ABCB1 2
17391969 10.1016/j.bmc.2007.03.021 HL-60 2

Data from ChEMBL 36 via Core Engine