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Compound Detail

CHEMBL399910

PINOCEMBRIN
🧪 Phase II
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🧪 Phase II
O=C1C[C@@H](c2ccccc2)Oc2cc(O)cc(O)c21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL399910
Name PINOCEMBRIN
Phase Phase II
Structure Type MOL
InChI Key URFCJEUYXNAHFI-ZDUSSCGKSA-N

Known Names

(2s)-pinocembrin Dihydrochrysin Galangin flavanone NSC-279005 NSC-43318 Pinocembrin
13
Targets
21
Activities
2
Assay Types
0
PK Parameters
20
Publications
6
Known Names
1
Indications

Molecular Properties

256.3
MW (Da)
2.80
ALogP
4
HBA
2
HBD
66.8
PSA (Ų)
0.82
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula C15H12O4
MW 256.26
Aromatic Rings 2
Heavy Atoms 19
NP-Likeness 1.65

Indications

Ischemic Stroke

Activity Summary

IC50 15 meas. best 6.05
EC50 6 meas. best 4.76

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Aromatase
CHEMBL1978
 IC50 6.05 6.05 900.0 1
Cytochrome P450 1A2
CHEMBL3356
 IC50 5.83 5.83 1491.0 1
Cytochrome P450 1B1
CHEMBL4878
 IC50 5.78 5.78 1679.0 1
Taenia crassiceps
CHEMBL612894
 IC50 5.7 5.7 2000.0 1
Unchecked
CHEMBL612545
 IC50 5.37 5.37 4300.0 1
Cytochrome P450 1A1
CHEMBL2231
 IC50 5.1 5.1 7906.0 1
Zika virus
CHEMBL4296612
 EC50 4.76 4.76 17440.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.74 4.445 18100.0 2
B16-F10
CHEMBL612656
 IC50 4.52 4.52 30100.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 4.17 4.145 68000.0 2
4-hydroxyphenylpyruvate dioxygenase
CHEMBL2242740
 IC50 4.14 4.14 73000.0 1
HT-1080
CHEMBL614580
 IC50 4.14 4.14 72800.0 1
HT-1080
CHEMBL614580
 EC50 4.03 4.03 92400.0 1
NCI-H187
CHEMBL2366276
 IC50 4.02 4.02 95530.0 1
KB
CHEMBL398
 IC50 4.0 4.0 99160.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Aromatase IC50 = 900.0 nM 6.05 Inhibition of aromatase (unknown origin) -
Cytochrome P450 1A2 IC50 = 1491.0 nM 5.83 Inhibition of human CYP1A2 by EROD assay 20696580
Cytochrome P450 1B1 IC50 = 1679.0 nM 5.78 Inhibition of human CYP1B1 by EROD assay 20696580
Taenia crassiceps IC50 = 2000.0 nM 5.7 Cysticidal activity against Taenia crassiceps cysts after 11 days by trypan blue... 28231520
Unchecked IC50 = 4300.0 nM 5.37 Inhibition of Saccharomyces cerevisiae alpha-glucosidase using p-nitrophenyl alp... 30835120
Cytochrome P450 1A1 IC50 = 7906.0 nM 5.1 Inhibition of human CYP1A1 by EROD assay 20696580
Zika virus EC50 = 17440.0 nM 4.76 Antiviral activity against Zika virus PRVABC59 Puerto Rico infected in human JEG... 31549836
NON-PROTEIN TARGET IC50 = 18100.0 nM 4.74 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-... 23743282
B16-F10 IC50 = 30100.0 nM 4.52 Cytotoxicity against mouse B16-F10 cells assessed as reduction in cell viability... 27720556
NON-PROTEIN TARGET EC50 = 68000.0 nM 4.17 Antiproliferative activity against mouse B16-BL6 cells after 72 hrs by MTT assay 12027739
NON-PROTEIN TARGET IC50 = 71000.0 nM 4.15 Cytotoxicity against mouse Colon 26-L5 cells after 72 hrs by MTT assay 19689125
HT-1080 IC50 = 72800.0 nM 4.14 Cytotoxicity against human HT1080 cells after 72 hrs by MTT assay 19689125
4-hydroxyphenylpyruvate dioxygenase IC50 = 73000.0 nM 4.14 Inhibition of Arabidopsis thaliana HPPD expressed in Escherichia coli JM105 usin... 28128559
NON-PROTEIN TARGET EC50 = 75600.0 nM 4.12 Antiproliferative activity against mouse 26-L5 cells after 72 hrs by MTT assay 12027739
HT-1080 EC50 = 92400.0 nM 4.03 Antiproliferative activity against human HT1080 cells after 72 hrs by MTT assay 12027739
NCI-H187 IC50 = 95530.0 nM 4.02 Cytotoxicity against human NCI-H187 cells after 5 days by Resazurin Microplate A... 20362442
KB IC50 = 99160.0 nM 4.0 Cytotoxicity against human KB cells after 3 days by Resazurin Microplate Assay 20362442

Literature References

PubMed DOI Target Context # Activities
22459211 10.1016/j.bmc.2012.02.039 Unchecked 11
26517554 10.1021/acs.jnatprod.5b00075 ADMET 10
19342224 10.1016/j.biortech.2009.02.050 Xanthogaleruca luteola 6
19342224 10.1016/j.biortech.2009.02.050 Epilachna 6
19342224 10.1016/j.biortech.2009.02.050 Spodoptera frugiperda 5
19719119 10.1021/jm900199u Aryl hydrocarbon receptor 4
19928832 10.1021/np900676y T47D 4
19928832 10.1021/np900676y MCF7 4
36731248 10.1016/j.bmc.2023.117187 Staphylococcus aureus 3
26517554 10.1021/acs.jnatprod.5b00075 Unchecked 3
1593282 10.1021/np50081a012 Unchecked 3
16621533 10.1016/j.bmcl.2005.12.075 Genome polyprotein 3
- 10.1007/s00044-013-0485-8 Mycobacterium tuberculosis 2
9287415 10.1021/np960581z L929 2
12027739 10.1021/np010486c NON-PROTEIN TARGET 2
21973101 10.1021/np200557e HT-29 2
30835120 10.1021/acs.jnatprod.8b00581 Unchecked 2
17637507 10.1016/j.bmc.2007.06.025 Serine/threonine-protein kinase pim-1 2
19236029 10.1021/np800698d Enterococcus faecalis 2
19682913 10.1016/j.bmc.2009.07.041 Tumor necrosis factor receptor superfamily member 10B 2

Data from ChEMBL 36 via Core Engine