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Compound Detail

CHEMBL559089

N-CAFFEOYLSEROTONIN
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O=C(/C=C/c1ccc(O)c(O)c1)NCCc1c[nH]c2ccc(O)cc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL559089
Name N-CAFFEOYLSEROTONIN
Phase Preclinical
Structure Type MOL
InChI Key YXKFALZVRFVXFA-QHHAFSJGSA-N
6
Targets
10
Activities
3
Assay Types
0
PK Parameters
9
Publications
0
Known Names

Molecular Properties

338.4
MW (Da)
2.66
ALogP
4
HBA
5
HBD
105.6
PSA (Ų)
0.36
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H18N2O4
MW 338.36
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness 0.40

Activity Summary

IC50 5 meas. best 4.82
EC50 3 meas. best 5.09
Ki 2 meas. best 4.19

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
No relevant target
CHEMBL2362975
 EC50 5.09 5.09 8100.0 2
B16
CHEMBL381
 IC50 4.82 4.82 15000.0 1
Radical scavenging activity
CHEMBL613712
 EC50 4.71 4.71 19400.0 1
Tyrosinase
CHEMBL5346
 IC50 4.55 4.55 28000.0 1
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 4.37 4.37 42500.0 1
Alpha-glucosidase MAL62
CHEMBL4357
 IC50 4.32 4.32 48200.0 1
Alpha-glucosidase MAL62
CHEMBL4357
 Ki 4.19 4.19 64400.0 1
Prostaglandin G/H synthase 2
CHEMBL230
 Ki 4.18 4.18 65500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
No relevant target EC50 = 8100.0 nM 5.09 Antioxidant activity assessed as DPPH free radical scavenging activity by spectr... 31376564
No relevant target EC50 = 8100.0 nM 5.09 Antioxidant activity assessed as DPPH radical scavenging activity measured after... 38107170
B16 IC50 = 15000.0 nM 4.82 Antimelanogenic activity in mouse B16 cells assessed as inhibition of intracellu... 19524439
Radical scavenging activity EC50 = 19400.0 nM 4.71 Antioxidant activity assessed as DPPH radical scavenging activity by spectrophot... 21377874
Tyrosinase IC50 = 28000.0 nM 4.55 Inhibition of catecholase activity of tyrosinase in mouse B16 cells assessed as ... 19524439
Prostaglandin G/H synthase 2 IC50 = 42500.0 nM 4.37 Inhibition of COX2 after 5 mins by spectrophotometric analysis 22386242
Alpha-glucosidase MAL62 IC50 = 48200.0 nM 4.32 Inhibition of yeast alpha-glucosidase using p-nitrophenyl-alpha-D-glucopyranosid... -
Alpha-glucosidase MAL62 Ki = 64400.0 nM 4.19 Uncompetitive inhibition of yeast alpha-glucosidase by Lineweaver-Burk plot anal... -
Prostaglandin G/H synthase 2 Ki = 65500.0 nM 4.18 Uncompetitive inhibition of COX2 by Lineweaver-Burk plot analysis 22386242

Literature References

PubMed DOI Target Context # Activities
19524439 10.1016/j.bmcl.2009.05.115 Tyrosinase 4
19524439 10.1016/j.bmcl.2009.05.115 B16 3
22386242 10.1016/j.bmcl.2012.02.002 Prostaglandin G/H synthase 2 3
- 10.1007/s00044-011-9699-9 Alpha-glucosidase MAL62 3
22386242 10.1016/j.bmcl.2012.02.002 Prostaglandin G/H synthase 1 2
21377874 10.1016/j.bmcl.2011.02.028 Radical scavenging activity 1
21377874 10.1016/j.bmcl.2011.02.028 Tyrosinase 1
31376564 10.1016/j.ejmech.2019.07.064 No relevant target 1
38107170 10.1039/d3md00560g No relevant target 1

Data from ChEMBL 36 via Core Engine