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Compound Detail

CHEMBL232202

ARBUTIN
🧪 Phase II
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🧪 Phase II
OC[C@H]1O[C@@H](Oc2ccc(O)cc2)[C@H](O)[C@@H](O)[C@@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL232202
Name ARBUTIN
Phase Phase II
Structure Type MOL
InChI Key BJRNKVDFDLYUGJ-RMPHRYRLSA-N
Active Moiety CHEMBL537

Known Names

Arbutin Arbutinum Arbutoside NSC-4036 Ursin
7
Targets
59
Activities
2
Assay Types
0
PK Parameters
20
Publications
5
Known Names
1
Indications
1
Mechanisms

Molecular Properties

272.2
MW (Da)
-1.43
ALogP
7
HBA
5
HBD
119.6
PSA (Ų)
0.46
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product Prodrug

Extended Properties

Molecular Formula C12H16O7
MW 272.25
Aromatic Rings 1
Heavy Atoms 19
NP-Likeness 2.00

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Tyrosinase inhibitor INHIBITOR Tyrosinase ✓ ✓

Indications

Melanosis

Activity Summary

IC50 55 meas. best 5.66
EC50 4 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 5.66 5.66 2200.0 1
Tyrosinase
CHEMBL1973
 IC50 4.52 4.52 30260.0 1
Tyrosinase
CHEMBL5346
 IC50 4.52 4.29 30260.0 2
Mushroom tyrosinase
CHEMBL6066154
 IC50 4.4 4.4 40000.0 1
B16
CHEMBL381
 IC50 4.19 4.095 64000.0 2
Melan-a
CHEMBL4296474
 IC50 4.01 4.01 98050.0 1
Tyrosinase
CHEMBL3318
 IC50 4.0 4.0 100000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 2200.0 nM 5.66 Inhibition of melanin synthesis in NHEM after 24 hrs by liquid scintillation 19102656
Tyrosinase IC50 = 30260.0 nM 4.52 Inhibition of tyrosinase in Melan-a cells 17693086
Tyrosinase IC50 = 30260.0 nM 4.52 Inhibition of tyrosinase in mouse Melan-a cells by ELISA 20022495
Mushroom tyrosinase IC50 = 40000.0 nM 4.4 Inhibition of mushroom tyrosinase using L-[3,5-3H]-tyrosine as substrate incubat... 32787103
B16 IC50 = 64000.0 nM 4.19 Inhibition of alpha-MSH-stimulated melanogenesis in mouse B16 cells assessed as ... 31387790
Tyrosinase IC50 = 87500.0 nM 4.06 Inhibition of tyrosinase in mouse B16-F1 cells 30446440
Melan-a IC50 = 98050.0 nM 4.01 Inhibition of melanin formation in mouse Melan-a cells after 5 days by ELISA 20022495
B16 IC50 = 99000.0 nM 4.0 Inhibition of alpha-MSH-induced melanin synthesis in mouse B16 cells grown in a ... 21429753
Tyrosinase IC50 = 100000.0 nM 4.0 Inhibition of mushroom tyrosinase using L-tyrosine as a substrate after 30 mins ... 26824128

Literature References

PubMed DOI Target Context # Activities
26290401 10.1021/acs.jnatprod.5b00273 PBL 15
20189399 10.1016/j.bmc.2010.01.046 Unchecked 6
23270663 10.1016/j.bmc.2012.11.038 Unchecked 6
30520635 10.1021/acs.jnatprod.8b00167 B16-F10 6
19615910 10.1016/j.bmc.2009.06.057 Tyrosinase 6
24601675 10.1021/np401091f Unchecked 6
19615910 10.1016/j.bmc.2009.06.057 NON-PROTEIN TARGET 6
12444684 10.1021/np020128p Radical scavenging activity 5
30011202 10.1021/acs.jmedchem.8b00737 Tyrosinase 5
23376010 10.1016/j.bmc.2013.01.012 Unchecked 5
19615910 10.1016/j.bmc.2009.06.057 Unchecked 5
27756508 10.1016/j.bmc.2016.10.001 NON-PROTEIN TARGET 4
27756508 10.1016/j.bmc.2016.10.001 Mus musculus 4
22834923 10.1021/np3001078 Unchecked 3
30011202 10.1021/acs.jmedchem.8b00737 No relevant target 3
20729091 10.1016/j.bmc.2010.07.062 Tyrosinase 3
29763564 10.1021/acs.jmedchem.7b00967 Tyrosinase 3
30011202 10.1021/acs.jmedchem.8b00737 B16 3
29887353 10.1016/j.bmcl.2018.05.051 B16 3
27720556 10.1016/j.bmc.2016.09.054 B16-F10 3

Data from ChEMBL 36 via Core Engine