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Compound Detail

CHEMBL311498

CIANIDANOL
💊 Approved Drug
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💊 Approved Drug
Oc1cc(O)c2c(c1)O[C@H](c1ccc(O)c(O)c1)[C@@H](O)C2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL311498
Name CIANIDANOL
Phase Approved
Structure Type MOL
InChI Key PFTAWBLQPZVEMU-DZGCQCFKSA-N

Known Names

Catechin Catechin, d- Catechinic acid Catechuic acid Catergen Cianidanol D-catechol NSC-2819
20
Targets
71
Activities
4
Assay Types
3
PK Parameters
20
Publications
8
Known Names
1
Mechanisms

Molecular Properties

290.3
MW (Da)
1.55
ALogP
6
HBA
5
HBD
110.4
PSA (Ų)
0.51
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1977
Availability Withdrawn
Chirality Single Enantiomer

Flags

Withdrawn Natural Product

Extended Properties

Molecular Formula C15H14O6
MW 290.27
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness 2.30

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Unknown - - ✓ ✓

Drug Warnings

Withdrawn
hematological toxicity
Hemolytic Anemia
Country: France; Spain; Germany; Switzerland   Year: 1985

Activity Summary

IC50 50 meas. best 7.22
EC50 16 meas. best 4.59
Kd 4 meas. best 5.8
Ki 1 meas. best 6.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mushroom tyrosinase
CHEMBL6066154
 IC50 7.22 7.19 60.0 2
Arginase
CHEMBL3108635
 Ki 6.22 6.22 600.0 1
Sclerostin
CHEMBL3580487
 Kd 5.8 5.765 1579.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.79 5.3325 1610.0 4
Arginase
CHEMBL3108635
 IC50 5.77 5.77 1700.0 1
Unchecked
CHEMBL612545
 IC50 5.75 4.9457 1800.0 7
Prostaglandin G/H synthase 1
CHEMBL2949
 IC50 5.39 5.045 4100.0 2
Radical scavenging activity
CHEMBL613712
 IC50 5.37 4.84 4300.0 2
Plasmodium falciparum
CHEMBL364
 IC50 5.23 5.2067 5900.0 3
No relevant target
CHEMBL2362975
 IC50 4.62 4.62 23900.0 1
Melatonin receptor type 1A
CHEMBL1945
 IC50 4.59 4.59 25800.0 1
Melatonin receptor type 1A
CHEMBL1945
 EC50 4.59 4.59 25800.0 1
BV-2
CHEMBL614781
 IC50 4.58 4.58 26110.0 1
Beta-secretase 1
CHEMBL4822
 IC50 4.46 4.46 35000.0 1
Prostaglandin G/H synthase 1
CHEMBL221
 IC50 4.43 4.265 36700.0 2
Prostaglandin G/H synthase 1
CHEMBL2949
 Kd 4.39 4.39 40700.0 1
Melatonin receptor type 1B
CHEMBL1946
 IC50 4.33 4.33 47300.0 1
Melatonin receptor type 1B
CHEMBL1946
 EC50 4.33 4.33 47300.0 1
Prothrombin
CHEMBL204
 Kd 4.31 4.31 49200.0 1
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 4.3 4.3 49950.0 1
Plantago lanceolata
CHEMBL2367284
 EC50 4.26 4.26 55000.0 1
Prostaglandin G/H synthase 1
CHEMBL2860
 IC50 4.1 4.1 80000.0 1
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 4.03 4.03 93300.0 1
Dihydroorotate dehydrogenase (fumarate)
CHEMBL4295843
 IC50 4.01 4.005 98300.0 2

Pharmacokinetic Data

Parameter Value Units Species
Ke 10000.0 nM Homo sapiens
Ke 1180.0 nM Homo sapiens
Ke 320.0 nM Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mushroom tyrosinase IC50 = 60.0 nM 7.22 Inhibition of mushroom tyrosinase monophenolase activity 39026645
Mushroom tyrosinase IC50 = 70.0 nM 7.16 Inhibition of mushroom tyrosinase diphenolase activity 39026645
Arginase Ki = 600.0 nM 6.22 Noncompetitive inhibition of Leishmania amazonensis recombinant arginase express... 24521209
Sclerostin Kd = 1579.0 nM 5.8 Binding affinity to SOST (unknown origin) by SPR analysis 38677061
NON-PROTEIN TARGET IC50 = 1610.0 nM 5.79 Antioxidant activity assessed as superoxide-scavenging activity by nitrite metho... 9461655
Arginase IC50 = 1700.0 nM 5.77 Inhibition of Leishmania amazonensis recombinant arginase expressed in Escherich... 24521209
Unchecked IC50 = 1800.0 nM 5.75 Inhibition of recombinant rat liver arginase 37257213
Sclerostin Kd = 1845.0 nM 5.73 Binding affinity to SOST loop2 (unknown origin) by SPR analysis 38677061
NON-PROTEIN TARGET IC50 = 2310.0 nM 5.64 Antioxidant activity assessed as superoxide anion radical scavenging activity 17907781
Unchecked IC50 = 2900.0 nM 5.54 Inhibition of beta amyloid (1 to 40) fibril formation by thioflavin T staining-b... 19931462
Prostaglandin G/H synthase 1 IC50 = 4100.0 nM 5.39 Inhibition of peroxidase activity of COX1 in heep seminal vesicle by TMPD assay 15568761
Radical scavenging activity IC50 = 4300.0 nM 5.37 Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins ... 22377672
Unchecked IC50 = 5300.0 nM 5.28 Inhibition of beta amyloid (1 to 42) fibril formation by thioflavin T staining-b... 19931462
Plasmodium falciparum IC50 = 5900.0 nM 5.23 Antimalarial activity against chloroquine /mefloquine/pyrimethamine-resistant Pl... 25488841
Plasmodium falciparum IC50 = 6000.0 nM 5.22 Antimalarial activity against chloroquine-resistant/mefloquine-sensitive Plasmod... 25488841
Plasmodium falciparum IC50 = 6700.0 nM 5.17 Antimalarial activity against chloroquine-sensitive/mefloquine-resistant Plasmod... 25488841
NON-PROTEIN TARGET IC50 = 9520.0 nM 5.02 Antineuroinflammatory activity in human BV2 cells assessed as inhibition of LPS-... 27623545
NON-PROTEIN TARGET IC50 = 13100.0 nM 4.88 Antioxidant activity assessed as superoxide radical anion scavenging activity 10425115
Unchecked IC50 = 20200.0 nM 4.7 Free radical scavenging activity of DPPH was determined; value taken from refere... 14698182
Prostaglandin G/H synthase 1 IC50 = 20200.0 nM 4.7 Inhibition of cyclooxygenase activity of COX1 in sheep seminal vesicle in presen... 15568761

Literature References

PubMed DOI Target Context # Activities
24610996 10.1007/s00044-013-0829-4 Prothrombin 9
26517554 10.1021/acs.jnatprod.5b00075 ADMET 9
3430163 10.1021/np50052a004 Hepatocyte 8
27623545 10.1016/j.bmcl.2016.08.094 NON-PROTEIN TARGET 5
15568761 10.1021/np0498410 Prostaglandin G/H synthase 1 5
21824690 10.1016/j.ejmech.2011.07.031 HepG2 5
2045817 10.1021/np50073a022 Rattus norvegicus 4
21493073 10.1016/j.bmc.2011.03.040 3T3-L1 4
34965114 10.1021/acs.jnatprod.1c00738 Trypanosoma brucei rhodesiense 4
33530021 10.1016/j.bmc.2021.116043 Cytochrome c 4
23145924 10.1021/jf303290g Diplodia seriata 4
25769817 10.1016/j.bmcl.2015.02.048 Unchecked 3
11000034 10.1021/np000084p Unchecked 3
17685652 10.1021/np070194x Unchecked 3
26517554 10.1021/acs.jnatprod.5b00075 Unchecked 3
17166721 10.1016/j.bmc.2006.11.037 NON-PROTEIN TARGET 3
30145372 10.1016/j.ejmech.2018.08.033 Dihydroorotate dehydrogenase (fumarate) 3
19931462 10.1016/j.bmc.2009.10.063 Unchecked 3
21910441 10.1021/np100872k Unchecked 3
22377672 10.1016/j.bmc.2012.02.002 Unchecked 3

Data from ChEMBL 36 via Core Engine