Benzene-1,4-diol

ID: ALA537

Chembl Id: CHEMBL537

Cas Number: 123-31-9

PubChem CID: 785

Product Number: W13699

Max Phase: Approved

First Approval: 2002

Molecular Formula: C6H6O2

Molecular Weight: 110.11

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: Hydroquinone | CHEBI:17594 | CHEMBL537 | NCI-C55834 | NSC-9247 | hydroquinone|Benzene-1,4-diol|123-31-9|1,4-benzenediol|Quinol|1,4-Dihydroxybenzene|p-Benzenediol|p-Hydroquinone|p-Hydroxyphenol|4-Hydroxyphenol|p-Dihydroxybenzene|Benzoquinol|hydroquinol|Dihydroquinone|Eldoquin|p-Dioxybenzene|Solaquin forte|Eldopaque|Hydroquinole|Idrochinone|Tecquinol|Phiaquin|Benzohydroquinone|Hidroquinone|Arctuvin|Tequinol|Dihydroxybenzene|Eldopaque Forte|Eldoquin Forte|Derma-Blanch|Hydrochinon|Tenox HQ|Diak 5|BeShow More

Canonical SMILES:  Oc1ccc(O)cc1

Standard InChI:  InChI=1S/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H

Standard InChI Key:  QIGBRXMKCJKVMJ-UHFFFAOYSA-N

Alternative Forms

  1. Parent:

Associated Targets(Human)

CA1 Tclin Carbonic anhydrase I (13240 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA2 Tclin Carbonic anhydrase II (17698 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KB (17409 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA14 Tclin Carbonic anhydrase XIV (1305 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA12 Tclin Carbonic anhydrase XII (6231 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA9 Tclin Carbonic anhydrase IX (8255 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA7 Tclin Carbonic anhydrase VII (2318 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA6 Tclin Carbonic anhydrase VI (993 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA5B Tclin Carbonic anhydrase VB (957 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA5A Tclin Carbonic anhydrase VA (1168 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA4 Tclin Carbonic anhydrase IV (2163 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA3 Tclin Carbonic anhydrase III (753 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Lymphoblastoid cell (5959 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LMNA Tbio Prelamin-A/C (36751 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NFKB1 Tclin Nuclear factor NF-kappa-B p105 subunit (1459 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RECQL Tbio ATP-dependent DNA helicase Q1 (5575 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HSD17B10 Tchem Endoplasmic reticulum-associated amyloid beta-peptide-binding protein (20669 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RAB9A Tbio Ras-related protein Rab-9A (22488 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HIF1A Tchem Hypoxia-inducible factor 1 alpha (6027 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PMP22 Tbio Peripheral myelin protein 22 (699 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MTOR Tclin Serine/threonine-protein kinase mTOR (13850 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPT Tclin Microtubule-associated protein tau (95507 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HBB Tbio Hemoglobin beta chain (329 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BLM Tchem Bloom syndrome protein (4248 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NPC1 Tchem Niemann-Pick C1 protein (18985 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HPGD Tchem 15-hydroxyprostaglandin dehydrogenase [NAD+] (24926 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
THPO Tbio Thrombopoietin (834 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GMNN Tbio Geminin (128009 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MPHOSPH8 Tbio M-phase phosphoprotein 8 (656 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PIN1 Tchem Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (36611 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ATAD5 Tbio ATPase family AAA domain-containing protein 5 (122566 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RXRA Tclin Retinoid X receptor alpha (3637 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ATXN2 Tbio Ataxin-2 (54410 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ESR1 Tclin Estrogen receptor alpha (17718 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NR1H4 Tclin Bile acid receptor FXR (6228 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FEN1 Tchem Flap endonuclease 1 (12055 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AR Tclin Androgen Receptor (11781 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RGS4 Tchem Regulator of G-protein signaling 4 (13867 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PPARD Tchem Peroxisome proliferator-activated receptor delta (6293 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEK293 (82097 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SH-SY5Y (11521 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NR3C1 Tclin Glucocorticoid receptor (14987 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UGT1A10 Tbio UDP-glucuronosyltransferase 1-10 (257 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UGT1A7 Tbio UDP-glucuronosyltransferase 1-7 (106 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AHR Tclin Aryl hydrocarbon receptor (1071 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NFE2L2 Tchem Nuclear factor erythroid 2-related factor 2 (95332 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GLS Tchem Glutaminase kidney isoform, mitochondrial (16997 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CXCL8 Tchem Interleukin-8 (642 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RORC Tchem Nuclear receptor ROR-gamma (8495 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ARSA Tbio Cerebroside-sulfatase (655 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HL-60 (67320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
K562 (73714 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SIRT1 Tchem NAD-dependent deacetylase sirtuin 1 (3505 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
U-87 MG (3946 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
U-251 (51189 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TYR Tclin Tyrosinase (717 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC6 Tclin Histone deacetylase 6 (20808 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

L1210 (27553 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PPO2 Tyrosinase (3884 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ca15 Carbonic anhydrase 15 (173 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Porphyromonas gingivalis (651 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Streptococcus mutans (2687 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Melan-a (81 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bacillus subtilis (32866 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Micrococcus luteus (7463 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Candida albicans (78123 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Escherichia coli (133304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pseudomonas aeruginosa (123386 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Artemia salina (1320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Gambusia affinis (76 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trichophyton mentagrophytes (4846 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P388 (20296 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ca13 Carbonic anhydrase XIII (322 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cavia porcellus (23802 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rorc Nuclear receptor ROR-gamma (89407 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
nfo Endonuclease 4 (425 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
lef Anthrax lethal factor (7585 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrm1 Muscarinic acetylcholine receptor M1 (3437 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
polC DNA polymerase III (243 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Large T antigen (1457 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
pfk 6-phospho-1-fructokinase (7870 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ca Carbonic anhydrase (13 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pmp22 Peripheral myelin protein 22 (1279 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Anopheles gambiae (126 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma cruzi (99888 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
J774 (3120 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Danio rerio (3092 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ache Acetylcholinesterase (12221 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Melanocyte (41 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Neutrophil (13 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rep Replicase polyprotein 1ab (11336 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: YesFirst In Class: NoBlack Box: No
Chirality: YesAvailability: YesProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 110.11Molecular Weight (Monoisotopic): 110.0368AlogP: 1.10#Rotatable Bonds:
Polar Surface Area: 40.46Molecular Species: NEUTRALHBA: 2HBD: 2
#RO5 Violations: HBA (Lipinski): 2HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 9.68CX Basic pKa: CX LogP: 1.37CX LogD: 1.36
Aromatic Rings: 1Heavy Atoms: 8QED Weighted: 0.49Np Likeness Score: 0.59

References

1. Dunn WJ, Koehler MG, Grigoras S..  (1987)  The role of solvent-accessible surface area in determining partition coefficients.,  30  (7): [PMID:3599019] [10.1021/jm00390a002]
2. Selassie CD, Kapur S, Verma RP, Rosario M..  (2005)  Cellular apoptosis and cytotoxicity of phenolic compounds: a quantitative structure-activity relationship study.,  48  (23): [PMID:16279782] [10.1021/jm050567w]
3. Fujikawa M, Nakao K, Shimizu R, Akamatsu M..  (2007)  QSAR study on permeability of hydrophobic compounds with artificial membranes.,  15  (11): [PMID:17418579] [10.1016/j.bmc.2007.03.040]
4. Song S, Lee H, Jin Y, Ha YM, Bae S, Chung HY, Suh H..  (2007)  Syntheses of hydroxy substituted 2-phenyl-naphthalenes as inhibitors of tyrosinase.,  17  (2): [PMID:17064896] [10.1016/j.bmcl.2006.10.025]
5. Epifano F, Genovese S, Sosa S, Tubaro A, Curini M..  (2007)  Synthesis and anti-inflammatory activity of 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid and its ester derivatives.,  17  (20): [PMID:17768049] [10.1016/j.bmcl.2007.07.058]
6. Criton M, Le Mellay-Hamon V..  (2008)  Analogues of N-hydroxy-N'-phenylthiourea and N-hydroxy-N'-phenylurea as inhibitors of tyrosinase and melanin formation.,  18  (12): [PMID:18501598] [10.1016/j.bmcl.2008.04.079]
7. Innocenti A, Hilvo M, Scozzafava A, Parkkila S, Supuran CT..  (2008)  Carbonic anhydrase inhibitors: Inhibition of the new membrane-associated isoform XV with phenols.,  18  (12): [PMID:18501600] [10.1016/j.bmcl.2008.04.077]
8. De Rosa S, De Giulio A, Iodice C..  (1994)  Biological effects of prenylated hydroquinones: structure-activity relationship studies in antimicrobial, brine shrimp, and fish lethality assays.,  57  (12): [PMID:7714539] [10.1021/np50114a015]
9. Chen QC, Youn U, Min BS, Bae K..  (2008)  Pyronane monoterpenoids from the fruit of Gardenia jasminoides.,  71  (6): [PMID:18505286] [10.1021/np800002z]
10. Rho HS, Baek HS, Ahn SM, Yoo JW, Kim DH, Kim HG..  (2009)  Studies on depigmenting activities of dihydroxyl benzamide derivatives containing adamantane moiety.,  19  (5): [PMID:19181523] [10.1016/j.bmcl.2008.12.106]
11. Perry NB, Brennan NJ..  (1997)  Antimicrobial and cytotoxic phenolic glycoside esters from the New Zealand tree Toronia toru.,  60  (6): [PMID:9214736] [10.1021/np970013z]
12. Li CY, Lee EJ, Wu TS..  (2004)  Antityrosinase principles and constituents of the petals of Crocus sativus.,  67  (3): [PMID:15043425] [10.1021/np0302854]
13. Arisawa M, Funayama S, Pezzuto JM, Kinghorn AD, Cordell GA, Farnsworth NR..  (1984)  Potential anticancer agents XXXII. Hydroquinone from Ipomopsis aggregata.,  47  (2): [PMID:6736973] [10.1021/np50032a037]
14. Huss U, Ringbom T, Perera P, Bohlin L, Vasänge M..  (2002)  Screening of ubiquitous plant constituents for COX-2 inhibition with a scintillation proximity based assay.,  65  (11): [PMID:12444669] [10.1021/np020023m]
15. Li CY, Wu TS..  (2002)  Constituents of the stigmas of Crocus sativus and their tyrosinase inhibitory activity.,  65  (10): [PMID:12398542] [10.1021/np020188v]
16. Innocenti A, Vullo D, Scozzafava A, Supuran CT..  (2008)  Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid.,  16  (15): [PMID:18579385] [10.1016/j.bmc.2008.06.013]
17. Bodet C, Epifano F, Genovese S, Curini M, Grenier D..  (2008)  Effects of 3-(4'-geranyloxy-3'-methoxyphenyl)-2-trans propenoic acid and its ester derivatives on biofilm formation by two oral pathogens, Porphyromonas gingivalis and Streptococcus mutans.,  43  (8): [PMID:18093697] [10.1016/j.ejmech.2007.11.001]
18. Pérez-Garrido A, Morales Helguera A, Abellán Guillén A, Cordeiro MN, Garrido Escudero A..  (2009)  Convenient QSAR model for predicting the complexation of structurally diverse compounds with beta-cyclodextrins.,  17  (2): [PMID:19056282] [10.1016/j.bmc.2008.11.040]
19. Mori-Hongo M, Takimoto H, Katagiri T, Kimura M, Ikeda Y, Miyase T..  (2009)  Melanin synthesis inhibitors from Lespedeza floribunda.,  72  (2): [PMID:19132934] [10.1021/np800395j]
20. Mori-Hongo M, Yamaguchi H, Warashina T, Miyase T..  (2009)  Melanin synthesis inhibitors from Lespedeza cyrtobotrya.,  72  (1): [PMID:19102656] [10.1021/np800535g]
21. Ngoc TM, Lee I, Ha do T, Kim H, Min B, Bae K..  (2009)  Tyrosinase-inhibitory constituents from the twigs of Cinnamomum cassia.,  72  (6): [PMID:19555125] [10.1021/np900031q]
22. Seo WD, Ryu YB, Curtis-Long MJ, Lee CW, Ryu HW, Jang KC, Park KH..  (2010)  Evaluation of anti-pigmentary effect of synthetic sulfonylamino chalcone.,  45  (5): [PMID:20149498] [10.1016/j.ejmech.2010.01.049]
23. Choi J, Bae SJ, Ha YM, No JK, Lee EK, Lee JS, Song S, Lee H, Suh H, Yu BP, Chung HY..  (2010)  A newly synthesized, potent tyrosinase inhibitor: 5-(6-hydroxy-2-naphthyl)-1,2,3-benzenetriol.,  20  (16): [PMID:20619644] [10.1016/j.bmcl.2010.06.087]
24. Hwang S, Choi SY, Lee JH, Kim S, In J, Ha SK, Lee E, Kim TY, Kim SY, Choi S, Kim S..  (2010)  Identification of a potent and noncytotoxic inhibitor of melanin production.,  18  (15): [PMID:20615711] [10.1016/j.bmc.2010.06.034]
25. Yuan J, Johnson RL, Huang R, Wichterman J, Jiang H, Hayton K, Fidock DA, Wellems TE, Inglese J, Austin CP, Su XZ..  (2009)  Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.,  (10): [PMID:19734910] [10.1038/nchembio.215]
26. Diamandis P, Wildenhain J, Clarke ID, Sacher AG, Graham J, Bellows DS, Ling EK, Ward RJ, Jamieson LG, Tyers M, Dirks PB..  (2007)  Chemical genetics reveals a complex functional ground state of neural stem cells.,  (5): [PMID:17417631] [10.1038/nchembio873]
27. PubChem BioAssay data set, 
28. PubChem BioAssay data set, 
29. PubChem BioAssay data set, 
30. PubChem BioAssay data set, 
31. PubChem BioAssay data set, 
32. PubChem BioAssay data set, 
33. PubChem BioAssay data set, 
34. Fourches D, Barnes JC, Day NC, Bradley P, Reed JZ, Tropsha A..  (2010)  Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.,  23  (1): [PMID:20014752] [10.1021/tx900326k]
35. Unpublished dataset, 
36. Elam C, Lape M, Deye J, Zultowsky J, Stanton DT, Paula S..  (2011)  Discovery of novel SERCA inhibitors by virtual screening of a large compound library.,  46  (5): [PMID:21353727] [10.1016/j.ejmech.2011.01.069]
37. Abraham MH, Ibrahim A, Acree WE..  (2008)  Air to lung partition coefficients for volatile organic compounds and blood to lung partition coefficients for volatile organic compounds and drugs.,  43  (3): [PMID:17544548] [10.1016/j.ejmech.2007.04.002]
38. Oztürk Sarikaya SB, Topal F, Sentürk M, Gülçin I, Supuran CT..  (2011)  In vitro inhibition of α-carbonic anhydrase isozymes by some phenolic compounds.,  21  (14): [PMID:21669522] [10.1016/j.bmcl.2011.05.071]
39. PubChem BioAssay data set, 
40. Tukey RH, Strassburg CP..  (2000)  Human UDP-glucuronosyltransferases: metabolism, expression, and disease.,  40  (1): [PMID:10836148] [10.1146/annurev.pharmtox.40.1.581]
41. Cho JC, Rho HS, Joo YH, Lee CS, Lee J, Ahn SM, Kim JE, Shin SS, Park YH, Suh KD, Park SN..  (2012)  Depigmenting activities of kojic acid derivatives without tyrosinase inhibitory activities.,  22  (12): [PMID:22579419] [10.1016/j.bmcl.2012.04.046]
42. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 
43. Chiari ME, Vera DM, Palacios SM, Carpinella MC..  (2011)  Tyrosinase inhibitory activity of a 6-isoprenoid-substituted flavanone isolated from Dalea elegans.,  19  (11): [PMID:21561780] [10.1016/j.bmc.2011.04.025]
44. Prasain K, Nguyen TD, Gorman MJ, Barrigan LM, Peng Z, Kanost MR, Syed LU, Li J, Zhu KY, Hua DH..  (2012)  Redox potentials, laccase oxidation, and antilarval activities of substituted phenols.,  20  (5): [PMID:22300888] [10.1016/j.bmc.2012.01.021]
45. Georgiev L, Chochkova M, Totseva I, Seizova K, Marinova E, Ivanova G, Ninova M, Najdenski H, Milkova T.  (2013)  Anti-tyrosinase, antioxidant and antimicrobial activities of hydroxycinnamoylamides,  22  (9): [10.1007/s00044-012-0419-x]
46. PubChem BioAssay data set, 
47. PubChem BioAssay data set, 
48. Miliovsky M, Svinyarov I, Mitrev Y, Evstatieva Y, Nikolova D, Chochkova M, Bogdanov MG..  (2013)  A novel one-pot synthesis and preliminary biological activity evaluation of cis-restricted polyhydroxy stilbenes incorporating protocatechuic acid and cinnamic acid fragments.,  66  [PMID:23796767] [10.1016/j.ejmech.2013.05.040]
49. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]
50. PubChem BioAssay data set, 
51. PubChem BioAssay data set, 
52. PubChem BioAssay data set, 
53. Yasuda D, Takahashi K, Kakinoki T, Tanaka Y, Ohe T, Nakamura S, Mashino T.  (2013)  Synthesis, radical scavenging activity and structureactivity relationship of uric acid analogs,  (3): [10.1039/C2MD20287E]
54. Castillo-Garit JA, del Toro-Cortés O, Vega MC, Rolón M, Rojas de Arias A, Casañola-Martin GM, Escario JA, Gómez-Barrio A, Marrero-Ponce Y, Torrens F, Abad C..  (2015)  Bond-based bilinear indices for computational discovery of novel trypanosomicidal drug-like compounds through virtual screening.,  96  [PMID:25884114] [10.1016/j.ejmech.2015.03.063]
55. Won TH, Song IH, Kim KH, Yang WY, Lee SK, Oh DC, Oh WK, Oh KB, Shin J..  (2015)  Bioactive Metabolites from the Fruits of Psoralea corylifolia.,  78  (4): [PMID:25710081] [10.1021/np500834d]
56. Le HT, Hong BN, Lee YR, Cheon JH, Kang TH, Kim TW..  (2016)  Regulatory effect of hydroquinone-tetraethylene glycol conjugates on zebrafish pigmentation.,  26  (2): [PMID:26684849] [10.1016/j.bmcl.2015.09.059]
57. Alam MI, Alam MA, Alam O, Nargotra A, Taneja SC, Koul S..  (2016)  Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.,  114  [PMID:26986086] [10.1016/j.ejmech.2016.03.008]
58. Özgeriş B, Göksu S, Polat Köse L, Gülçin İ, Salmas RE, Durdagi S, Tümer F, Supuran CT..  (2016)  Acetylcholinesterase and carbonic anhydrase inhibitory properties of novel urea and sulfamide derivatives incorporating dopaminergic 2-aminotetralin scaffolds.,  24  (10): [PMID:27068142] [10.1016/j.bmc.2016.04.002]
59. Garcia-Jimenez A, Teruel-Puche JA, Berna J, Rodriguez-Lopez JN, Tudela J, Garcia-Ruiz PA, Garcia-Canovas F..  (2016)  Characterization of the action of tyrosinase on resorcinols.,  24  (18): [PMID:27480027] [10.1016/j.bmc.2016.07.048]
60. WHO Anatomical Therapeutic Chemical Classification, 
61. DrugMatrix,  [10.6019/CHEMBL3885881]
62. Entezari Heravi Y, Bua S, Nocentini A, Del Prete S, Saboury AA, Sereshti H, Capasso C, Gratteri P, Supuran CT..  (2017)  Inhibition of Malassezia globosa carbonic anhydrase with phenols.,  25  (9): [PMID:28343756] [10.1016/j.bmc.2017.03.026]
63. Veselinović JB, Veselinović AM, Ilic-Tomic T, Davis R, O'Connor K, Pavic A, Nikodinovic-Runic J..  (2017)  Potent anti-melanogenic activity and favorable toxicity profile of selected 4-phenyl hydroxycoumarins in the zebrafish model and the computational molecular modeling studies.,  25  (24): [PMID:29042224] [10.1016/j.bmc.2017.09.021]
64. Unpublished dataset, 
65. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]
66. Sherer C, Prabhu S, Adams D, Hayes J, Rowther F, Tolaymat I, Warr T, Snape TJ..  (2018)  Towards identifying potent new hits for glioblastoma.,  (11): [PMID:30568753] [10.1039/C8MD00436F]
67. Pillaiyar T, Namasivayam V, Manickam M, Jung SH..  (2018)  Inhibitors of Melanogenesis: An Updated Review.,  61  (17): [PMID:29763564] [10.1021/acs.jmedchem.7b00967]
68. Narang R, Kumar R, Kalra S, Nayak SK, Khatik GL, Kumar GN, Sudhakar K, Singh SK..  (2019)  Recent advancements in mechanistic studies and structure activity relationship of FoF1 ATP synthase inhibitor as antimicrobial agent.,  182  [PMID:31493745] [10.1016/j.ejmech.2019.111644]
69. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]
70. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]
71. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]
72. Verdoni M,Roudaut H,De Pomyers H,Gigmes D,Bertin D,Luis J,Bengeloune AH,Mabrouk K.  (2016)  ArgTX-636, a polyamine isolated from spider venom: A novel class of melanogenesis inhibitors.,  24  (22.0): [PMID:27647371] [10.1016/j.bmc.2016.08.023]
73. Roulier B,Pérès B,Haudecoeur R.  (2020)  Advances in the Design of Genuine Human Tyrosinase Inhibitors for Targeting Melanogenesis and Related Pigmentations.,  63  (22.0): [PMID:32787103] [10.1021/acs.jmedchem.0c00994]
74. Unpublished dataset, 
75. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]
76. Fu D, Yuan Y, Qin F, Xu Y, Cui X, Li G, Yao S, Deng Y, Tang Z..  (2021)  Design, synthesis and biological evaluation of tyrosinase-targeting PROTACs.,  226  [PMID:34628235] [10.1016/j.ejmech.2021.113850]