HYDROQUINONE

ID: ALA537

Max Phase: Approved

First Approval: 2002

Molecular Formula: C6H6O2

Molecular Weight: 110.11

Molecule Type: Small molecule

Associated Items:

Representations

Synonyms (5): Hydroquinone | CHEBI:17594 | CHEMBL537 | NCI-C55834 | NSC-9247
Synonyms from Alternative Forms(5):

    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

    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

    Properties

    Molecular Weight: 110.11Molecular Weight (Monoisotopic): 110.0368AlogP: 1.10#Rotatable Bonds: 0
    Polar Surface Area: 40.46Molecular Species: NEUTRALHBA: 2HBD: 2
    #RO5 Violations: 0HBA (Lipinski): 2HBD (Lipinski): 2#RO5 Violations (Lipinski): 0
    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

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    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]
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    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]
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