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Showing metabocard for Hydroquinone (HMDB0002434)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:53 UTC
Update Date2023-02-21 17:16:24 UTC
HMDB IDHMDB0002434
Secondary Accession Numbers
  • HMDB02434
Metabolite Identification
Common NameHydroquinone
DescriptionHydroquinone, also known as benzene-1,4-diol, is an aromatic organic compound which is a type of phenol, having the chemical formula C6H4(OH)2. Its chemical structure has two hydroxyl groups bonded to a benzene ring in a para position. Hydroquinone is commonly used as a biomarker for benzene exposure. The presence of hydroquinone in normal individuals stems mainly from direct dietary ingestion, catabolism of tyrosine and other substrates by gut bacteria, ingestion of arbutin-containing foods, cigarette smoking, and the use of some over-the-counter medicines. Hydroquinone is a white granular solid at room temperature and pressure. The hydroxyl groups of hydroquinone are quite weakly acidic. Hydroquinone can lose an H+ from one of the hydroxyls to form a monophenolate ion or lose an H+ from both to form a diphenolate ion. Hydroquinone has a variety of uses principally associated with its action as a reducing agent which is soluble in water. It is a major component of most photographic developers where, with the compound Metol, it reduces silver halides to elemental silver.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002434 (Hydroquinone)

  Mrv1652309272007412D          

  8  8  0  0  0  0            999 V2000
   -1.8971    0.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6115    0.9477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3261    0.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3261   -0.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6116   -0.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8971   -0.2896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1826    0.9478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0406   -0.7021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  7  1  0  0  0  0
  4  8  1  0  0  0  0
M  END
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3D MOL for HMDB0002434 (Hydroquinone)

HMDB0002434
     RDKit          3D
Hydroquinone
 14 14  0  0  0  0  0  0  0  0999 V2000
    2.7667   -0.3408    0.3924 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3965   -0.2106    0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5908   -1.2876   -0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7646   -1.1361   -0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3756    0.1001   -0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7400    0.2551   -0.5261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5778    1.1853   -0.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7727    1.0170    0.2217 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3707    0.4113    0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0467   -2.2705   -0.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4037   -1.9767   -0.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4296    0.1970    0.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0497    2.1709    0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3968    1.8856    0.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  2  1  0
  1  9  1  0
  3 10  1  0
  4 11  1  0
  6 12  1  0
  7 13  1  0
  8 14  1  0
M  END
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3D SDF for HMDB0002434 (Hydroquinone)

  Mrv1652309272007412D          

  8  8  0  0  0  0            999 V2000
   -1.8971    0.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6115    0.9477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3261    0.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3261   -0.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6116   -0.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8971   -0.2896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1826    0.9478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0406   -0.7021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  7  1  0  0  0  0
  4  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002434

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(O)C=C1

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

> <INCHI_KEY>
QIGBRXMKCJKVMJ-UHFFFAOYSA-N

> <FORMULA>
C6H6O2

> <MOLECULAR_WEIGHT>
110.1106

> <EXACT_MASS>
110.036779436

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
10.751706760439284

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
benzene-1,4-diol

> <ALOGPS_LOGP>
0.71

> <JCHEM_LOGP>
1.3661151726666665

> <ALOGPS_LOGS>
-0.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.553013032476033

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.676283592749463

> <JCHEM_PKA_STRONGEST_BASIC>
-5.887165947200477

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
30.0198

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.55e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-hydroquinone

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0002434 (Hydroquinone)

HMDB0002434
     RDKit          3D
Hydroquinone
 14 14  0  0  0  0  0  0  0  0999 V2000
    2.7667   -0.3408    0.3924 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3965   -0.2106    0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5908   -1.2876   -0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7646   -1.1361   -0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3756    0.1001   -0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7400    0.2551   -0.5261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5778    1.1853   -0.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7727    1.0170    0.2217 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3707    0.4113    0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0467   -2.2705   -0.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4037   -1.9767   -0.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4296    0.1970    0.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0497    2.1709    0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3968    1.8856    0.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  2  1  0
  1  9  1  0
  3 10  1  0
  4 11  1  0
  6 12  1  0
  7 13  1  0
  8 14  1  0
M  END
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PDB for HMDB0002434 (Hydroquinone)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      -3.541   0.999   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.875   1.769   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.209   0.999   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.209  -0.541   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.875  -1.311   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.541  -0.541   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.208   1.769   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -7.542  -1.311   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    1                                                            
CONECT    8    4                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for HMDB0002434 (Hydroquinone)

COMPND    HMDB0002434
HETATM    1  O1  UNL     1       2.767  -0.341   0.392  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.397  -0.211   0.161  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.591  -1.288  -0.138  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.765  -1.136  -0.364  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.376   0.100  -0.300  1.00  0.00           C  
HETATM    6  O2  UNL     1      -2.740   0.255  -0.526  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.578   1.185  -0.000  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.773   1.017   0.222  1.00  0.00           C  
HETATM    9  H1  UNL     1       3.371   0.411   0.609  1.00  0.00           H  
HETATM   10  H2  UNL     1       1.047  -2.270  -0.194  1.00  0.00           H  
HETATM   11  H3  UNL     1      -1.404  -1.977  -0.599  1.00  0.00           H  
HETATM   12  H4  UNL     1      -3.430   0.197   0.225  1.00  0.00           H  
HETATM   13  H5  UNL     1      -1.050   2.171   0.053  1.00  0.00           H  
HETATM   14  H6  UNL     1       1.397   1.886   0.458  1.00  0.00           H  
CONECT    1    2    9
CONECT    2    3    3    8
CONECT    3    4   10
CONECT    4    5    5   11
CONECT    5    6    7
CONECT    6   12
CONECT    7    8    8   13
CONECT    8   14
END
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SMILES for HMDB0002434 (Hydroquinone)

OC1=CC=C(O)C=C1
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INCHI for HMDB0002434 (Hydroquinone)

InChI=1S/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC6H6O2
Average Molecular Weight110.1106
Monoisotopic Molecular Weight110.036779436
IUPAC Namebenzene-1,4-diol
Traditional Nameα-hydroquinone
CAS Registry Number123-31-9
SMILES
OC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H
InChI KeyQIGBRXMKCJKVMJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroquinones. Hydroquinones are compounds containing a hydroquinone moiety, which consists of a benzene ring with a hydroxyl groups at positions 1 and 4.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentHydroquinones
Alternative Parents
Substituents
  • Hydroquinone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial applicationIndirect biological roleEnvironmental roleBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point172.3 °CNot Available
Boiling Point286.00 to 288.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility72 mg/mL at 25 °CNot Available
LogP0.59HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker119.0730932474
[M+H]+Baker128.78930932474
[M-H]-Not Available119.07http://allccs.zhulab.cn/database/detail?ID=AllCCS00001918
[M+H]+Not Available128.789http://allccs.zhulab.cn/database/detail?ID=AllCCS00001918
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Bone Marrow
  • Epidermis
  • Fibroblasts
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
UrineDetected and Quantified<1 nmol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.460 +/- 0.770 uMAdult (>18 years old)Both
Uremia		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Uremia
  1. Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
Associated OMIM IDsNone
DrugBank IDDB09526
Phenol Explorer Compound ID660
FooDB IDFDB000885
KNApSAcK IDC00002656
Chemspider ID764
KEGG Compound IDC00530
BioCyc IDHYDROQUINONE
BiGG IDNot Available
Wikipedia LinkHydroquinone
METLIN ID6681
PubChem Compound785
PDB IDNot Available
ChEBI ID17594
Food Biomarker OntologyNot Available
VMH IDHQN
MarkerDB IDNot Available
Good Scents IDrw1250911
References
Synthesis ReferenceMiyanohara, Isao; Yanagihara, Tadahisa. Hydroquinone. Jpn. Kokai Tokkyo Koho (1977), 4 pp.
Material Safety Data Sheet (MSDS)Not Available
General References

Enzymes

Enzyme Details
1. Tyrosinase
General function:
Involved in oxidoreductase activity
Specific function:
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:
TYR
Uniprot ID:
P14679
Molecular weight:
60392.69
Reactions
Hydroquinone + Oxygen → Quinone + Waterdetails
Enzyme Details
2. Serum paraoxonase/lactonase 3
General function:
Involved in arylesterase activity
Specific function:
Has low activity towards the organophosphate paraxon and aromatic carboxylic acid esters. Rapidly hydrolyzes lactones such as statin prodrugs (e.g. lovastatin). Hydrolyzes aromatic lactones and 5- or 6-member ring lactones with aliphatic substituents but not simple lactones or those with polar substituents.
Gene Name:
PON3
Uniprot ID:
Q15166
Molecular weight:
39607.185
Reactions
4-Hydroxyphenyl acetate + Water → Hydroquinone + Acetic aciddetails
Enzyme Details
3. Serum paraoxonase/arylesterase 1
General function:
Involved in arylesterase activity
Specific function:
Hydrolyzes the toxic metabolites of a variety of organophosphorus insecticides. Capable of hydrolyzing a broad spectrum of organophosphate substrates and lactones, and a number of aromatic carboxylic acid esters. Mediates an enzymatic protection of low density lipoproteins against oxidative modification and the consequent series of events leading to atheroma formation.
Gene Name:
PON1
Uniprot ID:
P27169
Molecular weight:
39730.99
Reactions
4-Hydroxyphenyl acetate + Water → Hydroquinone + Acetic aciddetails
Enzyme Details
4. Serum paraoxonase/arylesterase 2
General function:
Involved in arylesterase activity
Specific function:
Capable of hydrolyzing lactones and a number of aromatic carboxylic acid esters. Has antioxidant activity. Is not associated with high density lipoprotein. Prevents LDL lipid peroxidation, reverses the oxidation of mildly oxidized LDL, and inhibits the ability of MM-LDL to induce monocyte chemotaxis.
Gene Name:
PON2
Uniprot ID:
Q15165
Molecular weight:
39380.535
Reactions
4-Hydroxyphenyl acetate + Water → Hydroquinone + Acetic aciddetails
Enzyme Details
5. Ribosyldihydronicotinamide dehydrogenase [quinone]
General function:
Involved in electron carrier activity
Specific function:
The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:
NQO2
Uniprot ID:
P16083
Molecular weight:
25918.4
Enzyme Details
6. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Hydroquinone → 3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxane-2-carboxylic aciddetails
Enzyme Details
7. NAD(P)H dehydrogenase [quinone] 1
General function:
Involved in electron carrier activity
Specific function:
The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinons involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:
NQO1
Uniprot ID:
P15559
Molecular weight:
30867.405