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Showing metabocard for 1,3-Benzenediol (HMDB0032037)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:47:23 UTC
Update Date2023-02-21 17:21:30 UTC
HMDB IDHMDB0032037
Secondary Accession Numbers
  • HMDB32037
Metabolite Identification
Common Name1,3-Benzenediol
Description1,3-Benzenediol, also known as resorcin or m-hydroquinone, belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3. 1,3-Benzenediol exists in all living organisms, ranging from bacteria to humans. 1,3-Benzenediol is a creamy, hawthorn, and musty tasting compound. 1,3-Benzenediol has been detected, but not quantified, in several different foods, such as alcoholic beverages, cereals and cereal products, coffee and coffee products, eggplants, and java plums. This could make 1,3-benzenediol a potential biomarker for the consumption of these foods. 1,3-Benzenediol is a potentially toxic compound. In addition, exogenous ochronosis is associated with prolonged exposure to resorcinol . Data regarding the specific mechanisms of action of resorcinol does not appear to be readily accessible in the literature. Nevertheless, the role played by iodide ions in the irreversible inactivation of the enzymes is not yet fully elucidated . Resorcinol works by helping to remove hard, scaly, or roughened skin. In particular, it appears that resorcinol indicated for treating acne, dermatitis, or eczema in various skin care topical applications and peels revolves around the compound's ability to precipitate cutaneous proteins from the treated skin . In LPO and TPO, the resulting π-cation radical of the porphyrin can isomerize to a radical cation with the radical in an aromatic side chain of the enzyme . In vitro and in vivo studies have demonstrated that resorcinol can inhibit peroxidases in the thyroid and subsequently block the synthesis of thyroid hormones and cause goiter .
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0032037 (1,3-Benzenediol)

  Mrv1652305062021452D          

  8  8  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  2  1  2  0  0  0  0
  7  5  2  0  0  0  0
  4  7  1  0  0  0  0
  3  4  2  0  0  0  0
  2  3  1  0  0  0  0
  6  3  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
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3D MOL for HMDB0032037 (1,3-Benzenediol)

HMDB0032037
     RDKit          3D
1,3-Benzenediol
 14 14  0  0  0  0  0  0  0  0999 V2000
    2.5221   -1.0435   -0.1394 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2714   -0.4210   -0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1569    0.9524   -0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0791    1.5633   -0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2562    0.8312   -0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1264   -0.5423    0.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2824   -1.3128    0.0786 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1039   -1.1505   -0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9774   -1.2193    0.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0756    1.5327   -0.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1676    2.6406   -0.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2213    1.3203   -0.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1965   -0.9189    0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2222   -2.2322    0.0010 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
  6  7  1  0
  6  8  2  0
  8  2  1  0
  1  9  1  0
  3 10  1  0
  4 11  1  0
  5 12  1  0
  7 13  1  0
  8 14  1  0
M  END
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3D SDF for HMDB0032037 (1,3-Benzenediol)

  Mrv1652305062021452D          

  8  8  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  2  1  2  0  0  0  0
  7  5  2  0  0  0  0
  4  7  1  0  0  0  0
  3  4  2  0  0  0  0
  2  3  1  0  0  0  0
  6  3  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032037

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
GHMLBKRAJCXXBS-UHFFFAOYSA-N

> <FORMULA>
C6H6O2

> <MOLECULAR_WEIGHT>
110.1106

> <EXACT_MASS>
110.036779436

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
10.74786583441956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
benzene-1,3-diol

> <ALOGPS_LOGP>
0.70

> <JCHEM_LOGP>
1.3661151726666665

> <ALOGPS_LOGS>
-0.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.725686553960157

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.26428499493661

> <JCHEM_PKA_STRONGEST_BASIC>
-5.663505847935281

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
30.019799999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.23e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
resorcinol

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0032037 (1,3-Benzenediol)

HMDB0032037
     RDKit          3D
1,3-Benzenediol
 14 14  0  0  0  0  0  0  0  0999 V2000
    2.5221   -1.0435   -0.1394 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2714   -0.4210   -0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1569    0.9524   -0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0791    1.5633   -0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2562    0.8312   -0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1264   -0.5423    0.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2824   -1.3128    0.0786 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1039   -1.1505   -0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9774   -1.2193    0.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0756    1.5327   -0.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1676    2.6406   -0.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2213    1.3203   -0.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1965   -0.9189    0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2222   -2.2322    0.0010 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
  6  7  1  0
  6  8  2  0
  8  2  1  0
  1  9  1  0
  3 10  1  0
  4 11  1  0
  5 12  1  0
  7 13  1  0
  8 14  1  0
M  END
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PDB for HMDB0032037 (1,3-Benzenediol)

HEADER    PROTEIN                                 06-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-20         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000   3.080   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667  -1.540   0.000  0.00  0.00           O+0
CONECT    1    5    2                                                       
CONECT    2    1    3                                                       
CONECT    3    4    2    6                                                  
CONECT    4    7    3                                                       
CONECT    5    1    7                                                       
CONECT    6    3                                                            
CONECT    7    5    4    8                                                  
CONECT    8    7                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for HMDB0032037 (1,3-Benzenediol)

COMPND    HMDB0032037
HETATM    1  O1  UNL     1       2.522  -1.043  -0.139  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.271  -0.421  -0.106  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.157   0.952  -0.148  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.079   1.563  -0.115  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.256   0.831  -0.039  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.126  -0.542   0.002  1.00  0.00           C  
HETATM    7  O2  UNL     1      -2.282  -1.313   0.079  1.00  0.00           O  
HETATM    8  C6  UNL     1       0.104  -1.151  -0.031  1.00  0.00           C  
HETATM    9  H1  UNL     1       2.977  -1.219   0.762  1.00  0.00           H  
HETATM   10  H2  UNL     1       2.076   1.533  -0.208  1.00  0.00           H  
HETATM   11  H3  UNL     1      -0.168   2.641  -0.148  1.00  0.00           H  
HETATM   12  H4  UNL     1      -2.221   1.320  -0.014  1.00  0.00           H  
HETATM   13  H5  UNL     1      -3.196  -0.919   0.105  1.00  0.00           H  
HETATM   14  H6  UNL     1       0.222  -2.232   0.001  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   12
CONECT    6    7    8    8
CONECT    7   13
CONECT    8   14
END
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SMILES for HMDB0032037 (1,3-Benzenediol)

OC1=CC(O)=CC=C1
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INCHI for HMDB0032037 (1,3-Benzenediol)

InChI=1S/C6H6O2/c7-5-2-1-3-6(8)4-5/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-1,3-diol
Traditional Nameresorcinol
CAS Registry Number108-46-3
SMILES
OC1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C6H6O2/c7-5-2-1-3-6(8)4-5/h1-4,7-8H
InChI KeyGHMLBKRAJCXXBS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentResorcinols
Alternative Parents
Substituents
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 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
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationEnvironmental role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point111 °CNot Available
Boiling Point178.00 °C. @ 16.00 mm HgThe Good Scents Company Information System
Water Solubility717 mg/mL at 25 °CNot Available
LogP0.80Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB11085
Phenol Explorer Compound ID663
FooDB IDFDB008738
KNApSAcK IDC00002671
Chemspider ID4878
KEGG Compound IDC01751
BioCyc IDCPD-623
BiGG IDNot Available
Wikipedia LinkResorcinol
METLIN IDNot Available
PubChem Compound5054
PDB IDRCO
ChEBI ID27810
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1009421
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details
1. 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
1,3-Benzenediol → 3,4,5-trihydroxy-6-(3-hydroxyphenoxy)oxane-2-carboxylic aciddetails