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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:45 UTC
HMDB IDHMDB0001164
Secondary Accession Numbers
  • HMDB01164
Metabolite Identification
Common Nametrans-1,2-Dihydrobenzene-1,2-diol
Descriptiontrans-1,2-Dihydrobenzene-1,2-diol, also known as arene diol or trans-(+-)-3,5-cyclohexadiene-1,2-diol, belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions. trans-1,2-Dihydrobenzene-1,2-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563860685
Synonyms
ValueSource
Arene diolHMDB
cis-3,5-Cyclohexadiene-1,2-diol solutionHMDB
Racemic mixture OF (+)- and (-)-1,2-dihydroxy-1,2-dihydrobenzeneHMDB
Rel-(1R,2R)-cyclohexa-3,5-diene-1,2-diolHMDB
trans-(+-)-3,5-Cyclohexadiene-1,2-diolHMDB
trans-3,5-Cyclohexadiene-1,2-diolHMDB
trans-1,2-Dihydrobenzene-1,2-diolChEBI
Chemical FormulaC6H8O2
Average Molecular Weight112.1265
Monoisotopic Molecular Weight112.0524295
IUPAC Name(1R,2R)-cyclohexa-3,5-diene-1,2-diol
Traditional Namearene diol
CAS Registry Number103302-38-1
SMILES
O[C@@H]1C=CC=C[C@H]1O
InChI Identifier
InChI=1S/C6H8O2/c7-5-3-1-2-4-6(5)8/h1-8H/t5-,6-/m1/s1
InChI KeyYDRSQRPHLBEPTP-PHDIDXHHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct Parent1,2-diols
Alternative Parents
Substituents
  • Secondary alcohol
  • 1,2-diol
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility178 g/LALOGPS
logP-0.18ALOGPS
logP-0.21ChemAxon
logS0.2ALOGPS
pKa (Strongest Acidic)13.47ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity32.56 m³·mol⁻¹ChemAxon
Polarizability11.13 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zfu-9000000000-36be6170d6aeb143432bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00xu-9710000000-3400c66fcd577a2df022Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1900000000-d7121c202776bf3f1ff8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-5900000000-51396982b568c547b4fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-9000000000-db963106694d68d1163cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-983307a7cfa91742b0daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1900000000-185fc58f8f3b52505cddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ik9-9300000000-9f1f8262efe5adb2f0c9Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
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 IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022458
KNApSAcK IDNot Available
Chemspider ID131491
KEGG Compound IDC04221
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6046
PubChem Compound149186
PDB IDNot Available
ChEBI ID10702
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceSato, Tokuro; Fukuyama, Tomitaro; Suzuki, Taeko; Yoshikawa, Haruhisa. 1,2-Dihydro-1,2-dihydroxybenzene and several other substances in the metabolism of benzene. Journal of Biochemistry (Tokyo, Japan) (1963), 53 23-7.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:
AKR1C4
Uniprot ID:
P17516
Molecular weight:
37094.57
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2. Functions as a bi-directional 3-alpha-, 17-beta- and 20-alpha HSD. Can interconvert active androgens, estrogens and progestins with their cognate inactive metabolites. Preferentially transforms androstenedione (4-dione) to testosterone.
Gene Name:
AKR1C3
Uniprot ID:
P42330
Molecular weight:
36866.91
Reactions
trans-1,2-Dihydrobenzene-1,2-diol + NADP → Pyrocatechol + NADPHdetails
General function:
Involved in oxidoreductase activity
Specific function:
Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the intrahepatic bile acid concentration. Has a low bile-binding ability. May play a role in myelin formation.
Gene Name:
AKR1C1
Uniprot ID:
Q04828
Molecular weight:
36788.02
Reactions
trans-1,2-Dihydrobenzene-1,2-diol + NADP → Pyrocatechol + NADPHdetails
General function:
Involved in oxidoreductase activity
Specific function:
Works in concert with the 5-alpha/5-beta-steroid reductases to convert steroid hormones into the 3-alpha/5-alpha and 3-alpha/5-beta-tetrahydrosteroids. Catalyzes the inactivation of the most potent androgen 5-alpha-dihydrotestosterone (5-alpha-DHT) to 5-alpha-androstane-3-alpha,17-beta-diol (3-alpha-diol). Has a high bile-binding ability.
Gene Name:
AKR1C2
Uniprot ID:
P52895
Molecular weight:
15747.91
Reactions
trans-1,2-Dihydrobenzene-1,2-diol + NADP → Pyrocatechol + NADPHdetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
DHDH
Uniprot ID:
Q9UQ10
Molecular weight:
36381.705
Reactions
trans-1,2-Dihydrobenzene-1,2-diol + NADP → Pyrocatechol + NADPHdetails