1,2-Dihydroxybenzene

Identification

Name
1,2-Dihydroxybenzene
Accession Number
DB02232  (EXPT00830)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
C.I.-76500 / NSC-1573
Categories
UNII
LF3AJ089DQ
CAS number
120-80-9
Weight
Average: 110.1106
Monoisotopic: 110.036779436
Chemical Formula
C6H6O2
InChI Key
YCIMNLLNPGFGHC-UHFFFAOYSA-N
InChI
InChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H
IUPAC Name
benzene-1,2-diol
SMILES
OC1=CC=CC=C1O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCatechol 1,2-dioxygenaseNot AvailableAcinetobacter sp. (strain ADP1)
UBiphenyl-2,3-diol 1,2-dioxygenaseNot AvailableBurkholderia xenovorans (strain LB400)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Disulfiram Action PathwayDrug action
Tyrosine MetabolismMetabolic
AlkaptonuriaDisease
Monoamine Oxidase-A Deficiency (MAO-A)Disease
Tyrosine MetabolismMetabolic
Tyrosinemia, Transient, of the NewbornDisease
HawkinsinuriaDisease
Tyrosinemia Type IDisease
Dopamine beta-Hydroxylase DeficiencyDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0000957
KEGG Compound
C15571
PubChem Compound
289
PubChem Substance
46507748
ChemSpider
13837760
BindingDB
26188
ChEBI
18135
ChEMBL
CHEMBL280998
HET
CAQ
PDB Entries
1dlt / 1knd / 1xep / 2buq / 2buy / 2pum / 3fw4 / 3hhy / 3mi5 / 3o4m
show 9 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)105 °CPhysProp
boiling point (°C)245 °CPhysProp
water solubility4.61E+005 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP0.88HANSCH,C ET AL. (1995)
logS0.62ADME Research, USCD
pKa9.45 (at 25 °C)SERJEANT,EP & DEMPSEY,B (1979)
Predicted Properties
PropertyValueSource
Water Solubility75.0 mg/mLALOGPS
logP0.74ALOGPS
logP1.37ChemAxon
logS-0.17ALOGPS
pKa (Strongest Acidic)9.34ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.02 m3·mol-1ChemAxon
Polarizability10.69 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9782
Blood Brain Barrier+0.5
Caco-2 permeable+0.8824
P-glycoprotein substrateNon-substrate0.7207
P-glycoprotein inhibitor INon-inhibitor0.9705
P-glycoprotein inhibitor IINon-inhibitor0.9926
Renal organic cation transporterNon-inhibitor0.9134
CYP450 2C9 substrateNon-substrate0.8247
CYP450 2D6 substrateNon-substrate0.8574
CYP450 3A4 substrateNon-substrate0.7305
CYP450 1A2 substrateNon-inhibitor0.8949
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9579
CYP450 2C19 inhibitorNon-inhibitor0.9348
CYP450 3A4 inhibitorNon-inhibitor0.957
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7461
Ames testNon AMES toxic0.6674
CarcinogenicityNon-carcinogens0.8689
BiodegradationReady biodegradable0.6877
Rat acute toxicity2.5957 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9322
hERG inhibition (predictor II)Non-inhibitor0.8953
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0udr-1950000000-16187bb35dcb40c26e78
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-03di-8900000000-4e15f35dca47661de590
GC-MS Spectrum - EI-BGC-MSsplash10-03di-9600000000-032a40483dec93738075
GC-MS Spectrum - EI-BGC-MSsplash10-03di-7900000000-83f892852c355a3863e9
GC-MS Spectrum - EI-BGC-MSsplash10-03di-9400000000-90885264baa17f65d954
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udr-1950000000-16187bb35dcb40c26e78
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udr-1930000000-24d2e0a8e36245d9e187
Mass Spectrum (Electron Ionization)MSsplash10-03di-9600000000-b8e03f4f3ea89044828e
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-01ox-9400000000-d59dce8c5e56b026f8b2
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-014i-9000000000-632cabc9b371835019c1
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-02t9-9200000000-ac902cb99981017de3b5
MS/MS Spectrum - EI-B (VARIAN MAT-44) , PositiveLC-MS/MSsplash10-03di-8900000000-95af3d2738de98d27f26
MS/MS Spectrum - EI-B (Unknown) , PositiveLC-MS/MSsplash10-03di-9600000000-032a40483dec93738075
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-03di-7900000000-f5cb1c53768e05ca1530
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0a4i-0900000000-c94dab4d218dbb3bb108
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, NegativeLC-MS/MSsplash10-0a4i-1900000000-edd8ba1e77bbb2f76304
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-66523f3122b954e6400f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-1900000000-5fd776e479836f7464af
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-9000000000-2c46a1375dbb634ef735
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0900000000-986c93875cb12d90fa90
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0900000000-a301685abb4194689ca3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9500000000-2017b42835ace86f16ee
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0a4i-0900000000-c94dab4d218dbb3bb108
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0a4i-1900000000-edd8ba1e77bbb2f76304
MS/MS Spectrum - , negativeLC-MS/MSsplash10-0a4i-0900000000-12053747e62e910151ad
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as catechols. These are compounds containing a 1,2-benzenediol moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenols
Sub Class
Benzenediols
Direct Parent
Catechols
Alternative Parents
1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Organooxygen compounds / Hydrocarbon derivatives
Substituents
Catechol / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Monocyclic benzene moiety / Organic oxygen compound / Hydrocarbon derivative / Organooxygen compound / Aromatic homomonocyclic compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
catechols (CHEBI:18135) / a catechol (CATECHOL)

Targets

Kind
Protein
Organism
Acinetobacter sp. (strain ADP1)
Pharmacological action
Unknown
General Function
Ferric iron binding
Specific Function
Not Available
Gene Name
catA
Uniprot ID
P07773
Uniprot Name
Catechol 1,2-dioxygenase
Molecular Weight
34347.02 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Burkholderia xenovorans (strain LB400)
Pharmacological action
Unknown
General Function
Ferrous iron binding
Specific Function
Shows a preference for catechols with groups immediately adjacent to the hydroxyl substituents.
Gene Name
bphC
Uniprot ID
P47228
Uniprot Name
Biphenyl-2,3-diol 1,2-dioxygenase
Molecular Weight
32470.515 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on October 01, 2018 13:16