2',6'-Dichloro-Biphenyl-2,6-Diol

Identification

Generic Name
2',6'-Dichloro-Biphenyl-2,6-Diol
DrugBank Accession Number
DB03259
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 255.097
Monoisotopic: 253.990134914
Chemical Formula
C12H8Cl2O2
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as polychlorinated biphenyls. These are organic compounds containing at least two chlorine atoms attached to either benzene ring of the biphenyl moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Biphenyls and derivatives
Direct Parent
Polychlorinated biphenyls
Alternative Parents
Dichlorobenzenes / Catechols / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Aryl chlorides / Organooxygen compounds / Organochlorides / Hydrocarbon derivatives
Substituents
1,3-dichlorobenzene / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Catechol / Chlorobenzene / Halobenzene / Hydrocarbon derivative
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
catechols, hydroxybiphenyls, dichlorobenzene (CHEBI:49509)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
MCZUCSAAGDCHHN-UHFFFAOYSA-N
InChI
InChI=1S/C12H8Cl2O2/c13-8-4-2-5-9(14)11(8)7-3-1-6-10(15)12(7)16/h1-6,15-16H
IUPAC Name
2',6'-dichloro-[1,1'-biphenyl]-2,3-diol
SMILES
OC1=CC=CC(=C1O)C1=C(Cl)C=CC=C1Cl

References

General References
Not Available
PubChem Compound
446948
PubChem Substance
46508347
ChemSpider
394175
ChEBI
49509
ZINC
ZINC000002047793
PDBe Ligand
BP6
PDB Entries
1lkd

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0784 mg/mLALOGPS
logP4.23ALOGPS
logP4.22Chemaxon
logS-3.5ALOGPS
pKa (Strongest Acidic)8.92Chemaxon
pKa (Strongest Basic)-6.3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area40.46 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity64.77 m3·mol-1Chemaxon
Polarizability23.64 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.995
Blood Brain Barrier+0.7743
Caco-2 permeable+0.7866
P-glycoprotein substrateNon-substrate0.6984
P-glycoprotein inhibitor INon-inhibitor0.9468
P-glycoprotein inhibitor IINon-inhibitor0.9555
Renal organic cation transporterNon-inhibitor0.8937
CYP450 2C9 substrateNon-substrate0.7918
CYP450 2D6 substrateNon-substrate0.8828
CYP450 3A4 substrateNon-substrate0.6225
CYP450 1A2 substrateInhibitor0.8026
CYP450 2C9 inhibitorInhibitor0.8196
CYP450 2D6 inhibitorNon-inhibitor0.8743
CYP450 2C19 inhibitorInhibitor0.6554
CYP450 3A4 inhibitorNon-inhibitor0.9158
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7321
Ames testNon AMES toxic0.9415
CarcinogenicityNon-carcinogens0.7793
BiodegradationNot ready biodegradable0.9784
Rat acute toxicity2.6414 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9439
hERG inhibition (predictor II)Non-inhibitor0.7426
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
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-1000-1290000000-9b5d4bbe07c8c0ff2b45
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0090000000-abd52df513db44bb0ba5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-2090000000-dd6b4ff7a757688f5e64
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0190000000-05e0c83b4769d489c54f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ox-0910000000-e8d103d5b0e193d8c4bd
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9010000000-d1261fb491aa0a62a226
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9100000000-82c3544001c570f09ccb
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-148.14116
predicted
DeepCCS 1.0 (2019)
[M+H]+150.53673
predicted
DeepCCS 1.0 (2019)
[M+Na]+156.56136
predicted
DeepCCS 1.0 (2019)

Targets

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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. [Article]
  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. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52