NAV

Dibromothymoquinone

Identification

Generic Name
Dibromothymoquinone
DrugBank Accession Number
DB04646
Background

At low concentrations, this compound inhibits reduction of conventional hydrophilic electron acceptors, probably acting as a plastoquinone antagonist. At higher concentrations, it acts as an electron acceptor, intercepting electrons either before or at the site of its inhibitory activity. [PubChem]

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 321.993
Monoisotopic: 319.904754858
Chemical Formula
C10H10Br2O2
Synonyms
  • 2,5-dibromo-3-isopropyl-6-methyl-1,4-benzoquinone
  • 2,5-dibromo-3-isopropyl-6-methylbenzoquinone
  • 2,5-dibromo-3-methyl-6-(1-methylethyl)-2,5-cyclohexadiene-1,4-dione
  • 2,5-dibromo-3-methyl-6-(1-methylethyl)cyclohexa-2,5-diene-1,4-dione
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UApocytochrome fNot AvailableMastigocladus laminosus
UCytochrome b6-f complex subunit 5Not AvailableMastigocladus laminosus
UCytochrome b6-f complex subunit 6Not AvailableMastigocladus laminosus
UCytochrome b6-f complex subunit 7Not AvailableMastigocladus laminosus
UCytochrome b6-f complex subunit 8Not AvailableMastigocladus laminosus
UCytochrome b6Not AvailableMastigocladus laminosus
UCytochrome b6-f complex iron-sulfur subunitNot AvailableMastigocladus laminosus
UCytochrome b6-f complex subunit 4Not AvailableMastigocladus laminosus
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
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbonyl compounds
Direct Parent
P-benzoquinones
Alternative Parents
Vinylogous halides / Alpha-haloketones / Vinyl bromides / Bromoalkenes / Organobromides / Organic oxides / Hydrocarbon derivatives
Substituents
Aliphatic homomonocyclic compound / Alpha-haloketone / Bromoalkene / Haloalkene / Hydrocarbon derivative / Organic oxide / Organobromide / Organohalogen compound / P-benzoquinone / Vinyl bromide
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
benzoquinones (CHEBI:19371) / a bromoaromatic compound, a quinone (CPD-10338)
Affected organisms
Not Available

Chemical Identifiers

UNII
0BY5UFN2U6
CAS number
29096-93-3
InChI Key
GHHZELQYJPWSMG-UHFFFAOYSA-N
InChI
InChI=1S/C10H10Br2O2/c1-4(2)6-8(12)9(13)5(3)7(11)10(6)14/h4H,1-3H3
IUPAC Name
2,5-dibromo-3-methyl-6-(propan-2-yl)cyclohexa-2,5-diene-1,4-dione
SMILES
CC(C)C1=C(Br)C(=O)C(C)=C(Br)C1=O

References

General References
Not Available
PubChem Compound
34474
PubChem Substance
46505309
ChemSpider
31724
ChEBI
19371
ChEMBL
CHEMBL1231418
ZINC
ZINC000002011646
PDBe Ligand
BNT
PDB Entries
2d2c / 4g86

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 Solubility0.132 mg/mLALOGPS
logP3.01ALOGPS
logP3.65Chemaxon
logS-3.4ALOGPS
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area34.14 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity64.11 m3·mol-1Chemaxon
Polarizability24.3 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8762
Caco-2 permeable+0.7279
P-glycoprotein substrateNon-substrate0.7073
P-glycoprotein inhibitor IInhibitor0.5365
P-glycoprotein inhibitor IINon-inhibitor0.9581
Renal organic cation transporterNon-inhibitor0.8685
CYP450 2C9 substrateNon-substrate0.8693
CYP450 2D6 substrateNon-substrate0.8448
CYP450 3A4 substrateSubstrate0.5249
CYP450 1A2 substrateNon-inhibitor0.8192
CYP450 2C9 inhibitorInhibitor0.5
CYP450 2D6 inhibitorNon-inhibitor0.8003
CYP450 2C19 inhibitorNon-inhibitor0.61
CYP450 3A4 inhibitorNon-inhibitor0.8425
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6524
Ames testNon AMES toxic0.7274
CarcinogenicityNon-carcinogens0.7008
BiodegradationNot ready biodegradable0.9138
Rat acute toxicity2.2966 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8729
hERG inhibition (predictor II)Non-inhibitor0.9479
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-MSsplash10-05mo-9661000000-b9ad2502d13f1a25325d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0009000000-8db12168710e43966eda
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0549000000-15e02ebf7d3f81f95f0e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0009000000-3873ad1e52afc8a2a336
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-016r-4019000000-a310c9b67b5479010e39
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014m-4911000000-c6c5cd6e9b265b91fa16
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-5292000000-7a5687613b0b2ad182d0
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]-148.0281
predicted
DeepCCS 1.0 (2019)
[M+H]+150.38611
predicted
DeepCCS 1.0 (2019)
[M+Na]+157.14305
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Apocytochrome f
Kind
Protein
Organism
Mastigocladus laminosus
Pharmacological action
Unknown
General Function
Iron ion binding
Specific Function
Component of the cytochrome b6-f complex, which mediates electron transfer between photosystem II (PSII) and photosystem I (PSI), cyclic electron flow around PSI, and state transitions.
Gene Name
petA
Uniprot ID
P83793
Uniprot Name
Cytochrome f
Molecular Weight
36449.73 Da
References
  1. 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]
Details2. Cytochrome b6-f complex subunit 5
Kind
Protein
Organism
Mastigocladus laminosus
Pharmacological action
Unknown
General Function
Electron transporter, transferring electrons within cytochrome b6/f complex of photosystem ii activity
Specific Function
Component of the cytochrome b6-f complex, which mediates electron transfer between photosystem II (PSII) and photosystem I (PSI), cyclic electron flow around PSI, and state transitions. PetG is req...
Gene Name
petG
Uniprot ID
P83797
Uniprot Name
Cytochrome b6-f complex subunit 5
Molecular Weight
4014.67 Da
References
  1. 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]
Details3. Cytochrome b6-f complex subunit 6
Kind
Protein
Organism
Mastigocladus laminosus
Pharmacological action
Unknown
General Function
Electron transporter, transferring electrons within cytochrome b6/f complex of photosystem ii activity
Specific Function
Component of the cytochrome b6-f complex, which mediates electron transfer between photosystem II (PSII) and photosystem I (PSI), cyclic electron flow around PSI, and state transitions (PubMed:1452...
Gene Name
petL
Uniprot ID
P83795
Uniprot Name
Cytochrome b6-f complex subunit 6
Molecular Weight
3502.415 Da
References
  1. 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]
Details4. Cytochrome b6-f complex subunit 7
Kind
Protein
Organism
Mastigocladus laminosus
Pharmacological action
Unknown
General Function
Electron carrier activity
Specific Function
Component of the cytochrome b6-f complex, which mediates electron transfer between photosystem II (PSII) and photosystem I (PSI), cyclic electron flow around PSI, and state transitions.
Gene Name
petM
Uniprot ID
P83796
Uniprot Name
Cytochrome b6-f complex subunit 7
Molecular Weight
3841.59 Da
References
  1. 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]
Details5. Cytochrome b6-f complex subunit 8
Kind
Protein
Organism
Mastigocladus laminosus
Pharmacological action
Unknown
General Function
Electron transporter, transferring electrons within cytochrome b6/f complex of photosystem ii activity
Specific Function
Component of the cytochrome b6-f complex, which mediates electron transfer between photosystem II (PSII) and photosystem I (PSI), cyclic electron flow around PSI, and state transitions.
Gene Name
petN
Uniprot ID
P83798
Uniprot Name
Cytochrome b6-f complex subunit 8
Molecular Weight
3275.95 Da
References
  1. 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]
Details6. Cytochrome b6
Kind
Protein
Organism
Mastigocladus laminosus
Pharmacological action
Unknown
General Function
Oxidoreductase activity
Specific Function
Component of the cytochrome b6-f complex, which mediates electron transfer between photosystem II (PSII) and photosystem I (PSI), cyclic electron flow around PSI, and state transitions.
Gene Name
petB
Uniprot ID
P83791
Uniprot Name
Cytochrome b6
Molecular Weight
24226.45 Da
References
  1. 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]
Details7. Cytochrome b6-f complex iron-sulfur subunit
Kind
Protein
Organism
Mastigocladus laminosus
Pharmacological action
Unknown
General Function
Ubiquinol-cytochrome-c reductase activity
Specific Function
Component of the cytochrome b6-f complex, which mediates electron transfer between photosystem II (PSII) and photosystem I (PSI), cyclic electron flow around PSI, and state transitions.
Gene Name
petC
Uniprot ID
P83794
Uniprot Name
Cytochrome b6-f complex iron-sulfur subunit
Molecular Weight
19401.11 Da
References
  1. 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]
Details8. Cytochrome b6-f complex subunit 4
Kind
Protein
Organism
Mastigocladus laminosus
Pharmacological action
Unknown
General Function
Oxidoreductase activity
Specific Function
Component of the cytochrome b6-f complex, which mediates electron transfer between photosystem II (PSII) and photosystem I (PSI), cyclic electron flow around PSI, and state transitions.
Gene Name
petD
Uniprot ID
P83792
Uniprot Name
Cytochrome b6-f complex subunit 4
Molecular Weight
17673.965 Da
References
  1. 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 September 11, 2007 17:49 / Updated at June 12, 2020 16:52