Cannabis Compound Database: Showing Compound Card for Quinone (CDB005109)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (7) Show 13 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 19:10:13 UTC

Updated at

2021-01-04 18:59:20 UTC

CannabisDB ID

CDB005109

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Quinone

Description

Quinone also known as 1,4-benzoquinone, p-BQ or cyclohexadienedione, belongs to the class of organic compounds known as quinones. These are heterocyclic compounds containing two C=O bonds. Quinones are oxidized derivatives of aromatic compounds and are often readily made from reactive aromatic compounds with electron-donating substituents such as phenols and catechols, which increase the nucleophilicity of the ring and contributes to the large redox potential needed to break aromaticity. Quinone exists as a solid characterized by yellow prisms, with a penetrating odor resembling that of chlorine. It is used as a chemical intermediate, a polymerization inhibitor, an oxidizing agent, a photographic chemical, and a tanning agent. Occupational exposure to quinone may occur in the dye, textile, chemical, tanning, and cosmetic industries. Acute exposure to high levels of quinone, via inhalation in humans, is highly irritating to the eyes, resulting in discoloration of the conjunctiva and cornea. Chronic dermal contact to quinone in humans may result in skin ulceration, while chronic inhalation exposure may result in visual disturbances. Derivatives of quinones are common constituents of biologically relevant molecules. Some serve as electron acceptors in electron transport chains such as those in photosynthesis (plastoquinone, phylloquinone), and aerobic respiration (ubiquinone). Quinone is a common constituent of biologically relevant molecules (e.g. Vitamin K1 is phylloquinone). The auto-oxidation of the neurotransmitter dopamine and its precursor L-Dopa generates dopamine quinone which inhibits the functioning of dopamine transporter (DAT) and the TH enzyme leading to low mitochondrial ATP production (PMID: 24653659 ). Quinone is a constituent of tobacco and marijuana (cannabis) smoke and is formed during the combustion of cannabis ( Ref:DOI ). Quinone is quite toxic and is believed to be the causative agent for smoke-induced emphysema (PMID: 25057895 ). Rodent studies have shown that smoking causes progressive accumulation of quinone in the lung which leads to destruction of alveolar cells and emphysema. The pathogenesis involves arylation, oxidative stress, inflammation, and apoptosis (PMID: 25057895 ). The lung damage caused by smoke-generated quinone could be prevented by high doses of ascorbic acid (vitamin C), a known antagonist for quinone.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,4-Benzochinon	ChEBI
2,5-Cyclohexadiene-1,4-dione	ChEBI
Benzo-1,4-quinone	ChEBI
Benzoquinone	ChEBI
p-Benzoquinone	ChEBI
p-Chinon	ChEBI
p-Quinone	ChEBI
Para-benzoquinone	ChEBI
Chinone	Kegg
1,4-Benzoquinone	Kegg
1,4-Benzoquine	HMDB
1,4-Cyclohexadiene dioxide	HMDB
1,4-Cyclohexadienedione	HMDB
1,4-Diossibenzene	HMDB
1,4-Dioxy-benzol	HMDB
1,4-Dioxybenzene	HMDB
2,5-Cyclohexadiene-1-4-dione	HMDB
Benzo-chinon	HMDB
Chinon	HMDB
Cyclohexadiene-1,4-dione	HMDB
Cyclohexadienedione	HMDB
Eldoquin	HMDB
Para-quinone	HMDB
Quinone1,4-benzoquinone	HMDB
Semiquinone anion	HMDB
Semiquinone radicals	HMDB

Chemical Formula

C₆H₄O₂

Average Molecular Weight

108.09

Monoisotopic Molecular Weight

108.0211

IUPAC Name

cyclohexa-2,5-diene-1,4-dione

Traditional Name

quinone

CAS Registry Number

106-51-4

SMILES

O=C1C=CC(=O)C=C1

InChI Identifier

InChI=1S/C6H4O2/c7-5-1-2-6(8)4-3-5/h1-4H

InChI Key

AZQWKYJCGOJGHM-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Substituents

P-benzoquinone
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

benzoquinone (CHEBI:16509 )
a small molecule (P-BENZOQUINONE )

Ontology

Ingestion

Source:

Biological:

Plant:

Poaceae

Biological location:

Subcellular:

Tissue and substructures:

Skeletal muscle

Cell and elements:

Cell:

Biofluid and excreta:

Urine

Organ and components:

Role

Environmental role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	115.7 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	11.1 mg/mL at 18 °C	Not Available
logP	0.20	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	0.21	ALOGPS
logP	1.02	ChemAxon
logS	-0.38	ALOGPS
pKa (Strongest Basic)	-7.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	31.03 m³·mol⁻¹	ChemAxon
Polarizability	9.75 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0zgi-9200000000-8777cde0dbcbb2157cdd	2014-09-20	View Spectrum
GC-MS	Quinone, non-derivatized, GC-MS Spectrum	splash10-0zgi-9500000000-c8bfbbc465fad7929f87	Spectrum
GC-MS	Quinone, non-derivatized, GC-MS Spectrum	splash10-00xr-1900000000-9b99afb0e9c6350434a4	Spectrum
GC-MS	Quinone, non-derivatized, GC-MS Spectrum	splash10-0zgi-9500000000-c8bfbbc465fad7929f87	Spectrum
GC-MS	Quinone, non-derivatized, GC-MS Spectrum	splash10-00xr-1900000000-9b99afb0e9c6350434a4	Spectrum
Predicted GC-MS	Quinone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-9500000000-6664b553a87d4fc15f94	Spectrum
Predicted GC-MS	Quinone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-7900000000-fca2433f986ba378f8c9	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00or-9000000000-6897ef153b4119e50ceb	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014u-9000000000-9bddbff45c6d0d3e0cf1	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive	splash10-0zgi-9500000000-c8bfbbc465fad7929f87	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-QFT 7V, negative	splash10-014i-1900000000-6d13549d8c534563dc9b	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-QFT 9V, negative	splash10-014i-1900000000-af62dc0334e009fe3e5b	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-QFT 14V, negative	splash10-014i-3900000000-1167cf77177c0761168e	2020-07-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-d886efcfed5b0135bcd5	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1900000000-7f5c75e048ee2f454e33	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9100000000-db1ffa9cf092dd5e4551	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-648d78080240a1294e4c	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-648d78080240a1294e4c	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-5900000000-0f04c7bee6397237ee21	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-2c6cb60a5040c6239920	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-4900000000-f1f9c8ded0fe97bb684d	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9000000000-3c2c54b9382bddbdf0df	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-62ea0dd9303aae554ccd	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-2900000000-7966cc06756dd3b8c736	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-28217a7272677bec662a	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Riboflavin Metabolism
Pyrimidine Metabolism
Beta Ureidopropionase Deficiency		Not Available
UMP Synthase Deficiency (Orotic Aciduria)		Not Available
Dihydropyrimidinase Deficiency		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Tyrosinase	TYR	11q14-q21	P14679	details
Ribosyldihydronicotinamide dehydrogenase [quinone]	NQO2	6p25.2	P16083	details
Amiloride-sensitive amine oxidase [copper-containing]	ABP1	7q36.1	P19801	details
Membrane primary amine oxidase	AOC3	17q21	Q16853	details
Retina-specific copper amine oxidase	AOC2	17q21	O75106	details
Quinone oxidoreductase	CRYZ	1p31.1	Q08257	details
NAD(P)H dehydrogenase [quinone] 1	NQO1	16q22.1	P15559	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Ribosyldihydronicotinamide dehydrogenase [quinone]	NQO2	6p25.2	P16083	details
Amiloride-sensitive amine oxidase [copper-containing]	ABP1	7q36.1	P19801	details
Membrane primary amine oxidase	AOC3	17q21	Q16853	details
Retina-specific copper amine oxidase	AOC2	17q21	O75106	details
Quinone oxidoreductase	CRYZ	1p31.1	Q08257	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Amiloride-sensitive amine oxidase [copper-containing]	ABP1	7q36.1	P19801	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0003364

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB005755

KNApSAcK ID

Not Available

Chemspider ID

4489

KEGG Compound ID

C00472

BioCyc ID

P-BENZOQUINONE

BiGG ID

Not Available

Wikipedia Link

1,4-Benzoquinone

METLIN ID

6905

PubChem Compound

4650

PDB ID

Not Available

ChEBI ID

16509

References

General References

Dorszewska J, Prendecki M, Lianeri M, Kozubski W: Molecular Effects of L-dopa Therapy in Parkinson's Disease. Curr Genomics. 2014 Feb;15(1):11-7. doi: 10.2174/1389202914666131210213042. [PubMed:24653659 ]
Ghosh A, Ganguly S, Dey N, Banerjee S, Das A, Chattopadhyay DJ, Chatterjee IB: Causation of cigarette smoke-induced emphysema by p-benzoquinone and its prevention by vitamin C. Am J Respir Cell Mol Biol. 2015 Mar;52(3):315-22. doi: 10.1165/rcmb.2013-0545OC. [PubMed:25057895 ]

Only showing the first 10 proteins. There are 13 proteins in total.

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Enzymes

Enzyme Details

1. Tyrosinase

General function:: Involved in oxidoreductase activity
Specific function:: This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:: TYR
Uniprot ID:: P14679
Molecular weight:: 60392.69

Enzyme Details

2. Ribosyldihydronicotinamide dehydrogenase [quinone]

General function:: Involved in electron carrier activity
Specific function:: The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:: NQO2
Uniprot ID:: P16083
Molecular weight:: 25918.4

Enzyme Details

3. Amiloride-sensitive amine oxidase [copper-containing]

General function:: Involved in copper ion binding
Specific function:: Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:: ABP1
Uniprot ID:: P19801
Molecular weight:: 85377.1

Enzyme Details

4. Membrane primary amine oxidase

General function:: Involved in copper ion binding
Specific function:: Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity. May play a role in adipogenesis.
Gene Name:: AOC3
Uniprot ID:: Q16853
Molecular weight:: 84621.27

Enzyme Details

5. Retina-specific copper amine oxidase

General function:: Involved in copper ion binding
Specific function:: Has a monoamine oxidase activity with substrate specificity for 2-phenylethylamine and tryptamine. May play a role in adipogenesis. May be a critical modulator of signal transmission in retina.
Gene Name:: AOC2
Uniprot ID:: O75106
Molecular weight:: 80515.11

Enzyme Details

6. Quinone oxidoreductase

General function:: Involved in zinc ion binding
Specific function:: Does not have alcohol dehydrogenase activity. Binds NADP and acts through a one-electron transfer process. Orthoquinones, such as 1,2-naphthoquinone or 9,10-phenanthrenequinone, are the best substrates (in vitro). May act in the detoxification of xenobiotics. Interacts with (AU)-rich elements (ARE) in the 3'-UTR of target mRNA species. Enhances the stability of mRNA coding for BCL2. NADPH binding interferes with mRNA binding.
Gene Name:: CRYZ
Uniprot ID:: Q08257
Molecular weight:: 35206.36

Enzyme Details

7. NAD(P)H dehydrogenase [quinone] 1

General function:: Involved in electron carrier activity
Specific function:: The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinons involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:: NQO1
Uniprot ID:: P15559
Molecular weight:: 30867.405

Only showing the first 10 proteins. There are 13 proteins in total.

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Showing Compound Card for Quinone (CDB005109)

Structure for CDB005109 (Quinone)

Enzymes