MiMeDB: Showing metabocard for Quinone (MMDBc0031144)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 00:37:02 UTC

Update Date

2024-10-07 04:39:46 UTC

Metabolite ID

MMDBc0031144

Metabolite Identification

Common Name

Quinone

Description

Quinone is also called 1,4-benzoquinone or cyclohexadienedione. 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. 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).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D 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

Molecular Formula

C₆H₄O₂

Average Mass

108.0948

Monoisotopic Mass

108.021129372

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	45.4 g/L	ALOGPS
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

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0zgi-9500000000-c8bfbbc465fad7929f87	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00xr-1900000000-9b99afb0e9c6350434a4	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0zgi-9500000000-c8bfbbc465fad7929f87	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00xr-1900000000-9b99afb0e9c6350434a4	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9500000000-6664b553a87d4fc15f94	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-7900000000-fca2433f986ba378f8c9	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00or-9000000000-6897ef153b4119e50ceb	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014u-9000000000-9bddbff45c6d0d3e0cf1	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive	splash10-0zgi-9500000000-c8bfbbc465fad7929f87	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-QFT 7V, negative	splash10-014i-1900000000-6d13549d8c534563dc9b	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-QFT 9V, negative	splash10-014i-1900000000-af62dc0334e009fe3e5b	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-QFT 14V, negative	splash10-014i-3900000000-1167cf77177c0761168e	2020-07-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-d886efcfed5b0135bcd5	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1900000000-7f5c75e048ee2f454e33	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9100000000-db1ffa9cf092dd5e4551	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-648d78080240a1294e4c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-648d78080240a1294e4c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-5900000000-0f04c7bee6397237ee21	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-2c6cb60a5040c6239920	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-4900000000-f1f9c8ded0fe97bb684d	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9000000000-3c2c54b9382bddbdf0df	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-62ea0dd9303aae554ccd	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-2900000000-7966cc06756dd3b8c736	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-28217a7272677bec662a	2021-09-24	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0zgi-9200000000-8777cde0dbcbb2157cdd	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, experimental)		2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)		2014-09-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Bone Marrow
Fibroblasts
Kidney
Liver
Neuron
Skeletal Muscle
Urine

Tissue Locations

Bone Marrow
Fibroblasts
Kidney
Liver
Neuron
Skeletal Muscle

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191760	Tyrosinase	Unknown	P14679	Homo sapiens
MMDBp0191809	Ribosyldihydronicotinamide dehydrogenase [quinone]	Unknown	P16083	Homo sapiens
MMDBp0192057	Amiloride-sensitive amine oxidase [copper-containing]	Unknown	P19801	Homo sapiens
MMDBp0192060	Membrane primary amine oxidase	Unknown	Q16853	Homo sapiens
MMDBp0192061	Retina-specific copper amine oxidase	Unknown	O75106	Homo sapiens
MMDBp0192651	Quinone oxidoreductase	Unknown	Q08257	Homo sapiens
MMDBp0193201	NAD(P)H dehydrogenase [quinone] 1	Unknown	P15559	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	2	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Leaves	Pimpinella anisum	FooDB	31437929
Plant	Fruit	Olea europaea	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Bone marrow	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Blood	Detected but not Quantified				HMDB

External Links

HMDB ID

HMDB0003364

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Mu D, Medzihradszky KF, Adams GW, Mayer P, Hines WM, Burlingame AL, Smith AJ, Cai D, Klinman JP: Primary structures for a mammalian cellular and serum copper amine oxidase. J Biol Chem. 1994 Apr 1;269(13):9926-32. [PubMed:8144587 ]
Smith MT: The mechanism of benzene-induced leukemia: a hypothesis and speculations on the causes of leukemia. Environ Health Perspect. 1996 Dec;104 Suppl 6:1219-25. doi: 10.1289/ehp.961041219. [PubMed:9118896 ]
Soucek P: Cytochrome P450 destruction by quinones: comparison of effects in rat and human liver microsomes. Chem Biol Interact. 1999 Aug 1;121(3):223-36. doi: 10.1016/s0009-2797(99)00100-3. [PubMed:10462055 ]
Yamazaki H, Shibata A, Suzuki M, Nakajima M, Shimada N, Guengerich FP, Yokoi T: Oxidation of troglitazone to a quinone-type metabolite catalyzed by cytochrome P-450 2C8 and P-450 3A4 in human liver microsomes. Drug Metab Dispos. 1999 Nov;27(11):1260-6. [PubMed:10534310 ]
Roberg K, Johansson U, Ollinger K: Lysosomal release of cathepsin D precedes relocation of cytochrome c and loss of mitochondrial transmembrane potential during apoptosis induced by oxidative stress. Free Radic Biol Med. 1999 Dec;27(11-12):1228-37. doi: 10.1016/s0891-5849(99)00146-x. [PubMed:10641715 ]
Toyota T, Ueno Y: [Clinical effect and side effect of troglitazone]. Nihon Rinsho. 2000 Feb;58(2):376-82. [PubMed:10707561 ]
He K, Woolf TF, Kindt EK, Fielder AE, Talaat RE: Troglitazone quinone formation catalyzed by human and rat CYP3A: an atypical CYP oxidation reaction. Biochem Pharmacol. 2001 Jul 15;62(2):191-8. doi: 10.1016/s0006-2952(01)00653-0. [PubMed:11389877 ]
Bello RI, Gomez-Diaz C, Navarro F, Alcain FJ, Villalba JM: Expression of NAD(P)H:quinone oxidoreductase 1 in HeLa cells: role of hydrogen peroxide and growth phase. J Biol Chem. 2001 Nov 30;276(48):44379-84. doi: 10.1074/jbc.M107168200. Epub 2001 Sep 20. [PubMed:11567026 ]
Siegel D, Ryder J, Ross D: NAD(P)H: quinone oxidoreductase 1 expression in human bone marrow endothelial cells. Toxicol Lett. 2001 Dec 15;125(1-3):93-8. doi: 10.1016/s0378-4274(01)00426-x. [PubMed:11701227 ]
Terman A, Neuzil J, Kagedal K, Ollinger K, Brunk UT: Decreased apoptotic response of inclusion-cell disease fibroblasts: a consequence of lysosomal enzyme missorting? Exp Cell Res. 2002 Mar 10;274(1):9-15. doi: 10.1006/excr.2001.5441. [PubMed:11855852 ]
Park S, Geddes TJ, Javitch JA, Kuhn DM: Dopamine prevents nitration of tyrosine hydroxylase by peroxynitrite and nitrogen dioxide: is nitrotyrosine formation an early step in dopamine neuronal damage? J Biol Chem. 2003 Aug 1;278(31):28736-42. doi: 10.1074/jbc.M304362200. Epub 2003 May 27. [PubMed:12771134 ]
Hasegawa T, Matsuzaki M, Takeda A, Kikuchi A, Furukawa K, Shibahara S, Itoyama Y: Increased dopamine and its metabolites in SH-SY5Y neuroblastoma cells that express tyrosinase. J Neurochem. 2003 Oct;87(2):470-5. doi: 10.1046/j.1471-4159.2003.02008.x. [PubMed:14511124 ]
Xu L, Eiseman JL, Egorin MJ, D'Argenio DZ: Physiologically-based pharmacokinetics and molecular pharmacodynamics of 17-(allylamino)-17-demethoxygeldanamycin and its active metabolite in tumor-bearing mice. J Pharmacokinet Pharmacodyn. 2003 Jun;30(3):185-219. doi: 10.1023/a:1025542026488. [PubMed:14571691 ]
He K, Talaat RE, Woolf TF: Incorporation of an oxygen from water into troglitazone quinone by cytochrome P450 and myeloperoxidase. Drug Metab Dispos. 2004 Apr;32(4):442-6. doi: 10.1124/dmd.32.4.442. [PubMed:15039298 ]
Gaskell M, McLuckie KI, Farmer PB: Comparison of the repair of DNA damage induced by the benzene metabolites hydroquinone and p-benzoquinone: a role for hydroquinone in benzene genotoxicity. Carcinogenesis. 2005 Mar;26(3):673-80. doi: 10.1093/carcin/bgi007. Epub 2004 Dec 23. [PubMed:15618234 ]
Fabiani R, De Bartolomeo A, Morozzi G: Involvement of oxygen free radicals in the serum-mediated increase of benzoquinone genotoxicity. Environ Mol Mutagen. 2005 Oct;46(3):156-63. doi: 10.1002/em.20146. [PubMed:15920754 ]
Kwasnicka-Crawford DA, Vincent SR: Role of a novel dual flavin reductase (NR1) and an associated histidine triad protein (DCS-1) in menadione-induced cytotoxicity. Biochem Biophys Res Commun. 2005 Oct 21;336(2):565-71. doi: 10.1016/j.bbrc.2005.08.129. [PubMed:16140270 ]

Showing metabocard for Quinone (MMDBc0031144)

MOL for #<Metabolite:0x0000559d050604a8>

3D MOL for #<Metabolite:0x0000559d050604a8>

3D SDF for #<Metabolite:0x0000559d050604a8>

3D-SDF for #<Metabolite:0x0000559d050604a8>

PDB for #<Metabolite:0x0000559d050604a8>

3D PDB for #<Metabolite:0x0000559d050604a8>

SMILES for #<Metabolite:0x0000559d050604a8>

INCHI for #<Metabolite:0x0000559d050604a8>

Structure for #<Metabolite:0x0000559d050604a8>

3D Structure for #<Metabolite:0x0000559d050604a8>