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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-04-06 16:21:13 UTC

Update Date

2023-02-21 17:17:44 UTC

HMDB ID

HMDB0012219

Secondary Accession Numbers

HMDB12219

Metabolite Identification

Common Name

Dopamine quinone

Description

Dopamine quinone, also known as DoQ, belongs to the class of organic compounds known as o-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 2-positions, respectively. Dopamine quinone has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make dopamine quinone a potential biomarker for the consumption of these foods. Dopamine quinone is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Dopamine quinone.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-(2-Aminoethyl)-1,2-benzoquinone	ChEBI
4-(2-Aminoethyl)-O-benzoquinone	ChEBI
Dopamine O-quinone	ChEBI
DoQ	ChEBI
4-(2-Aminoethyl)-3,5-cyclohexadiene-1,2-dione	HMDB
Dopaminoquinone	HMDB
Dopamine quinone	ChEBI

Chemical Formula

C₈H₉NO₂

Average Molecular Weight

151.1626

Monoisotopic Molecular Weight

151.063328537

IUPAC Name

4-(2-aminoethyl)cyclohexa-3,5-diene-1,2-dione

Traditional Name

4-(2-aminoethyl)cyclohexa-3,5-diene-1,2-dione

CAS Registry Number

50673-96-6

SMILES

NCCC1=CC(=O)C(=O)C=C1

InChI Identifier

InChI=1S/C8H9NO2/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5H,3-4,9H2

InChI Key

PQPXZWUZIOASKS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 2-positions, respectively.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

O-benzoquinones

Alternative Parents

Substituents

O-benzoquinone
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Primary aliphatic amine
Amine
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

primary amino compound (CHEBI:74684 )
benzoquinones (CHEBI:74684 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0012219)

Organ

Liver (HMDB: HMDB0012219)
Kidney (HMDB: HMDB0012219)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0012219)

Cellular substructure

Cytoplasm (HMDB: HMDB0012219)

Source

Endogenous

Endogenous (HMDB: HMDB0012219)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Biological role

Drug metabolite (HMDB: HMDB0012219)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.8 g/L	ALOGPS
logP	-0.29	ALOGPS
logP	0.47	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Basic)	9.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.16 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	43.65 m³·mol⁻¹	ChemAxon
Polarizability	15.25 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	133.24	31661259
DarkChem	[M-H]-	128.528	31661259
DeepCCS	[M+H]+	135.442	30932474
DeepCCS	[M-H]-	131.612	30932474
DeepCCS	[M-2H]-	169.244	30932474
DeepCCS	[M+Na]+	144.783	30932474
AllCCS	[M+H]+	132.6	32859911
AllCCS	[M+H-H2O]+	128.1	32859911
AllCCS	[M+NH4]+	136.8	32859911
AllCCS	[M+Na]+	138.0	32859911
AllCCS	[M-H]-	131.7	32859911
AllCCS	[M+Na-2H]-	133.0	32859911
AllCCS	[M+HCOO]-	134.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.81 minutes	32390414
Predicted by Siyang on May 30, 2022	9.1004 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.05 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	204.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	635.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	319.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	87.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	198.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	54.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	265.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	267.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	659.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	671.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	75.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	670.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	204.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	222.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	635.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	489.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	150.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dopamine quinone	NCCC1=CC(=O)C(=O)C=C1	2444.8	Standard polar	33892256
Dopamine quinone	NCCC1=CC(=O)C(=O)C=C1	1618.6	Standard non polar	33892256
Dopamine quinone	NCCC1=CC(=O)C(=O)C=C1	1635.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dopamine quinone,1TMS,isomer #1	C[Si](C)(C)NCCC1=CC(=O)C(=O)C=C1	1901.4	Semi standard non polar	33892256
Dopamine quinone,1TMS,isomer #1	C[Si](C)(C)NCCC1=CC(=O)C(=O)C=C1	1865.9	Standard non polar	33892256
Dopamine quinone,1TMS,isomer #1	C[Si](C)(C)NCCC1=CC(=O)C(=O)C=C1	2450.9	Standard polar	33892256
Dopamine quinone,2TMS,isomer #1	C[Si](C)(C)N(CCC1=CC(=O)C(=O)C=C1)[Si](C)(C)C	2009.6	Semi standard non polar	33892256
Dopamine quinone,2TMS,isomer #1	C[Si](C)(C)N(CCC1=CC(=O)C(=O)C=C1)[Si](C)(C)C	1926.8	Standard non polar	33892256
Dopamine quinone,2TMS,isomer #1	C[Si](C)(C)N(CCC1=CC(=O)C(=O)C=C1)[Si](C)(C)C	2573.3	Standard polar	33892256
Dopamine quinone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=CC(=O)C(=O)C=C1	2090.6	Semi standard non polar	33892256
Dopamine quinone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=CC(=O)C(=O)C=C1	2064.8	Standard non polar	33892256
Dopamine quinone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC1=CC(=O)C(=O)C=C1	2642.5	Standard polar	33892256
Dopamine quinone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC1=CC(=O)C(=O)C=C1)[Si](C)(C)C(C)(C)C	2461.7	Semi standard non polar	33892256
Dopamine quinone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC1=CC(=O)C(=O)C=C1)[Si](C)(C)C(C)(C)C	2336.1	Standard non polar	33892256
Dopamine quinone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC1=CC(=O)C(=O)C=C1)[Si](C)(C)C(C)(C)C	2744.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dopamine quinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9500000000-ef1bf7d630ebccb27612	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dopamine quinone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine quinone 10V, Positive-QTOF	splash10-0udr-0900000000-a79fe17dcebf8308ec75	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine quinone 20V, Positive-QTOF	splash10-0f79-5900000000-9ae3251a4e04828a914d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine quinone 40V, Positive-QTOF	splash10-0udi-9000000000-2007ca180d8e71fefdaa	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine quinone 10V, Negative-QTOF	splash10-0udi-0900000000-d3204bd01097e42a8e80	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine quinone 20V, Negative-QTOF	splash10-0udi-1900000000-59396481eef4024dbc1a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine quinone 40V, Negative-QTOF	splash10-001i-6900000000-e422635d58753efcc89e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine quinone 10V, Negative-QTOF	splash10-0udi-0900000000-c294e68376c4342ea785	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine quinone 20V, Negative-QTOF	splash10-0fk9-0900000000-fc8d545a45210a4b6d0f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine quinone 40V, Negative-QTOF	splash10-00di-3900000000-371582e5c2291956c5c3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine quinone 10V, Positive-QTOF	splash10-000i-0900000000-349fa2c875285e427b0f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine quinone 20V, Positive-QTOF	splash10-000i-2900000000-b14c99e939a3320e005c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dopamine quinone 40V, Positive-QTOF	splash10-016r-9400000000-c9df5da7a11ac517aa9c	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028863

KNApSAcK ID

Not Available

Chemspider ID

142759

KEGG Compound ID

C17755

BioCyc ID

CPD-8851

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162602

PDB ID

Not Available

ChEBI ID

74684

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Sulzer D, Zecca L: Intraneuronal dopamine-quinone synthesis: a review. Neurotox Res. 2000 Feb;1(3):181-95. [PubMed:12835101 ]

Showing metabocard for Dopamine quinone (HMDB0012219)

MOL for HMDB0012219 (Dopamine quinone)

3D MOL for HMDB0012219 (Dopamine quinone)

3D SDF for HMDB0012219 (Dopamine quinone)

3D-SDF for HMDB0012219 (Dopamine quinone)

PDB for HMDB0012219 (Dopamine quinone)

3D PDB for HMDB0012219 (Dopamine quinone)

SMILES for HMDB0012219 (Dopamine quinone)

INCHI for HMDB0012219 (Dopamine quinone)

Structure for HMDB0012219 (Dopamine quinone)

3D Structure for HMDB0012219 (Dopamine quinone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra