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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:42 UTC

HMDB ID

HMDB0000318

Secondary Accession Numbers

HMDB0005870
HMDB00318
HMDB05870

Metabolite Identification

Common Name

3,4-Dihydroxyphenylglycol

Description

3,4-Dihydroxyphenylglycol, also known as DHPG or DOPEG, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. 3,4-Dihydroxyphenylglycol is an extremely weak basic (essentially neutral) compound. 3,4-Dihydroxyphenylglycol exists in all living organisms, ranging from bacteria to plants to humans. It is a potent antioxidant (PMID: 30007612 ). In mammals, 3,4-Dihydroxyphenylglycol is the primary metabolite of norepinephrine and is generated through the action of the enzyme monoamine oxidase (MAO). DHPG is then further metabolized by the enzyme Catechol-O-methyltransferase (COMT) to 3-methoxy-4-hydroxyphenylglycol (MHPG). Within humans, 3,4-dihydroxyphenylglycol participates in a number of enzymatic reactions. In particular, 3,4-dihydroxyphenylglycol can be biosynthesized from 3,4-dihydroxymandelaldehyde; which is mediated by the enzyme alcohol dehydrogenase 1A. In addition, 3,4-dihydroxyphenylglycol and guaiacol can be converted into vanylglycol and pyrocatechol through its interaction with the enzyme catechol O-methyltransferase. Outside of the human body, 3,4-dihydroxyphenylglycol is found, on average, in the highest concentration in olives. High levels of DHPG (up to 368 mg/kg of dry weight) have been found in the pulp of natural black olives. This could make 3,4-dihydroxyphenylglycol a potential biomarker for the consumption of olives and olive oil. 3,4-Dihydroxyphenylglycol has been linked to Menkes disease (PMID: 19234788 ). DHPG level are lower in Menkes patients (3.57 ¬± 0.40 nM) than healthy infants 8.91 ¬± 0.77 nM). Menkes disease (also called ‚Äúkinky hair disease‚Äù) is an X-linked recessive neurodevelopmental disorder caused by defects in a gene that encodes a copper-transporting ATPase (ATP7A). Affected infants typically appear healthy at birth and show normal neurodevelopment for 2-3 months. Subsequently there is loss of milestones (e.g., smiling, visual tracking, head control) and death in late infancy or childhood (PMID: 19234788 ).

Structure

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

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3,4-Dihydroxyphenylglycol                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0       5.241   2.695   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.908   4.235   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.907  -2.695   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.574  -4.235   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.574   1.925   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.574   0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.908   2.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.241  -0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.908  -0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.241  -1.925   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.908  -1.925   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.574  -2.695   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2    7                                                            
CONECT    3   10                                                            
CONECT    4   12                                                            
CONECT    5    1    6    7                                                  
CONECT    6    5    8    9                                                  
CONECT    7    2    5                                                       
CONECT    8    6   10                                                       
CONECT    9    6   11                                                       
CONECT   10    3    8   12                                                  
CONECT   11    9   12                                                       
CONECT   12    4   10   11                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(3,4-Dihydroxyphenyl)ethylene glycol	ChEBI
1-(3,4-Dihydroxyphenyl)-1,2-ethanediol	ChEBI
2-Hydroxy-2-(3,4-dihydroxy)phenylethanol	ChEBI
3,4-Dihydroxyphenethyl glycol	ChEBI
3,4-Dihydroxyphenylethyl glycol	ChEBI
beta,3,4-Trihydroxy phenethyl alcohol	ChEBI
DHPG	ChEBI
Dihydroxyphenylethylene glycol	ChEBI
DOPEG	ChEBI
b,3,4-Trihydroxy phenethyl alcohol	Generator
Β,3,4-trihydroxy phenethyl alcohol	Generator
3,4-Dihydroxyphenylethyleneglycol	HMDB
4-(1,2-Dihydroxyethyl)-1,2-benzenediol	HMDB
DL-3,4-Dihydroxyphenylglycol	HMDB
Dihydroxyphenylethylene glycol, (+-)-isomer	HMDB
Dihydroxyphenylethylene glycol, (S)-isomer	HMDB
Dihydroxyphenylglycine	HMDB

Chemical Formula

C₈H₁₀O₄

Average Molecular Weight

170.1626

Monoisotopic Molecular Weight

170.057908808

IUPAC Name

4-(1,2-dihydroxyethyl)benzene-1,2-diol

Traditional Name

3,4-dihydroxyphenylglycol

CAS Registry Number

28822-73-3

SMILES

OCC(O)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C8H10O4/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8-12H,4H2

InChI Key

MTVWFVDWRVYDOR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Secondary alcohol
1,2-diol
Organic oxygen compound
Hydrocarbon derivative
Aromatic alcohol
Primary alcohol
Organooxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

catechols (CHEBI:1387 )
tetrol (CHEBI:1387 )
a catechol (CPD-11878 )

Ontology

Physiological effect

Health effect

Circulatory system disorder

Vascular disorder

Atherosclerosis (PMID: 21475195)

Endocrine system disorder

Breast disorder

Breast cancer (PMID: 9468591)

Digestive system disorder

Gastrointestinal disorder

Lower gastrointestinal disorder

Ulcerative colitis (PMID: 33440385)

Cancer

Cervical cancer (PMID: 26566624)

Disposition

Biological location

Cell

All cells and tissues (HMDB: HMDB0285690)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0285690)

Golgi apparatus membrane (HMDB: HMDB0285690)
Cell membrane (HMDB: HMDB0285690)

Source

Endogenous

Endogenous (HMDB: HMDB0285690)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Phosphatidylcholine Biosynthesis (HMDB: HMDB0285690)

Cellular process

Apoptosis (PMID: 23350810)
Cell proliferation (PMID: 23350810)

Biochemical process

Lipid transport (PMID: 21979151)

Role

Biological role

Nutrient (PMID: 28411170)

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	130 - 132 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-1.01	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	16.7 g/L	ALOGPS
logP	-0.72	ALOGPS
logP	-0.032	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	42.8 m³·mol⁻¹	ChemAxon
Polarizability	16.57 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	137.631	31661259
DarkChem	[M-H]-	133.487	31661259
AllCCS	[M+H]+	137.914	32859911
AllCCS	[M-H]-	134.165	32859911
DeepCCS	[M+H]+	138.09	30932474
DeepCCS	[M-H]-	134.339	30932474
DeepCCS	[M-2H]-	171.951	30932474
DeepCCS	[M+Na]+	147.489	30932474
AllCCS	[M+H]+	137.9	32859911
AllCCS	[M+H-H2O]+	133.6	32859911
AllCCS	[M+NH4]+	142.0	32859911
AllCCS	[M+Na]+	143.1	32859911
AllCCS	[M-H]-	134.2	32859911
AllCCS	[M+Na-2H]-	135.3	32859911
AllCCS	[M+HCOO]-	136.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dihydroxyphenylglycol	OCC(O)C1=CC(O)=C(O)C=C1	3293.2	Standard polar	33892256
3,4-Dihydroxyphenylglycol	OCC(O)C1=CC(O)=C(O)C=C1	1795.3	Standard non polar	33892256
3,4-Dihydroxyphenylglycol	OCC(O)C1=CC(O)=C(O)C=C1	1824.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dihydroxyphenylglycol,1TMS,isomer #1	C[Si](C)(C)OCC(O)C1=CC=C(O)C(O)=C1	1916.3	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,1TMS,isomer #2	C[Si](C)(C)OC(CO)C1=CC=C(O)C(O)=C1	1893.8	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,1TMS,isomer #3	C[Si](C)(C)OC1=CC(C(O)CO)=CC=C1O	1830.8	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,1TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C(O)CO)C=C1O	1851.5	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,2TMS,isomer #1	C[Si](C)(C)OCC(O[Si](C)(C)C)C1=CC=C(O)C(O)=C1	1858.4	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,2TMS,isomer #2	C[Si](C)(C)OCC(O)C1=CC=C(O[Si](C)(C)C)C(O)=C1	1838.9	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,2TMS,isomer #3	C[Si](C)(C)OCC(O)C1=CC=C(O)C(O[Si](C)(C)C)=C1	1828.5	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,2TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C(CO)O[Si](C)(C)C)C=C1O	1815.5	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,2TMS,isomer #5	C[Si](C)(C)OC1=CC(C(CO)O[Si](C)(C)C)=CC=C1O	1794.5	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,2TMS,isomer #6	C[Si](C)(C)OC1=CC=C(C(O)CO)C=C1O[Si](C)(C)C	1855.5	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,3TMS,isomer #1	C[Si](C)(C)OCC(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O)=C1	1798.5	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,3TMS,isomer #2	C[Si](C)(C)OCC(O[Si](C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C)=C1	1804.3	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,3TMS,isomer #3	C[Si](C)(C)OCC(O)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	1840.3	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,3TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C(CO)O[Si](C)(C)C)C=C1O[Si](C)(C)C	1822.5	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,4TMS,isomer #1	C[Si](C)(C)OCC(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	1824.3	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(O)C1=CC=C(O)C(O)=C1	2138.4	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(CO)C1=CC=C(O)C(O)=C1	2118.8	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(C(O)CO)=CC=C1O	2065.0	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C(O)CO)C=C1O	2092.4	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O)=C1	2352.5	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	2318.6	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC(O)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	2302.7	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C(CO)O[Si](C)(C)C(C)(C)C)C=C1O	2289.9	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC(C(CO)O[Si](C)(C)C(C)(C)C)=CC=C1O	2277.5	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC=C(C(O)CO)C=C1O[Si](C)(C)C(C)(C)C	2338.5	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	2506.5	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	2505.2	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	2539.9	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C(CO)O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2513.2	Semi standard non polar	33892256
3,4-Dihydroxyphenylglycol,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	2732.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (4 TMS)	splash10-0a59-0965000000-0c949d05cfff1600a5db	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Dihydroxyphenylglycol EI-B (Non-derivatized)	splash10-00y3-8900000000-0cb05419b964f5d6016b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (Non-derivatized)	splash10-0a59-0965000000-0c949d05cfff1600a5db	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-EI-TOF (Non-derivatized)	splash10-0a4j-0936000000-6334bc60ea77682060ca	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ly9-2900000000-9512bd346f5c1a6474d1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (4 TMS) - 70eV, Positive	splash10-0a4l-3009500000-7ac807311c5bfb441ee9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxyphenylglycol GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-00fr-2900000000-fbceba2f96c4ee1154ae	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-000i-9300000000-dd28ad7f56904a5c7c7e	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0bvi-9200000000-b9f4f1a5509344427d53	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol EI-B (HITACHI M-52) , Positive-QTOF	splash10-00y3-8900000000-0cb05419b964f5d6016b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol , negative-QTOF	splash10-0udi-0900000000-d656bf5821ba57e34cfa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 35V, Negative-QTOF	splash10-0uk9-0900000000-d35e76633f689d86ec71	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 35V, Negative-QTOF	splash10-00di-0900000000-98bd90051b89e92f7383	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 10V, Positive-QTOF	splash10-00di-0900000000-785c9bdff21d7558b9b4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 20V, Positive-QTOF	splash10-0fk9-1900000000-953cf944dd232b8d7832	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 40V, Positive-QTOF	splash10-0zg0-7900000000-cb8414fe82a1c814f764	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 10V, Negative-QTOF	splash10-014i-0900000000-a3cd8f79f0fba00900c3	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 20V, Negative-QTOF	splash10-0aor-1900000000-ecff175233ea65fe5f8f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 40V, Negative-QTOF	splash10-0a4i-7900000000-f8265f1946f33cedd546	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 10V, Negative-QTOF	splash10-0gb9-0900000000-e314b75f5fe1649a113b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 20V, Negative-QTOF	splash10-0fl0-0900000000-1e4c5e4e19625ce53572	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 40V, Negative-QTOF	splash10-052f-9400000000-637155f483cd289f34ec	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 10V, Positive-QTOF	splash10-000i-0900000000-73931a09199f234b44b2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 20V, Positive-QTOF	splash10-0nmr-3900000000-563a89742bb8d15cecc4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylglycol 40V, Positive-QTOF	splash10-0ue9-9100000000-5934a8f5824689891a5d	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	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, 100 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	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
Extracellular

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Urine

Tissue Locations

Adrenal Medulla
Brain
Neuron
Prostate

Pathways

Name	SMPDB/PathBank	KEGG
Tyrosine metabolism	Not Available
Alkaptonuria		Not Available
Hawkinsinuria		Not Available
Tyrosinemia Type I		Not Available
Tyrosinemia, transient, of the newborn		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.008 +/- 0.005 uM	Infant (0-1 year old)	Not Specified	Normal	18256395	details
Blood	Detected and Quantified	0.006 +/- 0.0016 uM	Adult (>18 years old)	Both	Normal	6877032	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.009 +/- 0.003 uM	Newborn (0-30 days old)	Both	Normal	18256395	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.204 +/- 0.0674 uM	Adult (>18 years old)	Not Specified	Normal	3773351	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.25 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.002 +/- 0.001 uM	Infant (0-1 year old)	Not Specified	Menkes syndrome	18256395	details
Blood	Detected and Quantified	0.004 +/- 0.002 uM	Newborn (0-30 days old)	Both	Menkes syndrome	18256395	details

Associated Disorders and Diseases

Disease References

Menkes disease
Kaler SG, Holmes CS, Goldstein DS, Tang J, Godwin SC, Donsante A, Liew CJ, Sato S, Patronas N: Neonatal diagnosis and treatment of Menkes disease. N Engl J Med. 2008 Feb 7;358(6):605-14. doi: 10.1056/NEJMoa070613. [PubMed:18256395 ]

Associated OMIM IDs

309400 (Menkes disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

661

FooDB ID

FDB020084

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

5307

PubChem Compound

91528

PDB ID

Not Available

ChEBI ID

1387

Food Biomarker Ontology

Not Available

VMH ID

34DHOXPEG

MarkerDB ID

MDB00000143

Good Scents ID

Not Available

References

Synthesis Reference

Hunter L W; Rorie D K; Yaksh T L; Tyce G M Concurrent separation of catecholamines, dihydroxyphenylglycol, vasoactive intestinal peptide, and neuropeptide Y in superfusate and tissue extract. Analytical biochemistry (1988), 173(2), 340-52.

Material Safety Data Sheet (MSDS)

Not Available

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Julien C, Rodriguez C, Sacquet J, Cuisinaud G, Sassard J: Liquid-chromatographic determination of free and total 3,4-dihydroxyphenylglycol and 3-methoxy-4-hydroxyphenylglycol in urine. Clin Chem. 1988 May;34(5):966-9. [PubMed:3370800 ]
Nakada T, Sasagawa I, Kubota Y, Suzuki H, Ishigooka M, Watanabe M: Dihydroxyphenylglycol in pheochromocytoma: its diagnostic use for norepinephrine dominant tumor. J Urol. 1996 Jan;155(1):14-8. [PubMed:7490813 ]
Eisenhofer G, Brush JE, Cannon RO 3rd, Stull R, Kopin IJ, Goldstein DS: Plasma dihydroxyphenylalanine and total body and regional noradrenergic activity in humans. J Clin Endocrinol Metab. 1989 Feb;68(2):247-55. [PubMed:2563731 ]
Divers WA Jr, Wilkes MM, Babaknia A, Yen SS: Maternal smoking and elevation of catecholamines and metabolites in the amniotic fluid. Am J Obstet Gynecol. 1981 Nov 15;141(6):625-8. [PubMed:7315891 ]
Graham PE, Smythe GA, Edwards GA, Lazarus L: Laboratory diagnosis of phaeochromocytoma: which analytes should we measure? Ann Clin Biochem. 1993 Mar;30 ( Pt 2):129-34. [PubMed:8466142 ]
Machida M, Sakaguchi A, Kamada S, Fujimoto T, Takechi S, Kakinoki S, Nomura A: Simultaneous analysis of human plasma catecholamines by high-performance liquid chromatography with a reversed-phase triacontylsilyl silica column. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Jan 18;830(2):249-54. Epub 2005 Nov 21. [PubMed:16301006 ]
Eisenhofer G, Kopin IJ, Goldstein DS: Catecholamine metabolism: a contemporary view with implications for physiology and medicine. Pharmacol Rev. 2004 Sep;56(3):331-49. [PubMed:15317907 ]
Baskys A, Fang L, Bayazitov I: Activation of neuroprotective pathways by metabotropic group I glutamate receptors: a potential target for drug discovery? Ann N Y Acad Sci. 2005 Aug;1053:55-73. [PubMed:16179509 ]
Esler MD, Lambert GW, Ferrier C, Kaye DM, Wallin BG, Kalff V, Kelly MJ, Jennings GL: Central nervous system noradrenergic control of sympathetic outflow in normotensive and hypertensive humans. Clin Exp Hypertens. 1995 Jan-Feb;17(1-2):409-23. [PubMed:7735286 ]
Divers WA, Wilkes MM, Babaknia A, Hill LM, Quilligan EJ, Yen SS: Amniotic fluid catecholamines and metabolites in intrauterine growth retardation. Am J Obstet Gynecol. 1981 Nov 15;141(6):608-10. [PubMed:7315888 ]
Elsworth JD, Roth RH, Redmond DE Jr: Relative importance of 3-methoxy-4-hydroxyphenylglycol and 3,4-dihydroxyphenylglycol as norepinephrine metabolites in rat, monkey, and humans. J Neurochem. 1983 Sep;41(3):786-93. [PubMed:6875564 ]
Loo H, Scatton B, Dennis T, Benkelfat C, Gay C, Poirier-Littre MF, Garreau M, Vanelle JM, Olie JP, Deniker P: [Study of noradrenaline metabolism in depressed patients by the determination of plasma dihydroxyphenylethylene glycol]. Encephale. 1983;9(4):297-316. [PubMed:6671452 ]
Bermudez-Oria A, Rodriguez-Gutierrez G, Rodriguez-Juan E, Gonzalez-Benjumea A, Fernandez-Bolanos J: Molecular interactions between 3,4-dihydroxyphenylglycol and pectin and antioxidant capacity of this complex in vitro. Carbohydr Polym. 2018 Oct 1;197:260-268. doi: 10.1016/j.carbpol.2018.05.089. Epub 2018 May 31. [PubMed:30007612 ]

Enzymes

Enzyme Details

1. Catechol O-methyltransferase

General function:: Involved in magnesium ion binding
Specific function:: Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:: COMT
Uniprot ID:: P21964
Molecular weight:: 30036.77

Reactions

S-Adenosylmethionine + 3,4-Dihydroxyphenylglycol → S-Adenosylhomocysteine + Vanylglycol	details

Enzyme Details

2. Alcohol dehydrogenase 4

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH4
Uniprot ID:: P08319
Molecular weight:: 40221.335

Reactions

3,4-Dihydroxyphenylglycol + NAD → 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen Ion	details

Enzyme Details

3. Alcohol dehydrogenase class-3

General function:: Involved in zinc ion binding
Specific function:: Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
Gene Name:: ADH5
Uniprot ID:: P11766
Molecular weight:: 39723.945

Reactions

3,4-Dihydroxyphenylglycol + NAD → 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen Ion	details

Enzyme Details

4. Alcohol dehydrogenase 1B

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH1B
Uniprot ID:: P00325
Molecular weight:: 39835.17

Reactions

3,4-Dihydroxyphenylglycol + NAD → 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen Ion	details

Enzyme Details

5. Alcohol dehydrogenase class 4 mu/sigma chain

General function:: Involved in zinc ion binding
Specific function:: Could function in retinol oxidation for the synthesis of retinoic acid, a hormone important for cellular differentiation. Medium-chain (octanol) and aromatic (m-nitrobenzaldehyde) compounds are the best substrates. Ethanol is not a good substrate but at the high ethanol concentrations reached in the digestive tract, it plays a role in the ethanol oxidation and contributes to the first pass ethanol metabolism.
Gene Name:: ADH7
Uniprot ID:: P40394
Molecular weight:: 41480.985

Reactions

3,4-Dihydroxyphenylglycol + NAD → 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen Ion	details

Enzyme Details

6. Alcohol dehydrogenase 1A

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH1A
Uniprot ID:: P07327
Molecular weight:: 39858.37

Reactions

3,4-Dihydroxyphenylglycol + NAD → 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen Ion	details

Enzyme Details

7. Alcohol dehydrogenase 6

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH6
Uniprot ID:: P28332
Molecular weight:: 39072.275

Reactions

3,4-Dihydroxyphenylglycol + NAD → 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen Ion	details

Enzyme Details

8. Alcohol dehydrogenase 1C

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH1C
Uniprot ID:: P00326
Molecular weight:: 39867.27

Reactions

3,4-Dihydroxyphenylglycol + NAD → 3,4-Dihydroxymandelaldehyde + NADH + Hydrogen Ion	details

Showing metabocard for 3,4-Dihydroxyphenylglycol (HMDB0000318)

MOL for HMDB0000318 (3,4-Dihydroxyphenylglycol)

3D MOL for HMDB0000318 (3,4-Dihydroxyphenylglycol)

3D SDF for HMDB0000318 (3,4-Dihydroxyphenylglycol)

3D-SDF for HMDB0000318 (3,4-Dihydroxyphenylglycol)

PDB for HMDB0000318 (3,4-Dihydroxyphenylglycol)

3D PDB for HMDB0000318 (3,4-Dihydroxyphenylglycol)

SMILES for HMDB0000318 (3,4-Dihydroxyphenylglycol)

INCHI for HMDB0000318 (3,4-Dihydroxyphenylglycol)

Structure for HMDB0000318 (3,4-Dihydroxyphenylglycol)

3D Structure for HMDB0000318 (3,4-Dihydroxyphenylglycol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

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