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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-05-22 19:02:18 UTC

Update Date

2023-02-21 17:17:16 UTC

HMDB ID

HMDB0006242

Secondary Accession Numbers

HMDB0004057
HMDB04057
HMDB06242

Metabolite Identification

Common Name

3,4-Dihydroxymandelaldehyde

Description

3,4-Dihydroxymandelaldehyde, also known as DHMAL or DHPGALD, belongs to the class of organic compounds known as phenylacetaldehydes. Phenylacetaldehydes are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde. Aldehyde dehydrogenases are a group of NAD(P)+ -dependent enzymes that catalyze the oxidation of aldehydes, such as those derived from catecholamines, to their corresponding carboxylic acids. There is an increasing body of evidence suggesting that these compounds are neurotoxic, and it has been recently hypothesized that neurodegenerative disorders may be associated with increased levels of this biogenic aldehyde. It is possible to speculate that reduced detoxification of 3,4- dihydroxymandelaldehyde from impaired or deficient aldehyde dehydrogenase function may be a contributing factor in the suggested neurotoxicity of these compounds. 3,4-Dihydroxymandelaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). 3,4-Dihydroxymandelaldehyde exists in all living organisms, ranging from bacteria to humans. Within humans, 3,4-dihydroxymandelaldehyde participates in a number of enzymatic reactions. In particular, 3,4-dihydroxymandelaldehyde can be biosynthesized from norepinephrine through the action of the enzyme amine oxidase [flavin-containing] a. In addition, 3,4-dihydroxymandelaldehyde and methylamine can be biosynthesized from epinephrine through its interaction with the enzyme amine oxidase [flavin-containing] a. In humans, 3,4-dihydroxymandelaldehyde is involved in the metabolic disorder called tyrosinemia type I. Outside of the human body, 3,4-Dihydroxymandelaldehyde has been detected, but not quantified in, several different foods, such as wild carrots, kohlrabis, angelica, sunburst squash (pattypan squash), and peachs. This could make 3,4-dihydroxymandelaldehyde a potential biomarker for the consumption of these foods. To date, 19 aldehyde dehydrogenase genes have been identified in the human genome. Several pharmaceutical agents and environmental toxins are also known to disrupt or inhibit aldehyde dehydrogenase function. Mutations in these genes and subsequent inborn errors in aldehyde metabolism are the molecular basis of several diseases. 3,4- dihydroxymandelaldehyde generates a free radical and activates mitochondrial permeability transition, a mechanism implicated in neuron death. 3,4-Dihydroxymandelaldehyde is the monoamine oxidase (MAO) aldehyde metabolite of both norepinephrine and epinephrine.

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      31.754  -6.399   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      30.421 -11.789   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      33.088 -13.329   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      35.755  -7.169   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      33.088  -8.709   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      33.088  -7.169   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.754  -9.479   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      34.422  -9.479   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.754 -11.019   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      34.422 -11.019   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      33.088 -11.789   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      34.422  -6.399   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    9                                                            
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5    6    7    8                                                  
CONECT    6    1    5   12                                                  
CONECT    7    5    9                                                       
CONECT    8    5   10                                                       
CONECT    9    2    7   11                                                  
CONECT   10    8   11                                                       
CONECT   11    3    9   10                                                  
CONECT   12    4    6                                                       
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-Dihydroxymandelic aldehyde	ChEBI
3,4-Dihydroxyphenylglycolaldehyde	ChEBI
3,4-Dihydroxyphenylglycolic aldehyde	ChEBI
alpha,3,4-Trihydroxybenzeneacetaldehyde	ChEBI
alpha,3,4-Trihydroxyphenylacetaldehyde	ChEBI
DHMAL	ChEBI
DHPGALD	ChEBI
DOPEGAL	ChEBI
a,3,4-Trihydroxybenzeneacetaldehyde	Generator
Α,3,4-trihydroxybenzeneacetaldehyde	Generator
a,3,4-Trihydroxyphenylacetaldehyde	Generator
Α,3,4-trihydroxyphenylacetaldehyde	Generator
a,3,4-Trihydroxy-benzeneacetaldehyde	HMDB
alpha,3,4-Trihydroxy-benzeneacetaldehyde	HMDB

Chemical Formula

C₈H₈O₄

Average Molecular Weight

168.1467

Monoisotopic Molecular Weight

168.042258744

IUPAC Name

2-(3,4-dihydroxyphenyl)-2-hydroxyacetaldehyde

Traditional Name

dhmal

CAS Registry Number

13023-73-9

SMILES

OC(C=O)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C8H8O4/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-4,8,10-12H

InChI Key

YUGMCLJIWGEKCK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylacetaldehydes. Phenylacetaldehydes are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylacetaldehydes

Direct Parent

Phenylacetaldehydes

Alternative Parents

Substituents

Phenylacetaldehyde
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alpha-hydroxyaldehyde
Secondary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aldehyde
Aromatic alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

catechols (CHEBI:27852 )
aldehyde (CHEBI:27852 )
a small molecule (DIHYDROXYPHENYLGLYCOLALDEHYDE )

Ontology

Not Available

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	11 g/L	ALOGPS
logP	0.2	ALOGPS
logP	0.13	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	9.2	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	41.74 m³·mol⁻¹	ChemAxon
Polarizability	15.68 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]+	136.149	31661259
DarkChem	[M-H]-	132.883	31661259
DeepCCS	[M+H]+	135.514	30932474
DeepCCS	[M-H]-	132.742	30932474
DeepCCS	[M-2H]-	168.916	30932474
DeepCCS	[M+Na]+	144.123	30932474
AllCCS	[M+H]+	137.1	32859911
AllCCS	[M+H-H2O]+	132.7	32859911
AllCCS	[M+NH4]+	141.2	32859911
AllCCS	[M+Na]+	142.3	32859911
AllCCS	[M-H]-	132.6	32859911
AllCCS	[M+Na-2H]-	133.6	32859911
AllCCS	[M+HCOO]-	134.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dihydroxymandelaldehyde	OC(C=O)C1=CC(O)=C(O)C=C1	3267.4	Standard polar	33892256
3,4-Dihydroxymandelaldehyde	OC(C=O)C1=CC(O)=C(O)C=C1	1599.0	Standard non polar	33892256
3,4-Dihydroxymandelaldehyde	OC(C=O)C1=CC(O)=C(O)C=C1	1696.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dihydroxymandelaldehyde,1TMS,isomer #1	C[Si](C)(C)OC(C=O)C1=CC=C(O)C(O)=C1	1812.4	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,1TMS,isomer #2	C[Si](C)(C)OC1=CC(C(O)C=O)=CC=C1O	1745.4	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C(O)C=O)C=C1O	1770.2	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,1TMS,isomer #4	C[Si](C)(C)OC=C(O)C1=CC=C(O)C(O)=C1	2017.5	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C(C=O)O[Si](C)(C)C)C=C1O	1806.9	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,2TMS,isomer #2	C[Si](C)(C)OC1=CC(C(C=O)O[Si](C)(C)C)=CC=C1O	1789.7	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,2TMS,isomer #3	C[Si](C)(C)OC=C(O[Si](C)(C)C)C1=CC=C(O)C(O)=C1	2087.8	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,2TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C(O)C=O)C=C1O[Si](C)(C)C	1778.6	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,2TMS,isomer #5	C[Si](C)(C)OC=C(O)C1=CC=C(O)C(O[Si](C)(C)C)=C1	1944.5	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,2TMS,isomer #6	C[Si](C)(C)OC=C(O)C1=CC=C(O[Si](C)(C)C)C(O)=C1	1969.4	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C(C=O)O[Si](C)(C)C)C=C1O[Si](C)(C)C	1833.3	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,3TMS,isomer #2	C[Si](C)(C)OC=C(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O)=C1	2034.0	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,3TMS,isomer #3	C[Si](C)(C)OC=C(O[Si](C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C)=C1	2007.0	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,3TMS,isomer #4	C[Si](C)(C)OC=C(O)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	1983.5	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,4TMS,isomer #1	C[Si](C)(C)OC=C(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	2060.3	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,4TMS,isomer #1	C[Si](C)(C)OC=C(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	1993.4	Standard non polar	33892256
3,4-Dihydroxymandelaldehyde,4TMS,isomer #1	C[Si](C)(C)OC=C(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	2023.7	Standard polar	33892256
3,4-Dihydroxymandelaldehyde,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(C=O)C1=CC=C(O)C(O)=C1	2055.7	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(C(O)C=O)=CC=C1O	1985.0	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C(O)C=O)C=C1O	2009.6	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC=C(O)C1=CC=C(O)C(O)=C1	2284.1	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C(C=O)O[Si](C)(C)C(C)(C)C)C=C1O	2277.0	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(C(C=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	2268.7	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O)=C1	2572.1	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C(O)C=O)C=C1O[Si](C)(C)C(C)(C)C	2264.6	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC=C(O)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	2476.1	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC=C(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	2519.4	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C(C=O)O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2525.3	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	2773.6	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	2752.8	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC=C(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	2723.1	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=C(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	2960.1	Semi standard non polar	33892256
3,4-Dihydroxymandelaldehyde,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=C(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	2790.0	Standard non polar	33892256
3,4-Dihydroxymandelaldehyde,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=C(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	2462.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxymandelaldehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-06ri-1900000000-d14339278a251a7d9df1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxymandelaldehyde GC-MS (3 TMS) - 70eV, Positive	splash10-01b9-7079000000-441c5f66bee2b8f14be7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxymandelaldehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxymandelaldehyde 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 - 3,4-Dihydroxymandelaldehyde 10V, Positive-QTOF	splash10-014i-0900000000-01c8f9ca75c86beb7118	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelaldehyde 20V, Positive-QTOF	splash10-0gb9-0900000000-30165da526b8042721a9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelaldehyde 40V, Positive-QTOF	splash10-0kn9-9800000000-24ef8505a6b8f892128d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelaldehyde 10V, Negative-QTOF	splash10-014i-0900000000-2ce2cd9a3f1a5d4737b3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelaldehyde 20V, Negative-QTOF	splash10-0aor-0900000000-a9b6cf257bb2c852ffd9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelaldehyde 40V, Negative-QTOF	splash10-0a4i-6900000000-1f2d65b1c1a32c4ea1fd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelaldehyde 10V, Negative-QTOF	splash10-014j-0900000000-876434025a3e5951556f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelaldehyde 20V, Negative-QTOF	splash10-00di-0900000000-667ec91845715350734f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelaldehyde 40V, Negative-QTOF	splash10-052f-9200000000-1663e47bc16a5fa465e4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelaldehyde 10V, Positive-QTOF	splash10-0fki-0900000000-d67f635e503103dc887e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelaldehyde 20V, Positive-QTOF	splash10-0r7i-4900000000-0f535b7035498a1a6303	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxymandelaldehyde 40V, Positive-QTOF	splash10-0ue9-9200000000-344fc9120de4f34191d3	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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+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

Not Available

Tissue Locations

Not Available

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

Not Available

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

FDB030386

KNApSAcK ID

Not Available

Chemspider ID

133725

KEGG Compound ID

C05577

BioCyc ID

DIHYDROXYPHENYLGLYCOLALDEHYDE

BiGG ID

46056

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

151725

PDB ID

Not Available

ChEBI ID

27852

Food Biomarker Ontology

Not Available

VMH ID

34DHMALD

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Marchitti SA, Deitrich RA, Vasiliou V: Neurotoxicity and metabolism of the catecholamine-derived 3,4-dihydroxyphenylacetaldehyde and 3,4-dihydroxyphenylglycolaldehyde: the role of aldehyde dehydrogenase. Pharmacol Rev. 2007 Jun;59(2):125-50. Epub 2007 Mar 22. [PubMed:17379813 ]
Burke WJ, Li SW, Chung HD, Ruggiero DA, Kristal BS, Johnson EM, Lampe P, Kumar VB, Franko M, Williams EA, Zahm DS: Neurotoxicity of MAO metabolites of catecholamine neurotransmitters: role in neurodegenerative diseases. Neurotoxicology. 2004 Jan;25(1-2):101-15. [PubMed:14697885 ]
Burke WJ, Li SW, Zahm DS, Macarthur H, Kolo LL, Westfall TC, Anwar M, Glickstein SB, Ruggiero DA: Catecholamine monoamine oxidase a metabolite in adrenergic neurons is cytotoxic in vivo. Brain Res. 2001 Feb 9;891(1-2):218-27. [PubMed:11164826 ]

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

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Amine oxidase [flavin-containing] B

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:: MAOB
Uniprot ID:: P27338
Molecular weight:: 58762.475

Reactions

Norepinephrine + Water + Oxygen → 3,4-Dihydroxymandelaldehyde + Ammonia + Hydrogen peroxide	details
Epinephrine + Water + Oxygen → 3,4-Dihydroxymandelaldehyde + Methylamine + Hydrogen peroxide	details

Enzyme Details

2. Amine oxidase [flavin-containing] A

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
Molecular weight:: 59681.27

Reactions

Norepinephrine + Water + Oxygen → 3,4-Dihydroxymandelaldehyde + Ammonia + Hydrogen peroxide	details
Epinephrine + Water + Oxygen → 3,4-Dihydroxymandelaldehyde + Methylamine + Hydrogen peroxide	details

Enzyme Details

3. Aldehyde dehydrogenase, dimeric NADP-preferring

General function:: Involved in oxidoreductase activity
Specific function:: ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:: ALDH3A1
Uniprot ID:: P30838
Molecular weight:: 50394.57

Reactions

3,4-Dihydroxymandelaldehyde + NAD + Water → 3,4-Dihydroxymandelic acid + NADH + Hydrogen Ion	details
3,4-Dihydroxymandelaldehyde + NADP + Water → 3,4-Dihydroxymandelic acid + NADPH + Hydrogen Ion	details

Enzyme Details

4. Aldehyde dehydrogenase family 1 member A3

General function:: Involved in oxidoreductase activity
Specific function:: Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:: ALDH1A3
Uniprot ID:: P47895
Molecular weight:: 56107.995

Reactions

3,4-Dihydroxymandelaldehyde + NAD + Water → 3,4-Dihydroxymandelic acid + NADH + Hydrogen Ion	details
3,4-Dihydroxymandelaldehyde + NADP + Water → 3,4-Dihydroxymandelic acid + NADPH + Hydrogen Ion	details

Enzyme Details

5. 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

6. Aldehyde dehydrogenase family 3 member B2

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: ALDH3B2
Uniprot ID:: P48448
Molecular weight:: 42623.62

Reactions

3,4-Dihydroxymandelaldehyde + NAD + Water → 3,4-Dihydroxymandelic acid + NADH + Hydrogen Ion	details
3,4-Dihydroxymandelaldehyde + NADP + Water → 3,4-Dihydroxymandelic acid + NADPH + Hydrogen Ion	details

Enzyme Details

7. Aldehyde dehydrogenase family 3 member B1

General function:: Involved in oxidoreductase activity
Specific function:: Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:: ALDH3B1
Uniprot ID:: P43353
Molecular weight:: 51839.245

Reactions

3,4-Dihydroxymandelaldehyde + NAD + Water → 3,4-Dihydroxymandelic acid + NADH + Hydrogen Ion	details
3,4-Dihydroxymandelaldehyde + NADP + Water → 3,4-Dihydroxymandelic acid + NADPH + Hydrogen Ion	details

Enzyme Details

8. 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

9. 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

10. 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

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

Show all enzymes and transporters

Showing metabocard for 3,4-Dihydroxymandelaldehyde (HMDB0006242)

MOL for HMDB0006242 (3,4-Dihydroxymandelaldehyde)

3D MOL for HMDB0006242 (3,4-Dihydroxymandelaldehyde)

3D SDF for HMDB0006242 (3,4-Dihydroxymandelaldehyde)

3D-SDF for HMDB0006242 (3,4-Dihydroxymandelaldehyde)

PDB for HMDB0006242 (3,4-Dihydroxymandelaldehyde)

3D PDB for HMDB0006242 (3,4-Dihydroxymandelaldehyde)

SMILES for HMDB0006242 (3,4-Dihydroxymandelaldehyde)

INCHI for HMDB0006242 (3,4-Dihydroxymandelaldehyde)

Structure for HMDB0006242 (3,4-Dihydroxymandelaldehyde)

3D Structure for HMDB0006242 (3,4-Dihydroxymandelaldehyde)

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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