MiMeDB: Showing metabocard for 3,4-Dihydroxymandelaldehyde (MMDBc0047947)

Plant

Animal

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:18:06 UTC

Update Date

2024-10-09 19:46:54 UTC

Metabolite ID

MMDBc0047947

Metabolite Identification

Common Name

3,4-Dihydroxymandelaldehyde

Description

3,4-Dihydroxymandelaldehyde is the monoamine oxidase (MAO) aldehyde metabolite of both norepinephrine and epinephrine. 3,4- dihydroxymandelaldehyde generates a free radical and activates mitochondrial permeability transition, a mechanism implicated in neuron death. 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. 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. To date, 19 aldehyde dehydrogenase genes have been identified in the human genome. Mutations in these genes and subsequent inborn errors in aldehyde metabolism are the molecular basis of several diseases. Several pharmaceutical agents and environmental toxins are also known to disrupt or inhibit aldehyde dehydrogenase function. (PMID: 17379813 , 14697885 , 11164826 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(3,4-Dihydroxyphenyl)-2-hydroxyacetaldehyde	ChEBI
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

Molecular Formula

C₈H₈O₄

Average Mass

168.1467

Monoisotopic Mass

168.042258744

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

13023-73-9

SMILES

Not Available

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

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	168.7
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	145.3
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	52.8
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	264.3
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	264.1
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	283.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	627.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	409.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	493.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	148.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	354.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	166.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	70.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	303.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	580.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	43.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	191.0
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	782.4
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	572.0

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_1	C[Si](C)(C)OC(C=O)C1=CC=C(O)C(O)=C1	standard non polar	2025-10-24	1859.97
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_2	C[Si](C)(C)OC1=CC(C(O)C=O)=CC=C1O	standard non polar	2025-10-24	1725.6
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_3	C[Si](C)(C)OC1=CC=C(C(O)C=O)C=C1O	standard non polar	2025-10-24	1851.57
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_4	C[Si](C)(C)OC=C(O)C1=CC=C(O)C(O)=C1	standard non polar	2025-10-24	1894.69
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_5	C[Si](C)(C)OC1=CC=C(C(C=O)O[Si](C)(C)C)C=C1O	standard non polar	2025-10-24	1972.97
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_6	C[Si](C)(C)OC1=CC(C(C=O)O[Si](C)(C)C)=CC=C1O	standard non polar	2025-10-24	1419.22
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_7	C[Si](C)(C)OC=C(O[Si](C)(C)C)C1=CC=C(O)C(O)=C1	standard non polar	2025-10-24	1918.59
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_8	C[Si](C)(C)OC1=CC=C(C(O)C=O)C=C1O[Si](C)(C)C	standard non polar	2025-10-24	1979.8
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_9	C[Si](C)(C)OC=C(O)C1=CC=C(O)C(O[Si](C)(C)C)=C1	standard non polar	2025-10-24	1615.66
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_10	C[Si](C)(C)OC=C(O)C1=CC=C(O[Si](C)(C)C)C(O)=C1	standard non polar	2025-10-24	2181.5
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_11	C[Si](C)(C)OC1=CC=C(C(C=O)O[Si](C)(C)C)C=C1O[Si](C)(C)C	standard non polar	2025-10-24	1857.18
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_12	C[Si](C)(C)OC=C(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O)=C1	standard non polar	2025-10-24	1614.99
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_13	C[Si](C)(C)OC=C(O[Si](C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C)=C1	standard non polar	2025-10-24	971.858
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_14	C[Si](C)(C)OC=C(O)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	standard non polar	2025-10-24	1645.32
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_15	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	standard non polar	2025-10-24	1744.96
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_1	C[Si](C)(C)OC(C=O)C1=CC=C(O)C(O)=C1	standard polar	2025-10-24	1963.74
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_2	C[Si](C)(C)OC1=CC(C(O)C=O)=CC=C1O	standard polar	2025-10-24	2428.54
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_3	C[Si](C)(C)OC1=CC=C(C(O)C=O)C=C1O	standard polar	2025-10-24	1886.51
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_4	C[Si](C)(C)OC=C(O)C1=CC=C(O)C(O)=C1	standard polar	2025-10-24	2193.11
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_5	C[Si](C)(C)OC1=CC=C(C(C=O)O[Si](C)(C)C)C=C1O	standard polar	2025-10-24	1979.21
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_6	C[Si](C)(C)OC1=CC(C(C=O)O[Si](C)(C)C)=CC=C1O	standard polar	2025-10-24	1919.97
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_7	C[Si](C)(C)OC=C(O[Si](C)(C)C)C1=CC=C(O)C(O)=C1	standard polar	2025-10-24	1614.08
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_8	C[Si](C)(C)OC1=CC=C(C(O)C=O)C=C1O[Si](C)(C)C	standard polar	2025-10-24	1718.74
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_9	C[Si](C)(C)OC=C(O)C1=CC=C(O)C(O[Si](C)(C)C)=C1	standard polar	2025-10-24	1863.6
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_10	C[Si](C)(C)OC=C(O)C1=CC=C(O[Si](C)(C)C)C(O)=C1	standard polar	2025-10-24	1921.77
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_11	C[Si](C)(C)OC1=CC=C(C(C=O)O[Si](C)(C)C)C=C1O[Si](C)(C)C	standard polar	2025-10-24	1499.57
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_12	C[Si](C)(C)OC=C(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O)=C1	standard polar	2025-10-24	2114.36
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_13	C[Si](C)(C)OC=C(O[Si](C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C)=C1	standard polar	2025-10-24	1912.49
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_14	C[Si](C)(C)OC=C(O)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	standard polar	2025-10-24	2300.09
Gas Chromatography	3,4-Dihydroxymandelaldehyde_TMS_15	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	standard polar	2025-10-24	1679.81

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191832	Amine oxidase [flavin-containing] B	Unknown	P27338	Homo sapiens
MMDBp0191840	Amine oxidase [flavin-containing] A	Unknown	P21397	Homo sapiens
MMDBp0191962	Aldehyde dehydrogenase, dimeric NADP-preferring	Unknown	P30838	Homo sapiens
MMDBp0191964	Aldehyde dehydrogenase family 1 member A3	Unknown	P47895	Homo sapiens
MMDBp0192165	Alcohol dehydrogenase 4	Unknown	P08319	Homo sapiens
MMDBp0192188	Aldehyde dehydrogenase family 3 member B2	Unknown	P48448	Homo sapiens
MMDBp0192189	Aldehyde dehydrogenase family 3 member B1	Unknown	P43353	Homo sapiens
MMDBp0192400	Alcohol dehydrogenase class-3	Unknown	P11766	Homo sapiens
MMDBp0192402	Alcohol dehydrogenase 1B	Unknown	P00325	Homo sapiens
MMDBp0192403	Alcohol dehydrogenase class 4 mu/sigma chain	Unknown	P40394	Homo sapiens
MMDBp0192404	Alcohol dehydrogenase 1A	Unknown	P07327	Homo sapiens
MMDBp0192405	Alcohol dehydrogenase 6	Unknown	P28332	Homo sapiens
MMDBp0192406	Alcohol dehydrogenase 1C	Unknown	P00326	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated 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/Eubacteria	Firmicutes	210	Human feces; Pig ; Human ; Cattle ; Human subgingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	118	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	78	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	28	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	3	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	2		Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

27852

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

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. doi: 10.1016/s0006-8993(00)03199-1. [PubMed:11164826 ]
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. doi: 10.1016/S0161-813X(03)00090-1. [PubMed:14697885 ]
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. doi: 10.1124/pr.59.2.1. Epub 2007 Mar 22. [PubMed:17379813 ]

Showing metabocard for 3,4-Dihydroxymandelaldehyde (MMDBc0047947)

MOL for #<Metabolite:0x00007f9aa10deb00>

3D MOL for #<Metabolite:0x00007f9aa10deb00>

3D SDF for #<Metabolite:0x00007f9aa10deb00>

3D-SDF for #<Metabolite:0x00007f9aa10deb00>

PDB for #<Metabolite:0x00007f9aa10deb00>

3D PDB for #<Metabolite:0x00007f9aa10deb00>

SMILES for #<Metabolite:0x00007f9aa10deb00>

INCHI for #<Metabolite:0x00007f9aa10deb00>

Structure for #<Metabolite:0x00007f9aa10deb00>

3D Structure for #<Metabolite:0x00007f9aa10deb00>