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Showing metabocard for 3,4-Dihydroxyphenylacetaldehyde (HMDB0003791)

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enzymes (9) Show 9 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 04:52:53 UTC
Update Date2023-02-21 17:16:49 UTC
HMDB IDHMDB0003791
Secondary Accession Numbers
  • HMDB0006256
  • HMDB0006778
  • HMDB03791
  • HMDB06256
  • HMDB06778
Metabolite Identification
Common Name3,4-Dihydroxyphenylacetaldehyde
Description3,4-Dihydroxyphenylacetaldehyde (DOPAL) is a metabolite of the monoamine oxidase-catalyzed oxidative deamination of dopamine. Aldehydes are highly reactive molecules formed during the biotransformation of numerous endogenous and exogenous compounds, including biogenic amines. DOPAL 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 (i.e.: 4-hydroxy-2-nonenal) are also known to disrupt or inhibit aldehyde dehydrogenase function. (PMID: 17379813 , 14697885 , 11164826 , 16956664 .
Structure
Data?1676999809
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0003791 (3,4-Dihydroxyphenylacetaldehyde)


  Mrv1652309042000302D          

 11 11  0  0  0  0            999 V2000
   21.6414  -12.7731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0704  -11.9481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7849  -16.4857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0704  -15.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7849  -15.6607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3559  -13.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0704  -12.7731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0704  -14.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3559  -14.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7849  -13.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7849  -14.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  0  0  0  0
  3  5  2  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  6  7  2  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  2  0  0  0  0
  8 11  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
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3D MOL for HMDB0003791 (3,4-Dihydroxyphenylacetaldehyde)

HMDB0003791
     RDKit          3D
3,4-Dihydroxyphenylacetaldehyde
 19 19  0  0  0  0  0  0  0  0999 V2000
    2.2971    0.8336    1.5746 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8113    0.7817    0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0570    0.3416   -0.7409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6623    0.0051   -0.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3605   -1.2827    0.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9415   -1.6535    0.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9320   -0.6861    0.3276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2389   -0.9800    0.6673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6229    0.6090   -0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6378    1.5546   -0.0695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182    0.9751   -0.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8513    1.0578    0.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6006   -0.5766   -1.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1247    1.0746   -1.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1362   -2.0116    0.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2026   -2.6405    0.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4657   -1.9125    0.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4352    2.5071   -0.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1063    2.0032   -0.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  2  0
 11  4  1  0
  2 12  1  0
  3 13  1  0
  3 14  1  0
  5 15  1  0
  6 16  1  0
  8 17  1  0
 10 18  1  0
 11 19  1  0
M  END
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3D SDF for HMDB0003791 (3,4-Dihydroxyphenylacetaldehyde)


  Mrv1652309042000302D          

 11 11  0  0  0  0            999 V2000
   21.6414  -12.7731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0704  -11.9481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7849  -16.4857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0704  -15.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7849  -15.6607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3559  -13.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0704  -12.7731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0704  -14.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3559  -14.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7849  -13.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7849  -14.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  0  0  0  0
  3  5  2  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  6  7  2  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  2  0  0  0  0
  8 11  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003791

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=C(O)C=C(CC=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,4-5,10-11H,3H2

> <INCHI_KEY>
IADQVXRMSNIUEL-UHFFFAOYSA-N

> <FORMULA>
C8H8O3

> <MOLECULAR_WEIGHT>
152.1473

> <EXACT_MASS>
152.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.778587155159714

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)acetaldehyde

> <ALOGPS_LOGP>
1.15

> <JCHEM_LOGP>
0.8452472096666666

> <ALOGPS_LOGS>
-1.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.722398872622591

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.273193828046429

> <JCHEM_PKA_STRONGEST_BASIC>
-6.289341908676513

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
40.402

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.72e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dopal

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0003791 (3,4-Dihydroxyphenylacetaldehyde)

HMDB0003791
     RDKit          3D
3,4-Dihydroxyphenylacetaldehyde
 19 19  0  0  0  0  0  0  0  0999 V2000
    2.2971    0.8336    1.5746 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8113    0.7817    0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0570    0.3416   -0.7409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6623    0.0051   -0.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3605   -1.2827    0.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9415   -1.6535    0.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9320   -0.6861    0.3276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2389   -0.9800    0.6673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6229    0.6090   -0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6378    1.5546   -0.0695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182    0.9751   -0.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8513    1.0578    0.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6006   -0.5766   -1.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1247    1.0746   -1.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1362   -2.0116    0.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2026   -2.6405    0.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4657   -1.9125    0.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4352    2.5071   -0.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1063    2.0032   -0.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  2  0
 11  4  1  0
  2 12  1  0
  3 13  1  0
  3 14  1  0
  5 15  1  0
  6 16  1  0
  8 17  1  0
 10 18  1  0
 11 19  1  0
M  END
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PDB for HMDB0003791 (3,4-Dihydroxyphenylacetaldehyde)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0      40.397 -23.843   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      43.065 -22.303   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      44.398 -30.773   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      43.065 -28.463   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      44.398 -29.233   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      41.731 -24.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      43.065 -23.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      43.065 -26.923   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      41.731 -26.153   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      44.398 -24.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      44.398 -26.153   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3    5                                                            
CONECT    4    5    8                                                       
CONECT    5    3    4                                                       
CONECT    6    1    7    9                                                  
CONECT    7    2    6   10                                                  
CONECT    8    4    9   11                                                  
CONECT    9    6    8                                                       
CONECT   10    7   11                                                       
CONECT   11    8   10                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0003791 (3,4-Dihydroxyphenylacetaldehyde)

COMPND    HMDB0003791
HETATM    1  O1  UNL     1       2.297   0.834   1.575  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.811   0.782   0.475  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.057   0.342  -0.741  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.662   0.005  -0.373  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.361  -1.283   0.001  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.942  -1.654   0.358  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.932  -0.686   0.328  1.00  0.00           C  
HETATM    8  O2  UNL     1      -3.239  -0.980   0.667  1.00  0.00           O  
HETATM    9  C7  UNL     1      -1.623   0.609  -0.049  1.00  0.00           C  
HETATM   10  O3  UNL     1      -2.638   1.555  -0.070  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.318   0.975  -0.406  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.851   1.058   0.338  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.601  -0.577  -1.108  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.125   1.075  -1.563  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.136  -2.012   0.018  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.203  -2.641   0.651  1.00  0.00           H  
HETATM   17  H6  UNL     1      -3.466  -1.913   0.940  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.435   2.507  -0.342  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.106   2.003  -0.698  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4   13   14
CONECT    4    5    5   11
CONECT    5    6   15
CONECT    6    7    7   16
CONECT    7    8    9
CONECT    8   17
CONECT    9   10   11   11
CONECT   10   18
CONECT   11   19
END
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SMILES for HMDB0003791 (3,4-Dihydroxyphenylacetaldehyde)

OC1=C(O)C=C(CC=O)C=C1
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INCHI for HMDB0003791 (3,4-Dihydroxyphenylacetaldehyde)

InChI=1S/C8H8O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,4-5,10-11H,3H2
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2-(3,4-Dihydroxyphenyl)ethanalChEBI
DOPALChEBI
ProtocatechuatealdehydeChEBI
DHPAA aldehydeMeSH
3,4-Dihydroxy-benzeneacetaldehydeHMDB
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
IUPAC Name2-(3,4-dihydroxyphenyl)acetaldehyde
Traditional Namedopal
CAS Registry Number5707-55-1
SMILES
OC1=C(O)C=C(CC=O)C=C1
InChI Identifier
InChI=1S/C8H8O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,4-5,10-11H,3H2
InChI KeyIADQVXRMSNIUEL-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetaldehydes
Direct ParentPhenylacetaldehydes
Alternative Parents
Substituents
  • Phenylacetaldehyde
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alpha-hydrogen aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Route of exposureSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.005Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility8.72 g/LALOGPS
logP1.15ALOGPS
logP0.85ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)9.27ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.4 m³·mol⁻¹ChemAxon
Polarizability14.78 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.78331661259
DarkChem[M-H]-129.2631661259
DeepCCS[M+H]+131.26630932474
DeepCCS[M-H]-127.53530932474
DeepCCS[M-2H]-165.14730932474
DeepCCS[M+Na]+140.68530932474
AllCCS[M+H]+132.732859911
AllCCS[M+H-H2O]+128.232859911
AllCCS[M+NH4]+136.932859911
AllCCS[M+Na]+138.132859911
AllCCS[M-H]-130.032859911
AllCCS[M+Na-2H]-131.332859911
AllCCS[M+HCOO]-132.832859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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. 2.51 minutes32390414
Predicted by Siyang on May 30, 202210.026 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.25 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid41.3 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1043.6 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid319.1 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid111.0 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid189.4 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid83.9 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid459.6 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid384.2 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)160.0 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid747.9 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid313.5 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1001.8 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid233.0 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid267.3 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate550.5 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA305.6 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water194.7 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,4-DihydroxyphenylacetaldehydeOC1=C(O)C=C(CC=O)C=C12779.5Standard polar33892256
3,4-DihydroxyphenylacetaldehydeOC1=C(O)C=C(CC=O)C=C11505.4Standard non polar33892256
3,4-DihydroxyphenylacetaldehydeOC1=C(O)C=C(CC=O)C=C11641.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,4-Dihydroxyphenylacetaldehyde,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(CC=O)C=C1O1621.3Semi standard non polar33892256
3,4-Dihydroxyphenylacetaldehyde,1TMS,isomer #2C[Si](C)(C)OC1=CC(CC=O)=CC=C1O1591.1Semi standard non polar33892256
3,4-Dihydroxyphenylacetaldehyde,1TMS,isomer #3C[Si](C)(C)OC=CC1=CC=C(O)C(O)=C11907.9Semi standard non polar33892256
3,4-Dihydroxyphenylacetaldehyde,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(CC=O)C=C1O[Si](C)(C)C1667.7Semi standard non polar33892256
3,4-Dihydroxyphenylacetaldehyde,2TMS,isomer #2C[Si](C)(C)OC=CC1=CC=C(O[Si](C)(C)C)C(O)=C11872.0Semi standard non polar33892256
3,4-Dihydroxyphenylacetaldehyde,2TMS,isomer #3C[Si](C)(C)OC=CC1=CC=C(O)C(O[Si](C)(C)C)=C11851.2Semi standard non polar33892256
3,4-Dihydroxyphenylacetaldehyde,3TMS,isomer #1C[Si](C)(C)OC=CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11895.6Semi standard non polar33892256
3,4-Dihydroxyphenylacetaldehyde,3TMS,isomer #1C[Si](C)(C)OC=CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11924.0Standard non polar33892256
3,4-Dihydroxyphenylacetaldehyde,3TMS,isomer #1C[Si](C)(C)OC=CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11916.2Standard polar33892256
3,4-Dihydroxyphenylacetaldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CC=O)C=C1O1882.3Semi standard non polar33892256
3,4-Dihydroxyphenylacetaldehyde,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(CC=O)=CC=C1O1851.9Semi standard non polar33892256
3,4-Dihydroxyphenylacetaldehyde,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC=CC1=CC=C(O)C(O)=C12153.5Semi standard non polar33892256
3,4-Dihydroxyphenylacetaldehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CC=O)C=C1O[Si](C)(C)C(C)(C)C2146.2Semi standard non polar33892256
3,4-Dihydroxyphenylacetaldehyde,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC=CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C12358.1Semi standard non polar33892256
3,4-Dihydroxyphenylacetaldehyde,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC=CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C12324.6Semi standard non polar33892256
3,4-Dihydroxyphenylacetaldehyde,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12621.9Semi standard non polar33892256
3,4-Dihydroxyphenylacetaldehyde,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12571.4Standard non polar33892256
3,4-Dihydroxyphenylacetaldehyde,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12259.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxyphenylacetaldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-3900000000-7f82d1d31cd24be9e8652017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxyphenylacetaldehyde GC-MS (2 TMS) - 70eV, Positivesplash10-00e9-8390000000-bba6c4376314951fb5ee2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dihydroxyphenylacetaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylacetaldehyde 10V, Positive-QTOFsplash10-0udi-0900000000-19827d81a06a62c2b70a2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylacetaldehyde 20V, Positive-QTOFsplash10-0udr-2900000000-479d55c57638faa6d9cd2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylacetaldehyde 40V, Positive-QTOFsplash10-0udl-9400000000-cadc5e95515b4cecf1f72015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylacetaldehyde 10V, Negative-QTOFsplash10-0udi-0900000000-b0ef024b4e5895ddea082015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylacetaldehyde 20V, Negative-QTOFsplash10-0udi-2900000000-352f5ee2c302c824867e2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylacetaldehyde 40V, Negative-QTOFsplash10-0006-9500000000-96da2068f1ed3e30ae472015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylacetaldehyde 10V, Positive-QTOFsplash10-0pb9-0900000000-588f3b3d236131a4fa7a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylacetaldehyde 20V, Positive-QTOFsplash10-0a4i-3900000000-d3765e83b72ff4e9c9332021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylacetaldehyde 40V, Positive-QTOFsplash10-0zfr-9100000000-63064bac00f3091d89c32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylacetaldehyde 10V, Negative-QTOFsplash10-00di-0900000000-b75a7231958cf1fc53ec2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylacetaldehyde 20V, Negative-QTOFsplash10-00di-0900000000-ed865ca228b5007b7ed42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dihydroxyphenylacetaldehyde 40V, Negative-QTOFsplash10-00kf-9100000000-7cc4c0962b7233330b8c2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023227
KNApSAcK IDC00052036
Chemspider ID106504
KEGG Compound IDC04043
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3,4-Dihydroxyphenylacetaldehyde
METLIN IDNot Available
PubChem Compound119219
PDB IDNot Available
ChEBI ID27978
Food Biomarker OntologyNot Available
VMH ID34DHPAC
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Florang VR, Rees JN, Brogden NK, Anderson DG, Hurley TD, Doorn JA: Inhibition of the oxidative metabolism of 3,4-dihydroxyphenylacetaldehyde, a reactive intermediate of dopamine metabolism, by 4-hydroxy-2-nonenal. Neurotoxicology. 2007 Jan;28(1):76-82. Epub 2006 Aug 1. [PubMed:16956664 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]

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
Dopamine + Water + Oxygen → 3,4-Dihydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxidedetails
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
Dopamine + Water + Oxygen → 3,4-Dihydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxidedetails
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-Dihydroxyphenylacetaldehyde + NAD + Water → 3,4-Dihydroxybenzeneacetic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxyphenylacetaldehyde + NADP + Water → 3,4-Dihydroxybenzeneacetic acid + NADPH + Hydrogen Iondetails
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-Dihydroxyphenylacetaldehyde + NAD + Water → 3,4-Dihydroxybenzeneacetic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxyphenylacetaldehyde + NADP + Water → 3,4-Dihydroxybenzeneacetic acid + NADPH + Hydrogen Iondetails
Enzyme Details
5. Amiloride-sensitive amine oxidase [copper-containing]
General function:
Involved in copper ion binding
Specific function:
Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:
ABP1
Uniprot ID:
P19801
Molecular weight:
85377.1
Enzyme Details
6. Membrane primary amine oxidase
General function:
Involved in copper ion binding
Specific function:
Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity. May play a role in adipogenesis.
Gene Name:
AOC3
Uniprot ID:
Q16853
Molecular weight:
84621.27
Reactions
Dopamine + Water + Oxygen → 3,4-Dihydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxidedetails
Enzyme Details
7. Retina-specific copper amine oxidase
General function:
Involved in copper ion binding
Specific function:
Has a monoamine oxidase activity with substrate specificity for 2-phenylethylamine and tryptamine. May play a role in adipogenesis. May be a critical modulator of signal transmission in retina.
Gene Name:
AOC2
Uniprot ID:
O75106
Molecular weight:
80515.11
Reactions
Dopamine + Water + Oxygen → 3,4-Dihydroxyphenylacetaldehyde + Ammonia + Hydrogen peroxidedetails
Enzyme Details
8. 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-Dihydroxyphenylacetaldehyde + NAD + Water → 3,4-Dihydroxybenzeneacetic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxyphenylacetaldehyde + NADP + Water → 3,4-Dihydroxybenzeneacetic acid + NADPH + Hydrogen Iondetails
Enzyme Details
9. 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-Dihydroxyphenylacetaldehyde + NAD + Water → 3,4-Dihydroxybenzeneacetic acid + NADH + Hydrogen Iondetails
3,4-Dihydroxyphenylacetaldehyde + NADP + Water → 3,4-Dihydroxybenzeneacetic acid + NADPH + Hydrogen Iondetails