Showing metabocard for 3,4-Dihydroxymandelaldehyde (MMDBc0047947)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-23 23:18:06 UTC
Update Date2022-09-01 02:02:42 UTC
Metabolite IDMMDBc0047947
Metabolite Identification
Common Name3,4-Dihydroxymandelaldehyde
Description3,4-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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f5abd6933d0>


  Mrv0541 02231220342D          

 12 12  0  0  0  0            999 V2000
   17.0112   -3.4279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2967   -6.3154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7257   -7.1404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1545   -3.8404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7257   -4.6653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7257   -3.8404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0112   -5.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4401   -5.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0112   -5.9028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4401   -5.9028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7257   -6.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4401   -3.4279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  9  1  0  0  0  0
  3 11  1  0  0  0  0
  4 12  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
  6 12  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  2  0  0  0  0
  9 11  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f5abd6933d0>

HMDB0006242
     RDKit          3D
3,4-Dihydroxymandelaldehyde
 20 20  0  0  0  0  0  0  0  0999 V2000
   -3.4250    1.4079    0.8680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6471    1.0950   -0.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1249   -0.2839   -0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6444   -1.0877    0.9009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6299   -0.2936   -0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0145   -1.5154    0.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3904   -1.5486    0.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1715   -0.4189   -0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5558   -0.5363   -0.0154 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5305    0.7936   -0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2886    1.9359   -0.3133 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1360    0.8407   -0.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3442    1.8439   -0.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4587   -0.7531   -1.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8770   -1.4283    1.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5886   -2.4253    0.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9134   -2.4967    0.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1845    0.2335   -0.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9054    2.8547   -0.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3509    1.7826   -0.3274 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12  5  1  0
  2 13  1  0
  3 14  1  0
  4 15  1  0
  6 16  1  0
  7 17  1  0
  9 18  1  0
 11 19  1  0
 12 20  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f5abd6933d0>


  Mrv0541 02231220342D          

 12 12  0  0  0  0            999 V2000
   17.0112   -3.4279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2967   -6.3154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7257   -7.1404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1545   -3.8404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7257   -4.6653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7257   -3.8404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0112   -5.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4401   -5.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0112   -5.9028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4401   -5.9028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7257   -6.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4401   -3.4279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  9  1  0  0  0  0
  3 11  1  0  0  0  0
  4 12  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
  6 12  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  2  0  0  0  0
  9 11  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047947

> <DATABASE_NAME>
MIME

> <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

> <FORMULA>
C8H8O4

> <MOLECULAR_WEIGHT>
168.1467

> <EXACT_MASS>
168.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
15.682386444439553

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.20

> <JCHEM_LOGP>
0.13008874899999998

> <ALOGPS_LOGS>
-1.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.480209015536303

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.197489149638058

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7544012525555255

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
41.7402

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dhmal

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f5abd6933d0>

HMDB0006242
     RDKit          3D
3,4-Dihydroxymandelaldehyde
 20 20  0  0  0  0  0  0  0  0999 V2000
   -3.4250    1.4079    0.8680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6471    1.0950   -0.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1249   -0.2839   -0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6444   -1.0877    0.9009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6299   -0.2936   -0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0145   -1.5154    0.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3904   -1.5486    0.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1715   -0.4189   -0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5558   -0.5363   -0.0154 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5305    0.7936   -0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2886    1.9359   -0.3133 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1360    0.8407   -0.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3442    1.8439   -0.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4587   -0.7531   -1.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8770   -1.4283    1.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5886   -2.4253    0.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9134   -2.4967    0.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1845    0.2335   -0.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9054    2.8547   -0.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3509    1.7826   -0.3274 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12  5  1  0
  2 13  1  0
  3 14  1  0
  4 15  1  0
  6 16  1  0
  7 17  1  0
  9 18  1  0
 11 19  1  0
 12 20  1  0
M  END
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PDB for #<Metabolite:0x00007f5abd6933d0>

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
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3D PDB for #<Metabolite:0x00007f5abd6933d0>

COMPND    HMDB0006242
HETATM    1  O1  UNL     1      -3.425   1.408   0.868  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.647   1.095  -0.017  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.125  -0.284  -0.112  1.00  0.00           C  
HETATM    4  O2  UNL     1      -2.644  -1.088   0.901  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.630  -0.294  -0.094  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.015  -1.515   0.054  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.390  -1.549   0.074  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.171  -0.419  -0.046  1.00  0.00           C  
HETATM    9  O3  UNL     1       3.556  -0.536  -0.015  1.00  0.00           O  
HETATM   10  C7  UNL     1       1.531   0.794  -0.192  1.00  0.00           C  
HETATM   11  O4  UNL     1       2.289   1.936  -0.313  1.00  0.00           O  
HETATM   12  C8  UNL     1       0.136   0.841  -0.214  1.00  0.00           C  
HETATM   13  H1  UNL     1      -2.344   1.844  -0.734  1.00  0.00           H  
HETATM   14  H2  UNL     1      -2.459  -0.753  -1.076  1.00  0.00           H  
HETATM   15  H3  UNL     1      -1.877  -1.428   1.423  1.00  0.00           H  
HETATM   16  H4  UNL     1      -0.589  -2.425   0.151  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.913  -2.497   0.189  1.00  0.00           H  
HETATM   18  H6  UNL     1       4.184   0.234  -0.096  1.00  0.00           H  
HETATM   19  H7  UNL     1       1.905   2.855  -0.423  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.351   1.783  -0.327  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    5   14
CONECT    4   15
CONECT    5    6    6   12
CONECT    6    7   16
CONECT    7    8    8   17
CONECT    8    9   10
CONECT    9   18
CONECT   10   11   12   12
CONECT   11   19
CONECT   12   20
END
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SMILES for #<Metabolite:0x00007f5abd6933d0>

OC(C=O)C1=CC(O)=C(O)C=C1
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INCHI for #<Metabolite:0x00007f5abd6933d0>

InChI=1S/C8H8O4/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-4,8,10-12H
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Synonyms
ValueSource
3,4-Dihydroxymandelic aldehydeChEBI
3,4-DihydroxyphenylglycolaldehydeChEBI
3,4-Dihydroxyphenylglycolic aldehydeChEBI
alpha,3,4-TrihydroxybenzeneacetaldehydeChEBI
alpha,3,4-TrihydroxyphenylacetaldehydeChEBI
DHMALChEBI
DHPGALDChEBI
DOPEGALChEBI
a,3,4-TrihydroxybenzeneacetaldehydeGenerator
Α,3,4-trihydroxybenzeneacetaldehydeGenerator
a,3,4-TrihydroxyphenylacetaldehydeGenerator
Α,3,4-trihydroxyphenylacetaldehydeGenerator
a,3,4-Trihydroxy-benzeneacetaldehydeHMDB
alpha,3,4-Trihydroxy-benzeneacetaldehydeHMDB
Molecular FormulaC8H8O4
Average Mass168.1467
Monoisotopic Mass168.042258744
IUPAC Name2-(3,4-dihydroxyphenyl)-2-hydroxyacetaldehyde
Traditional Namedhmal
CAS Registry Number13023-73-9
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 KeyYUGMCLJIWGEKCK-UHFFFAOYSA-N