Showing metabocard for 3,4-Dihydroxyphenylacetaldehyde (MMDBc0029730)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:39:17 UTC
Update Date2024-04-30 19:41:33 UTC
Metabolite IDMMDBc0029730
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. 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.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fdb4d655ee8>


  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
Download

3D MOL for #<Metabolite:0x00007fdb4d655ee8>

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 #<Metabolite:0x00007fdb4d655ee8>


  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>
MMDBc0029730

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x00007fdb4d655ee8>

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 #<Metabolite:0x00007fdb4d655ee8>

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 #<Metabolite:0x00007fdb4d655ee8>

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 #<Metabolite:0x00007fdb4d655ee8>

OC1=C(O)C=C(CC=O)C=C1
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INCHI for #<Metabolite:0x00007fdb4d655ee8>

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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Synonyms
ValueSource
2-(3,4-Dihydroxyphenyl)ethanalChEBI
DOPALChEBI
ProtocatechuatealdehydeChEBI
DHPAA aldehydeMeSH
3,4-Dihydroxy-benzeneacetaldehydeHMDB
Molecular FormulaC8H8O3
Average Mass152.1473
Monoisotopic Mass152.047344122
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