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Showing metabocard for 3-Methoxy-4-hydroxyphenylglycolaldehyde (HMDB0004061)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (6) Show 6 proteinsXML
enzymes (6) Show 6 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 10:08:18 UTC
Update Date2023-02-21 17:16:52 UTC
HMDB IDHMDB0004061
Secondary Accession Numbers
  • HMDB0006776
  • HMDB04061
  • HMDB06776
Metabolite Identification
Common Name3-Methoxy-4-hydroxyphenylglycolaldehyde
Description3-Methoxy-4-hydroxyphenylglycolaldehyde, also known as 4-hydroxy-3-methoxy mandelaldehyde, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 3-Methoxy-4-hydroxyphenylglycolaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Methoxy-4-hydroxyphenylglycolaldehyde is the monoamine oxidase (MAO) aldehyde metabolite of metanephrine. 3-Methoxy-4-hydroxyphenylglycolaldehyde exists in all living organisms, ranging from bacteria to humans. Within humans, 3-methoxy-4-hydroxyphenylglycolaldehyde participates in a number of enzymatic reactions. In particular, 3-methoxy-4-hydroxyphenylglycolaldehyde can be biosynthesized from normetanephrine; which is mediated by the enzyme amine oxidase [flavin-containing] a. In addition, 3-methoxy-4-hydroxyphenylglycolaldehyde can be biosynthesized from metanephrine through the action of the enzyme amine oxidase [flavin-containing] a. Metanephrine is an O-methylated metabolite formed by catechol-O-methyltransferase (COMT) from epinephrine. In humans, 3-methoxy-4-hydroxyphenylglycolaldehyde is involved in the metabolic disorder called the monoamine oxidase-a deficiency (mao-a) pathway. Outside of the human body, 3-Methoxy-4-hydroxyphenylglycolaldehyde has been detected, but not quantified in, several different foods, such as chervils, kai-lans, calabash, custard apples, and tea. This could make 3-methoxy-4-hydroxyphenylglycolaldehyde a potential biomarker for the consumption of these foods. Catecholamines are substantially increased during stress, exercise or smoking and could result in clinically important platelet activation if their action was not rapidly regulated. Catecholamines play an important role in platelet activation and aggregation, epinephrine being the most potent one. The inhibitory effects of methoxy phenolic derivatives on epinephrine-induced platelet aggregation may possibly be attributed to their free radical scavenging properties. There is substantial evidence to conclude that an internal rapid autoregulation of epinephrine-induced platelet aggregation, caused by its metabolic degradation products, takes place in vivo.
Structure
Data?1676999812
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0004061 (3-Methoxy-4-hydroxyphenylglycolaldehyde)


  Mrv0541 02231219522D          

 13 13  0  0  0  0            999 V2000
   27.5218  -11.7090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2364   -8.8214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9508  -12.5340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3797   -9.2339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9508   -9.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8073  -11.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6653   -8.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2364  -11.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9508  -11.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9508  -10.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2364  -10.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6653  -11.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6653  -10.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  8  1  0  0  0  0
  2  5  1  0  0  0  0
  3  9  1  0  0  0  0
  4  7  2  0  0  0  0
  5  7  1  0  0  0  0
  5 10  1  0  0  0  0
  8  9  2  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  2  0  0  0  0
 10 13  1  0  0  0  0
 12 13  2  0  0  0  0
M  END
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3D MOL for HMDB0004061 (3-Methoxy-4-hydroxyphenylglycolaldehyde)

HMDB0004061
     RDKit          3D
3-Methoxy-4-hydroxyphenylglycolaldehyde
 23 23  0  0  0  0  0  0  0  0999 V2000
   -2.5889    0.8434    1.5966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5816   -0.0579    0.5079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4014   -0.3019   -0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2374    0.3263    0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9458    0.0815   -0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2294    0.7002   -0.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1190    2.0651    0.1606 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8386   -0.0386    1.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9919   -1.2380    0.9288 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9045   -0.8041   -1.4892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2401   -1.4378   -1.8927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211   -1.1934   -1.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6027   -1.8336   -1.6259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8710    0.5548    2.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3140    1.8460    1.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5974    0.9373    2.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2155    1.0288    1.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9038    0.5954   -0.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8593    2.2992    0.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1637    0.4368    1.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8267   -1.0166   -2.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2486   -2.1422   -2.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4631   -1.6508   -1.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  5 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  6 18  1  0
  7 19  1  0
  8 20  1  0
 10 21  1  0
 11 22  1  0
 13 23  1  0
M  END
Download

3D SDF for HMDB0004061 (3-Methoxy-4-hydroxyphenylglycolaldehyde)


  Mrv0541 02231219522D          

 13 13  0  0  0  0            999 V2000
   27.5218  -11.7090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2364   -8.8214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9508  -12.5340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3797   -9.2339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9508   -9.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8073  -11.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6653   -8.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2364  -11.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9508  -11.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9508  -10.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2364  -10.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6653  -11.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6653  -10.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  8  1  0  0  0  0
  2  5  1  0  0  0  0
  3  9  1  0  0  0  0
  4  7  2  0  0  0  0
  5  7  1  0  0  0  0
  5 10  1  0  0  0  0
  8  9  2  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  2  0  0  0  0
 10 13  1  0  0  0  0
 12 13  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004061

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(=C1)C(O)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O4/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-5,8,11-12H,1H3

> <INCHI_KEY>
VISAJVAPYPFKCL-UHFFFAOYSA-N

> <FORMULA>
C9H10O4

> <MOLECULAR_WEIGHT>
182.1733

> <EXACT_MASS>
182.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
17.671285440421318

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetaldehyde

> <ALOGPS_LOGP>
0.49

> <JCHEM_LOGP>
0.27598280499999994

> <ALOGPS_LOGS>
-1.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.947572767111232

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.903212004669111

> <JCHEM_PKA_STRONGEST_BASIC>
-3.756563475609691

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
46.22250000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.13e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0004061 (3-Methoxy-4-hydroxyphenylglycolaldehyde)

HMDB0004061
     RDKit          3D
3-Methoxy-4-hydroxyphenylglycolaldehyde
 23 23  0  0  0  0  0  0  0  0999 V2000
   -2.5889    0.8434    1.5966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5816   -0.0579    0.5079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4014   -0.3019   -0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2374    0.3263    0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9458    0.0815   -0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2294    0.7002   -0.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1190    2.0651    0.1606 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8386   -0.0386    1.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9919   -1.2380    0.9288 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9045   -0.8041   -1.4892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2401   -1.4378   -1.8927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211   -1.1934   -1.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6027   -1.8336   -1.6259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8710    0.5548    2.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3140    1.8460    1.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5974    0.9373    2.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2155    1.0288    1.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9038    0.5954   -0.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8593    2.2992    0.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1637    0.4368    1.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8267   -1.0166   -2.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2486   -2.1422   -2.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4631   -1.6508   -1.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  5 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  6 18  1  0
  7 19  1  0
  8 20  1  0
 10 21  1  0
 11 22  1  0
 13 23  1  0
M  END
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PDB for HMDB0004061 (3-Methoxy-4-hydroxyphenylglycolaldehyde)

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      51.374 -21.857   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      52.708 -16.467   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      54.041 -23.397   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      56.709 -17.237   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      54.041 -17.237   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      50.040 -21.087   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      55.375 -16.467   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      52.708 -21.087   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      54.041 -21.857   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      54.041 -18.777   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      52.708 -19.547   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      55.375 -21.087   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      55.375 -19.547   0.000  0.00  0.00           C+0
CONECT    1    6    8                                                       
CONECT    2    5                                                            
CONECT    3    9                                                            
CONECT    4    7                                                            
CONECT    5    2    7   10                                                  
CONECT    6    1                                                            
CONECT    7    4    5                                                       
CONECT    8    1    9   11                                                  
CONECT    9    3    8   12                                                  
CONECT   10    5   11   13                                                  
CONECT   11    8   10                                                       
CONECT   12    9   13                                                       
CONECT   13   10   12                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for HMDB0004061 (3-Methoxy-4-hydroxyphenylglycolaldehyde)

COMPND    HMDB0004061
HETATM    1  C1  UNL     1      -2.589   0.843   1.597  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.582  -0.058   0.508  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.401  -0.302  -0.158  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.237   0.326   0.233  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.946   0.082  -0.435  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.229   0.700  -0.089  1.00  0.00           C  
HETATM    7  O2  UNL     1       2.119   2.065   0.161  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.839  -0.039   1.021  1.00  0.00           C  
HETATM    9  O3  UNL     1       2.992  -1.238   0.929  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.905  -0.804  -1.489  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.240  -1.438  -1.893  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.421  -1.193  -1.226  1.00  0.00           C  
HETATM   13  O4  UNL     1      -2.603  -1.834  -1.626  1.00  0.00           O  
HETATM   14  H1  UNL     1      -1.871   0.555   2.379  1.00  0.00           H  
HETATM   15  H2  UNL     1      -2.314   1.846   1.159  1.00  0.00           H  
HETATM   16  H3  UNL     1      -3.597   0.937   2.035  1.00  0.00           H  
HETATM   17  H4  UNL     1      -0.215   1.029   1.073  1.00  0.00           H  
HETATM   18  H5  UNL     1       2.904   0.595  -0.969  1.00  0.00           H  
HETATM   19  H6  UNL     1       2.859   2.299   0.769  1.00  0.00           H  
HETATM   20  H7  UNL     1       3.164   0.437   1.931  1.00  0.00           H  
HETATM   21  H8  UNL     1       1.827  -1.017  -2.036  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.249  -2.142  -2.739  1.00  0.00           H  
HETATM   23  H10 UNL     1      -3.463  -1.651  -1.135  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3
CONECT    3    4    4   12
CONECT    4    5   17
CONECT    5    6   10   10
CONECT    6    7    8   18
CONECT    7   19
CONECT    8    9    9   20
CONECT   10   11   21
CONECT   11   12   12   22
CONECT   12   13
CONECT   13   23
END
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SMILES for HMDB0004061 (3-Methoxy-4-hydroxyphenylglycolaldehyde)

COC1=C(O)C=CC(=C1)C(O)C=O
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INCHI for HMDB0004061 (3-Methoxy-4-hydroxyphenylglycolaldehyde)

InChI=1S/C9H10O4/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-5,8,11-12H,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
4-Hydroxy-3-methoxy mandelaldehydeHMDB
4-Hydroxy-3-methoxymandelaldehydeHMDB
4-Hydroxy-3-methoxyphenylglycolaldehydeHMDB
a,4-Dihydroxy-3-methoxy-benzeneacetaldehydeHMDB
Chemical FormulaC9H10O4
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
IUPAC Name2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetaldehyde
Traditional Name2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetaldehyde
CAS Registry Number17592-23-3
SMILES
COC1=C(O)C=CC(=C1)C(O)C=O
InChI Identifier
InChI=1S/C9H10O4/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-5,8,11-12H,1H3
InChI KeyVISAJVAPYPFKCL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenylacetaldehyde
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Ether
  • Aromatic alcohol
  • Organooxygen compound
  • Aldehyde
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • 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
LogP0.517Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.13 g/LALOGPS
logP0.49ALOGPS
logP0.28ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)9.9ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.22 m³·mol⁻¹ChemAxon
Polarizability17.67 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+140.65731661259
DarkChem[M-H]-138.39931661259
DeepCCS[M+H]+139.3930932474
DeepCCS[M-H]-136.7930932474
DeepCCS[M-2H]-172.77830932474
DeepCCS[M+Na]+148.31630932474
AllCCS[M+H]+140.432859911
AllCCS[M+H-H2O]+136.232859911
AllCCS[M+NH4]+144.432859911
AllCCS[M+Na]+145.532859911
AllCCS[M-H]-137.332859911
AllCCS[M+Na-2H]-138.232859911
AllCCS[M+HCOO]-139.232859911

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. Predicted by Afia on May 17, 2022.2.51 minutes32390414
Predicted by Siyang on May 30, 20229.0385 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.38 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid54.1 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid979.9 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid280.1 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid93.3 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid164.3 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid51.8 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid274.0 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 Acid299.0 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)113.4 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid643.3 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid148.5 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid825.2 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid191.4 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid225.2 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate493.0 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA321.4 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water153.7 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Methoxy-4-hydroxyphenylglycolaldehydeCOC1=C(O)C=CC(=C1)C(O)C=O3004.7Standard polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehydeCOC1=C(O)C=CC(=C1)C(O)C=O1589.9Standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehydeCOC1=C(O)C=CC(=C1)C(O)C=O1592.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Methoxy-4-hydroxyphenylglycolaldehyde,1TMS,isomer #1COC1=CC(C(O)C=O)=CC=C1O[Si](C)(C)C1728.2Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,1TMS,isomer #2COC1=CC(C(C=O)O[Si](C)(C)C)=CC=C1O1748.8Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,1TMS,isomer #3COC1=CC(C(O)=CO[Si](C)(C)C)=CC=C1O1901.8Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,2TMS,isomer #1COC1=CC(C(C=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C1787.7Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,2TMS,isomer #2COC1=CC(C(O)=CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C1936.9Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,2TMS,isomer #3COC1=CC(C(=CO[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O1995.0Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,3TMS,isomer #1COC1=CC(C(=CO[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C2022.3Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,3TMS,isomer #1COC1=CC(C(=CO[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C1965.8Standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,3TMS,isomer #1COC1=CC(C(=CO[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C2133.8Standard polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,1TBDMS,isomer #1COC1=CC(C(O)C=O)=CC=C1O[Si](C)(C)C(C)(C)C1978.9Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,1TBDMS,isomer #2COC1=CC(C(C=O)O[Si](C)(C)C(C)(C)C)=CC=C1O2001.6Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,1TBDMS,isomer #3COC1=CC(C(O)=CO[Si](C)(C)C(C)(C)C)=CC=C1O2169.5Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,2TBDMS,isomer #1COC1=CC(C(C=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2280.1Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,2TBDMS,isomer #2COC1=CC(C(O)=CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2466.3Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,2TBDMS,isomer #3COC1=CC(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O2496.0Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,3TBDMS,isomer #1COC1=CC(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2735.0Semi standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,3TBDMS,isomer #1COC1=CC(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2617.0Standard non polar33892256
3-Methoxy-4-hydroxyphenylglycolaldehyde,3TBDMS,isomer #1COC1=CC(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2475.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2900000000-c3b751a80e98556beecd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde GC-MS (2 TMS) - 70eV, Positivesplash10-00di-5193000000-6e22ae7f509439b91a972017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde 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-Methoxy-4-hydroxyphenylglycolaldehyde 10V, Positive-QTOFsplash10-001i-0900000000-241e0f5c9b5867f24f802017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde 20V, Positive-QTOFsplash10-0fsi-0900000000-ad05d32557d49f4e68532017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde 40V, Positive-QTOFsplash10-0abj-6900000000-3b0305c2b5932c3966b52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde 10V, Negative-QTOFsplash10-001i-0900000000-6784d8af6231fa2706032017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde 20V, Negative-QTOFsplash10-0kn9-0900000000-8395d2966f8d730d3dd32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde 40V, Negative-QTOFsplash10-0a4i-7900000000-348d28ad54efde88e76b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde 10V, Negative-QTOFsplash10-001i-0900000000-e0b0d2106fad76afa1fe2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde 20V, Negative-QTOFsplash10-0pi3-3900000000-cdf305b3288279dea0a12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde 40V, Negative-QTOFsplash10-056r-5900000000-4c8fbae5388a3e0a51002021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde 10V, Positive-QTOFsplash10-00kr-0900000000-656cb77ee0208456f90b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde 20V, Positive-QTOFsplash10-00dl-4900000000-e5c44a99eda118e291d32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methoxy-4-hydroxyphenylglycolaldehyde 40V, Positive-QTOFsplash10-0fj3-9500000000-b4df271139281b8e52ff2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C 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+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 IDFDB023294
KNApSAcK IDNot Available
Chemspider ID389601
KEGG Compound IDC05583
BioCyc IDNot Available
BiGG ID46069
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440729
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH ID3M4HPGA
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kawamura M, Eisenhofer G, Kopin IJ, Kador PF, Lee YS, Fujisawa S, Sato S: Aldose reductase: an aldehyde scavenging enzyme in the intraneuronal metabolism of norepinephrine in human sympathetic ganglia. Auton Neurosci. 2002 Mar 18;96(2):131-9. [PubMed:11958479 ]
  2. Evangelou AM, Malamas MP, Vezyraki P, Karkabounas SC: Is epinephrine-induced platelet aggregation autoregulated by its metabolic degradation products in vivo? In Vivo. 1998 May-Jun;12(3):321-5. [PubMed:9706478 ]

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
Normetanephrine + Water + Oxygen → 3-Methoxy-4-hydroxyphenylglycolaldehyde + Ammonia + Hydrogen peroxidedetails
Metanephrine + Water + Oxygen → 3-Methoxy-4-hydroxyphenylglycolaldehyde + Hydrogen peroxide + Methylaminedetails
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
Normetanephrine + Water + Oxygen → 3-Methoxy-4-hydroxyphenylglycolaldehyde + Ammonia + Hydrogen peroxidedetails
Metanephrine + Water + Oxygen → 3-Methoxy-4-hydroxyphenylglycolaldehyde + Hydrogen peroxide + Methylaminedetails
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-Methoxy-4-hydroxyphenylglycolaldehyde + NAD + Water → Vanillylmandelic acid + NADH + Hydrogen Iondetails
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water → Vanillylmandelic 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-Methoxy-4-hydroxyphenylglycolaldehyde + NAD + Water → Vanillylmandelic acid + NADH + Hydrogen Iondetails
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water → Vanillylmandelic acid + NADPH + Hydrogen Iondetails
Enzyme Details
5. 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-Methoxy-4-hydroxyphenylglycolaldehyde + NAD + Water → Vanillylmandelic acid + NADH + Hydrogen Iondetails
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water → Vanillylmandelic acid + NADPH + Hydrogen Iondetails
Enzyme Details
6. 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-Methoxy-4-hydroxyphenylglycolaldehyde + NAD + Water → Vanillylmandelic acid + NADH + Hydrogen Iondetails
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water → Vanillylmandelic acid + NADPH + Hydrogen Iondetails