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Showing metabocard for 5-Hydroxyindoleacetaldehyde (HMDB0004073)

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enzymes (11) Show 11 proteins
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 10:19:52 UTC
Update Date2023-02-21 17:16:53 UTC
HMDB IDHMDB0004073
Secondary Accession Numbers
  • HMDB04073
Metabolite Identification
Common Name5-Hydroxyindoleacetaldehyde
Description5-Hydroxyindoleacetaldehyde, also known as 5-HIAL, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. Within humans, 5-hydroxyindoleacetaldehyde participates in a number of enzymatic reactions. In particular, 5-hydroxyindoleacetaldehyde can be biosynthesized from serotonin through its interaction with the enzyme kynurenine 3-monooxygenase. In humans, 5-hydroxyindoleacetaldehyde is involved in tryptophan metabolism. Outside of the human body, 5-hydroxyindoleacetaldehyde has been detected, but not quantified in, several different foods, such as garden rhubarbs, black radish, oriental wheat, garden tomato, and wild leeks. This could make 5-hydroxyindoleacetaldehyde a potential biomarker for the consumption of these foods. 5-Hydroxyindoleacetaldehyde is a biogenic aldehyde of serotonin derived from the action of monoamine oxidase (MAO) (PMID: 11306106 , 2470392 ).
Structure
Data?1676999813
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0004073 (5-Hydroxyindoleacetaldehyde)


  Mrv1652302102019252D          

 13 14  0  0  0  0            999 V2000
 9997.0764 9999.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8215 9998.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3735 9998.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1805 9998.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.295810000.3109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8834 9999.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4354 9998.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1891 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.102810000.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9036 9998.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6180 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3324 9998.9064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1185 9997.2425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  3 13  1  0  0  0  0
M  END
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3D MOL for HMDB0004073 (5-Hydroxyindoleacetaldehyde)

HMDB0004073
     RDKit          3D
5-Hydroxyindoleacetaldehyde
 22 23  0  0  0  0  0  0  0  0999 V2000
    3.9208    0.5828   -0.1005 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5393   -0.5579   -0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1285   -0.9524   -0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2096    0.1717    0.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4247    1.4933    0.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2263    2.1511    0.4762 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7229    1.2401    0.2151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1094    1.3397    0.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9018    0.2489   -0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3523   -1.0071   -0.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1550   -2.1032   -0.6756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9766   -1.0901   -0.3079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1846    0.0013   -0.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2815   -1.3770   -0.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8108   -1.4841   -0.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856   -1.6886    0.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3488    1.9978    0.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1179    3.1733    0.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5430    2.3195    0.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9854    0.3222   -0.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5223   -2.7103    0.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5404   -2.0710   -0.4913 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  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13  4  1  0
 13  7  1  0
  2 14  1  0
  3 15  1  0
  3 16  1  0
  5 17  1  0
  6 18  1  0
  8 19  1  0
  9 20  1  0
 11 21  1  0
 12 22  1  0
M  END
Download

3D SDF for HMDB0004073 (5-Hydroxyindoleacetaldehyde)


  Mrv1652302102019252D          

 13 14  0  0  0  0            999 V2000
 9997.0764 9999.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8215 9998.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3735 9998.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1805 9998.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.295810000.3109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8834 9999.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4354 9998.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1891 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.102810000.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9036 9998.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6180 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3324 9998.9064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1185 9997.2425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  3 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004073

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC2=C(NC=C2CC=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H9NO2/c12-4-3-7-6-11-10-2-1-8(13)5-9(7)10/h1-2,4-6,11,13H,3H2

> <INCHI_KEY>
OBFAPCIUSYHFIE-UHFFFAOYSA-N

> <FORMULA>
C10H9NO2

> <MOLECULAR_WEIGHT>
175.184

> <EXACT_MASS>
175.063328537

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
17.84929534452678

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(5-hydroxy-1H-indol-3-yl)acetaldehyde

> <ALOGPS_LOGP>
1.93

> <JCHEM_LOGP>
1.2475745243333334

> <ALOGPS_LOGS>
-2.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.496225334909536

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.553565809357778

> <JCHEM_PKA_STRONGEST_BASIC>
-5.507986134106482

> <JCHEM_POLAR_SURFACE_AREA>
53.089999999999996

> <JCHEM_REFRACTIVITY>
49.50760000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxyindoleacetaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0004073 (5-Hydroxyindoleacetaldehyde)

HMDB0004073
     RDKit          3D
5-Hydroxyindoleacetaldehyde
 22 23  0  0  0  0  0  0  0  0999 V2000
    3.9208    0.5828   -0.1005 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5393   -0.5579   -0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1285   -0.9524   -0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2096    0.1717    0.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4247    1.4933    0.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2263    2.1511    0.4762 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7229    1.2401    0.2151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1094    1.3397    0.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9018    0.2489   -0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3523   -1.0071   -0.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1550   -2.1032   -0.6756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9766   -1.0901   -0.3079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1846    0.0013   -0.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2815   -1.3770   -0.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8108   -1.4841   -0.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856   -1.6886    0.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3488    1.9978    0.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1179    3.1733    0.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5430    2.3195    0.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9854    0.3222   -0.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5223   -2.7103    0.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5404   -2.0710   -0.4913 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  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13  4  1  0
 13  7  1  0
  2 14  1  0
  3 15  1  0
  3 16  1  0
  5 17  1  0
  6 18  1  0
  8 19  1  0
  9 20  1  0
 11 21  1  0
 12 22  1  0
M  END
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PDB for HMDB0004073 (5-Hydroxyindoleacetaldehyde)

HEADER    PROTEIN                                 10-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-FEB-20         0                                  
HETATM    1  C   UNK     0    8661.2098665.593   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8660.7338664.128   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8661.7648662.984   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8663.2708663.304   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    8663.4858667.247   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8662.7168665.913   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8663.7468664.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.1538665.395   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.9928666.927   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.4878664.625   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.8208665.395   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8669.1548664.625   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8661.2888661.519   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    7                                                       
CONECT    5    6    9                                                       
CONECT    6    7    5    1                                                  
CONECT    7    6    8    4                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    5                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    3                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END
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3D PDB for HMDB0004073 (5-Hydroxyindoleacetaldehyde)

COMPND    HMDB0004073
HETATM    1  O1  UNL     1       3.921   0.583  -0.101  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.539  -0.558  -0.151  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.128  -0.952  -0.061  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.210   0.172   0.113  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.425   1.493   0.414  1.00  0.00           C  
HETATM    6  N1  UNL     1       0.226   2.151   0.476  1.00  0.00           N  
HETATM    7  C5  UNL     1      -0.723   1.240   0.215  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.109   1.340   0.142  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.902   0.249  -0.148  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.352  -1.007  -0.383  1.00  0.00           C  
HETATM   11  O2  UNL     1      -3.155  -2.103  -0.676  1.00  0.00           O  
HETATM   12  C9  UNL     1      -0.977  -1.090  -0.308  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.185   0.001  -0.017  1.00  0.00           C  
HETATM   14  H1  UNL     1       4.282  -1.377  -0.273  1.00  0.00           H  
HETATM   15  H2  UNL     1       1.811  -1.484  -0.992  1.00  0.00           H  
HETATM   16  H3  UNL     1       1.986  -1.689   0.777  1.00  0.00           H  
HETATM   17  H4  UNL     1       2.349   1.998   0.590  1.00  0.00           H  
HETATM   18  H5  UNL     1       0.118   3.173   0.690  1.00  0.00           H  
HETATM   19  H6  UNL     1      -2.543   2.320   0.324  1.00  0.00           H  
HETATM   20  H7  UNL     1      -3.985   0.322  -0.207  1.00  0.00           H  
HETATM   21  H8  UNL     1      -3.522  -2.710   0.067  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.540  -2.071  -0.491  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   14
CONECT    3    4   15   16
CONECT    4    5    5   13
CONECT    5    6   17
CONECT    6    7   18
CONECT    7    8    8   13
CONECT    8    9   19
CONECT    9   10   10   20
CONECT   10   11   12
CONECT   11   21
CONECT   12   13   13   22
END
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SMILES for HMDB0004073 (5-Hydroxyindoleacetaldehyde)

OC1=CC2=C(NC=C2CC=O)C=C1
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INCHI for HMDB0004073 (5-Hydroxyindoleacetaldehyde)

InChI=1S/C10H9NO2/c12-4-3-7-6-11-10-2-1-8(13)5-9(7)10/h1-2,4-6,11,13H,3H2
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View in JSmolView Stereo Labels
Synonyms
ValueSource
5-HialChEBI
5-Hydroxyindole-3-acetaldehydeChEBI
(5-Hydroxy-1H-indol-3-yl)acetaldehydeHMDB
(5-Hydroxyindol-3-yl)acetaldehydeHMDB
5-Hydroxy-1H-indole-3-acetaldehydeHMDB
HydroxyindoleacetaldehydeHMDB
5-HydroxytryptaldehydeHMDB
Chemical FormulaC10H9NO2
Average Molecular Weight175.184
Monoisotopic Molecular Weight175.063328537
IUPAC Name2-(5-hydroxy-1H-indol-3-yl)acetaldehyde
Traditional Namehydroxyindoleacetaldehyde
CAS Registry Number1892-21-3
SMILES
OC1=CC2=C(NC=C2CC=O)C=C1
InChI Identifier
InChI=1S/C10H9NO2/c12-4-3-7-6-11-10-2-1-8(13)5-9(7)10/h1-2,4-6,11,13H,3H2
InChI KeyOBFAPCIUSYHFIE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassHydroxyindoles
Direct ParentHydroxyindoles
Alternative Parents
Substituents
  • Hydroxyindole
  • 3-alkylindole
  • Indole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Substituted pyrrole
  • Benzenoid
  • Alpha-hydrogen aldehyde
  • Pyrrole
  • Heteroaromatic compound
  • Azacycle
  • Aldehyde
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
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
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.32 g/LALOGPS
logP1.93ALOGPS
logP1.25ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)9.55ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.51 m³·mol⁻¹ChemAxon
Polarizability17.85 ųChemAxon
Number of Rings2ChemAxon
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]+138.1331661259
DarkChem[M-H]-136.52731661259
DeepCCS[M+H]+134.2430932474
DeepCCS[M-H]-131.37530932474
DeepCCS[M-2H]-167.63230932474
DeepCCS[M+Na]+142.69930932474
AllCCS[M+H]+137.832859911
AllCCS[M+H-H2O]+133.432859911
AllCCS[M+NH4]+141.932859911
AllCCS[M+Na]+143.132859911
AllCCS[M-H]-137.332859911
AllCCS[M+Na-2H]-137.732859911
AllCCS[M+HCOO]-138.232859911

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, 2022.3.46 minutes32390414
Predicted by Siyang on May 30, 202210.0241 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.44 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid28.3 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1448.6 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid325.5 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid112.2 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid180.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid319.1 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid447.8 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 Acid337.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)148.8 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid728.5 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid290.3 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1189.4 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid353.8 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid242.4 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate536.2 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA261.6 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water153.0 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-HydroxyindoleacetaldehydeOC1=CC2=C(NC=C2CC=O)C=C13276.0Standard polar33892256
5-HydroxyindoleacetaldehydeOC1=CC2=C(NC=C2CC=O)C=C12046.4Standard non polar33892256
5-HydroxyindoleacetaldehydeOC1=CC2=C(NC=C2CC=O)C=C12083.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Hydroxyindoleacetaldehyde,1TMS,isomer #1C[Si](C)(C)OC1=CC=C2[NH]C=C(CC=O)C2=C12043.9Semi standard non polar33892256
5-Hydroxyindoleacetaldehyde,1TMS,isomer #2C[Si](C)(C)OC=CC1=C[NH]C2=CC=C(O)C=C122233.3Semi standard non polar33892256
5-Hydroxyindoleacetaldehyde,1TMS,isomer #3C[Si](C)(C)N1C=C(CC=O)C2=CC(O)=CC=C212066.6Semi standard non polar33892256
5-Hydroxyindoleacetaldehyde,2TMS,isomer #1C[Si](C)(C)OC=CC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C122284.5Semi standard non polar33892256
5-Hydroxyindoleacetaldehyde,2TMS,isomer #1C[Si](C)(C)OC=CC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C122171.1Standard non polar33892256
5-Hydroxyindoleacetaldehyde,2TMS,isomer #1C[Si](C)(C)OC=CC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C122415.6Standard polar33892256
5-Hydroxyindoleacetaldehyde,2TMS,isomer #2C[Si](C)(C)OC1=CC=C2C(=C1)C(CC=O)=CN2[Si](C)(C)C2071.3Semi standard non polar33892256
5-Hydroxyindoleacetaldehyde,2TMS,isomer #2C[Si](C)(C)OC1=CC=C2C(=C1)C(CC=O)=CN2[Si](C)(C)C2059.1Standard non polar33892256
5-Hydroxyindoleacetaldehyde,2TMS,isomer #2C[Si](C)(C)OC1=CC=C2C(=C1)C(CC=O)=CN2[Si](C)(C)C2192.4Standard polar33892256
5-Hydroxyindoleacetaldehyde,2TMS,isomer #3C[Si](C)(C)OC=CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C122325.3Semi standard non polar33892256
5-Hydroxyindoleacetaldehyde,2TMS,isomer #3C[Si](C)(C)OC=CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C122350.5Standard non polar33892256
5-Hydroxyindoleacetaldehyde,2TMS,isomer #3C[Si](C)(C)OC=CC1=CN([Si](C)(C)C)C2=CC=C(O)C=C122389.3Standard polar33892256
5-Hydroxyindoleacetaldehyde,3TMS,isomer #1C[Si](C)(C)OC=CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C122310.8Semi standard non polar33892256
5-Hydroxyindoleacetaldehyde,3TMS,isomer #1C[Si](C)(C)OC=CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C122344.5Standard non polar33892256
5-Hydroxyindoleacetaldehyde,3TMS,isomer #1C[Si](C)(C)OC=CC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C122253.1Standard polar33892256
5-Hydroxyindoleacetaldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2[NH]C=C(CC=O)C2=C12312.0Semi standard non polar33892256
5-Hydroxyindoleacetaldehyde,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC=CC1=C[NH]C2=CC=C(O)C=C122476.4Semi standard non polar33892256
5-Hydroxyindoleacetaldehyde,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C=C(CC=O)C2=CC(O)=CC=C212318.3Semi standard non polar33892256
5-Hydroxyindoleacetaldehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C122766.1Semi standard non polar33892256
5-Hydroxyindoleacetaldehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C122606.4Standard non polar33892256
5-Hydroxyindoleacetaldehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C122611.5Standard polar33892256
5-Hydroxyindoleacetaldehyde,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(CC=O)=CN2[Si](C)(C)C(C)(C)C2545.0Semi standard non polar33892256
5-Hydroxyindoleacetaldehyde,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(CC=O)=CN2[Si](C)(C)C(C)(C)C2479.6Standard non polar33892256
5-Hydroxyindoleacetaldehyde,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(CC=O)=CN2[Si](C)(C)C(C)(C)C2385.9Standard polar33892256
5-Hydroxyindoleacetaldehyde,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC=CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C122766.7Semi standard non polar33892256
5-Hydroxyindoleacetaldehyde,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC=CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C122741.8Standard non polar33892256
5-Hydroxyindoleacetaldehyde,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC=CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C122550.1Standard polar33892256
5-Hydroxyindoleacetaldehyde,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C122968.3Semi standard non polar33892256
5-Hydroxyindoleacetaldehyde,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C122929.1Standard non polar33892256
5-Hydroxyindoleacetaldehyde,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C122532.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxyindoleacetaldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-0900000000-82ea66debc45b5a549122017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxyindoleacetaldehyde GC-MS (1 TMS) - 70eV, Positivesplash10-00xr-4590000000-148aa38d23d73f5990a52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxyindoleacetaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxyindoleacetaldehyde 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 - 5-Hydroxyindoleacetaldehyde 10V, Positive-QTOFsplash10-004i-0900000000-34afefea4e019e0298522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyindoleacetaldehyde 20V, Positive-QTOFsplash10-057j-0900000000-c324c5351368276b781e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyindoleacetaldehyde 40V, Positive-QTOFsplash10-05ng-2900000000-b5cae8ea903e8b80ef0c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyindoleacetaldehyde 10V, Negative-QTOFsplash10-00di-0900000000-f492ed9bb605e0b7b03b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyindoleacetaldehyde 20V, Negative-QTOFsplash10-00di-0900000000-9fb25b933c4987b62dee2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyindoleacetaldehyde 40V, Negative-QTOFsplash10-001i-2900000000-0c78360f8596defdda872016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyindoleacetaldehyde 10V, Positive-QTOFsplash10-002b-0900000000-8c82c2093e14f3857e5c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyindoleacetaldehyde 20V, Positive-QTOFsplash10-002b-0900000000-6c3085f4067426eeb1f32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyindoleacetaldehyde 40V, Positive-QTOFsplash10-0159-1900000000-fc0d25838e197398d0902021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyindoleacetaldehyde 10V, Negative-QTOFsplash10-00di-0900000000-ce155c63a4e18d1808952021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyindoleacetaldehyde 20V, Negative-QTOFsplash10-0089-0900000000-3967b0a653903263d9182021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyindoleacetaldehyde 40V, Negative-QTOFsplash10-014i-0900000000-b3f6f7944533b77bfd8b2021-09-24Wishart 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 Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothEnthesitis-related arthritis details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030573
KNApSAcK IDNot Available
Chemspider ID67261
KEGG Compound IDC05634
BioCyc IDNot Available
BiGG ID46165
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound74688
PDB IDNot Available
ChEBI ID50157
Food Biomarker OntologyNot Available
VMH ID5HOXINDACT
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceMarchand, B.; Streffer, Ch. Synthesis of 5-hydroxy-3-indolylacetaldehyde. Angew. Chem. (1959), 71 575.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Some M, Svensson S, Hoog JO, Helander A: Studies on the interaction between ethanol and serotonin metabolism in rat, using deuterated ethanol and 4-methylpyrazole. Biochem Pharmacol. 2000 Feb 15;59(4):385-91. [PubMed:10644046 ]
  2. Keung WM: Biogenic aldehyde(s) derived from the action of monoamine oxidase may mediate the antidipsotropic effect of daidzin. Chem Biol Interact. 2001 Jan 30;130-132(1-3):919-30. doi: 10.1016/s0009-2797(00)00245-3. [PubMed:11306106 ]
  3. Helander A, Tottmar O: Reactions of biogenic aldehydes with hemoglobin. Alcohol. 1989 Jan-Feb;6(1):71-5. doi: 10.1016/0741-8329(89)90076-1. [PubMed:2470392 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details
1. Aldehyde oxidase
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular weight:
147916.735
Reactions
5-Hydroxyindoleacetaldehyde + Oxygen + Water → 5-Hydroxyindoleacetic acid + Hydrogen peroxidedetails
Enzyme Details
2. 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
Serotonin + Water + Oxygen → 5-Hydroxyindoleacetaldehyde + Ammonia + Hydrogen peroxidedetails
Enzyme Details
3. 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
Serotonin + Water + Oxygen → 5-Hydroxyindoleacetaldehyde + Ammonia + Hydrogen peroxidedetails
Enzyme Details
4. 4-trimethylaminobutyraldehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Molecular weight:
56291.485
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water → 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
Enzyme Details
5. Alpha-aminoadipic semialdehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water → 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
Enzyme Details
6. 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
Enzyme Details
7. Aldehyde dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water → 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
Enzyme Details
8. Fatty aldehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water → 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
Enzyme Details
9. Aldehyde dehydrogenase X, mitochondrial
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.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Reactions
5-Hydroxyindoleacetaldehyde + NAD + Water → 5-Hydroxyindoleacetic acid + Hydrogen Ion + NADHdetails
Enzyme Details
10. Indolethylamine N-methyltransferase
General function:
Involved in methyltransferase activity
Specific function:
Functions as thioether S-methyltransferase and is active with a variety of thioethers and the corresponding selenium and tellurium compounds, including 3-methylthiopropionaldehyde, dimethyl selenide, dimethyl telluride, 2-methylthioethylamine, 2-methylthioethanol, methyl-n-propyl sulfide and diethyl sulfide. Plays an important role in the detoxification of selenium compounds (By similarity). Catalyzes the N-methylation of tryptamine and structurally related compounds.
Gene Name:
INMT
Uniprot ID:
O95050
Molecular weight:
28833.695

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters