Showing metabocard for Indoleacetaldehyde (MMDBc0032968)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:29:17 UTC
Update Date2024-04-30 19:56:51 UTC
Metabolite IDMMDBc0032968
Metabolite Identification
Common NameIndoleacetaldehyde
DescriptionIndoleacetaldehyde, also known as tryptaldehyde, belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Indoleacetaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Indoleacetaldehyde exists in all living species, ranging from bacteria to humans. Within humans, indoleacetaldehyde participates in a number of enzymatic reactions. In particular, indoleacetaldehyde can be biosynthesized from tryptamine; which is mediated by the enzyme kynurenine 3-monooxygenase. In addition, indoleacetaldehyde can be converted into indoleacetic acid; which is catalyzed by the enzyme aldehyde dehydrogenase, mitochondrial. In humans, indoleacetaldehyde is involved in tryptophan metabolism. Outside of the human body, indoleacetaldehyde has been detected, but not quantified in, several different foods, such as nuts, turmerics, Alaska blueberries, summer savouries, and black raspberries. This could make indoleacetaldehyde a potential biomarker for the consumption of these foods. Indoleacetaldehyde is also a substrate for amine oxidase and 4-trimethylaminobutyraldehyde dehydrogenase.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fa4ecd3f048>


  Mrv1652309042000192D          

 12 13  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
  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
M  END
Download

3D MOL for #<Metabolite:0x00007fa4ecd3f048>

HMDB0001190
     RDKit          3D
Indoleacetaldehyde
 21 22  0  0  0  0  0  0  0  0999 V2000
    2.4745    0.2264   -1.4945 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8820    0.7961   -0.5068 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1835    0.6789    0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9934   -0.1941    0.6621 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8782   -1.4995    1.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3525   -1.9509    0.7890 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0789   -0.9818    0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3678   -0.9711   -0.3258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8356    0.1739   -0.9159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0146    1.2746   -1.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7338    1.2321   -0.5048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2272    0.1015    0.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7848    1.4312   -0.5044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8878    0.3062    1.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9252    1.7122    1.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6774   -2.0486    1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7523   -2.9043    0.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9730   -1.8522   -0.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8648    0.2107   -1.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4147    2.1605   -1.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0713    2.0983   -0.5670 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
 11 12  2  0
 12  4  1  0
 12  7  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  5 16  1  0
  6 17  1  0
  8 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fa4ecd3f048>


  Mrv1652309042000192D          

 12 13  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
  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
M  END
> <DATABASE_ID>
MMDBc0032968

> <DATABASE_NAME>
MIME

> <SMILES>
O=CCC1=CNC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C10H9NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,6-7,11H,5H2

> <INCHI_KEY>
WHOOUMGHGSPMGR-UHFFFAOYSA-N

> <FORMULA>
C10H9NO

> <MOLECULAR_WEIGHT>
159.1846

> <EXACT_MASS>
159.068413915

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
16.871541819986895

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.32

> <JCHEM_LOGP>
1.5511398459999997

> <ALOGPS_LOGS>
-2.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.36531159224378

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.729744726395769

> <JCHEM_PKA_STRONGEST_BASIC>
-7.051475135375678

> <JCHEM_POLAR_SURFACE_AREA>
32.86

> <JCHEM_REFRACTIVITY>
47.5267

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
indole-3-acetaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for #<Metabolite:0x00007fa4ecd3f048>

HMDB0001190
     RDKit          3D
Indoleacetaldehyde
 21 22  0  0  0  0  0  0  0  0999 V2000
    2.4745    0.2264   -1.4945 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8820    0.7961   -0.5068 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1835    0.6789    0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9934   -0.1941    0.6621 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8782   -1.4995    1.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3525   -1.9509    0.7890 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0789   -0.9818    0.1645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3678   -0.9711   -0.3258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8356    0.1739   -0.9159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0146    1.2746   -1.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7338    1.2321   -0.5048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2272    0.1015    0.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7848    1.4312   -0.5044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8878    0.3062    1.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9252    1.7122    1.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6774   -2.0486    1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7523   -2.9043    0.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9730   -1.8522   -0.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8648    0.2107   -1.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4147    2.1605   -1.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0713    2.0983   -0.5670 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
 11 12  2  0
 12  4  1  0
 12  7  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  5 16  1  0
  6 17  1  0
  8 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
M  END
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PDB for #<Metabolite:0x00007fa4ecd3f048>

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  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
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
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                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END
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3D PDB for #<Metabolite:0x00007fa4ecd3f048>

COMPND    HMDB0001190
HETATM    1  O1  UNL     1       2.474   0.226  -1.495  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.882   0.796  -0.507  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.183   0.679   0.796  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.993  -0.194   0.662  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.878  -1.499   1.090  1.00  0.00           C  
HETATM    6  N1  UNL     1      -0.353  -1.951   0.789  1.00  0.00           N  
HETATM    7  C5  UNL     1      -1.079  -0.982   0.165  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.368  -0.971  -0.326  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.836   0.174  -0.916  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.015   1.275  -1.004  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.734   1.232  -0.505  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.227   0.102   0.095  1.00  0.00           C  
HETATM   13  H1  UNL     1       3.785   1.431  -0.504  1.00  0.00           H  
HETATM   14  H2  UNL     1       2.888   0.306   1.571  1.00  0.00           H  
HETATM   15  H3  UNL     1       1.925   1.712   1.110  1.00  0.00           H  
HETATM   16  H4  UNL     1       1.677  -2.049   1.590  1.00  0.00           H  
HETATM   17  H5  UNL     1      -0.752  -2.904   0.983  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.973  -1.852  -0.236  1.00  0.00           H  
HETATM   19  H7  UNL     1      -3.865   0.211  -1.317  1.00  0.00           H  
HETATM   20  H8  UNL     1      -2.415   2.161  -1.474  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.071   2.098  -0.567  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4   14   15
CONECT    4    5    5   12
CONECT    5    6   16
CONECT    6    7   17
CONECT    7    8    8   12
CONECT    8    9   18
CONECT    9   10   10   19
CONECT   10   11   20
CONECT   11   12   12   21
END
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SMILES for #<Metabolite:0x00007fa4ecd3f048>

O=CCC1=CNC2=C1C=CC=C2
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INCHI for #<Metabolite:0x00007fa4ecd3f048>

InChI=1S/C10H9NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,6-7,11H,5H2
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Synonyms
ValueSource
1H-Indole-3-acetaldehydeChEBI
2-(indol-3-yl)AcetaldehydeChEBI
Indole-3-acetaldehydeChEBI
1H-indol-3-YlacetaldehydeHMDB
2-(3-Indolyl)acetaldehydeHMDB
indol-3-YlacetaldehydeHMDB
TryptaldehydeHMDB
Molecular FormulaC10H9NO
Average Mass159.1846
Monoisotopic Mass159.068413915
IUPAC Name2-(1H-indol-3-yl)acetaldehyde
Traditional Nameindole-3-acetaldehyde
CAS Registry Number2591-98-2
SMILES
O=CCC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C10H9NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,6-7,11H,5H2
InChI KeyWHOOUMGHGSPMGR-UHFFFAOYSA-N