Showing metabocard for Indole-3-carboxaldehyde (MMDBc0000271)

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Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:48:17 UTC
Update Date2024-04-30 19:31:44 UTC
Metabolite IDMMDBc0000271
Metabolite Identification
Common NameIndole-3-carboxaldehyde
DescriptionIndole-3-carboxaldehyde (IAld or I3A), also known as 3-formylindole or 3-indolealdehyde, belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. I3A is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, I3A is a biologically active metabolite which acts as a receptor agonist at the aryl hydrocarbon receptor in intestinal immune cells. It stimulates the production of interleukin-22 which facilitates mucosal reactivity (PMID: 27102537 ). I3A is a microbially derived tryptophan metabolite produced by Clostridium and Lactobacillus (PMID: 30120222 , 27102537  ). I3A has also been found in the urine of patients with untreated phenylketonuria (PMID: 5073866 ). Outside of the human body, I3A has been detected, but not quantified in, several different foods, such as beans, Brussels sprouts, cucumbers, cereals and cereal products, and white cabbages. This could make I3A a potential biomarker for the consumption of these foods.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fd5f9b35a70>

  Mrv1652309042000372D          

 11 12  0  0  0  0            999 V2000
   -1.6433    0.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8982   -0.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3462   -1.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5392   -0.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4239    1.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363    0.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2843   -0.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4693    0.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3830    0.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1838   -0.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8982    0.1498    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  2  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007fd5f9b35a70>

HMDB0029737
     RDKit          3D
Indole-3-carboxaldehyde
 18 19  0  0  0  0  0  0  0  0999 V2000
    1.1584   -3.0297   -0.0692 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8863   -2.0467    0.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3729   -0.6857    0.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1181    0.4298    0.5595 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2717    1.4778    0.4761 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0378    1.0515    0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1755    1.6835   -0.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3216    0.9989   -0.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2809   -0.3785   -0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0763   -1.0138   -0.3757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0686   -0.3271   -0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9213   -2.2655    0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1704    0.4246    0.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5418    2.4606    0.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2499    2.7652    0.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2758    1.4857   -0.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1578   -0.9484   -0.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0095   -2.0820   -0.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  3  1  0
 11  6  1  0
  2 12  1  0
  4 13  1  0
  5 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fd5f9b35a70>

  Mrv1652309042000372D          

 11 12  0  0  0  0            999 V2000
   -1.6433    0.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8982   -0.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3462   -1.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5392   -0.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4239    1.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363    0.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2843   -0.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4693    0.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3830    0.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1838   -0.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8982    0.1498    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  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000271

> <DATABASE_NAME>
MIME

> <SMILES>
O=CC1=CNC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C9H7NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-6,10H

> <INCHI_KEY>
OLNJUISKUQQNIM-UHFFFAOYSA-N

> <FORMULA>
C9H7NO

> <MOLECULAR_WEIGHT>
145.158

> <EXACT_MASS>
145.052763851

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.996254284774686

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1H-indole-3-carbaldehyde

> <ALOGPS_LOGP>
1.92

> <JCHEM_LOGP>
1.7845101536666665

> <ALOGPS_LOGS>
-1.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.542810230152927

> <JCHEM_PKA_STRONGEST_BASIC>
-7.253462701456542

> <JCHEM_POLAR_SURFACE_AREA>
32.86

> <JCHEM_REFRACTIVITY>
43.7285

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.46e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
indole-3-carboxaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for #<Metabolite:0x00007fd5f9b35a70>

HMDB0029737
     RDKit          3D
Indole-3-carboxaldehyde
 18 19  0  0  0  0  0  0  0  0999 V2000
    1.1584   -3.0297   -0.0692 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8863   -2.0467    0.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3729   -0.6857    0.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1181    0.4298    0.5595 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2717    1.4778    0.4761 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0378    1.0515    0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1755    1.6835   -0.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3216    0.9989   -0.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2809   -0.3785   -0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0763   -1.0138   -0.3757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0686   -0.3271   -0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9213   -2.2655    0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1704    0.4246    0.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5418    2.4606    0.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2499    2.7652    0.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2758    1.4857   -0.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1578   -0.9484   -0.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0095   -2.0820   -0.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  3  1  0
 11  6  1  0
  2 12  1  0
  4 13  1  0
  5 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
M  END
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PDB for #<Metabolite:0x00007fd5f9b35a70>

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      -3.067   0.477   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.543  -0.987   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.513  -2.131   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.007  -1.811   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -0.791   2.131   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -1.561   0.798   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.531  -0.347   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.876   0.280   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.715   1.811   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.210  -0.490   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.543   0.280   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                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END
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3D PDB for #<Metabolite:0x00007fd5f9b35a70>

COMPND    HMDB0029737
HETATM    1  O1  UNL     1       1.158  -3.030  -0.069  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.886  -2.047   0.219  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.373  -0.686   0.252  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.118   0.430   0.559  1.00  0.00           C  
HETATM    5  N1  UNL     1       1.272   1.478   0.476  1.00  0.00           N  
HETATM    6  C4  UNL     1       0.038   1.051   0.130  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.176   1.684  -0.090  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.322   0.999  -0.444  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.281  -0.379  -0.593  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.076  -1.014  -0.376  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.069  -0.327  -0.021  1.00  0.00           C  
HETATM   12  H1  UNL     1       2.921  -2.266   0.443  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.170   0.425   0.812  1.00  0.00           H  
HETATM   14  H3  UNL     1       1.542   2.461   0.654  1.00  0.00           H  
HETATM   15  H4  UNL     1      -1.250   2.765   0.017  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.276   1.486  -0.618  1.00  0.00           H  
HETATM   17  H6  UNL     1      -3.158  -0.948  -0.869  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.009  -2.082  -0.482  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4    4   11
CONECT    4    5   13
CONECT    5    6   14
CONECT    6    7    7   11
CONECT    7    8   15
CONECT    8    9    9   16
CONECT    9   10   17
CONECT   10   11   11   18
END
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SMILES for #<Metabolite:0x00007fd5f9b35a70>

O=CC1=CNC2=C1C=CC=C2
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INCHI for #<Metabolite:0x00007fd5f9b35a70>

InChI=1S/C9H7NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-6,10H
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Synonyms
Molecular FormulaC9H7NO
Average Mass145.158
Monoisotopic Mass145.052763851
IUPAC Name1H-indole-3-carbaldehyde
Traditional Nameindole-3-carboxaldehyde
CAS Registry Number487-89-8
SMILES
O=CC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C9H7NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-6,10H
InChI KeyOLNJUISKUQQNIM-UHFFFAOYSA-N