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Showing metabocard for Indole-3-carboxaldehyde (HMDB0029737)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:32:19 UTC
Update Date2023-02-21 17:19:11 UTC
HMDB IDHMDB0029737
Secondary Accession Numbers
  • HMDB29737
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 a pyrrole ring fused to benzene to form 2,3-benzopyrrole. 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 ). 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
Data?1676999951
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0029737 (Indole-3-carboxaldehyde)

  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
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3D MOL for HMDB0029737 (Indole-3-carboxaldehyde)

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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3D SDF for HMDB0029737 (Indole-3-carboxaldehyde)

  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>
HMDB0029737

> <DATABASE_NAME>
hmdb

> <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 HMDB0029737 (Indole-3-carboxaldehyde)

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 HMDB0029737 (Indole-3-carboxaldehyde)

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 HMDB0029737 (Indole-3-carboxaldehyde)

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 HMDB0029737 (Indole-3-carboxaldehyde)

O=CC1=CNC2=C1C=CC=C2
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INCHI for HMDB0029737 (Indole-3-carboxaldehyde)

InChI=1S/C9H7NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-6,10H
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC9H7NO
Average Molecular Weight145.158
Monoisotopic Molecular Weight145.052763851
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
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct ParentIndoles
Alternative Parents
Substituents
  • Indole
  • Aryl-aldehyde
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Vinylogous amide
  • Azacycle
  • Aldehyde
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point197 - 199 °CNot Available
Boiling Point339.10 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility2927 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.68Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000934
KNApSAcK IDC00000112
Chemspider ID9838
KEGG Compound IDC08493
BioCyc IDINDOLE-3-CARBOXALDEHYDE
BiGG IDNot Available
Wikipedia LinkIndole-3-carboxaldehyde
METLIN IDNot Available
PubChem Compound10256
PDB IDI3A
ChEBI ID28238
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1251521
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Roager HM, Licht TR: Microbial tryptophan catabolites in health and disease. Nat Commun. 2018 Aug 17;9(1):3294. doi: 10.1038/s41467-018-05470-4. [PubMed:30120222 ]
  2. Zhang LS, Davies SS: Microbial metabolism of dietary components to bioactive metabolites: opportunities for new therapeutic interventions. Genome Med. 2016 Apr 21;8(1):46. doi: 10.1186/s13073-016-0296-x. [PubMed:27102537 ]
  3. Kochen W, Buhner R, Otting W: [Identification of oxindole and 3-indolecarbaldehyde in the urine of patients with untreated phenylketonuria]. Hoppe Seylers Z Physiol Chem. 1972 Jul;353(7):1017-22. [PubMed:5073866 ]
  4. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details
1. Aryl hydrocarbon receptor
General function:
Involved in transcription regulator activity
Specific function:
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues
Gene Name:
AHR
Uniprot ID:
P35869
Molecular weight:
96146.7