Showing metabocard for 3-(1H-indol-3-yl)propanoic acid (MMDBc0055325)

Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-17 19:49:14 UTC
Update Date2025-10-07 16:09:03 UTC
Metabolite IDMMDBc0055325
Metabolite Identification
Common Name3-(1H-indol-3-yl)propanoic acid
Description3-(1H-indol-3-yl)propanoic acid is a member of the indole-carboxylic acid chemical class, functioning as a metabolite produced by gut microbiota. Its chemical structure features an indole ring linked to a propanoic acid moiety, which is pivotal in various biochemical pathways. In vivo studies have demonstrated that this compound exhibits favorable pharmacokinetic properties and tolerability in animal models, suggesting its potential utility in therapeutic applications (PMID:29229639 ). Additionally, 3-(1H-indol-3-yl)propanoic acid has been utilized in the synthesis of bismuth(III) complexes, showcasing its versatility in coordination chemistry. These complexes, including [Bi(IPA)3], highlight the compound's significance beyond its metabolic role, indicating its potential applications in materials science and medicinal chemistry (PMID:29229639 ). As a metabolite, 3-(1H-indol-3-yl)propanoic acid may also play a role in modulating gut health and influencing systemic metabolic pathways, although specific biological mechanisms require further elucidation.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00005643233dfcb8>


  Mrv1652306172221492D          

 14 15  0  0  0  0            999 V2000
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -1.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329   -1.9399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -1.4984    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  8  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  3  2  0  0  0  0
  9  8  1  0  0  0  0
 10  4  2  0  0  0  0
 10  9  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  2  0  0  0  0
 14 11  1  0  0  0  0
M  CHG  1  14  -1
M  END
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3D MOL for #<Metabolite:0x00005643233dfcb8>

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3D SDF for #<Metabolite:0x00005643233dfcb8>

  Mrv1652306172221492D          

 14 15  0  0  0  0            999 V2000
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -1.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329   -1.9399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -1.4984    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  8  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  3  2  0  0  0  0
  9  8  1  0  0  0  0
 10  4  2  0  0  0  0
 10  9  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  2  0  0  0  0
 14 11  1  0  0  0  0
M  CHG  1  14  -1
M  END
> <DATABASE_ID>
MMDBc0055325

> <DATABASE_NAME>
MIME

> <SMILES>
[O-]C(=O)CCC1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C11H11NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6H2,(H,13,14)/p-1

> <INCHI_KEY>
GOLXRNDWAUTYKT-UHFFFAOYSA-M

> <FORMULA>
C11H10NO2

> <MOLECULAR_WEIGHT>
188.207

> <EXACT_MASS>
188.071702146

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
19.53141665909218

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(1H-indol-3-yl)propanoate

> <JCHEM_LOGP>
2.154324763333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.175193522886932

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.8029322038078455

> <JCHEM_POLAR_SURFACE_AREA>
55.92

> <JCHEM_REFRACTIVITY>
63.8902

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-(1H-indol-3-yl)propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00005643233dfcb8>
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PDB for #<Metabolite:0x00005643233dfcb8>
HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.680  -1.012   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.204  -2.477   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       3.235  -3.621   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.698  -2.797   0.000  0.00  0.00           O-1
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    9                                                       
CONECT    4    2   10                                                       
CONECT    5    6    8                                                       
CONECT    6    5   11                                                       
CONECT    7    8   12                                                       
CONECT    8    5    7    9                                                  
CONECT    9    3    8   10                                                  
CONECT   10    4    9   12                                                  
CONECT   11    6   13   14                                                  
CONECT   12    7   10                                                       
CONECT   13   11                                                            
CONECT   14   11                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

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3D PDB for #<Metabolite:0x00005643233dfcb8>
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SMILES for #<Metabolite:0x00005643233dfcb8>
[O-]C(=O)CCC1=CNC2=CC=CC=C12
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INCHI for #<Metabolite:0x00005643233dfcb8>
InChI=1S/C11H11NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6H2,(H,13,14)/p-1
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Synonyms
ValueSource
IndolepropionateChEBI
Indolepropionic acidGenerator
3-(1H-indol-3-yl)Propanoic acidGenerator
Molecular FormulaC11H10NO2
Average Mass188.207
Monoisotopic Mass188.071702146
IUPAC Name3-(1H-indol-3-yl)propanoate
Traditional Name3-(1H-indol-3-yl)propanoate
CAS Registry NumberNot Available
SMILES
[O-]C(=O)CCC1=CNC2=CC=CC=C12
InChI Identifier
InChI=1S/C11H11NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6H2,(H,13,14)/p-1
InChI KeyGOLXRNDWAUTYKT-UHFFFAOYSA-M