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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-05-22 14:17:36 UTC

Update Date

2021-10-13 04:37:29 UTC

HMDB ID

HMDB0002096

Secondary Accession Numbers

HMDB02096

Metabolite Identification

Common Name

3-Indolebutyric acid

Description

3-Indolebutyric acid is an indolic tryptophan metabolite occasionally found in human urine. (PMID:7130309 ). 3-Indolebutyric acid is a plasma and urinary tryptophan-related metabolite related to metabolic and skin diseases. (PMID:15206797 ). Plasma levels of tryptophan metabolites in the umbilical vein and artery are significantly higher than those in the maternal vein. (PMID:1506727 ). 3-Indolebutyric acid has been shown to accelerated glucose uptake in the rat diaphragm. (PMID:6025019 ). 3-Indolebutyric acid is also a microbial netabolite, urinary indole-3-butyrate is produced by Clostridia sp. (PMID:6630445 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0002096
     RDKit          3D
3-Indolebutyric acid
 28 29  0  0  0  0  0  0  0  0999 V2000
    3.6273    1.5852   -1.5201 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9854    1.2117   -0.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2183    1.5096    0.1630 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0596    0.3910    0.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7422    0.1356   -0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9162   -0.7125    0.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4176   -1.0452    0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8010   -2.2297   -0.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0868   -2.1594   -0.8595 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5319   -0.9331   -0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7781   -0.3440   -0.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9637    0.9591   -0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9530    1.6794    0.3470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7396    1.0644    0.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5179   -0.2197    0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8940    0.8121    0.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5366   -0.6072    0.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8032    0.9044    1.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9273   -0.3776   -1.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2512    1.1045   -0.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4457   -1.6308    0.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7804   -0.0871    1.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1563   -3.0848   -0.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6889   -2.8768   -1.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6005   -0.8366   -1.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9231    1.4742   -0.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0837    2.6961    0.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9455    1.6172    0.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15  7  1  0
 15 10  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  8 23  1  0
  9 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
M  END


  Mrv1652307172020252D          

 15 16  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6127   -0.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3271    0.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3271    0.9749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0416   -0.2625    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  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002096

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CCCC1=CNC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C12H13NO2/c14-12(15)7-3-4-9-8-13-11-6-2-1-5-10(9)11/h1-2,5-6,8,13H,3-4,7H2,(H,14,15)

> <INCHI_KEY>
JTEDVYBZBROSJT-UHFFFAOYSA-N

> <FORMULA>
C12H13NO2

> <MOLECULAR_WEIGHT>
203.2371

> <EXACT_MASS>
203.094628665

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
22.02662640087978

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(1H-indol-3-yl)butanoic acid

> <ALOGPS_LOGP>
2.38

> <JCHEM_LOGP>
2.5988934283333327

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.171275210037287

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.861797772063651

> <JCHEM_POLAR_SURFACE_AREA>
53.089999999999996

> <JCHEM_REFRACTIVITY>
57.6541

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.56e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-indolebutyric acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002096
     RDKit          3D
3-Indolebutyric acid
 28 29  0  0  0  0  0  0  0  0999 V2000
    3.6273    1.5852   -1.5201 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9854    1.2117   -0.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2183    1.5096    0.1630 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0596    0.3910    0.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7422    0.1356   -0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9162   -0.7125    0.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4176   -1.0452    0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8010   -2.2297   -0.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0868   -2.1594   -0.8595 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5319   -0.9331   -0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7781   -0.3440   -0.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9637    0.9591   -0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9530    1.6794    0.3470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7396    1.0644    0.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5179   -0.2197    0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8940    0.8121    0.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5366   -0.6072    0.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8032    0.9044    1.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9273   -0.3776   -1.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2512    1.1045   -0.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4457   -1.6308    0.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7804   -0.0871    1.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1563   -3.0848   -0.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6889   -2.8768   -1.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6005   -0.8366   -1.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9231    1.4742   -0.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0837    2.6961    0.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9455    1.6172    0.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15  7  1  0
 15 10  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  8 23  1  0
  9 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
M  END

HEADER    PROTEIN                                 17-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUL-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  C   UNK     0       3.543   0.280   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.877  -0.490   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.211   0.280   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.211   1.820   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       7.544  -0.490   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   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0002096
HETATM    1  O1  UNL     1       3.627   1.585  -1.520  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.985   1.212  -0.400  1.00  0.00           C  
HETATM    3  O2  UNL     1       5.218   1.510   0.163  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.060   0.391   0.423  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.742   0.136  -0.280  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.916  -0.712   0.667  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.418  -1.045   0.117  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.801  -2.230  -0.465  1.00  0.00           C  
HETATM    9  N1  UNL     1      -2.087  -2.159  -0.860  1.00  0.00           N  
HETATM   10  C7  UNL     1      -2.532  -0.933  -0.532  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.778  -0.344  -0.710  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.964   0.959  -0.263  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.953   1.679   0.347  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.740   1.064   0.504  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.518  -0.220   0.076  1.00  0.00           C  
HETATM   16  H1  UNL     1       5.894   0.812   0.418  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.537  -0.607   0.587  1.00  0.00           H  
HETATM   18  H3  UNL     1       2.803   0.904   1.384  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.927  -0.378  -1.250  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.251   1.104  -0.485  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.446  -1.631   0.982  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.780  -0.087   1.593  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.156  -3.085  -0.586  1.00  0.00           H  
HETATM   24  H9  UNL     1      -2.689  -2.877  -1.335  1.00  0.00           H  
HETATM   25  H10 UNL     1      -4.600  -0.837  -1.174  1.00  0.00           H  
HETATM   26  H11 UNL     1      -4.923   1.474  -0.373  1.00  0.00           H  
HETATM   27  H12 UNL     1      -3.084   2.696   0.703  1.00  0.00           H  
HETATM   28  H13 UNL     1      -0.945   1.617   0.978  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   16
CONECT    4    5   17   18
CONECT    5    6   19   20
CONECT    6    7   21   22
CONECT    7    8    8   15
CONECT    8    9   23
CONECT    9   10   24
CONECT   10   11   11   15
CONECT   11   12   25
CONECT   12   13   13   26
CONECT   13   14   27
CONECT   14   15   15   28
END

HMDB0002096
     RDKit          3D
3-Indolebutyric acid
 28 29  0  0  0  0  0  0  0  0999 V2000
    3.6273    1.5852   -1.5201 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9854    1.2117   -0.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2183    1.5096    0.1630 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0596    0.3910    0.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7422    0.1356   -0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9162   -0.7125    0.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4176   -1.0452    0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8010   -2.2297   -0.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0868   -2.1594   -0.8595 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5319   -0.9331   -0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7781   -0.3440   -0.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9637    0.9591   -0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9530    1.6794    0.3470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7396    1.0644    0.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5179   -0.2197    0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8940    0.8121    0.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5366   -0.6072    0.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8032    0.9044    1.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9273   -0.3776   -1.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2512    1.1045   -0.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4457   -1.6308    0.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7804   -0.0871    1.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1563   -3.0848   -0.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6889   -2.8768   -1.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6005   -0.8366   -1.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9231    1.4742   -0.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0837    2.6961    0.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9455    1.6172    0.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15  7  1  0
 15 10  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  8 23  1  0
  9 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1H-Indole-3-butanoic acid	ChEBI
3-Indolyl-gamma-butyric acid	ChEBI
4-(indol-3-yl)Butyric acid	ChEBI
4-indol-3-Ylbutyric acid	ChEBI
IBA	ChEBI
Indole-3-butanoic acid	ChEBI
Indolebutyric acid	ChEBI
Seradix	ChEBI
Indole-3-butyric acid	Kegg
1H-Indole-3-butanoate	Generator
3-Indolyl-g-butyrate	Generator
3-Indolyl-g-butyric acid	Generator
3-Indolyl-gamma-butyrate	Generator
3-Indolyl-γ-butyrate	Generator
3-Indolyl-γ-butyric acid	Generator
4-(indol-3-yl)Butyrate	Generator
4-indol-3-Ylbutyrate	Generator
Indole-3-butanoate	Generator
Indolebutyrate	Generator
Indole-3-butyrate	Generator
3-Indolebutyrate	Generator
Indolebutyric acid, monoammonium salt	MeSH
Indolebutyric acid, monopotassium salt	MeSH
Indolebutyric acid, monosodium salt	MeSH
1H-Indole-3-butyrate	HMDB
1H-Indole-3-butyric acid	HMDB
3-Indole butyrate	HMDB
3-Indole butyric acid	HMDB
3-Indolylbutyric acid	HMDB
3-Iodolebutyrate	HMDB
4-(1H-indol-3-yl)-Butyrate	HMDB
4-(1H-indol-3-yl)-Butyric acid	HMDB
4-(1H-indol-3-yl)Butanoate	HMDB
4-(1H-Indol-3-yl)butanoic acid	HMDB
4-(3-1H-Indolyl)butyrate	HMDB
4-(3-1H-Indolyl)butyric acid	HMDB
4-(3-Indole)-butyrate	HMDB
4-(3-Indole)-butyric acid	HMDB
4-(3-Indolyl)butyrate	HMDB
4-(3-Indolyl)butyric acid	HMDB
4-(Indolyl)- butyrate	HMDB
4-(Indolyl)- butyric acid	HMDB
4-indol-3-Ylbutyric-acid	HMDB
b-Indolebutyrate	HMDB
b-Indolebutyric acid	HMDB
beta-Indolebutyrate	HMDB
beta-Indolebutyric acid	HMDB
Indole 3-butyrate	HMDB
Indole 3-butyric acid	HMDB
Indole-3 butyrate	HMDB
Indole-3 butyric acid	HMDB
Indole-3-butrylate	HMDB
Indole-3-butrylic acid	HMDB
Indolyl-3-butyrate	HMDB
Indolyl-3-butyric acid	HMDB
3-Indolebutyric acid	ChEBI
4-(1H-Indol-3-yl)butyric acid	HMDB
4-(3-Indolyl)butanoic acid	HMDB
4-(Indol-3-yl)butanoate	HMDB
[3-(3-Indolyl)propyl]carboxylic acid	HMDB
beta-IBA	HMDB
beta-Indolylbutyric acid	HMDB
gamma-(Indol-3-yl)butyric acid	HMDB
gamma-(Indole-3)-butyric acid	HMDB
β-IBA	HMDB
β-Indolebutyric acid	HMDB
β-Indolylbutyric acid	HMDB
γ-(Indol-3-yl)butyric acid	HMDB
γ-(Indole-3)-butyric acid	HMDB

Chemical Formula

C₁₂H₁₃NO₂

Average Molecular Weight

203.2371

Monoisotopic Molecular Weight

203.094628665

IUPAC Name

4-(1H-indol-3-yl)butanoic acid

Traditional Name

3-indolebutyric acid

CAS Registry Number

133-32-4

SMILES

OC(=O)CCCC1=CNC2=C1C=CC=C2

InChI Identifier

InChI=1S/C12H13NO2/c14-12(15)7-3-4-9-8-13-11-6-2-1-5-10(9)11/h1-2,5-6,8,13H,3-4,7H2,(H,14,15)

InChI Key

JTEDVYBZBROSJT-UHFFFAOYSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indol-3-yl carboxylic acid (CHEBI:33070 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	124.5 °C	Not Available
Boiling Point	426.56 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.25 mg/mL at 20 °C	Not Available
LogP	2.30	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.36 g/L	ALOGPS
logP	2.38	ALOGPS
logP	2.6	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	4.86	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.09 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	57.65 m³·mol⁻¹	ChemAxon
Polarizability	22.03 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	146.663	31661259
DarkChem	[M-H]-	145.748	31661259
DeepCCS	[M+H]+	141.218	30932474
DeepCCS	[M-H]-	138.77	30932474
DeepCCS	[M-2H]-	174.375	30932474
DeepCCS	[M+Na]+	149.622	30932474
AllCCS	[M+H]+	145.9	32859911
AllCCS	[M+H-H2O]+	141.8	32859911
AllCCS	[M+NH4]+	149.7	32859911
AllCCS	[M+Na]+	150.8	32859911
AllCCS	[M-H]-	148.8	32859911
AllCCS	[M+Na-2H]-	149.0	32859911
AllCCS	[M+HCOO]-	149.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Indolebutyric acid	OC(=O)CCCC1=CNC2=C1C=CC=C2	3428.6	Standard polar	33892256
3-Indolebutyric acid	OC(=O)CCCC1=CNC2=C1C=CC=C2	1900.3	Standard non polar	33892256
3-Indolebutyric acid	OC(=O)CCCC1=CNC2=C1C=CC=C2	2091.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Indolebutyric acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCCC1=C[NH]C2=CC=CC=C12	2140.6	Semi standard non polar	33892256
3-Indolebutyric acid,1TMS,isomer #2	C[Si](C)(C)N1C=C(CCCC(=O)O)C2=CC=CC=C21	2196.4	Semi standard non polar	33892256
3-Indolebutyric acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCCC1=CN([Si](C)(C)C)C2=CC=CC=C12	2168.8	Semi standard non polar	33892256
3-Indolebutyric acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCCC1=CN([Si](C)(C)C)C2=CC=CC=C12	2114.8	Standard non polar	33892256
3-Indolebutyric acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCCC1=CN([Si](C)(C)C)C2=CC=CC=C12	2343.5	Standard polar	33892256
3-Indolebutyric acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCC1=C[NH]C2=CC=CC=C12	2393.6	Semi standard non polar	33892256
3-Indolebutyric acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C(CCCC(=O)O)C2=CC=CC=C21	2435.6	Semi standard non polar	33892256
3-Indolebutyric acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2617.8	Semi standard non polar	33892256
3-Indolebutyric acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2557.0	Standard non polar	33892256
3-Indolebutyric acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2559.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3-Indolebutyric acid GC-MS (1 TMS)	splash10-000x-0910000000-7c2b4d74ecedb117caf3	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Indolebutyric acid GC-MS (2 TMS)	splash10-0udi-0391000000-c62444bc1faa5f67d652	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Indolebutyric acid EI-B (Non-derivatized)	splash10-001i-0920000000-a53e6a97ea38d50751b7	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Indolebutyric acid GC-MS (Non-derivatized)	splash10-000x-0910000000-7c2b4d74ecedb117caf3	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Indolebutyric acid GC-MS (Non-derivatized)	splash10-0udi-0391000000-c62444bc1faa5f67d652	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Indolebutyric acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-005c-2900000000-6403d086e6b2ec4ac0d3	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Indolebutyric acid GC-MS (1 TMS) - 70eV, Positive	splash10-05j0-7920000000-fc57e474504223a4e838	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Indolebutyric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Indolebutyric acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0f79-0970000000-7543d99fe8a1f2b0de25	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Indolebutyric acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-00lu-0900000000-b46d8f64c372b7348dbd	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Indolebutyric acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-00lu-2900000000-ccb02800c683b0a921ee	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Indolebutyric acid EI-B (HITACHI M-68) , Positive-QTOF	splash10-001i-0920000000-a53e6a97ea38d50751b7	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-0udi-0090000000-d6f784c6fec287fbd7c4	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-0udi-0590000000-22d2baa6bbf6262cb3cf	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-014i-1900000000-21352951c1447c77df39	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-014i-2900000000-184013bb3b879000bdf1	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-014i-2900000000-cd1951f573aa0d883a8c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-0f79-1930000000-d04d53f6788d45ef881f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-002u-2900000000-e52b6e60b86d650a9c2e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-0032-8900000000-f17437c2c96f7f7f4ed2	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-017j-9500000000-8e79159a3b4ebf3488d8	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-014i-5900000000-afb8479ad9268699e823	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ , negative-QTOF	splash10-0udi-0090000000-d6f784c6fec287fbd7c4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ , negative-QTOF	splash10-0udi-0590000000-22d2baa6bbf6262cb3cf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ , negative-QTOF	splash10-014i-1900000000-21352951c1447c77df39	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ , negative-QTOF	splash10-014i-2900000000-184013bb3b879000bdf1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ , negative-QTOF	splash10-014i-2900000000-cd1951f573aa0d883a8c	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Indolebutyric acid 10V, Positive-QTOF	splash10-0udr-0960000000-cbabcf60da67d36a7a52	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Indolebutyric acid 20V, Positive-QTOF	splash10-0pbl-2910000000-66aadf35b92473e5d20e	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Indolebutyric acid 40V, Positive-QTOF	splash10-0006-5900000000-3eb3c75b1c9c299f55b5	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Indolebutyric acid 10V, Negative-QTOF	splash10-0udi-0290000000-534678e83a3a049ca362	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Indolebutyric acid 20V, Negative-QTOF	splash10-0zfr-1890000000-baeca4f8b84a743b76a0	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Indolebutyric acid 40V, Negative-QTOF	splash10-0a4l-9700000000-72990cf325b9dadb784a	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Neuron
Platelet

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22800120	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Schizophrenia	22800120	details

Associated Disorders and Diseases

Disease References

Schizophrenia
Cai HL, Li HD, Yan XZ, Sun B, Zhang Q, Yan M, Zhang WY, Jiang P, Zhu RH, Liu YP, Fang PF, Xu P, Yuan HY, Zhang XH, Hu L, Yang W, Ye HS: Metabolomic analysis of biochemical changes in the plasma and urine of first-episode neuroleptic-naive schizophrenia patients after treatment with risperidone. J Proteome Res. 2012 Aug 3;11(8):4338-50. doi: 10.1021/pr300459d. Epub 2012 Jul 26. [PubMed:22800120 ]

Associated OMIM IDs

181500 (Schizophrenia)

External Links

DrugBank ID

DB02740

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Indole-3-butyric_acid

METLIN ID

6485

PubChem Compound

8617

PDB ID

Not Available

ChEBI ID

33070

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1190841

References

Synthesis Reference

Polaczkowa, W.; Porowska, N. 3-Indolebutyric acid. Przemysl Chemiczny (1950), 6 340-3.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Merle M, Gilbert A, Fredenucci JF, Petry D, Foliguet B, Mosnier M: Experimental and clinical study of the effect of naftidrofuryl on the recovery from peripheral nerve lesions. Microsurgery. 1994;15(3):179-86. [PubMed:8015423 ]
Hirsch JL, Bensoussan JJ, Mosnier M, Lehert P: [Evaluation of the efficacy and tolerance of naftidrofuryl in patients presenting with exertional angina. Multicenter double-blind versus placebo study]. Ann Cardiol Angeiol (Paris). 1999 Feb;48(2):137-45. [PubMed:12555338 ]
Meininger V, Chaineau E, Soudiere B: [Effect of naftidrofuryl (LS129) on axonal growth]. Rev Neurol (Paris). 1994;150(2):115-22. [PubMed:7863151 ]
Eguchi K, Kamimura S, Yonezawa M, Mitsui Y, Mizutani Y, Kudo T: [Tryptophan and its metabolite concentrations in human plasma during the perinatal period]. Nihon Sanka Fujinka Gakkai Zasshi. 1992 Jun;44(6):663-8. [PubMed:1506727 ]
Tonelli D, Gattavecchia E, Gandolfi M: Thin-layer chromatographic determination of indolic tryptophan metabolites in human urine using Sep-Pak C18 extraction. J Chromatogr. 1982 Sep 10;231(2):283-9. [PubMed:7130309 ]
Marklova E, Albahri Z, Nozickova M: HPLC profiling of Trp-related metabolites in humans. Adv Exp Med Biol. 2003;527:739-44. [PubMed:15206797 ]
Silverstein MN, Wakim KG, Bahn RC: The influence of tryptophan metabolites on tissue uptake of glucose. Metabolism. 1967 May;16(5):410-2. [PubMed:6025019 ]
Lombard GL, Dowell VR Jr: Comparison of three reagents for detecting indole production by anaerobic bacteria in microtest systems. J Clin Microbiol. 1983 Sep;18(3):609-13. [PubMed:6630445 ]

Enzymes

Enzyme Details

1. Beta-2-microglobulin precursor [Contains: Beta-2-microglobulin variant pI 5.3]

General function:: Not Available
Specific function:: Beta-2-microglobulin is the beta-chain of major histocompatibility complex class I molecules
Gene Name:: B2M
Uniprot ID:: P61769
Molecular weight:: 13715.0

References

Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Showing metabocard for 3-Indolebutyric acid (HMDB0002096)

MOL for HMDB0002096 (3-Indolebutyric acid)

3D MOL for HMDB0002096 (3-Indolebutyric acid)

3D SDF for HMDB0002096 (3-Indolebutyric acid)

3D-SDF for HMDB0002096 (3-Indolebutyric acid)

PDB for HMDB0002096 (3-Indolebutyric acid)

3D PDB for HMDB0002096 (3-Indolebutyric acid)

SMILES for HMDB0002096 (3-Indolebutyric acid)

INCHI for HMDB0002096 (3-Indolebutyric acid)

Structure for HMDB0002096 (3-Indolebutyric acid)

3D Structure for HMDB0002096 (3-Indolebutyric acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References