NP-MRD: Showing NP-Card for 3-Indolebutyric acid (NP0000481)

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Record Information

Version

1.0

Created at

2006-05-22 14:17:36 UTC

Updated at

2024-04-19 10:06:57 UTC

NP-MRD ID

NP0000481

Secondary Accession Numbers

None

Natural Product 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>
NP0000481

> <DATABASE_NAME>
NP-MRD

> <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

View in JSmol

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
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
Indolebutyric acid, monosodium salt	HMDB
Indolebutyric acid, monoammonium salt	HMDB
Indolebutyric acid, monopotassium salt	HMDB
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
3-Indolebutyric acid	ChEBI

Chemical Formula

C₁₂H₁₃NO₂

Average Mass

203.2371 Da

Monoisotopic Mass

203.09463 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-25	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-25	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-25	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-25	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.133705802 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201.216488466 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, simulated)	Varshavi.d26			2021-08-09	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Arabidopsis thaliana	KNApSAcK Database	22123792
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Nicotiana tabacum	KNApSAcK Database	22123792
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Pisum sativum	KNApSAcK Database	22123792
Solanum tuberosum	KNApSAcK Database	22123792
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Tropaeolum majus	LOTUS Database	35616633
Zea mays	LOTUS Database	35616633
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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 )

Physical Properties

State

Solid

Experimental 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 CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).

Predicted 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

External Links

HMDB ID

HMDB0002096

DrugBank ID

DB02740

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

rw1190841

References

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. doi: 10.1128/jcm.18.3.609-613.1983. [PubMed:6630445 ]

Showing NP-Card for 3-Indolebutyric acid (NP0000481)

MOL for NP0000481 (3-Indolebutyric acid)

3D MOL for NP0000481 (3-Indolebutyric acid)

3D SDF for NP0000481 (3-Indolebutyric acid)

3D-SDF for NP0000481 (3-Indolebutyric acid)

PDB for NP0000481 (3-Indolebutyric acid)

3D PDB for NP0000481 (3-Indolebutyric acid)

SMILES for NP0000481 (3-Indolebutyric acid)

INCHI for NP0000481 (3-Indolebutyric acid)

Structure for NP0000481 (3-Indolebutyric acid)

3D Structure for NP0000481 (3-Indolebutyric acid)