Showing metabocard for Indole-3-methyl acetate (MMDBc0000477)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:38:39 UTC
Update Date2024-04-30 19:32:34 UTC
Metabolite IDMMDBc0000477
Metabolite Identification
Common NameIndole-3-methyl acetate
DescriptionIndole-3-methyl acetate, also known as methyl indole-3-acetate (methyl-IAA), is a catabolite of tryptophan converted by the gut microbiota. After absorption through the intestinal epithelium, tryptophan catabolites enter the bloodstream and are later excreted in the urine (PMID: 30120222 ). Pediatric enthesitis-related arthritis (ERA) patients (i.e. spondyloarthropathy associated with inflammatory bowel disease) have intestinal inflammation and decreased gut microbial diversity. Such alterations in the gut microbiota resulted in the reduction of tryptophan metabolism and several tryptophan metabolites in pediatric ERA fecal samples, including indole-3-methyl acetate (PMID: 27786174 ). Indole-3-methyl acetate is found in apple, and has been isolated from immature seeds of beach pea (Lathyrus maritimus), Vicia amurensis, wild soybean (Glycine soja), lobiya (Vigna catiang var. sinensis) and hyacinth bean (Dolichos lablab).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f923abb62e0>


  Mrv1652301282019172D          

 14 15  0  0  0  0            999 V2000
 9997.0764 9999.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8215 9998.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3735 9998.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1805 9998.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.295810000.3109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8834 9999.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4354 9998.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1891 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.102810000.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9036 9998.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6180 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3324 9998.9064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.617910000.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.0469 9999.3189    0.0000 C   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 14  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f923abb62e0>

HMDB0029738
     RDKit          3D
Indole-3-methyl acetate
 25 26  0  0  0  0  0  0  0  0999 V2000
    4.3798    0.9714    0.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3535    0.6804   -0.8003 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1293    0.1839   -0.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9093   -0.0146    0.8014 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0878   -0.1101   -1.4492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1295   -0.6928   -0.8200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4725   -2.0471   -0.8029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6241   -2.2199   -0.1445 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0515   -0.9968    0.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1905   -0.6537    0.9977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3859    0.6779    1.2963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4725    1.6304    0.8863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3570    1.2939    0.1812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1357   -0.0497   -0.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8537    0.0081    0.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1597    1.5968   -0.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0355    1.4903    1.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5418   -0.8755   -2.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8054    0.8251   -1.9681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0796   -2.8646   -1.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1076   -3.1198    0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8784   -1.4272    1.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2563    1.0085    1.8567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6534    2.6812    1.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6204    2.0241   -0.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  6  1  0
 14  9  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  0
  5 19  1  0
  7 20  1  0
  8 21  1  0
 10 22  1  0
 11 23  1  0
 12 24  1  0
 13 25  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f923abb62e0>


  Mrv1652301282019172D          

 14 15  0  0  0  0            999 V2000
 9997.0764 9999.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8215 9998.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3735 9998.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1805 9998.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.295810000.3109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8834 9999.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4354 9998.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1891 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.102810000.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9036 9998.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6180 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3324 9998.9064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.617910000.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.0469 9999.3189    0.0000 C   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 14  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000477

> <DATABASE_NAME>
MIME

> <SMILES>
COC(=O)CC1=CNC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C11H11NO2/c1-14-11(13)6-8-7-12-10-5-3-2-4-9(8)10/h2-5,7,12H,6H2,1H3

> <INCHI_KEY>
KTHADMDGDNYQRX-UHFFFAOYSA-N

> <FORMULA>
C11H11NO2

> <MOLECULAR_WEIGHT>
189.2105

> <EXACT_MASS>
189.078978601

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
19.777863703154345

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-(1H-indol-3-yl)acetate

> <ALOGPS_LOGP>
2.61

> <JCHEM_LOGP>
1.8556501543333335

> <ALOGPS_LOGS>
-2.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.044118914611719

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0781988457999905

> <JCHEM_POLAR_SURFACE_AREA>
42.09

> <JCHEM_REFRACTIVITY>
53.2212

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 1H-indol-3-ylacetate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f923abb62e0>

HMDB0029738
     RDKit          3D
Indole-3-methyl acetate
 25 26  0  0  0  0  0  0  0  0999 V2000
    4.3798    0.9714    0.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3535    0.6804   -0.8003 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1293    0.1839   -0.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9093   -0.0146    0.8014 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0878   -0.1101   -1.4492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1295   -0.6928   -0.8200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4725   -2.0471   -0.8029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6241   -2.2199   -0.1445 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0515   -0.9968    0.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1905   -0.6537    0.9977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3859    0.6779    1.2963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4725    1.6304    0.8863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3570    1.2939    0.1812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1357   -0.0497   -0.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8537    0.0081    0.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1597    1.5968   -0.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0355    1.4903    1.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5418   -0.8755   -2.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8054    0.8251   -1.9681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0796   -2.8646   -1.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1076   -3.1198    0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8784   -1.4272    1.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2563    1.0085    1.8567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6534    2.6812    1.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6204    2.0241   -0.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  6  1  0
 14  9  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  0
  5 19  1  0
  7 20  1  0
  8 21  1  0
 10 22  1  0
 11 23  1  0
 12 24  1  0
 13 25  1  0
M  END
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PDB for #<Metabolite:0x00007f923abb62e0>

HEADER    PROTEIN                                 28-JAN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-JAN-20         0                                  
HETATM    1  C   UNK     0    8661.2098665.593   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8660.7338664.128   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8661.7648662.984   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8663.2708663.304   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    8663.4858667.247   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8662.7168665.913   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8663.7468664.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.1538665.395   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.9928666.927   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.4878664.625   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.8208665.395   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8669.1548664.625   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8667.8208666.935   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    8670.4888665.395   0.000  0.00  0.00           C+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   13                                                  
CONECT   12   11   14                                                       
CONECT   13   11                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END
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3D PDB for #<Metabolite:0x00007f923abb62e0>

COMPND    HMDB0029738
HETATM    1  C1  UNL     1       4.380   0.971   0.132  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.354   0.680  -0.800  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.129   0.184  -0.409  1.00  0.00           C  
HETATM    4  O2  UNL     1       1.909  -0.015   0.801  1.00  0.00           O  
HETATM    5  C3  UNL     1       1.088  -0.110  -1.449  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.129  -0.693  -0.820  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.472  -2.047  -0.803  1.00  0.00           C  
HETATM    8  N1  UNL     1      -1.624  -2.220  -0.145  1.00  0.00           N  
HETATM    9  C6  UNL     1      -2.051  -0.997   0.277  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.190  -0.654   0.998  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.386   0.678   1.296  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.473   1.630   0.886  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.357   1.294   0.181  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.136  -0.050  -0.134  1.00  0.00           C  
HETATM   15  H1  UNL     1       4.854   0.008   0.488  1.00  0.00           H  
HETATM   16  H2  UNL     1       5.160   1.597  -0.345  1.00  0.00           H  
HETATM   17  H3  UNL     1       4.035   1.490   1.034  1.00  0.00           H  
HETATM   18  H4  UNL     1       1.542  -0.875  -2.130  1.00  0.00           H  
HETATM   19  H5  UNL     1       0.805   0.825  -1.968  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.080  -2.865  -1.245  1.00  0.00           H  
HETATM   21  H7  UNL     1      -2.108  -3.120   0.019  1.00  0.00           H  
HETATM   22  H8  UNL     1      -3.878  -1.427   1.302  1.00  0.00           H  
HETATM   23  H9  UNL     1      -4.256   1.009   1.857  1.00  0.00           H  
HETATM   24  H10 UNL     1      -2.653   2.681   1.134  1.00  0.00           H  
HETATM   25  H11 UNL     1      -0.620   2.024  -0.156  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   18   19
CONECT    6    7    7   14
CONECT    7    8   20
CONECT    8    9   21
CONECT    9   10   10   14
CONECT   10   11   22
CONECT   11   12   12   23
CONECT   12   13   24
CONECT   13   14   14   25
END
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SMILES for #<Metabolite:0x00007f923abb62e0>

COC(=O)CC1=CNC2=C1C=CC=C2
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INCHI for #<Metabolite:0x00007f923abb62e0>

InChI=1S/C11H11NO2/c1-14-11(13)6-8-7-12-10-5-3-2-4-9(8)10/h2-5,7,12H,6H2,1H3
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Synonyms
ValueSource
beta-Indolylacetic acid methyl esterChEBI
Indole-3-acetic acid, methyl esterChEBI
Methyl 3-indolylacetateChEBI
Methyl beta-indoleacetateChEBI
Methyl beta-indolylacetateChEBI
Methyl indol-3-ylacetateChEBI
b-Indolylacetate methyl esterGenerator
b-Indolylacetic acid methyl esterGenerator
beta-Indolylacetate methyl esterGenerator
Β-indolylacetate methyl esterGenerator
Β-indolylacetic acid methyl esterGenerator
Indole-3-acetate, methyl esterGenerator
Methyl 3-indolylacetic acidGenerator
Methyl b-indoleacetateGenerator
Methyl b-indoleacetic acidGenerator
Methyl beta-indoleacetic acidGenerator
Methyl β-indoleacetateGenerator
Methyl β-indoleacetic acidGenerator
Methyl b-indolylacetateGenerator
Methyl b-indolylacetic acidGenerator
Methyl beta-indolylacetic acidGenerator
Methyl β-indolylacetateGenerator
Methyl β-indolylacetic acidGenerator
Methyl indol-3-ylacetic acidGenerator
Indole-3-methyl acetic acidGenerator
1H-Indole-3-acetic acid, methyl esterHMDB
beta -Indolylacetic acid methyl esterHMDB
IAA methyl esterHMDB
Indole-3-acetic acid methyl esterHMDB
INDOLE-3-acetIC ACID methylesterHMDB
MeiaaHMDB
Methyl 1H-indol-3-ylacetateHMDB
Methyl 2-(1H-indol-3-yl)acetateHMDB
Methyl beta -indoleacetateHMDB
Methyl beta -indolylacetateHMDB
Methyl iaaHMDB
Methyl indole-3-acetateHMDB
Methylester OF 3-indoleacetic acidHMDB
Methyl (indol-3-yl)acetic acidGenerator
(1H-Indol-3-yl)acetic acid methyl esterHMDB
Indolyl-3-acetic acid methyl esterHMDB
Methyl 1H-indole-3-acetateHMDB
Methyl-IAAHMDB
Molecular FormulaC11H11NO2
Average Mass189.2105
Monoisotopic Mass189.078978601
IUPAC Namemethyl 2-(1H-indol-3-yl)acetate
Traditional Namemethyl 1H-indol-3-ylacetate
CAS Registry NumberNot Available
SMILES
COC(=O)CC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C11H11NO2/c1-14-11(13)6-8-7-12-10-5-3-2-4-9(8)10/h2-5,7,12H,6H2,1H3
InChI KeyKTHADMDGDNYQRX-UHFFFAOYSA-N