Hmdb loader

Showing metabocard for Indoleacrylic acid (HMDB0000734)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:07 UTC
HMDB IDHMDB0000734
Secondary Accession Numbers
  • HMDB00734
Metabolite Identification
Common NameIndoleacrylic acid
DescriptionIndoleacrylic acid (CAS: 1204-06-4), also known as indoleacrylate, IA, and IAcrA, is a member of the class of compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. Indoleacrylic acid is practically insoluble (in water) and a weak acidic compound (based on its pKa). Within the cell, indoleacrylic acid is primarily located in the membrane (predicted from logP). Indoleacrylic acid is best known as a plant growth hormone (a natural auxin), whereas its biological role in animals is still unknown. A two-stage production of this compound is likely: intestinal microorganisms catabolize tryptophan to indole derivatives which are then absorbed and converted into indoleacrylic acid and its glycine conjugate, indolylacryloylglycine (IAcrGly). Indolylacryloylglycine excretion in urine is especially pronounced in some myopathies, namely in boys with Duchenne muscular dystrophy (PMID: 10707769 ). It has been recently found that indoleacrylic acid promotes intestinal epithelial barrier function and mitigates inflammatory responses. Stimulating indoleacrylic acid production could promote anti-inflammatory responses and have therapeutic benefits (PMID: 28704649 ). Urinary Indole-3-acrylate is produced by Clostridium sporogenes (PMID: 29168502 ). Indoleacrylic acid is also a metabolite of Peptostreptococcus (PMID: 28704649 , 29168502 ).
Structure
Data?1676999707
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000734 (Indoleacrylic acid)


  Mrv1652304202022142D          

 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
10002.0468 9999.3188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.3323 9998.0813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.3324 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
 9999.9036 9998.9064    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
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 12 10  1  0  0  0  0
 12 11  2  0  0  0  0
 13 12  1  0  0  0  0
 14 13  2  0  0  0  0
  8 14  1  0  0  0  0
M  END
Download

3D MOL for HMDB0000734 (Indoleacrylic acid)

HMDB0000734
     RDKit          3D
Indoleacrylic acid
 23 24  0  0  0  0  0  0  0  0999 V2000
    4.3339   -1.3555    0.6904 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8877   -0.2533    0.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7861    0.7586    0.0326 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4258   -0.0153    0.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5678   -0.9688    0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1452   -0.9407    0.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6196   -2.0789    0.6518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9185   -1.8008    0.4909 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0511   -0.5232    0.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1420    0.2568   -0.2400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9804    1.5536   -0.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7372    2.0835   -0.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6232    1.3254   -0.4466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7557    0.0190   -0.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6191    1.5350   -0.5756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1274    0.9407   -0.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0915   -1.9077    0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2293   -3.0273    0.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7121   -2.4668    0.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1315   -0.1739   -0.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8418    2.1783   -0.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5908    3.1146   -1.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3487    1.7466   -0.5291 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  2  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
  3 15  1  0
  4 16  1  0
  5 17  1  0
  7 18  1  0
  8 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
 13 23  1  0
M  END
Download

3D SDF for HMDB0000734 (Indoleacrylic acid)


  Mrv1652304202022142D          

 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
10002.0468 9999.3188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.3323 9998.0813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.3324 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
 9999.9036 9998.9064    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
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 12 10  1  0  0  0  0
 12 11  2  0  0  0  0
 13 12  1  0  0  0  0
 14 13  2  0  0  0  0
  8 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000734

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)\C=C\C1=CNC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C11H9NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-7,12H,(H,13,14)/b6-5+

> <INCHI_KEY>
PLVPPLCLBIEYEA-AATRIKPKSA-N

> <FORMULA>
C11H9NO2

> <MOLECULAR_WEIGHT>
187.198

> <EXACT_MASS>
187.063328534

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
19.34464224554396

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(1H-indol-3-yl)prop-2-enoic acid

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
2.234848253

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.393868468603337

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.650101023193603

> <JCHEM_POLAR_SURFACE_AREA>
53.089999999999996

> <JCHEM_REFRACTIVITY>
54.146400000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(1H-indol-3-yl)prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000734 (Indoleacrylic acid)

HMDB0000734
     RDKit          3D
Indoleacrylic acid
 23 24  0  0  0  0  0  0  0  0999 V2000
    4.3339   -1.3555    0.6904 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8877   -0.2533    0.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7861    0.7586    0.0326 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4258   -0.0153    0.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5678   -0.9688    0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1452   -0.9407    0.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6196   -2.0789    0.6518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9185   -1.8008    0.4909 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0511   -0.5232    0.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1420    0.2568   -0.2400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9804    1.5536   -0.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7372    2.0835   -0.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6232    1.3254   -0.4466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7557    0.0190   -0.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6191    1.5350   -0.5756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1274    0.9407   -0.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0915   -1.9077    0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2293   -3.0273    0.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7121   -2.4668    0.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1315   -0.1739   -0.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8418    2.1783   -0.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5908    3.1146   -1.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3487    1.7466   -0.5291 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  2  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
  3 15  1  0
  4 16  1  0
  5 17  1  0
  7 18  1  0
  8 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
 13 23  1  0
M  END
Download

PDB for HMDB0000734 (Indoleacrylic acid)

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-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  O   UNK     0    8670.4878665.395   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8669.1548663.085   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8669.1548664.625   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8667.8208665.395   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8666.4878664.625   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   14                                                  
CONECT    9    8    5                                                       
CONECT   10   12                                                            
CONECT   11   12                                                            
CONECT   12   10   11   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13    8                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END
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3D PDB for HMDB0000734 (Indoleacrylic acid)

COMPND    HMDB0000734
HETATM    1  O1  UNL     1       4.334  -1.355   0.690  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.888  -0.253   0.310  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.786   0.759   0.033  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.426  -0.015   0.153  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.568  -0.969   0.414  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.145  -0.941   0.327  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.620  -2.079   0.652  1.00  0.00           C  
HETATM    8  N1  UNL     1      -1.918  -1.801   0.491  1.00  0.00           N  
HETATM    9  C6  UNL     1      -2.051  -0.523   0.071  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.142   0.257  -0.240  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.980   1.554  -0.649  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.737   2.084  -0.752  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.623   1.325  -0.447  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.756   0.019  -0.032  1.00  0.00           C  
HETATM   15  H1  UNL     1       4.619   1.535  -0.576  1.00  0.00           H  
HETATM   16  H2  UNL     1       2.127   0.941  -0.172  1.00  0.00           H  
HETATM   17  H3  UNL     1       2.092  -1.908   0.746  1.00  0.00           H  
HETATM   18  H4  UNL     1      -0.229  -3.027   0.979  1.00  0.00           H  
HETATM   19  H5  UNL     1      -2.712  -2.467   0.662  1.00  0.00           H  
HETATM   20  H6  UNL     1      -4.131  -0.174  -0.155  1.00  0.00           H  
HETATM   21  H7  UNL     1      -3.842   2.178  -0.898  1.00  0.00           H  
HETATM   22  H8  UNL     1      -1.591   3.115  -1.077  1.00  0.00           H  
HETATM   23  H9  UNL     1       0.349   1.747  -0.529  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   15
CONECT    4    5    5   16
CONECT    5    6   17
CONECT    6    7    7   14
CONECT    7    8   18
CONECT    8    9   19
CONECT    9   10   10   14
CONECT   10   11   20
CONECT   11   12   12   21
CONECT   12   13   22
CONECT   13   14   14   23
END
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SMILES for HMDB0000734 (Indoleacrylic acid)

OC(=O)\C=C\C1=CNC2=C1C=CC=C2
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INCHI for HMDB0000734 (Indoleacrylic acid)

InChI=1S/C11H9NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-7,12H,(H,13,14)/b6-5+
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View in JSmolView Stereo Labels
Synonyms
ValueSource
3-(3-Indolyl)acrylic acidChEBI
3-Indoleacrylic acidChEBI
3-Indolylacrylic acidChEBI
Indole-3-acrylic acidChEBI
Indole-3beta-acrylic acidChEBI
trans-3-Indoleacrylic acidChEBI
trans-beta-Indoleacrylic acidChEBI
3-(3-Indolyl)acrylateGenerator
3-IndoleacrylateGenerator
3-IndolylacrylateGenerator
Indole-3-acrylateGenerator
Indole-3b-acrylateGenerator
Indole-3b-acrylic acidGenerator
Indole-3beta-acrylateGenerator
Indole-3β-acrylateGenerator
Indole-3β-acrylic acidGenerator
trans-3-IndoleacrylateGenerator
trans-b-IndoleacrylateGenerator
trans-b-Indoleacrylic acidGenerator
trans-beta-IndoleacrylateGenerator
trans-Β-indoleacrylateGenerator
trans-Β-indoleacrylic acidGenerator
IndoleacrylateGenerator
(e)-3-(indol-3-yl)AcrylateHMDB
Indoleacrylic acid, (e)-isomerHMDB
Indoleacrylic acid, sodium saltHMDB
Indole acrylic acidHMDB
(2E)-3-(1H-indol-3-yl)-2-Propenoic acidHMDB
(e)-3-(1H-indol-3-yl)-2-Propenoic acidHMDB
(e)-3-(1H-indol-3-yl)Prop-2-enoic acidHMDB
(e)-Indole-3-acrylic acidHMDB
3-(1H-indol-3-yl)-2-Propenoic acidHMDB
3-(1H-indol-3-yl)Acrylic acidHMDB
3-(indol-3-yl)Prop-2-enoic acidHMDB
3-beta-Indoleacrylic acidHMDB
3-Β-indoleacrylic acidHMDB
IAHMDB
IAcrAHMDB
Indoleacrylic acidChEBI
Chemical FormulaC11H9NO2
Average Molecular Weight187.198
Monoisotopic Molecular Weight187.063328534
IUPAC Name(2E)-3-(1H-indol-3-yl)prop-2-enoic acid
Traditional Name(2E)-3-(1H-indol-3-yl)prop-2-enoic acid
CAS Registry Number29953-71-7
SMILES
OC(=O)\C=C\C1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C11H9NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-7,12H,(H,13,14)/b6-5+
InChI KeyPLVPPLCLBIEYEA-AATRIKPKSA-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
  • Substituted pyrrole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point180 - 186 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg134.53430932474
[M-H]-Not Available134.534http://allccs.zhulab.cn/database/detail?ID=AllCCS00000329
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.22 g/LALOGPS
logP2.29ALOGPS
logP2.23ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity54.15 m³·mol⁻¹ChemAxon
Polarizability19.34 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+137.08530932474
DeepCCS[M-H]-134.68930932474
DeepCCS[M-2H]-169.53630932474
DeepCCS[M+Na]+143.99530932474
AllCCS[M+H]+140.432859911
AllCCS[M+H-H2O]+136.032859911
AllCCS[M+NH4]+144.432859911
AllCCS[M+Na]+145.632859911
AllCCS[M-H]-140.532859911
AllCCS[M+Na-2H]-140.632859911
AllCCS[M+HCOO]-140.832859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.5.13 minutes32390414
Predicted by Siyang on May 30, 202211.2773 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.87 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1919.8 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid362.0 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid129.3 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid208.0 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid302.3 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid397.1 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid344.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)122.7 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1000.4 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid381.3 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1161.5 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid328.4 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid338.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate401.4 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA310.0 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water45.4 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Indoleacrylic acidOC(=O)\C=C\C1=CNC2=C1C=CC=C23270.3Standard polar33892256
Indoleacrylic acidOC(=O)\C=C\C1=CNC2=C1C=CC=C22105.2Standard non polar33892256
Indoleacrylic acidOC(=O)\C=C\C1=CNC2=C1C=CC=C22194.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Indoleacrylic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=C[NH]C2=CC=CC=C122232.4Semi standard non polar33892256
Indoleacrylic acid,1TMS,isomer #2C[Si](C)(C)N1C=C(/C=C/C(=O)O)C2=CC=CC=C212350.6Semi standard non polar33892256
Indoleacrylic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=CN([Si](C)(C)C)C2=CC=CC=C122410.3Semi standard non polar33892256
Indoleacrylic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=CN([Si](C)(C)C)C2=CC=CC=C122298.3Standard non polar33892256
Indoleacrylic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=CN([Si](C)(C)C)C2=CC=CC=C122288.4Standard polar33892256
Indoleacrylic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=C[NH]C2=CC=CC=C122506.1Semi standard non polar33892256
Indoleacrylic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=C(/C=C/C(=O)O)C2=CC=CC=C212599.5Semi standard non polar33892256
Indoleacrylic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122812.7Semi standard non polar33892256
Indoleacrylic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122673.4Standard non polar33892256
Indoleacrylic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122502.5Standard polar33892256
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 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 IDFDB112378
KNApSAcK IDNot Available
Chemspider ID4524636
KEGG Compound IDNot Available
BioCyc IDCPD-11578
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5375048
PDB IDNot Available
ChEBI ID132244
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceMoffatt, J. S. Preparation of b-3-indolylacrylic acid. Journal of the Chemical Society (1957), 1442-3.; Bauguess, Lyle C.; Berg, Clarence P. The availability of indole derivatives for supplementing diets deficient in tryptophan. Proceedings of the Iowa Academy of Science (1933), 40 110-11.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Marklova E: Where does indolylacrylic acid come from? Amino Acids. 1999;17(4):401-13. [PubMed:10707769 ]
  2. Wlodarska M, Luo C, Kolde R, d'Hennezel E, Annand JW, Heim CE, Krastel P, Schmitt EK, Omar AS, Creasey EA, Garner AL, Mohammadi S, O'Connell DJ, Abubucker S, Arthur TD, Franzosa EA, Huttenhower C, Murphy LO, Haiser HJ, Vlamakis H, Porter JA, Xavier RJ: Indoleacrylic Acid Produced by Commensal Peptostreptococcus Species Suppresses Inflammation. Cell Host Microbe. 2017 Jul 12;22(1):25-37.e6. doi: 10.1016/j.chom.2017.06.007. [PubMed:28704649 ]
  3. Dodd D, Spitzer MH, Van Treuren W, Merrill BD, Hryckowian AJ, Higginbottom SK, Le A, Cowan TM, Nolan GP, Fischbach MA, Sonnenburg JL: A gut bacterial pathway metabolizes aromatic amino acids into nine circulating metabolites. Nature. 2017 Nov 30;551(7682):648-652. doi: 10.1038/nature24661. Epub 2017 Nov 22. [PubMed:29168502 ]