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Showing metabocard for indole-3-acetyl-proline (HMDB0304386)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-24 09:23:31 UTC
Update Date2021-09-24 09:23:31 UTC
HMDB IDHMDB0304386
Secondary Accession NumbersNone
Metabolite Identification
Common Nameindole-3-acetyl-proline
DescriptionIndole-3-acetyl-proline is also known as iaa-pro. Indole-3-acetyl-proline is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Indole-3-acetyl-proline can be found in a number of food items such as dill, black crowberry, savoy cabbage, and arrowhead, which makes indole-3-acetyl-proline a potential biomarker for the consumption of these food products.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0304386 (indole-3-acetyl-proline)


  Mrv1533005141521452D          

 20 22  0  0  0  0            999 V2000
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    1.7103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2450    1.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2450    2.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    3.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9754    2.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1504    2.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2621    3.0922    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.2621    1.6632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7575    0.3126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  1  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  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  1  0  0  0  0
 13 15  2  0  0  0  0
  8 12  1  0  0  0  0
  7 16  2  0  0  0  0
  4 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  3 20  1  0  0  0  0
M  CHG  1  14  -1
M  END
Download

3D MOL for HMDB0304386 (indole-3-acetyl-proline)

HMDB0304386
     RDKit          3D
indole-3-acetyl-proline
 35 37  0  0  0  0  0  0  0  0999 V2000
   -3.5454   -0.6864    3.3569 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9697   -0.0273    2.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4745    1.2093    2.7837 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.8859   -0.6488    1.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1703   -0.6076    0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1728    0.7471   -0.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7358    1.2108   -0.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9738    0.0712    0.2316 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382   -0.3000   -0.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1415   -1.3319    0.4327 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1672    0.5166   -0.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5192   -0.0561   -1.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0436   -0.7646   -2.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3158   -1.0958   -1.9417 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6843   -0.6331   -0.7243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8585   -0.7096   -0.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9254   -0.1257    1.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8175    0.5250    1.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6471    0.5978    1.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5596    0.0168   -0.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5748   -1.7179    1.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1913   -1.4106   -0.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0646   -0.6430    1.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8653    1.4535    0.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4876    0.6638   -1.3898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3856    1.5288   -1.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7063    2.0362    0.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3649    0.5630   -1.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2047    1.5467   -0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4979   -1.0126   -3.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9184   -1.6320   -2.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7295   -1.2115   -0.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8457   -0.1616    1.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8559    0.9882    2.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7579    1.1014    1.3860 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  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  8  4  1  0
 20 12  1  0
 20 15  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
 11 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
M  CHG  1   3  -1
M  END
Download

3D SDF for HMDB0304386 (indole-3-acetyl-proline)


  Mrv1533005141521452D          

 20 22  0  0  0  0            999 V2000
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    1.7103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2450    1.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2450    2.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    3.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9754    2.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1504    2.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2621    3.0922    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.2621    1.6632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7575    0.3126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  1  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  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  1  0  0  0  0
 13 15  2  0  0  0  0
  8 12  1  0  0  0  0
  7 16  2  0  0  0  0
  4 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  3 20  1  0  0  0  0
M  CHG  1  14  -1
M  END
> <DATABASE_ID>
HMDB0304386

> <DATABASE_NAME>
hmdb

> <SMILES>
[O-]C(=O)C1CCCN1C(=O)CC1=CNC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H16N2O3/c18-14(17-7-3-6-13(17)15(19)20)8-10-9-16-12-5-2-1-4-11(10)12/h1-2,4-5,9,13,16H,3,6-8H2,(H,19,20)/p-1

> <INCHI_KEY>
STGVBTJKCSSKNP-UHFFFAOYSA-M

> <FORMULA>
C15H15N2O3

> <MOLECULAR_WEIGHT>
271.297

> <EXACT_MASS>
271.108815931

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.476297617133184

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[2-(1H-indol-3-yl)acetyl]pyrrolidine-2-carboxylate

> <ALOGPS_LOGP>
1.69

> <JCHEM_LOGP>
1.4459026786666658

> <ALOGPS_LOGS>
-2.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.057809965571316

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.0363726512037115

> <JCHEM_PKA_STRONGEST_BASIC>
-2.321503879975618

> <JCHEM_POLAR_SURFACE_AREA>
76.23

> <JCHEM_REFRACTIVITY>
84.27570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.89e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[2-(1H-indol-3-yl)acetyl]pyrrolidine-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0304386 (indole-3-acetyl-proline)

HMDB0304386
     RDKit          3D
indole-3-acetyl-proline
 35 37  0  0  0  0  0  0  0  0999 V2000
   -3.5454   -0.6864    3.3569 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9697   -0.0273    2.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4745    1.2093    2.7837 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.8859   -0.6488    1.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1703   -0.6076    0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1728    0.7471   -0.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7358    1.2108   -0.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9738    0.0712    0.2316 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382   -0.3000   -0.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1415   -1.3319    0.4327 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1672    0.5166   -0.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5192   -0.0561   -1.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0436   -0.7646   -2.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3158   -1.0958   -1.9417 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6843   -0.6331   -0.7243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8585   -0.7096   -0.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9254   -0.1257    1.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8175    0.5250    1.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6471    0.5978    1.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5596    0.0168   -0.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5748   -1.7179    1.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1913   -1.4106   -0.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0646   -0.6430    1.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8653    1.4535    0.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4876    0.6638   -1.3898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3856    1.5288   -1.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7063    2.0362    0.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3649    0.5630   -1.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2047    1.5467   -0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4979   -1.0126   -3.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9184   -1.6320   -2.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7295   -1.2115   -0.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8457   -0.1616    1.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8559    0.9882    2.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7579    1.1014    1.3860 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  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  8  4  1  0
 20 12  1  0
 20 15  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
 11 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
M  CHG  1   3  -1
M  END
Download

PDB for HMDB0304386 (indole-3-acetyl-proline)

HEADER    PROTEIN                                 14-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-15         0                                  
HETATM    1  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.250   1.728   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -2.726   3.192   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -4.191   3.668   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.191   5.208   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.726   5.684   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.821   4.438   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.281   4.438   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.489   5.772   0.000  0.00  0.00           O-1
HETATM   15  O   UNK     0       0.489   3.105   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -3.281   0.583   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    1    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13    8                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    7                                                            
CONECT   17    4   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    3                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END
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3D PDB for HMDB0304386 (indole-3-acetyl-proline)

COMPND    HMDB0304386
HETATM    1  O1  UNL     1      -3.545  -0.686   3.357  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.970  -0.027   2.447  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.475   1.209   2.784  1.00  0.00           O1-
HETATM    4  C2  UNL     1      -2.886  -0.649   1.115  1.00  0.00           C  
HETATM    5  C3  UNL     1      -4.170  -0.608   0.343  1.00  0.00           C  
HETATM    6  C4  UNL     1      -4.173   0.747  -0.326  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.736   1.211  -0.237  1.00  0.00           C  
HETATM    8  N1  UNL     1      -1.974   0.071   0.232  1.00  0.00           N  
HETATM    9  C6  UNL     1      -0.638  -0.300  -0.075  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.141  -1.332   0.433  1.00  0.00           O  
HETATM   11  C7  UNL     1       0.167   0.517  -0.984  1.00  0.00           C  
HETATM   12  C8  UNL     1       1.519  -0.056  -1.152  1.00  0.00           C  
HETATM   13  C9  UNL     1       2.044  -0.765  -2.209  1.00  0.00           C  
HETATM   14  N2  UNL     1       3.316  -1.096  -1.942  1.00  0.00           N  
HETATM   15  C10 UNL     1       3.684  -0.633  -0.724  1.00  0.00           C  
HETATM   16  C11 UNL     1       4.859  -0.710  -0.010  1.00  0.00           C  
HETATM   17  C12 UNL     1       4.925  -0.126   1.230  1.00  0.00           C  
HETATM   18  C13 UNL     1       3.818   0.525   1.737  1.00  0.00           C  
HETATM   19  C14 UNL     1       2.647   0.598   1.018  1.00  0.00           C  
HETATM   20  C15 UNL     1       2.560   0.017  -0.232  1.00  0.00           C  
HETATM   21  H1  UNL     1      -2.575  -1.718   1.224  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.191  -1.411  -0.417  1.00  0.00           H  
HETATM   23  H3  UNL     1      -5.065  -0.643   1.008  1.00  0.00           H  
HETATM   24  H4  UNL     1      -4.865   1.453   0.155  1.00  0.00           H  
HETATM   25  H5  UNL     1      -4.488   0.664  -1.390  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.386   1.529  -1.240  1.00  0.00           H  
HETATM   27  H7  UNL     1      -2.706   2.036   0.511  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.365   0.563  -1.969  1.00  0.00           H  
HETATM   29  H9  UNL     1       0.205   1.547  -0.578  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.498  -1.013  -3.120  1.00  0.00           H  
HETATM   31  H11 UNL     1       3.918  -1.632  -2.590  1.00  0.00           H  
HETATM   32  H12 UNL     1       5.730  -1.211  -0.387  1.00  0.00           H  
HETATM   33  H13 UNL     1       5.846  -0.162   1.838  1.00  0.00           H  
HETATM   34  H14 UNL     1       3.856   0.988   2.710  1.00  0.00           H  
HETATM   35  H15 UNL     1       1.758   1.101   1.386  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    4    5    8   21
CONECT    5    6   22   23
CONECT    6    7   24   25
CONECT    7    8   26   27
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   28   29
CONECT   12   13   13   20
CONECT   13   14   30
CONECT   14   15   31
CONECT   15   16   16   20
CONECT   16   17   32
CONECT   17   18   18   33
CONECT   18   19   34
CONECT   19   20   20   35
END
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SMILES for HMDB0304386 (indole-3-acetyl-proline)

[O-]C(=O)C1CCCN1C(=O)CC1=CNC2=C1C=CC=C2
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INCHI for HMDB0304386 (indole-3-acetyl-proline)

InChI=1S/C15H16N2O3/c18-14(17-7-3-6-13(17)15(19)20)8-10-9-16-12-5-2-1-4-11(10)12/h1-2,4-5,9,13,16H,3,6-8H2,(H,19,20)/p-1
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1-[2-(1H-indol-3-yl)Acetyl]pyrrolidine-2-carboxylic acidGenerator
Indole-3-acetyl-proMetaCyc
IAA-proMetaCyc
Chemical FormulaC15H15N2O3
Average Molecular Weight271.297
Monoisotopic Molecular Weight271.108815931
IUPAC Name1-[2-(1H-indol-3-yl)acetyl]pyrrolidine-2-carboxylate
Traditional Name1-[2-(1H-indol-3-yl)acetyl]pyrrolidine-2-carboxylate
CAS Registry NumberNot Available
SMILES
[O-]C(=O)C1CCCN1C(=O)CC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C15H16N2O3/c18-14(17-7-3-6-13(17)15(19)20)8-10-9-16-12-5-2-1-4-11(10)12/h1-2,4-5,9,13,16H,3,6-8H2,(H,19,20)/p-1
InChI KeySTGVBTJKCSSKNP-UHFFFAOYSA-M
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Proline or derivatives
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Carboxylic acid
  • Organoheterocyclic compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic anion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP1.69ALOGPS
logP1.45ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4.04ChemAxon
pKa (Strongest Basic)-2.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area76.23 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity84.28 m³·mol⁻¹ChemAxon
Polarizability27.48 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+163.20132859911
AllCCS[M+H-H2O]+159.60832859911
AllCCS[M+Na]+167.49532859911
AllCCS[M+NH4]+166.53632859911
AllCCS[M-H]-164.65732859911
AllCCS[M+Na-2H]-164.25532859911
AllCCS[M+HCOO]-163.93332859911
DeepCCS[M+H]+154.70330932474
DeepCCS[M-H]-152.32930932474
DeepCCS[M-2H]-185.46130932474
DeepCCS[M+Na]+160.78130932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
indole-3-acetyl-proline,1TMS,isomer #1C[Si](C)(C)N1C=C(CC(=O)N2CCCC2C(=O)[O-])C2=CC=CC=C212593.4Semi standard non polar33892256
indole-3-acetyl-proline,1TMS,isomer #1C[Si](C)(C)N1C=C(CC(=O)N2CCCC2C(=O)[O-])C2=CC=CC=C212505.4Standard non polar33892256
indole-3-acetyl-proline,1TMS,isomer #1C[Si](C)(C)N1C=C(CC(=O)N2CCCC2C(=O)[O-])C2=CC=CC=C213306.0Standard polar33892256
indole-3-acetyl-proline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(CC(=O)N2CCCC2C(=O)[O-])C2=CC=CC=C212825.6Semi standard non polar33892256
indole-3-acetyl-proline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(CC(=O)N2CCCC2C(=O)[O-])C2=CC=CC=C212727.9Standard non polar33892256
indole-3-acetyl-proline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(CC(=O)N2CCCC2C(=O)[O-])C2=CC=CC=C213380.3Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - indole-3-acetyl-proline 10V, Negative-QTOFsplash10-00b9-0090000000-7b89181dd4012603cb692019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - indole-3-acetyl-proline 20V, Negative-QTOFsplash10-024i-3690000000-48759cda6f90fe91f2de2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - indole-3-acetyl-proline 40V, Negative-QTOFsplash10-014i-7900000000-f11a90d725db665908342019-02-23Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030931
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available