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Showing NP-Card for Indoleacetic acid (NP0000884)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2024-09-03 04:22:19 UTC
NP-MRD IDNP0000884
Natural Product DOIhttps://doi.org/10.57994/2820
Secondary Accession NumbersNone
Natural Product Identification
Common NameIndoleacetic acid
DescriptionIndoleacetic acid (IAA) is a breakdown product of tryptophan metabolism and is often produced by the action of bacteria in the mammalian gut. Some endogenous production of IAA in mammalian tissues also occurs. It may be produced by the decarboxylation of tryptamine or the oxidative deamination of tryptophan. IAA frequently occurs at low levels in urine and has been found in elevated levels in the urine of patients with phenylketonuria ((PMID: 13610897 ). Using material extracted from human urine, it was discovered by Kogl in 1933 that Indoleacetic acid is also an important plant hormone (PMID: 13610897 ). Specifically IAA is a member of the group of phytohormones called auxins. IAA is generally considered to be the most important native auxin. Plant cells synthesize IAA from tryptophan. (Wikipedia) IAA and some derivatives can be oxidised by horseradish peroxidase (HRP) to cytotoxic species. IAA is only toxic after oxidative decarboxylation; the effect of IAA/HRP is thought to be due in part to the formation of methylene-oxindole, which may conjugate with DNA bases and protein thiols. IAA/HRP could be used as the basis for targeted cancer, a potential new role for plant auxins in cancer therapy. (PMID: 11163327 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000884 (Indoleacetic acid)


  Mrv1652309272007322D          

 13 14  0  0  1  0            999 V2000
   -3.1806    2.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8950    2.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6095    2.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6096    1.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8951    0.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1805    1.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3960    0.9843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9110    1.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3959    2.3191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411    0.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3342    0.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0793   -0.7565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7821    0.6410    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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  7  8  2  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 13  2  0  0  0  0
 11 12  1  0  0  0  0
M  END
Download

3D MOL for NP0000884 (Indoleacetic acid)

HMDB0000197
     RDKit          3D
Indoleacetic acid
 22 23  0  0  0  0  0  0  0  0999 V2000
    2.1212   -0.6625    1.4322 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7217   -0.5866    0.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9297   -1.2027    0.1052 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0847    0.1974   -0.7693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7914    0.7740   -0.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4992    2.0709    0.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7993    2.1400    0.3777 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3841    0.9267    0.2614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6851    0.4937    0.4947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0095   -0.8250    0.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0215   -1.6830   -0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7178   -1.2678   -0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3953    0.0677   -0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9758   -2.2280    0.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7636    1.0410   -1.0050 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224   -0.4620   -1.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1849    2.9071    0.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3421    2.9825    0.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4302    1.1985    0.8351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0076   -1.2245    0.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2597   -2.7329   -0.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574   -1.9247   -0.7202 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  5  1  0
 13  8  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  6 17  1  0
  7 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
M  END
Download

3D SDF for NP0000884 (Indoleacetic acid)


  Mrv1652309272007322D          

 13 14  0  0  1  0            999 V2000
   -3.1806    2.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8950    2.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6095    2.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6096    1.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8951    0.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1805    1.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3960    0.9843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9110    1.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3959    2.3191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411    0.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3342    0.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0793   -0.7565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7821    0.6410    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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  7  8  2  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 13  2  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000884

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CC1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13)

> <INCHI_KEY>
SEOVTRFCIGRIMH-UHFFFAOYSA-N

> <FORMULA>
C10H9NO2

> <MOLECULAR_WEIGHT>
175.184

> <EXACT_MASS>
175.063328537

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
17.735695939781067

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(1H-indol-3-yl)acetic acid

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
1.709756098333333

> <ALOGPS_LOGS>
-2.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.189363501426207

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.661850493370194

> <JCHEM_POLAR_SURFACE_AREA>
53.089999999999996

> <JCHEM_REFRACTIVITY>
48.4521

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.38e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-indole-3-acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000884 (Indoleacetic acid)

HMDB0000197
     RDKit          3D
Indoleacetic acid
 22 23  0  0  0  0  0  0  0  0999 V2000
    2.1212   -0.6625    1.4322 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7217   -0.5866    0.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9297   -1.2027    0.1052 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0847    0.1974   -0.7693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7914    0.7740   -0.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4992    2.0709    0.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7993    2.1400    0.3777 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3841    0.9267    0.2614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6851    0.4937    0.4947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0095   -0.8250    0.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0215   -1.6830   -0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7178   -1.2678   -0.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3953    0.0677   -0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9758   -2.2280    0.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7636    1.0410   -1.0050 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224   -0.4620   -1.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1849    2.9071    0.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3421    2.9825    0.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4302    1.1985    0.8351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0076   -1.2245    0.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2597   -2.7329   -0.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574   -1.9247   -0.7202 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  5  1  0
 13  8  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  6 17  1  0
  7 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
M  END
Download

PDB for NP0000884 (Indoleacetic acid)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      -5.937   3.853   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.271   4.623   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.604   3.853   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.605   2.313   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.271   1.543   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.937   2.313   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.473   1.837   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.567   3.083   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -4.472   4.329   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -3.997   0.373   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.491   0.052   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.015  -1.412   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.460   1.197   0.000  0.00  0.00           O+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    8    6   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    1                                                       
CONECT   10    7   11                                                       
CONECT   11   10   13   12                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END
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3D PDB for NP0000884 (Indoleacetic acid)

COMPND    HMDB0000197
HETATM    1  O1  UNL     1       2.121  -0.662   1.432  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.722  -0.587   0.322  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.930  -1.203   0.105  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.085   0.197  -0.769  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.791   0.774  -0.319  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.499   2.071   0.036  1.00  0.00           C  
HETATM    7  N1  UNL     1      -0.799   2.140   0.378  1.00  0.00           N  
HETATM    8  C5  UNL     1      -1.384   0.927   0.261  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.685   0.494   0.495  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.009  -0.825   0.290  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.021  -1.683  -0.145  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.718  -1.268  -0.383  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.395   0.068  -0.174  1.00  0.00           C  
HETATM   14  H1  UNL     1       3.976  -2.228   0.131  1.00  0.00           H  
HETATM   15  H2  UNL     1       2.764   1.041  -1.005  1.00  0.00           H  
HETATM   16  H3  UNL     1       1.922  -0.462  -1.654  1.00  0.00           H  
HETATM   17  H4  UNL     1       1.185   2.907   0.045  1.00  0.00           H  
HETATM   18  H5  UNL     1      -1.342   2.983   0.697  1.00  0.00           H  
HETATM   19  H6  UNL     1      -3.430   1.199   0.835  1.00  0.00           H  
HETATM   20  H7  UNL     1      -4.008  -1.225   0.454  1.00  0.00           H  
HETATM   21  H8  UNL     1      -2.260  -2.733  -0.313  1.00  0.00           H  
HETATM   22  H9  UNL     1       0.057  -1.925  -0.720  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   14
CONECT    4    5   15   16
CONECT    5    6    6   13
CONECT    6    7   17
CONECT    7    8   18
CONECT    8    9    9   13
CONECT    9   10   19
CONECT   10   11   11   20
CONECT   11   12   21
CONECT   12   13   13   22
END
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SMILES for NP0000884 (Indoleacetic acid)

OC(=O)CC1=CNC2=CC=CC=C12
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INCHI for NP0000884 (Indoleacetic acid)

InChI=1S/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13)
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View in JSmol
Synonyms
ValueSource
(indol-3-yl)AcetateChEBI
(indol-3-yl)Acetic acidChEBI
2-(indol-3-yl)Ethanoic acidChEBI
3-IndolylessigsaeureChEBI
HeteroauxinChEBI
IAAChEBI
IESChEBI
Indole-3-acetic acidKegg
IndoleacetateKegg
(1H-indol-3-yl)AcetateKegg
2-(indol-3-yl)EthanoateGenerator
Indole-3-acetateGenerator
(1H-indol-3-yl)Acetic acidGenerator
(1H-indol-3-yl)-AcetateHMDB
(1H-indol-3-yl)-Acetic acidHMDB
1H-indol-3-YlacetateHMDB
1H-indol-3-Ylacetic acidHMDB
1H-Indole-3-acetateHMDB
1H-Indole-3-acetic acidHMDB
2-(1H-indol-3-yl)AcetateHMDB
2-(1H-indol-3-yl)Acetic acidHMDB
2-(3-Indolyl)acetateHMDB
2-(3-Indolyl)acetic acidHMDB
3-(Carboxymethyl)indoleHMDB
3-IAAHMDB
3-Indole-acetic acidHMDB
3-IndoleacetateHMDB
3-Indoleacetic acidHMDB
3-IndolylacetateHMDB
3-Indolylacetic acidHMDB
alpha-indol-3-yl-Acetic acidHMDB
b-IndoleacetateHMDB
b-Indoleacetic acidHMDB
b-IndolylacetateHMDB
b-Indolylacetic acidHMDB
beta-Indole-3-acetic acidHMDB
beta-IndoleacetateHMDB
beta-Indoleacetic acidHMDB
beta-IndolylacetateHMDB
beta-Indolylacetic acidHMDB
indol-3-YlacetateHMDB
indol-3-Ylacetic acidHMDB
Indolyl-3-acetateHMDB
Indolyl-3-acetic acidHMDB
IndolylacetateHMDB
Indolylacetic acidHMDB
Kyselina 3-indolyloctovaHMDB
RhizopinHMDB
Rhizopon aHMDB
Skatole carboxylateHMDB
Skatole carboxylic acidHMDB
Indoleacetic acid, calcium saltHMDB
Indoleacetic acid, monopotassium saltHMDB
Indoleacetic acid, monosodium saltHMDB
IES CPDHMDB
Indole acetic acidHMDB
Indoleacetic acid, alpha-(14)C-labeledHMDB
(R,R)-3,3'-Dithiobis(2-aminopropanoic acid)HMDB
(R-(R*,r*))-3,3'-dithiobis(2-aminopropanoic acid)HMDB
3,3'-Dithiobis-L-alanineHMDB
beta,Beta'-diamino-beta,beta'-dicarboxydiethyl disulfideHMDB
beta,Beta'-dithiodialanineHMDB
Bis(beta-amino-beta-carboxyethyl) disulfideHMDB
e921HMDB
L-alpha-Diamino-beta-dithiolactic acidHMDB
L-DicysteineHMDB
Oxidized L-cysteineHMDB
(R,R)-3,3'-Dithiobis(2-aminopropanoate)HMDB
(R-(R*,r*))-3,3'-dithiobis(2-aminopropanoate)HMDB
b,Beta'-diamino-b,beta'-dicarboxydiethyl disulfideHMDB
b,Beta'-diamino-b,beta'-dicarboxydiethyl disulphideHMDB
beta,Beta'-diamino-beta,beta'-dicarboxydiethyl disulphideHMDB
Β,beta'-diamino-β,beta'-dicarboxydiethyl disulfideHMDB
Β,beta'-diamino-β,beta'-dicarboxydiethyl disulphideHMDB
b,Beta'-dithiodialanineHMDB
Β,beta'-dithiodialanineHMDB
Bis(b-amino-b-carboxyethyl) disulfideHMDB
Bis(b-amino-b-carboxyethyl) disulphideHMDB
Bis(beta-amino-beta-carboxyethyl) disulphideHMDB
Bis(β-amino-β-carboxyethyl) disulfideHMDB
Bis(β-amino-β-carboxyethyl) disulphideHMDB
L-a-Diamino-b-dithiolactateHMDB
L-a-Diamino-b-dithiolactic acidHMDB
L-alpha-Diamino-beta-dithiolactateHMDB
L-Α-diamino-β-dithiolactateHMDB
L-Α-diamino-β-dithiolactic acidHMDB
(-)-CystineHMDB
(R-(R*,r*))-3,3'-dithiobisHMDB
2-Amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoateHMDB
2-Amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoic acidHMDB
2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoateHMDB
2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoic acidHMDB
3,3'-DithiobisHMDB
3,3'-Dithiobis[2-amino-[R-(r*,r*)]-propanoateHMDB
3,3'-Dithiobis[2-amino-[R-(r*,r*)]-propanoic acidHMDB
3,3'-DithiodialanineHMDB
b,B'-diamino-b,b'-dicarboxydiethyl disulfideHMDB
b,B'-dithiodialanineHMDB
beta,Beta'-dithiobisalanineHMDB
Bis(b-amino-beta-carboxyethyl) disulfideHMDB
Cysteine disulfideHMDB
CystinHMDB
CystineHMDB
Cystine acidHMDB
D(+)-3,3'-Dithiobis(2-aminopropanoateHMDB
D(+)-3,3'-Dithiobis(2-aminopropanoic acidHMDB
DicysteineHMDB
GelucystineHMDB
L-(-)-CystineHMDB
L-Cysteine disulfideHMDB
L-CystinHMDB
[R-(R*,r*)]-3,3'-dithiobisHMDB
L CystineHMDB
Copper cystinateHMDB
(+)-Lactic acidHMDB
(S)-(+)-Lactic acidHMDB
(S)-2-Hydroxypropanoic acidHMDB
(S)-2-Hydroxypropionic acidHMDB
L-(+)-alpha-Hydroxypropionic acidHMDB
L-(+)-Lactic acidHMDB
L-MilchsaeureHMDB
L-LactateHMDB
(+)-LactateHMDB
(S)-(+)-LactateHMDB
(S)-2-HydroxypropanoateHMDB
(S)-2-HydroxypropionateHMDB
L-(+)-a-HydroxypropionateHMDB
L-(+)-a-Hydroxypropionic acidHMDB
L-(+)-alpha-HydroxypropionateHMDB
L-(+)-Α-hydroxypropionateHMDB
L-(+)-Α-hydroxypropionic acidHMDB
L-(+)-LactateHMDB
(alpha)-LactateHMDB
(alpha)-Lactic acidHMDB
(S)-(+)-2-HydroxypropanoateHMDB
(S)-(+)-2-Hydroxypropanoic acidHMDB
(S)-2-Hydroxy-propanoateHMDB
(S)-2-Hydroxy-propanoic acidHMDB
(S)-LactateHMDB
(S)-Lactic acidHMDB
1-Hydroxyethane 1-carboxylateHMDB
1-Hydroxyethane 1-carboxylic acidHMDB
1-HydroxyethanecarboxylateHMDB
1-Hydroxyethanecarboxylic acidHMDB
2-HydroxypropanoateHMDB
2-Hydroxypropanoic acidHMDB
2-HydroxypropionateHMDB
a-HydroxypropanoateHMDB
a-Hydroxypropanoic acidHMDB
a-HydroxypropionateHMDB
a-Hydroxypropionic acidHMDB
alpha-HydroxypropanoateHMDB
alpha-Hydroxypropanoic acidHMDB
alpha-HydroxypropionateHMDB
alpha-Hydroxypropionic acidHMDB
L-(+)- Lactic acidHMDB
L-2-HydroxypropanoateHMDB
L-2-Hydroxypropanoic acidHMDB
LactateHMDB
Lactic acidHMDB
Milk acidHMDB
Sarcolactic acidHMDB
2-Hydroxypropionic acidHMDB
D-Lactic acidHMDB
D Lactic acidHMDB
Lactate, ammoniumHMDB
2 Hydroxypropanoic acidHMDB
2 Hydroxypropionic acidHMDB
Ammonium lactateHMDB
L Lactic acidHMDB
9-beta-D-Ribofuranosyl-9H-purin-6-olHMDB
9-beta-D-RibofuranosylhypoxanthineHMDB
Hypoxanthine D-ribosideHMDB
HypoxanthosineHMDB
iHMDB
InosinHMDB
InosinaHMDB
InosinumHMDB
InotinHMDB
9-b-D-Ribofuranosyl-9H-purin-6-olHMDB
9-Β-D-ribofuranosyl-9H-purin-6-olHMDB
9-b-D-RibofuranosylhypoxanthineHMDB
9-Β-D-ribofuranosylhypoxanthineHMDB
(-)-InosineHMDB
1,9-Dihydro-9-b-D-ribofuranosyl-6H-purin-6-oneHMDB
1,9-Dihydro-9-beta-D-ribofuranosyl-6H-purin-6-oneHMDB
1,9-Dihydro-9-beta-delta-ribofuranosyl-6H-purin-6-oneHMDB
9-b-D-Ribofuranosyl-hypoxanthineHMDB
9-beta-D-Ribofuranosyl-hypoxanthineHMDB
9-beta-delta-Ribofuranosyl-hypoxanthineHMDB
9-beta-delta-RibofuranosylhypoxanthineHMDB
9beta-D-RibofuranosylhypoxanthineHMDB
9beta-delta-RibofuranosylhypoxanthineHMDB
AtorelHMDB
beta-D-Ribofuranoside hypoxanthine-9HMDB
beta-delta-Ribofuranoside hypoxanthine-9HMDB
beta-InosineHMDB
HXRHMDB
Hypoxanthine 9-beta-D-ribofuranosideHMDB
Hypoxanthine 9-beta-delta-ribofuranosideHMDB
Hypoxanthine nucleosideHMDB
Hypoxanthine ribonucleosideHMDB
Hypoxanthine ribosideHMDB
Hypoxanthine-9 beta-D-ribofuranosideHMDB
Hypoxanthine-9 beta-delta-ribofuranosideHMDB
Hypoxanthine-9-beta-D-ribofuranosideHMDB
Hypoxanthine-9-beta-delta-ribofuranosideHMDB
Hypoxanthine-9-D-ribofuranosideHMDB
Hypoxanthine-9-delta-ribofuranosideHMDB
Hypoxanthine-riboseHMDB
Indole-3-carboxaldehydeHMDB
InoHMDB
InosieHMDB
Iso-prinosineHMDB
OxiaminHMDB
Panholic-LHMDB
Pantholic-LHMDB
RibonosineHMDB
SelferHMDB
TrophicardylHMDB
(2S)-6-(Acetylamino)-2-aminohexanoic acidHMDB
N(6)-ACETYLLYSINEHMDB
N(zeta)-AcetyllysineHMDB
N-epsilon-Acetyl-L-lysineHMDB
N-Epsilon-AcetyllysineHMDB
N(epsilon)-Acetyl-L-lysineHMDB
N(zeta)-Acetyl-L-lysineHMDB
(2S)-6-(Acetylamino)-2-aminohexanoateHMDB
N(Z)-AcetyllysineHMDB
N(Ζ)-acetyllysineHMDB
N(Z)-Acetyl-L-lysineHMDB
N(Ζ)-acetyl-L-lysineHMDB
e-Acetyl-L-lysineHMDB
e-N-Acetyl-L-lysineHMDB
e-N-AcetyllysineHMDB
epsilon-Acetyl-L-lysineHMDB
epsilon-N-Acetyl-L-lysineHMDB
epsilon-N-AcetyllysineHMDB
L-e-N-AcetyllysineHMDB
L-epsilon-N-AcetyllysineHMDB
N-e-Acetyl-L-lysineHMDB
N-e-AcetyllysineHMDB
N6-AcetyllysineHMDB
Ne-acetyl-L-lysineHMDB
Ne-acetyllysineHMDB
Omega-N-acetyl-L-lysineHMDB
W-N-Acetyl-L-lysineHMDB
N(6)-AcetyllsineHMDB
Omega-acetyllsineHMDB
beta-Alanyl-3-methyl-L-histidineHMDB
beta-Alanyl-N(pai)-methyl-L-histidineHMDB
b-Alanyl-3-methyl-L-histidineHMDB
Β-alanyl-3-methyl-L-histidineHMDB
b-Alanyl-N(pai)-methyl-L-histidineHMDB
Β-alanyl-N(pai)-methyl-L-histidineHMDB
L-AnserineHMDB
L-N-b-Alanyl-3-methyl-histidineHMDB
L-N-beta-Alanyl-3-methyl-histidineHMDB
N-b-Alanyl-3-methyl-L-histidineHMDB
N-beta-Alanyl-3-methyl-L-histidineHMDB
BalanineHMDB
Beta Alanyl 3 methylhistidineHMDB
Beta-Alanyl-3-methylhistidineHMDB
OphidineHMDB
3-(Carboxymethyl)-1H-indoleHMDB
3-Indolylmethylcarboxylic acidHMDB
alpha-IAAHMDB
Α-iaaHMDB
beta-IAAHMDB
Β-iaaHMDB
Β-indoleacetic acidHMDB
Indoleacetic acidChEBI
Chemical FormulaC10H9NO2
Average Mass175.1840 Da
Monoisotopic Mass175.06333 Da
IUPAC Name2-(1H-indol-3-yl)acetic acid
Traditional Nameβ-indole-3-acetic acid
CAS Registry Number87-51-4
SMILES
OC(=O)CC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13)
InChI KeySEOVTRFCIGRIMH-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-14View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-14View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-14View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-14View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-14View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-14View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Arabidopsis thalianaKNApSAcK Database
Balansia epichloeLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica oleraceaKNApSAcK Database
Brassica oleracea var. botrytisFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
Castanea crenataKNApSAcK Database
Castanea henryiKNApSAcK Database
CervidaeFooDB
Cervus canadensisFooDB
Chamaecyparis lawsonianaKNApSAcK Database
Citrus reticulataLOTUS Database
Citrus sinensisKNApSAcK Database
Citrus unshiuKNApSAcK Database
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Colletotrichum gloeosporioidesLOTUS Database
ColumbaFooDB
ColumbidaeFooDB
Corylus avellanaKNApSAcK Database
Cotinus coggygriaKNApSAcK Database
Cucurbita maximaLOTUS Database
Cucurbita pepoLOTUS Database
Dalbergia dolichopetalaKNApSAcK Database
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Diospyros kakiKNApSAcK Database
Dolichos lablabKNApSAcK Database
Dromaius novaehollandiaeFooDB
Elymus repensLOTUS Database
Epichloe festucaeLOTUS Database
Equus caballusFooDB
Euphorbia esculaKNApSAcK Database
Funaria hygrometricaLOTUS Database
Gallus gallusFooDB
Ginkgo bilobaLOTUS Database
Glycine maxFooDB
Glycine sojaKNApSAcK Database
Gossypium hirsutumLOTUS Database
Hebeloma hiemaleLOTUS Database
Heracleum steveniiLOTUS Database
Ipomoea batatasLOTUS Database
Ipomoea nilLOTUS Database
Isatis tinctoriaLOTUS Database
Lablab purpureusFooDB
Lagopus mutaFooDB
Lathyrus maritimusKNApSAcK Database
LeporidaeFooDB
Lepus timidusFooDB
Lygodium flexuosumKNApSAcK Database
Malus pumilaKNApSAcK Database
Marchantia polymorphaLOTUS Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Moringa oleiferaFooDB
Mus musculusLOTUS Database
Musa x paradisiacaFooDB
Nicotiana tabacumKNApSAcK Database
Numida meleagrisFooDB
OdocoileusFooDB
Origanum vulgareFooDB
OryctolagusFooDB
Ovis ariesFooDB
Panax ginsengKNApSAcK Database
Paraburkholderia phymatum-
Phaseolus mungoKNApSAcK Database
Phaseolus vulgarisKNApSAcK Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Phyllostachys reticulataLOTUS Database
Picea abiesKNApSAcK Database
Picea sitchensisKNApSAcK Database
Pinus contortaKNApSAcK Database
Pinus slyvestrisKNApSAcK Database
Pinus sylvestrisLOTUS Database
Pisum sativumKNApSAcK Database
Plagiochila arcticaLOTUS Database
Prunus cerasusKNApSAcK Database
Prunus domesticaKNApSAcK Database
Pseudomonas amygdaliLOTUS Database
Pseudomonas fluorescensLOTUS Database
Pseudomonas syringaeLOTUS Database
Pseudotsuga menziesiiKNApSAcK Database
Pythium aphanidermatumLOTUS Database
Quercus roburKNApSAcK Database
Raphanus sativusKNApSAcK Database
Rhizopus oryzaeFungi
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
Ricinus communisKNApSAcK Database
Salix atrocinereaLOTUS Database
Scheffersomyces spartinaeLOTUS Database
Solanum lycopersicumKNApSAcK Database
Solanum lycopersicum var. lycopersicumFooDB
Spinacia oleraceaFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Synechococcus elongatusLOTUS Database
Tachigali paniculataLOTUS Database
Tropaeolum majusLOTUS Database
Vicia amurensisKNApSAcK Database
Vigna mungoFooDB
Vigna unguiculata var. sesquipedalisKNApSAcK Database
Vitis viniferaKNApSAcK Database
Vitis vinifera L.FooDB
Zea maysKNApSAcK Database
Zea mays L.FooDB
Species Where Detected
Species NameSourceReference
Homo sapiensKNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
Rhizopus suinusKNApSAcK Database
Saccharomyces cerevisiaeKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct ParentIndole-3-acetic acid derivatives
Alternative Parents
Substituents
  • Indole-3-acetic acid derivative
  • 3-alkylindole
  • Indole
  • Substituted pyrrole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carbonyl group
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point168.5 °CNot Available
Boiling Point413.00 to 415.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1.5 mg/mLNot Available
LogP1.41Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility1.38 g/LALOGPS
logP1.87ALOGPS
logP1.71ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)4.66ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.45 m³·mol⁻¹ChemAxon
Polarizability17.74 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000197
DrugBank IDDB07950
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004267
KNApSAcK IDC00000100
Chemspider ID780
KEGG Compound IDC00954
BioCyc IDINDOLE_ACETATE_AUXIN
BiGG IDNot Available
Wikipedia LinkIndole-3-acetic_acid
METLIN IDNot Available
PubChem Compound802
PDB IDNot Available
ChEBI ID16411
Good Scents IDrw1251501
References
General References
  1. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
  2. Igari T, Tsuchizawa M, Shimamura T: Alteration of tryptophan metabolism in the synovial fluid of patients with rheumatoid arthritis and osteoarthritis. Tohoku J Exp Med. 1987 Oct;153(2):79-86. [PubMed:3500530 ]
  3. Carpenter LL, Anderson GM, Siniscalchi JM, Chappell PB, Price LH: Acute changes in cerebrospinal fluid 5-HIAA following oral paroxetine challenge in healthy humans. Neuropsychopharmacology. 2003 Feb;28(2):339-47. [PubMed:12589387 ]
  4. Owens MJ, Nemeroff CB: Role of serotonin in the pathophysiology of depression: focus on the serotonin transporter. Clin Chem. 1994 Feb;40(2):288-95. [PubMed:7508830 ]
  5. Tu JB, Wong CY: Serotonin metabolism in normal and abnormal infants during the perinatal period. Biol Neonate. 1976;29(3-4):187-93. [PubMed:133735 ]
  6. Blennow K, Wallin A, Gottfries CG, Mansson JE, Svennerholm L: Concentration gradients for monoamine metabolites in lumbar cerebrospinal fluid. J Neural Transm Park Dis Dement Sect. 1993;5(1):5-15. [PubMed:7679905 ]
  7. Morgan WW, Grant RW: Increased rate of disappearance of serum probenecid in barbital dependent rats. Eur J Pharmacol. 1976 Dec;40(2):349-57. [PubMed:1033074 ]
  8. Jellinger K, Riederer P: Brain monoamines in metabolic (endotoxic) coma. A preliminary biochemical study in human postmortem material. J Neural Transm. 1977;41(4):275-86. [PubMed:925688 ]
  9. Sarrias MJ, Cabre P, Martinez E, Artigas F: Relationship between serotoninergic measures in blood and cerebrospinal fluid simultaneously obtained in humans. J Neurochem. 1990 Mar;54(3):783-6. [PubMed:1689378 ]
  10. Kema IP, Meijer WG, Meiborg G, Ooms B, Willemse PH, de Vries EG: Profiling of tryptophan-related plasma indoles in patients with carcinoid tumors by automated, on-line, solid-phase extraction and HPLC with fluorescence detection. Clin Chem. 2001 Oct;47(10):1811-20. [PubMed:11568091 ]
  11. Bai F, Jones DC, Lau SS, Monks TJ: Serotonergic neurotoxicity of 3,4-(+/-)-methylenedioxyamphetamine and 3,4-(+/-)-methylendioxymethamphetamine (ecstasy) is potentiated by inhibition of gamma-glutamyl transpeptidase. Chem Res Toxicol. 2001 Jul;14(7):863-70. [PubMed:11453733 ]
  12. Ridges AP, Bishop FM, Lawton K, Goldberg IJ: Amine metabolism, thyroid function and response to clomipramine and maprotiline medication in depression. Postgrad Med J. 1980;56 Suppl 1:37-41. [PubMed:6156444 ]
  13. Raghuram TC, Krishnaswamy K: Serotonin metabolism is pellagra. Arch Neurol. 1975 Oct;32(10):708-10. [PubMed:1180737 ]
  14. Carling RS, Degg TJ, Allen KR, Bax ND, Barth JH: Evaluation of whole blood serotonin and plasma and urine 5-hydroxyindole acetic acid in diagnosis of carcinoid disease. Ann Clin Biochem. 2002 Nov;39(Pt 6):577-82. [PubMed:12564839 ]
  15. Taniguchi K, Okatani Y, Sagara Y: Serotonin metabolism in the fetus in preeclampsia. Asia Oceania J Obstet Gynaecol. 1994 Mar;20(1):77-86. [PubMed:7513511 ]
  16. Russo S, Boon JC, Kema IP, Willemse PH, den Boer JA, Korf J, de Vries EG: Patients with carcinoid syndrome exhibit symptoms of aggressive impulse dysregulation. Psychosom Med. 2004 May-Jun;66(3):422-5. [PubMed:15184706 ]
  17. Igari T, Shimamura T: Serotonin metabolism and its enzymic activities in joint diseases. Clin Orthop Relat Res. 1979 Mar-Apr;(139):232-49. [PubMed:455840 ]
  18. Bearcroft CP, Perrett D, Farthing MJ: Postprandial plasma 5-hydroxytryptamine in diarrhoea predominant irritable bowel syndrome: a pilot study. Gut. 1998 Jan;42(1):42-6. [PubMed:9505884 ]
  19. Ilkhanizadeh B, Owji AA, Tavangar SM, Vasei M, Tabei SM: Spot urine 5-hydroxy indole acetic acid and acute appendicitis. Hepatogastroenterology. 2001 May-Jun;48(39):609-13. [PubMed:11462886 ]
  20. Apak S, Kazez A, Ozel SK, Ustundag B, Akpolat N, Kizirgil A: Spot urine 5-hydroxyindoleacetic acid levels in the early diagnosis of acute appendicitis. J Pediatr Surg. 2005 Sep;40(9):1436-9. [PubMed:16150345 ]
  21. WEISSBACH H, KING W, SJOERDSMA A, UDENFRIEND S: Formation of indole-3-acetic acid and tryptamine in animals: a method for estimation of indole-3-acetic acid in tissues. J Biol Chem. 1959 Jan;234(1):81-6. [PubMed:13610897 ]
  22. Folkes LK, Wardman P: Oxidative activation of indole-3-acetic acids to cytotoxic species- a potential new role for plant auxins in cancer therapy. Biochem Pharmacol. 2001 Jan 15;61(2):129-36. [PubMed:11163327 ]