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Showing NP-Card for 2-Indolecarboxylic acid (NP0086936)

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Record Information
Version2.0
Created at2022-05-11 16:35:07 UTC
Updated at2022-05-11 16:35:07 UTC
NP-MRD IDNP0086936
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Indolecarboxylic acid
Description2-Indolecarboxylic acid, also known as indol-2-carboxylate or 2-carboxyindole, belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole. 2-Indolecarboxylic acid is a weakly acidic compound (based on its pKa). Outside of the human body, 2-Indolecarboxylic acid has been detected, but not quantified in, milk (cow). This could make 2-indolecarboxylic acid a potential biomarker for the consumption of these foods. 2-Indolecarboxylic acid is found in Strychnos cathayensis. 2-Indolecarboxylic acid was first documented in 1995 (PMID: 7592495). Lipid peroxidation with tert-butyl hydroperoxide is a source of free radicals (PMID 12236544 ) (PMID: 15537165) (PMID: 12236544).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0086936 (2-Indolecarboxylic acid)

4-Hydroxy-L-glutamate.mol
  Mrv0541 02231219282D          

 12 13  0  0  0  0            999 V2000
    0.2456    0.6674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7305    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2456   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5391   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2535   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9680   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9680    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2535    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5391    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5555    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9680    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9680   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  4  9  2  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  2 10  1  0  0  0  0
M  END
Download

3D MOL for NP0086936 (2-Indolecarboxylic acid)

     RDKit          3D

 19 20  0  0  0  0  0  0  0  0999 V2000
    3.7688   -1.0067    0.8488 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1258   -0.0302    0.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8349    1.0874   -0.0487 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6842   -0.0921    0.2529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8945    0.9298   -0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4369    0.5522   -0.2298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6026    1.1803   -0.6133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8107    0.5448   -0.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8582   -0.7260    0.0883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6736   -1.3315    0.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4406   -0.7188    0.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8336   -1.0747    0.5950 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1839    1.1123   -0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2095    1.8845   -0.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6116    2.1734   -1.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7263    1.0654   -0.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8087   -1.2309    0.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6701   -2.3290    0.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1041   -1.9902    1.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6 11  2  0
 11 12  1  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
 12  4  1  0
  7  6  1  0
  3 13  1  0
  5 14  1  0
 12 19  1  0
 10 18  1  0
  9 17  1  0
  8 16  1  0
  7 15  1  0
M  END
Download

3D SDF for NP0086936 (2-Indolecarboxylic acid)

4-Hydroxy-L-glutamate.mol
  Mrv0541 02231219282D          

 12 13  0  0  0  0            999 V2000
    0.2456    0.6674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7305    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2456   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5391   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2535   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9680   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9680    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2535    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5391    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5555    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9680    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9680   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  4  9  2  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  2 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086936

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC2=C(N1)C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C9H7NO2/c11-9(12)8-5-6-3-1-2-4-7(6)10-8/h1-5,10H,(H,11,12)

> <INCHI_KEY>
HCUARRIEZVDMPT-UHFFFAOYSA-N

> <FORMULA>
C9H7NO2

> <MOLECULAR_WEIGHT>
161.1574

> <EXACT_MASS>
161.047678473

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
16.172480278919686

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1H-indole-2-carboxylic acid

> <ALOGPS_LOGP>
1.79

> <JCHEM_LOGP>
1.6495918406666665

> <ALOGPS_LOGS>
-1.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.566380710465612

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5999552060906654

> <JCHEM_POLAR_SURFACE_AREA>
53.09

> <JCHEM_REFRACTIVITY>
44.2782

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.78e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
indole-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0086936 (2-Indolecarboxylic acid)

Download
PDB for NP0086936 (2-Indolecarboxylic acid)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 4-Hydroxy-L-glutamate.mol                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       0.458   1.246   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       1.364   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.458  -1.246   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.006  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.340  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.674  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.674   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.340   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.006   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.904   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.674   1.334   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.674  -1.334   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    1    4                                                  
CONECT   10   11   12    2                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0086936 (2-Indolecarboxylic acid)
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SMILES for NP0086936 (2-Indolecarboxylic acid)
OC(=O)C1=CC2=C(N1)C=CC=C2
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INCHI for NP0086936 (2-Indolecarboxylic acid)
InChI=1S/C9H7NO2/c11-9(12)8-5-6-3-1-2-4-7(6)10-8/h1-5,10H,(H,11,12)
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View in JSmol
Synonyms
ValueSource
2-IndolecarboxylateGenerator
indol-2-Carboxylic acidHMDB
indol-2-CarboxylateHMDB
1H-Indole-2-carboxylateHMDB
1H-Indole-2-carboxylic acidHMDB
2-CarboxyindoleHMDB
Indole-2-carboxylateHMDB
Indole-2-carboxylic acidHMDB
Chemical FormulaC9H7NO2
Average Mass161.1574 Da
Monoisotopic Mass161.04768 Da
IUPAC Name1H-indole-2-carboxylic acid
Traditional Nameindole-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C1=CC2=C(N1)C=CC=C2
InChI Identifier
InChI=1S/C9H7NO2/c11-9(12)8-5-6-3-1-2-4-7(6)10-8/h1-5,10H,(H,11,12)
InChI KeyHCUARRIEZVDMPT-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Strychnos cathayensisLOTUS Database
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIndoles and derivatives  
Sub ClassIndolecarboxylic acids and derivatives  
Direct ParentIndolecarboxylic acids and derivatives  
Alternative Parents
Substituents
  • Indolecarboxylic acid derivative
    • 

  • Indole
    • 

  • Pyrrole-2-carboxylic acid
    • 

  • Pyrrole-2-carboxylic acid or derivatives
    • 

  • Substituted pyrrole
    • 

  • Benzenoid
    • 

  • Pyrrole
    • 

  • Heteroaromatic compound
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Azacycle
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organic nitrogen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.79ALOGPS
logP1.65ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity44.28 m³·mol⁻¹ChemAxon
Polarizability16.17 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002285  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022948  
KNApSAcK IDNot Available
Chemspider ID65731  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6593  
PubChem Compound72899  
PDB IDNot Available
ChEBI ID130363  
Good Scents IDNot Available
References
General References
  1. Seal AN, Pratley JE, Haig T, An M: Identification and quantitation of compounds in a series of allelopathic and non-allelopathic rice root exudates. J Chem Ecol. 2004 Aug;30(8):1647-62. doi: 10.1023/b:joec.0000042074.96036.14. [PubMed:15537165  ] 
  2. Eaton RW, Chapman PJ: Formation of indigo and related compounds from indolecarboxylic acids by aromatic acid-degrading bacteria: chromogenic reactions for cloning genes encoding dioxygenases that act on aromatic acids. J Bacteriol. 1995 Dec;177(23):6983-8. doi: 10.1128/jb.177.23.6983-6988.1995. [PubMed:7592495  ] 
  3. Stetinova V, Smetanova L, Grossmann V, Anzenbacher P: In vitro and in vivo assessment of the antioxidant activity of melatonin and related indole derivatives. Gen Physiol Biophys. 2002 Jun;21(2):153-62. [PubMed:12236544  ]