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Showing NP-Card for 1h-indol-2-ylacetic acid (NP0158798)

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Record Information
Version1.0
Created at2022-09-02 16:26:59 UTC
Updated at2022-09-02 16:26:59 UTC
NP-MRD IDNP0158798
Secondary Accession NumbersNone
Natural Product Identification
Common Name1h-indol-2-ylacetic acid
DescriptionIndoleacetic acid, also known as indoleacetate, belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. Indoleacetic acid is a weakly acidic compound (based on its pKa). Indoleacetic acid can be biosynthesized from indoleacetaldehyde; which is catalyzed by the enzyme aldehyde dehydrogenase, mitochondrial. 1h-indol-2-ylacetic acid is found in Streptomyces fradiae. In humans, indoleacetic acid is involved in tryptophan metabolism.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0158798 (1h-indol-2-ylacetic acid)

Structure #1
  Mrv0541 02241206312D          

 13 14  0  0  0  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    2.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    2.9519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  7  2  0  0  0  0
  4  9  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  2  0  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  7  9  1  0  0  0  0
  8 11  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  2  0  0  0  0
 10 13  1  0  0  0  0
M  END
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3D MOL for NP0158798 (1h-indol-2-ylacetic acid)

     RDKit          3D

 22 23  0  0  0  0  0  0  0  0999 V2000
   -3.3491   -0.2199    1.7156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2437    0.3649    0.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6361    1.6921    0.3918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6683   -0.3803   -0.5423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1721   -0.3836   -0.3673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3228   -1.3683    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9841   -0.8752    0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1990   -1.4629    0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3315   -0.6680    0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2264    0.6627   -0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9944    1.1908   -0.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8454    0.4253   -0.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4301    0.7236   -0.6253 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0599    2.4571    0.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8543    0.0931   -1.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0511   -1.4263   -0.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6084   -2.3718    0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2624   -2.4867    0.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2972   -1.0808    0.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1188    1.2960   -0.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9711    2.2123   -0.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8342    1.6059   -0.9609 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13  5  1  0
 12  7  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  6 17  1  0
  8 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
 13 22  1  0
M  END
Download

3D SDF for NP0158798 (1h-indol-2-ylacetic acid)

Structure #1
  Mrv0541 02241206312D          

 13 14  0  0  0  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    2.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    2.9519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  7  2  0  0  0  0
  4  9  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  2  0  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  7  9  1  0  0  0  0
  8 11  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  2  0  0  0  0
 10 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0158798

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CC1=CC2=CC=CC=C2N1

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

> <INCHI_KEY>
QOPBEBWGSGFROG-UHFFFAOYSA-N

> <FORMULA>
C10H9NO2

> <MOLECULAR_WEIGHT>
175.184

> <EXACT_MASS>
175.063328537

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
18.13886442592368

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.78

> <JCHEM_LOGP>
1.6297572219999998

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.039994092670845

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.647244815649918

> <JCHEM_POLAR_SURFACE_AREA>
53.09

> <JCHEM_REFRACTIVITY>
48.3296

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1H-indol-2-ylacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0158798 (1h-indol-2-ylacetic acid)

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PDB for NP0158798 (1h-indol-2-ylacetic acid)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.090   4.176   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      -2.630   4.176   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.320   5.510   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    7                                                       
CONECT    4    2    9                                                       
CONECT    5    7    8                                                       
CONECT    6    8   10                                                       
CONECT    7    3    5    9                                                  
CONECT    8    5    6   11                                                  
CONECT    9    4    7   11                                                  
CONECT   10    6   12   13                                                  
CONECT   11    8    9                                                       
CONECT   12   10                                                            
CONECT   13   10                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

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3D PDB for NP0158798 (1h-indol-2-ylacetic acid)
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SMILES for NP0158798 (1h-indol-2-ylacetic acid)
OC(=O)CC1=CC2=CC=CC=C2N1
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INCHI for NP0158798 (1h-indol-2-ylacetic acid)
InChI=1S/C10H9NO2/c12-10(13)6-8-5-7-3-1-2-4-9(7)11-8/h1-5,11H,6H2,(H,12,13)
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View in JSmol
Synonyms
ValueSource
IndoleacetateGenerator
INDOLE-2-acetateGenerator
2-(1H-indol-2-yl)AcetateGenerator
Chemical FormulaC10H9NO2
Average Mass175.1840 Da
Monoisotopic Mass175.06333 Da
IUPAC Name2-(1H-indol-2-yl)acetic acid
Traditional Name1H-indol-2-ylacetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CC1=CC2=CC=CC=C2N1
InChI Identifier
InChI=1S/C10H9NO2/c12-10(13)6-8-5-7-3-1-2-4-9(7)11-8/h1-5,11H,6H2,(H,12,13)
InChI KeyQOPBEBWGSGFROG-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces fradiaeLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIndoles and derivatives  
Sub ClassIndolyl carboxylic acids and derivatives  
Direct ParentIndolyl carboxylic acids and derivatives  
Alternative Parents
Substituents
  • Indolyl carboxylic acid derivative
    • 

  • Indole
    • 

  • Substituted pyrrole
    • 

  • Benzenoid
    • 

  • Pyrrole
    • 

  • Heteroaromatic compound
    • 

  • Azacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP1.78ALOGPS
logP1.63ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.33 m³·mol⁻¹ChemAxon
Polarizability18.14 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIndole-3-acetic acid  
METLIN IDNot Available
PubChem Compound4371752  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]