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Showing NP-Card for indole acetic acid (NP0235005)

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Record Information
Version2.0
Created at2022-09-06 17:23:38 UTC
Updated at2022-09-06 17:23:38 UTC
NP-MRD IDNP0235005
Secondary Accession NumbersNone
Natural Product Identification
Common Nameindole acetic acid
Description3-Acetoxyindole, also known as indoxyl acetate, belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. indole acetic acid is found in Strychnos cathayensis. 3-Acetoxyindole is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0235005 (indole acetic acid)


  Mrv1533004191516412D          

 13 14  0  0  0  0            999 V2000
   -0.1781   -3.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    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   -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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  5 13  1  0  0  0  0
  8 13  1  0  0  0  0
M  END
Download

3D MOL for NP0235005 (indole acetic acid)

     RDKit          3D

 22 23  0  0  0  0  0  0  0  0999 V2000
    3.8882   -1.1283    0.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6603   -0.3026    0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4682    0.6094    0.9523 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6461   -0.5001   -0.8259 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4837    0.2584   -0.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2233    1.4431   -1.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0333    1.8367   -1.2033 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6329    0.9431   -0.3695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8853    0.9085    0.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2210   -0.1373    1.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2809   -1.1202    1.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0216   -1.0813    0.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6790   -0.0360   -0.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1022   -1.4100   -0.9930 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7682   -2.0898    0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7874   -0.5599    0.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9016    1.9821   -2.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5078    2.7063   -1.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6179    1.6693    0.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2222   -0.1940    1.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5532   -1.9552    1.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2741   -1.8422    0.8592 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  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
  1 14  1  0
  1 15  1  0
  1 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 NP0235005 (indole acetic acid)


  Mrv1533004191516412D          

 13 14  0  0  0  0            999 V2000
   -0.1781   -3.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    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   -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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  5 13  1  0  0  0  0
  8 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0235005

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C10H9NO2/c1-7(12)13-10-6-11-9-5-3-2-4-8(9)10/h2-6,11H,1H3

> <INCHI_KEY>
JBOPQACSHPPKEP-UHFFFAOYSA-N

> <FORMULA>
C10H9NO2

> <MOLECULAR_WEIGHT>
175.187

> <EXACT_MASS>
175.063328534

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
18.204171622294034

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1H-indol-3-yl acetate

> <ALOGPS_LOGP>
2.49

> <JCHEM_LOGP>
1.6792687833333333

> <ALOGPS_LOGS>
-1.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.889798755155624

> <JCHEM_PKA_STRONGEST_BASIC>
-7.1479538039739765

> <JCHEM_POLAR_SURFACE_AREA>
42.09

> <JCHEM_REFRACTIVITY>
48.276900000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.43e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
indole acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0235005 (indole acetic acid)

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PDB for NP0235005 (indole acetic acid)
HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.887  -3.189   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.650  -4.013   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    5    8                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

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3D PDB for NP0235005 (indole acetic acid)
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SMILES for NP0235005 (indole acetic acid)
CC(=O)OC1=CNC2=CC=CC=C12
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INCHI for NP0235005 (indole acetic acid)
InChI=1S/C10H9NO2/c1-7(12)13-10-6-11-9-5-3-2-4-8(9)10/h2-6,11H,1H3
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View in JSmol
Synonyms
ValueSource
Indoxyl acetateMeSH
Chemical FormulaC10H9NO2
Average Mass175.1870 Da
Monoisotopic Mass175.06333 Da
IUPAC Name1H-indol-3-yl acetate
Traditional Nameindole acetic acid
CAS Registry NumberNot Available
SMILES
CC(=O)OC1=CNC2=CC=CC=C12
InChI Identifier
InChI=1S/C10H9NO2/c1-7(12)13-10-6-11-9-5-3-2-4-8(9)10/h2-6,11H,1H3
InChI KeyJBOPQACSHPPKEP-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
Strychnos cathayensisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene  to form 2,3-benzopyrrole.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIndoles and derivatives  
Sub ClassIndoles  
Direct ParentIndoles  
Alternative Parents
Substituents
  • Indole
    • 

  • Substituted pyrrole
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Pyrrole
    • 

  • Carboxylic acid ester
    • 

  • Azacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP2.49ALOGPS
logP1.68ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)14.89ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area42.09 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.28 m³·mol⁻¹ChemAxon
Polarizability18.2 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 LinkNot Available
METLIN IDNot Available
PubChem Compound11841  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]