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Showing NP-Card for Indole 3-carboxylic acid methyl ester (NP0055025)

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Record Information
Version2.0
Created at2022-04-28 01:11:40 UTC
Updated at2022-04-28 01:11:40 UTC
NP-MRD IDNP0055025
Secondary Accession NumbersNone
Natural Product Identification
Common NameIndole 3-carboxylic acid methyl ester
DescriptionMethyl indole-3-carboxylate, also known as 3-carbomethoxyindole or 3-methoxycarbonylindole, 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. Indole 3-carboxylic acid methyl ester is found in Arabidopsis thaliana, Aristolochia cucurbitifolia, Aristolochia kaempferi, Balansia epichloe, Botryocladia leptopoda, Epichloe festucae, Himalaiella deltoidea, Ligularia dentata, Meehania urticifolia, Pachliopta aristolochiae, Penicillium herquei, Pinus sylvestris, Taraxacum mongolicum, Xylaria obovata and Zymoseptoria tritici. Methyl indole-3-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0055025 (Indole 3-carboxylic acid methyl ester)


  Mrv1533004201501142D          

 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 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -2.7631    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  1  0  0  0  0
  3  4  2  0  0  0  0
  3  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
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3D MOL for NP0055025 (Indole 3-carboxylic acid methyl ester)

     RDKit          3D

 22 23  0  0  0  0  0  0  0  0999 V2000
    4.1792    0.8133   -0.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0256    0.0102   -0.0127 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7423    0.4802   -0.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6096    1.6735   -0.6095 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5575   -0.3387   -0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5348   -1.6741    0.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7323   -2.1214    0.3871 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5527   -1.1138    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9195   -0.9783   -0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4794    0.2121   -0.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7036    1.3164   -0.7838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3353    1.1927   -0.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7655   -0.0035   -0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9278    0.3551   -0.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318    1.8059   -0.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5885    1.0065    0.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4052   -2.2681    0.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0862   -3.0735    0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5269   -1.8547    0.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5542    0.2653   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1631    2.2635   -1.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6836    2.0312   -0.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  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 NP0055025 (Indole 3-carboxylic acid methyl ester)


  Mrv1533004201501142D          

 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 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -2.7631    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  1  0  0  0  0
  3  4  2  0  0  0  0
  3  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>
NP0055025

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CNC2=CC=CC=C12

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

> <INCHI_KEY>
QXAUTQFAWKKNLM-UHFFFAOYSA-N

> <FORMULA>
C10H9NO2

> <MOLECULAR_WEIGHT>
175.187

> <EXACT_MASS>
175.063328534

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
18.198892947515823

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 1H-indole-3-carboxylate

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
2.0754847730000003

> <ALOGPS_LOGS>
-1.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.19891906866319

> <JCHEM_PKA_STRONGEST_BASIC>
-6.963504186585626

> <JCHEM_POLAR_SURFACE_AREA>
42.09

> <JCHEM_REFRACTIVITY>
49.169800000000016

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.43e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 1H-indole-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0055025 (Indole 3-carboxylic acid methyl ester)

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PDB for NP0055025 (Indole 3-carboxylic acid methyl ester)
HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.143  -4.334   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.680  -5.158   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                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    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 NP0055025 (Indole 3-carboxylic acid methyl ester)
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SMILES for NP0055025 (Indole 3-carboxylic acid methyl ester)
COC(=O)C1=CNC2=CC=CC=C12
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INCHI for NP0055025 (Indole 3-carboxylic acid methyl ester)
InChI=1S/C10H9NO2/c1-13-10(12)8-6-11-9-5-3-2-4-7(8)9/h2-6,11H,1H3
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View in JSmol
Synonyms
ValueSource
3-CarbomethoxyindoleChEBI
3-MethoxycarbonylindoleChEBI
Indole-3-carboxylic acid methyl esterChEBI
Indole-3-carboxylate methyl esterGenerator
Methyl indole-3-carboxylic acidGenerator
Chemical FormulaC10H9NO2
Average Mass175.1870 Da
Monoisotopic Mass175.06333 Da
IUPAC Namemethyl 1H-indole-3-carboxylate
Traditional Namemethyl 1H-indole-3-carboxylate
CAS Registry NumberNot Available
SMILES
COC(=O)C1=CNC2=CC=CC=C12
InChI Identifier
InChI=1S/C10H9NO2/c1-13-10(12)8-6-11-9-5-3-2-4-7(8)9/h2-6,11H,1H3
InChI KeyQXAUTQFAWKKNLM-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
Arabidopsis thalianaPlant
Aristolochia cucurbitifoliaLOTUS Database
Aristolochia kaempferiLOTUS Database
Balansia epichloeLOTUS Database
Botryocladia leptopodaLOTUS Database
Epichloe festucaeLOTUS Database
Jurinea deltoideaLOTUS Database
Ligularia dentataLOTUS Database
Meehania urticifoliaLOTUS Database
Pachliopta aristolochiaeLOTUS Database
Penicillium herqueiLOTUS Database
Pinus sylvestrisLOTUS Database
Taraxacum mongolicumLOTUS Database
Xylaria obovataLOTUS Database
Zymoseptoria triticiLOTUS Database
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-3-carboxylic acid or derivatives
    • 

  • Substituted pyrrole
    • 

  • Benzenoid
    • 

  • Pyrrole
    • 

  • Methyl ester
    • 

  • Vinylogous amide
    • 

  • Heteroaromatic compound
    • 

  • Carboxylic acid ester
    • 

  • Carboxylic acid derivative
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Azacycle
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic nitrogen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP2.5ALOGPS
logP2.08ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area42.09 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.17 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 IDCPDQT-423  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound589098  
PDB IDNot Available
ChEBI ID65019  
Good Scents IDNot Available
References
General References