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Showing NP-Card for (2r)-2-(1h-indol-3-yl)propanoic acid (NP0172711)

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Record Information
Version2.0
Created at2022-09-03 09:41:59 UTC
Updated at2022-09-03 09:42:00 UTC
NP-MRD IDNP0172711
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2r)-2-(1h-indol-3-yl)propanoic acid
Description(2R)-(3-indolyl) propionic acid 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. (2r)-2-(1h-indol-3-yl)propanoic acid is found in Colletotrichum fragariae. Based on a literature review very few articles have been published on (2r)-(3-indolyl) propionic acid.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0172711 ((2r)-2-(1h-indol-3-yl)propanoic acid)


  Mrv1652309032211422D          

 14 15  0  0  1  0            999 V2000
    1.4358   -2.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  1  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
   -0.1781   -3.1062    0.0000 O   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
    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
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  6 14  1  0  0  0  0
  9 14  1  0  0  0  0
M  END
Download

3D MOL for NP0172711 ((2r)-2-(1h-indol-3-yl)propanoic acid)

     RDKit          3D

 25 26  0  0  0  0  0  0  0  0999 V2000
    2.6778   -0.9516    0.6876 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5956    0.1373    0.6241 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1068    1.1431   -0.3290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5647    1.4801   -1.3955 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3226    1.7472    0.0514 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3276   -0.4616    0.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1055   -1.8050    0.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1552   -2.0212   -0.3535 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7608   -0.8266   -0.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0472   -0.4942   -0.7074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4108    0.8440   -0.6673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5055    1.8284   -0.3199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2071    1.5096   -0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8601    0.1583   -0.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863   -1.7814    1.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6454   -0.4845    0.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7108   -1.3464   -0.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5262    0.5430    1.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1901    1.3986   -0.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8318   -2.6220    0.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6200   -2.9508   -0.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7473   -1.2723   -0.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4234    1.0894   -0.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7836    2.8788   -0.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4702    2.2600    0.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  5  1  0
  3  4  2  0
  2  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  6  1  0
 14  9  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  1
  5 19  1  0
  7 20  1  0
  8 21  1  0
 10 22  1  0
 11 23  1  0
 12 24  1  0
 13 25  1  0
M  END
Download

3D SDF for NP0172711 ((2r)-2-(1h-indol-3-yl)propanoic acid)


  Mrv1652309032211422D          

 14 15  0  0  1  0            999 V2000
    1.4358   -2.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  1  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
   -0.1781   -3.1062    0.0000 O   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
    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
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  6 14  1  0  0  0  0
  9 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0172711

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](C(O)=O)C1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C11H11NO2/c1-7(11(13)14)9-6-12-10-5-3-2-4-8(9)10/h2-7,12H,1H3,(H,13,14)/t7-/m1/s1

> <INCHI_KEY>
WNVIEMRKZPPPOJ-SSDOTTSWSA-N

> <FORMULA>
C11H11NO2

> <MOLECULAR_WEIGHT>
189.214

> <EXACT_MASS>
189.078978598

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
19.801673859017317

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.32

> <JCHEM_LOGP>
2.2527423766666663

> <ALOGPS_LOGS>
-2.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.149285306465043

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.6762489338037705

> <JCHEM_POLAR_SURFACE_AREA>
53.089999999999996

> <JCHEM_REFRACTIVITY>
53.02660000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-(1H-indol-3-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0172711 ((2r)-2-(1h-indol-3-yl)propanoic acid)

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PDB for NP0172711 ((2r)-2-(1h-indol-3-yl)propanoic acid)
HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       2.680  -5.158   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.333  -5.798   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -0.887  -3.189   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    6    9                                                  
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

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3D PDB for NP0172711 ((2r)-2-(1h-indol-3-yl)propanoic acid)
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SMILES for NP0172711 ((2r)-2-(1h-indol-3-yl)propanoic acid)
C[C@@H](C(O)=O)C1=CNC2=CC=CC=C12
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INCHI for NP0172711 ((2r)-2-(1h-indol-3-yl)propanoic acid)
InChI=1S/C11H11NO2/c1-7(11(13)14)9-6-12-10-5-3-2-4-8(9)10/h2-7,12H,1H3,(H,13,14)/t7-/m1/s1
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View in JSmol
Synonyms
ValueSource
(2R)-(3-Indolyl) propionateGenerator
Chemical FormulaC11H11NO2
Average Mass189.2140 Da
Monoisotopic Mass189.07898 Da
IUPAC Name(2R)-2-(1H-indol-3-yl)propanoic acid
Traditional Name(2R)-2-(1H-indol-3-yl)propanoic acid
CAS Registry NumberNot Available
SMILES
C[C@@H](C(O)=O)C1=CNC2=CC=CC=C12
InChI Identifier
InChI=1S/C11H11NO2/c1-7(11(13)14)9-6-12-10-5-3-2-4-8(9)10/h2-7,12H,1H3,(H,13,14)/t7-/m1/s1
InChI KeyWNVIEMRKZPPPOJ-SSDOTTSWSA-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
Colletotrichum fragariaeLOTUS 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
    • 

  • Pyrrole
    • 

  • Heteroaromatic compound
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Azacycle
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Carbonyl group
    • 

  • 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
logP2.32ALOGPS
logP2.25ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4.68ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity53.03 m³·mol⁻¹ChemAxon
Polarizability19.8 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 ID29334515  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12230079  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]