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Showing NP-Card for 3,4-dihydroxy-1h-indole-2-carboxylic acid (NP0296482)

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Record Information
Version2.0
Created at2022-09-10 06:04:59 UTC
Updated at2022-09-10 06:04:59 UTC
NP-MRD IDNP0296482
Secondary Accession NumbersNone
Natural Product Identification
Common Name3,4-dihydroxy-1h-indole-2-carboxylic acid
DescriptionSCHEMBL48966 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. 3,4-dihydroxy-1h-indole-2-carboxylic acid is found in Beta vulgaris. Based on a literature review very few articles have been published on SCHEMBL48966.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0296482 (3,4-dihydroxy-1h-indole-2-carboxylic acid)


  Mrv1652309102208052D          

 14 15  0  0  0  0            999 V2000
   -0.5837   -1.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.0165    0.0000 O   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
    2.6378   -2.3479    0.0000 O   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
    1.1387   -1.3654    0.0000 C   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  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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  1  0  0  0  0
 10 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
  4 13  2  0  0  0  0
 13 14  1  0  0  0  0
M  END
Download

3D MOL for NP0296482 (3,4-dihydroxy-1h-indole-2-carboxylic acid)

     RDKit          3D

 21 22  0  0  0  0  0  0  0  0999 V2000
    3.7658    0.6615   -0.0591 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1193   -0.4142   -0.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7109   -1.6469   -0.0377 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6570   -0.3284   -0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7708   -1.3350    0.0283 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4969   -0.8994    0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6900   -1.6092    0.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8806   -0.8987    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8452    0.4696    0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6275    1.1660    0.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7050    2.5189    0.0525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4345    0.4716    0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8853    0.8418    0.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4444    2.0796   -0.0171 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5256   -1.8828   -0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0654   -2.3432    0.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7483   -2.6879    0.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8217   -1.4330    0.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7772    1.0210    0.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0746    3.2576    0.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1572    2.9909   -0.0184 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 13  2  0
 13 14  1  0
 13 12  1  0
 12 10  2  0
 10 11  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  1  0
  6 12  1  0
  3 15  1  0
 14 21  1  0
 11 20  1  0
  9 19  1  0
  8 18  1  0
  7 17  1  0
  5 16  1  0
M  END
Download

3D SDF for NP0296482 (3,4-dihydroxy-1h-indole-2-carboxylic acid)


  Mrv1652309102208052D          

 14 15  0  0  0  0            999 V2000
   -0.5837   -1.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.0165    0.0000 O   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
    2.6378   -2.3479    0.0000 O   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
    1.1387   -1.3654    0.0000 C   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  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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  1  0  0  0  0
 10 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
  4 13  2  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0296482

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=C(O)C2=C(O)C=CC=C2N1

> <INCHI_IDENTIFIER>
InChI=1S/C9H7NO4/c11-5-3-1-2-4-6(5)8(12)7(10-4)9(13)14/h1-3,10-12H,(H,13,14)

> <INCHI_KEY>
WHNCXIBKVUPNHR-UHFFFAOYSA-N

> <FORMULA>
C9H7NO4

> <MOLECULAR_WEIGHT>
193.158

> <EXACT_MASS>
193.037507709

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
17.793217197109133

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4-dihydroxy-1H-indole-2-carboxylic acid

> <JCHEM_LOGP>
1.6924611973333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.70514732772018

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.871934730874516

> <JCHEM_PKA_STRONGEST_BASIC>
-5.704027589007407

> <JCHEM_POLAR_SURFACE_AREA>
93.55

> <JCHEM_REFRACTIVITY>
48.24

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3,4-dihydroxy-1H-indole-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0296482 (3,4-dihydroxy-1h-indole-2-carboxylic acid)

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PDB for NP0296482 (3,4-dihydroxy-1h-indole-2-carboxylic acid)
HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  O   UNK     0      -1.090  -2.637   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.090   0.031   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.650  -4.013   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    6   13                                                  
CONECT   13   12    4   14                                                  
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

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3D PDB for NP0296482 (3,4-dihydroxy-1h-indole-2-carboxylic acid)
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SMILES for NP0296482 (3,4-dihydroxy-1h-indole-2-carboxylic acid)
OC(=O)C1=C(O)C2=C(O)C=CC=C2N1
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INCHI for NP0296482 (3,4-dihydroxy-1h-indole-2-carboxylic acid)
InChI=1S/C9H7NO4/c11-5-3-1-2-4-6(5)8(12)7(10-4)9(13)14/h1-3,10-12H,(H,13,14)
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View in JSmol
SynonymsNot Available
Chemical FormulaC9H7NO4
Average Mass193.1580 Da
Monoisotopic Mass193.03751 Da
IUPAC Name3,4-dihydroxy-1H-indole-2-carboxylic acid
Traditional Name3,4-dihydroxy-1H-indole-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C1=C(O)C2=C(O)C=CC=C2N1
InChI Identifier
InChI=1S/C9H7NO4/c11-5-3-1-2-4-6(5)8(12)7(10-4)9(13)14/h1-3,10-12H,(H,13,14)
InChI KeyWHNCXIBKVUPNHR-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
Beta vulgarisLOTUS 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
    • 

  • Hydroxyindole
    • 

  • Indole
    • 

  • Pyrrole-2-carboxylic acid or derivatives
    • 

  • Pyrrole-2-carboxylic acid
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Benzenoid
    • 

  • Substituted pyrrole
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous acid
    • 

  • Pyrrole
    • 

  • Azacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen 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
logP1.69ChemAxon
pKa (Strongest Acidic)4.87ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area93.55 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.24 m³·mol⁻¹ChemAxon
Polarizability17.79 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 ID67170345  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound54730558  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]