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Showing NP-Card for 1h-pyrrole-2,3-dicarboxylic acid (NP0328678)

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Record Information
Version2.0
Created at2022-09-12 12:21:33 UTC
Updated at2022-09-12 12:21:33 UTC
NP-MRD IDNP0328678
Secondary Accession NumbersNone
Natural Product Identification
Common Name1h-pyrrole-2,3-dicarboxylic acid
Description1H-pyrrole-2,3-dicarboxylic acid belongs to the class of organic compounds known as pyrrole 2-carboxylic acids. These are pyrrole carboxylic acids where the carboxyl group is attached at position C2. 1h-pyrrole-2,3-dicarboxylic acid is found in Parietaria officinalis. 1H-pyrrole-2,3-dicarboxylic acid is a weakly acidic compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0328678 (1h-pyrrole-2,3-dicarboxylic acid)


  Mrv1533004241502212D          

 11 11  0  0  0  0            999 V2000
    1.2822    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974    0.3323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558    1.6913    0.0000 O   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
  4  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
Download

3D MOL for NP0328678 (1h-pyrrole-2,3-dicarboxylic acid)

     RDKit          3D

 16 16  0  0  0  0  0  0  0  0999 V2000
    0.6122   -2.3279    0.5783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4497   -1.7425    0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6355   -2.4678    0.1865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4529   -0.3042    0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6076    0.4335   -0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2899    1.7567   -0.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0158    1.8577   -0.1806 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5503    0.6328    0.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9463    0.4191    0.3978 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7203    1.4394    0.3820 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5058   -0.7972    0.6893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9769   -2.8665   -0.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5963   -0.0230   -0.3695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0133    2.5375   -0.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5559    2.7593   -0.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1157   -1.3069    0.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  7  8  1  0
 11 16  1  0
  5 13  1  0
  6 14  1  0
  7 15  1  0
  3 12  1  0
M  END
Download

3D SDF for NP0328678 (1h-pyrrole-2,3-dicarboxylic acid)


  Mrv1533004241502212D          

 11 11  0  0  0  0            999 V2000
    1.2822    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974    0.3323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558    1.6913    0.0000 O   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
  4  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328678

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=C(C=CN1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H5NO4/c8-5(9)3-1-2-7-4(3)6(10)11/h1-2,7H,(H,8,9)(H,10,11)

> <INCHI_KEY>
OEUSNWDYXDEXDR-UHFFFAOYSA-N

> <FORMULA>
C6H5NO4

> <MOLECULAR_WEIGHT>
155.109

> <EXACT_MASS>
155.021857645

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
13.222737704952468

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1H-pyrrole-2,3-dicarboxylic acid

> <ALOGPS_LOGP>
0.42

> <JCHEM_LOGP>
0.2882968683333333

> <ALOGPS_LOGS>
-1.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.384223392000508

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.822191451664978

> <JCHEM_POLAR_SURFACE_AREA>
90.39

> <JCHEM_REFRACTIVITY>
35.206700000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1H-pyrrole-2,3-dicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0328678 (1h-pyrrole-2,3-dicarboxylic acid)

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PDB for NP0328678 (1h-pyrrole-2,3-dicarboxylic acid)
HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0       2.393   4.390   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.274   4.390   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.290  -0.290   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.651   1.651   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.795   0.620   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.971   3.157   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    4    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0328678 (1h-pyrrole-2,3-dicarboxylic acid)
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SMILES for NP0328678 (1h-pyrrole-2,3-dicarboxylic acid)
OC(=O)C1=C(C=CN1)C(O)=O
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INCHI for NP0328678 (1h-pyrrole-2,3-dicarboxylic acid)
InChI=1S/C6H5NO4/c8-5(9)3-1-2-7-4(3)6(10)11/h1-2,7H,(H,8,9)(H,10,11)
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View in JSmol
Synonyms
ValueSource
1H-Pyrrole-2,3-dicarboxylateGenerator
Pyrrole-2,3-dicarboxylic acidMeSH
Chemical FormulaC6H5NO4
Average Mass155.1090 Da
Monoisotopic Mass155.02186 Da
IUPAC Name1H-pyrrole-2,3-dicarboxylic acid
Traditional Name1H-pyrrole-2,3-dicarboxylic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C1=C(C=CN1)C(O)=O
InChI Identifier
InChI=1S/C6H5NO4/c8-5(9)3-1-2-7-4(3)6(10)11/h1-2,7H,(H,8,9)(H,10,11)
InChI KeyOEUSNWDYXDEXDR-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
Parietaria officinalisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrrole 2-carboxylic acids. These are pyrrole carboxylic acids where the carboxyl group is attached at position C2.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrroles  
Sub ClassPyrrole carboxylic acids and derivatives  
Direct ParentPyrrole 2-carboxylic acids  
Alternative Parents
Substituents
  • Pyrrole-2-carboxylic acid
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Substituted pyrrole
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous amide
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
logP0.42ALOGPS
logP0.29ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.82ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area90.39 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity35.21 m³·mol⁻¹ChemAxon
Polarizability13.22 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]