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Showing NP-Card for pyrrole-3-carboxylic acid (NP0262501)

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Record Information
Version2.0
Created at2022-09-08 05:20:07 UTC
Updated at2022-09-08 05:20:07 UTC
NP-MRD IDNP0262501
Secondary Accession NumbersNone
Natural Product Identification
Common Namepyrrole-3-carboxylic acid
DescriptionPyrrole-3-carboxylic acid belongs to the class of organic compounds known as pyrrole carboxylic acids. These are heterocyclic compounds containing a pyrrole ring bearing a carboxyl group. Pyrrole-3-carboxylic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. pyrrole-3-carboxylic acid is found in Penicillium chrysogenum. pyrrole-3-carboxylic acid was first documented in 2019 (PMID: 31055115). Based on a literature review a small amount of articles have been published on pyrrole-3-carboxylic acid (PMID: 34170100) (PMID: 33316671) (PMID: 33125976) (PMID: 33078449).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0262501 (pyrrole-3-carboxylic acid)


  Mrv1652309082207202D          

  8  8  0  0  0  0            999 V2000
   -0.1467    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
    1.2822    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
  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  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
M  END
Download

3D MOL for NP0262501 (pyrrole-3-carboxylic acid)

     RDKit          3D

 13 13  0  0  0  0  0  0  0  0999 V2000
    2.2502    1.3452   -0.9182 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7805    0.2974   -0.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6236   -0.7767   -0.2294 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3410    0.1509   -0.1838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2985   -0.9637    0.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6467   -0.7076    0.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8288    0.5597    0.0267 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6511    1.0941   -0.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9257   -0.8983    0.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1766   -1.9002    0.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4319   -1.3650    0.8057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7435    1.0624   -0.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4970    2.1018   -0.7362 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  8  2  0
  8  7  1  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  3  9  1  0
  8 13  1  0
  7 12  1  0
  6 11  1  0
  5 10  1  0
M  END
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3D SDF for NP0262501 (pyrrole-3-carboxylic acid)


  Mrv1652309082207202D          

  8  8  0  0  0  0            999 V2000
   -0.1467    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
    1.2822    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
  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  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
M  END
> <DATABASE_ID>
NP0262501

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CNC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C5H5NO2/c7-5(8)4-1-2-6-3-4/h1-3,6H,(H,7,8)

> <INCHI_KEY>
DOYOPBSXEIZLRE-UHFFFAOYSA-N

> <FORMULA>
C5H5NO2

> <MOLECULAR_WEIGHT>
111.1

> <EXACT_MASS>
111.032028405

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
10.222096758809684

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1H-pyrrole-3-carboxylic acid

> <JCHEM_LOGP>
0.7107128366666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.26619278114594

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.573138186171115

> <JCHEM_POLAR_SURFACE_AREA>
53.089999999999996

> <JCHEM_REFRACTIVITY>
28.073

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1H-pyrrole-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0262501 (pyrrole-3-carboxylic acid)

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PDB for NP0262501 (pyrrole-3-carboxylic acid)
HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  O   UNK     0      -0.274   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       2.393   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
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                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END

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3D PDB for NP0262501 (pyrrole-3-carboxylic acid)
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SMILES for NP0262501 (pyrrole-3-carboxylic acid)
OC(=O)C1=CNC=C1
Download
INCHI for NP0262501 (pyrrole-3-carboxylic acid)
InChI=1S/C5H5NO2/c7-5(8)4-1-2-6-3-4/h1-3,6H,(H,7,8)
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View in JSmol
Synonyms
ValueSource
Pyrrole-3-carboxylateGenerator
Chemical FormulaC5H5NO2
Average Mass111.1000 Da
Monoisotopic Mass111.03203 Da
IUPAC Name1H-pyrrole-3-carboxylic acid
Traditional Name1H-pyrrole-3-carboxylic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C1=CNC=C1
InChI Identifier
InChI=1S/C5H5NO2/c7-5(8)4-1-2-6-3-4/h1-3,6H,(H,7,8)
InChI KeyDOYOPBSXEIZLRE-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
Penicillium chrysogenumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrrole carboxylic acids. These are heterocyclic compounds containing a pyrrole ring bearing a carboxyl group.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrroles  
Sub ClassPyrrole carboxylic acids and derivatives  
Direct ParentPyrrole carboxylic acids  
Alternative Parents
Substituents
  • Pyrrole-3-carboxylic acid
    • 

  • Substituted pyrrole
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous amide
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • 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 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
logP0.71ChemAxon
pKa (Strongest Acidic)3.57ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity28.07 m³·mol⁻¹ChemAxon
Polarizability10.22 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 ID91277  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101030  
PDB IDNot Available
ChEBI ID68076  
Good Scents IDNot Available
References
General References
  1. Cui X, Lu G, Fang F, Xiong Y, Tian S, Wan Y, Xiao Y, Shen D, Wang H, Zhang J, Lee CS: Iron Self-Boosting Polymer Nanoenzyme for Low-Temperature Photothermal-Enhanced Ferrotherapy. ACS Appl Mater Interfaces. 2021 Jul 7;13(26):30274-30283. doi: 10.1021/acsami.1c01658. Epub 2021 Jun 25. [PubMed:34170100  ] 
  2. Koning JT, Bollmann UE, Bester K: Biodegradation of third-generation organic antifouling biocides and their hydrolysis products in marine model systems. J Hazard Mater. 2021 Mar 15;406:124755. doi: 10.1016/j.jhazmat.2020.124755. Epub  2020 Dec 3. [PubMed:33316671  ] 
  3. Song C, Li Y, Wang B, Hong Y, Xue C, Li Q, Shen E, Cui D: A novel anticoagulant affinity membrane for enhanced hemocompatibility and bilirubin removal. Colloids Surf B Biointerfaces. 2021 Jan;197:111430. doi: 10.1016/j.colsurfb.2020.111430. Epub 2020 Oct 22. [PubMed:33125976  ] 
  4. Rasal NK, Sonawane RB, Jagtap SV: Synthesis, biological evaluation, and in silico study of pyrazoline-conjugated 2,4-dimethyl-1H-pyrrole-3-carboxylic acid derivatives. Arch Pharm (Weinheim). 2021 Feb;354(2):e2000267. doi: 10.1002/ardp.202000267. Epub 2020 Oct 19. [PubMed:33078449  ] 
  5. Soylemez S, Goker S, Toppare L: A promising enzyme anchoring probe for selective ethanol sensing in beverages. Int J Biol Macromol. 2019 Jul 15;133:1228-1235. doi: 10.1016/j.ijbiomac.2019.05.001. Epub 2019 May 2. [PubMed:31055115  ] 
  6. LOTUS database [Link]