NP-MRD: Showing NP-Card for 4-(2-amino-3-bromophenyl)-1h-pyrrole-2-carboxylic acid (NP0204083)

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Record Information

Version

2.0

Created at

2022-09-04 23:41:37 UTC

Updated at

2022-09-04 23:41:37 UTC

NP-MRD ID

NP0204083

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(2-amino-3-bromophenyl)-1h-pyrrole-2-carboxylic acid

Description

88899-26-7 Belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond. 4-(2-amino-3-bromophenyl)-1h-pyrrole-2-carboxylic acid is found in Pseudomonas chlororaphis. Based on a literature review very few articles have been published on 88899-26-7.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052201412D          

 16 17  0  0  0  0            999 V2000
    1.3222    0.7634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    2.4134    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4186   -0.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1637   -1.3312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -1.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8538   -1.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1893   -2.7523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0333   -1.9124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0837   -0.5465    0.0000 C   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
  3  4  1  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  2  0  0  0  0
  2  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  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 12 16  2  0  0  0  0
  9 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0204083

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=C(Br)C=CC=C1C1=CNC(=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H9BrN2O2/c12-8-3-1-2-7(10(8)13)6-4-9(11(15)16)14-5-6/h1-5,14H,13H2,(H,15,16)

> <INCHI_KEY>
ZFBPVDVEOVIINM-UHFFFAOYSA-N

> <FORMULA>
C11H9BrN2O2

> <MOLECULAR_WEIGHT>
281.109

> <EXACT_MASS>
279.984741

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
24.222973435840686

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(2-amino-3-bromophenyl)-1H-pyrrole-2-carboxylic acid

> <JCHEM_LOGP>
2.2177659936666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.49740077146124

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.122377514025618

> <JCHEM_PKA_STRONGEST_BASIC>
2.573488644098126

> <JCHEM_POLAR_SURFACE_AREA>
79.11

> <JCHEM_REFRACTIVITY>
65.40990000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-(2-amino-3-bromophenyl)-1H-pyrrole-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  N   UNK     0       2.468   1.425   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       3.802   2.195   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.802   3.735   0.000  0.00  0.00           C+0
HETATM    4 Br   UNK     0       2.468   4.505   0.000  0.00  0.00          Br+0
HETATM    5  C   UNK     0       5.136   4.505   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.469   3.735   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.469   2.195   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.136   1.425   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.136  -0.115   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.381  -1.020   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       5.906  -2.485   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       4.366  -2.485   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.460  -3.731   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.087  -5.138   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.929  -3.570   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.890  -1.020   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    2    9                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   12    9                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₉BrN₂O₂

Average Mass

281.1090 Da

Monoisotopic Mass

279.98474 Da

IUPAC Name

4-(2-amino-3-bromophenyl)-1H-pyrrole-2-carboxylic acid

Traditional Name

4-(2-amino-3-bromophenyl)-1H-pyrrole-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

NC1=C(Br)C=CC=C1C1=CNC(=C1)C(O)=O

InChI Identifier

InChI=1S/C11H9BrN2O2/c12-8-3-1-2-7(10(8)13)6-4-9(11(15)16)14-5-6/h1-5,14H,13H2,(H,15,16)

InChI Key

ZFBPVDVEOVIINM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pseudomonas chlororaphis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrroles

Sub Class

Substituted pyrroles

Direct Parent

Phenylpyrroles

Alternative Parents

Substituents

3-phenylpyrrole
Aniline or substituted anilines
2-bromoaniline
Pyrrole-2-carboxylic acid or derivatives
Pyrrole-2-carboxylic acid
Bromobenzene
Halobenzene
Aryl bromide
Aryl halide
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Amino acid or derivatives
Amino acid
Azacycle
Carboxylic acid derivative
Carboxylic acid
Organohalogen compound
Primary amine
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organobromide
Organonitrogen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.22	ChemAxon
pKa (Strongest Acidic)	5.12	ChemAxon
pKa (Strongest Basic)	2.57	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.11 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	65.41 m³·mol⁻¹	ChemAxon
Polarizability	24.22 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28694571

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54543728

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-(2-amino-3-bromophenyl)-1h-pyrrole-2-carboxylic acid (NP0204083)

MOL for NP0204083 (4-(2-amino-3-bromophenyl)-1h-pyrrole-2-carboxylic acid)

3D MOL for NP0204083 (4-(2-amino-3-bromophenyl)-1h-pyrrole-2-carboxylic acid)

3D SDF for NP0204083 (4-(2-amino-3-bromophenyl)-1h-pyrrole-2-carboxylic acid)

3D-SDF for NP0204083 (4-(2-amino-3-bromophenyl)-1h-pyrrole-2-carboxylic acid)

PDB for NP0204083 (4-(2-amino-3-bromophenyl)-1h-pyrrole-2-carboxylic acid)

3D PDB for NP0204083 (4-(2-amino-3-bromophenyl)-1h-pyrrole-2-carboxylic acid)

SMILES for NP0204083 (4-(2-amino-3-bromophenyl)-1h-pyrrole-2-carboxylic acid)

INCHI for NP0204083 (4-(2-amino-3-bromophenyl)-1h-pyrrole-2-carboxylic acid)

Structure for NP0204083 (4-(2-amino-3-bromophenyl)-1h-pyrrole-2-carboxylic acid)

3D Structure for NP0204083 (4-(2-amino-3-bromophenyl)-1h-pyrrole-2-carboxylic acid)