NP-MRD: Showing NP-Card for Banegasine (NP0004645)

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Record Information

Version

2.0

Created at

2020-12-09 02:04:43 UTC

Updated at

2021-07-15 16:49:45 UTC

NP-MRD ID

NP0004645

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Banegasine

Provided By

NPAtlas

Description

4-(2-Aminophenyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid belongs to the class of organic compounds known as phenylpyrrolines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrroline ring through a CC or CN bond. Banegasine is found in Pseudomonas. Banegasine was first documented in 2003 (PMID: 12821455). Based on a literature review very few articles have been published on 4-(2-aminophenyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118083D          

 27 28  0  0  0  0            999 V2000
   -2.0210   -1.7655   -1.2181 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2041   -0.6947   -0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5128   -0.3538    0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7331    0.6770    0.9590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6451    1.3579    1.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3737    1.0157    1.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1142   -0.0292    0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2779   -0.3319   -0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7998   -1.2290   -0.9755 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2199   -1.1536   -1.0168 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5641    0.1856   -0.5947 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8523    0.1153    0.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4606   -0.9704    0.2957 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053    1.2743    0.6413 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4375    0.4525    0.3850 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0133   -1.5693   -2.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9021   -2.7410   -0.8202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3133   -0.9332   -0.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7335    0.9653    1.2749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8253    2.1845    2.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5490    1.5822    1.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2128   -1.9699   -1.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9071   -1.8768   -1.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5762    0.9086   -1.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3068    2.1121    0.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6835    0.0530    1.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2367    1.5236    0.3839 H   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
  4  5  2  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
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 11 15  1  0  0  0  0
  7  2  1  0  0  0  0
 15  8  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  3 18  1  0  0  0  0
  4 19  1  0  0  0  0
  5 20  1  0  0  0  0
  6 21  1  0  0  0  0
  9 22  1  0  0  0  0
 10 23  1  0  0  0  0
 11 24  1  6  0  0  0
 14 25  1  0  0  0  0
 15 26  1  0  0  0  0
 15 27  1  0  0  0  0
M  END


  Mrv1652306242118083D          

 27 28  0  0  0  0            999 V2000
   -2.0210   -1.7655   -1.2181 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2041   -0.6947   -0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5128   -0.3538    0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7331    0.6770    0.9590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6451    1.3579    1.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3737    1.0157    1.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1142   -0.0292    0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2779   -0.3319   -0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7998   -1.2290   -0.9755 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2199   -1.1536   -1.0168 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5641    0.1856   -0.5947 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8523    0.1153    0.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4606   -0.9704    0.2957 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053    1.2743    0.6413 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4375    0.4525    0.3850 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0133   -1.5693   -2.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9021   -2.7410   -0.8202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3133   -0.9332   -0.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7335    0.9653    1.2749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8253    2.1845    2.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5490    1.5822    1.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2128   -1.9699   -1.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9071   -1.8768   -1.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5762    0.9086   -1.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3068    2.1121    0.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6835    0.0530    1.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2367    1.5236    0.3839 H   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
  4  5  2  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
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 11 15  1  0  0  0  0
  7  2  1  0  0  0  0
 15  8  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  3 18  1  0  0  0  0
  4 19  1  0  0  0  0
  5 20  1  0  0  0  0
  6 21  1  0  0  0  0
  9 22  1  0  0  0  0
 10 23  1  0  0  0  0
 11 24  1  6  0  0  0
 14 25  1  0  0  0  0
 15 26  1  0  0  0  0
 15 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004645

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]1([H])N([H])C([H])=C(C2=C([H])C([H])=C([H])C([H])=C2N([H])[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N2O2/c12-9-4-2-1-3-8(9)7-5-10(11(14)15)13-6-7/h1-4,6,10,13H,5,12H2,(H,14,15)/t10-/m0/s1

> <INCHI_KEY>
KPYXDIVTPWLGHB-UHFFFAOYSA-N

> <FORMULA>
C11H12N2O2

> <MOLECULAR_WEIGHT>
204.229

> <EXACT_MASS>
204.089877634

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
21.38809245251842

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-4-(2-aminophenyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid

> <ALOGPS_LOGP>
0.33

> <JCHEM_LOGP>
-1.858768762931227

> <ALOGPS_LOGS>
-2.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.1857629585630427

> <JCHEM_PKA_STRONGEST_BASIC>
8.309004661668043

> <JCHEM_POLAR_SURFACE_AREA>
75.35

> <JCHEM_REFRACTIVITY>
57.2348

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-4-(2-aminophenyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  N   UNK     0      -2.021  -1.766  -1.218  0.00  0.00           N+0
HETATM    2  C   UNK     0      -2.204  -0.695  -0.306  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.513  -0.354   0.077  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.733   0.677   0.959  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.645   1.358   1.450  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.374   1.016   1.069  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.114  -0.029   0.173  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.278  -0.332  -0.184  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.800  -1.229  -0.976  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.220  -1.154  -1.017  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.564   0.186  -0.595  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.852   0.115   0.130  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.461  -0.970   0.296  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.405   1.274   0.641  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.438   0.453   0.385  0.00  0.00           C+0
HETATM   16  H   UNK     0      -2.013  -1.569  -2.252  0.00  0.00           H+0
HETATM   17  H   UNK     0      -1.902  -2.741  -0.820  0.00  0.00           H+0
HETATM   18  H   UNK     0      -4.313  -0.933  -0.350  0.00  0.00           H+0
HETATM   19  H   UNK     0      -4.734   0.965   1.275  0.00  0.00           H+0
HETATM   20  H   UNK     0      -2.825   2.184   2.157  0.00  0.00           H+0
HETATM   21  H   UNK     0      -0.549   1.582   1.484  0.00  0.00           H+0
HETATM   22  H   UNK     0       0.213  -1.970  -1.554  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.907  -1.877  -1.285  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.576   0.909  -1.421  0.00  0.00           H+0
HETATM   25  H   UNK     0       4.307   2.112   0.107  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.684   0.053   1.389  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.237   1.524   0.384  0.00  0.00           H+0
CONECT    1    2   16   17                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5   19                                                  
CONECT    5    4    6   20                                                  
CONECT    6    5    7   21                                                  
CONECT    7    6    8    2                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10   22                                                  
CONECT   10    9   11   23                                                  
CONECT   11   10   12   15   24                                             
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   25                                                       
CONECT   15   11    8   26   27                                             
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    3                                                            
CONECT   19    4                                                            
CONECT   20    5                                                            
CONECT   21    6                                                            
CONECT   22    9                                                            
CONECT   23   10                                                            
CONECT   24   11                                                            
CONECT   25   14                                                            
CONECT   26   15                                                            
CONECT   27   15                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
4-(2-Aminophenyl)-2,3-dihydro-1H-pyrrole-2-carboxylate	Generator

Chemical Formula

C₁₁H₁₂N₂O₂

Average Mass

204.2290 Da

Monoisotopic Mass

204.08988 Da

IUPAC Name

(2S)-4-(2-aminophenyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid

Traditional Name

(2S)-4-(2-aminophenyl)-2,3-dihydro-1H-pyrrole-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H12N2O2/c12-9-4-2-1-3-8(9)7-5-10(11(14)15)13-6-7/h1-4,6,10,13H,5,12H2,(H,14,15)

InChI Key

KPYXDIVTPWLGHB-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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	NPAtlas	12821455

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolines

Sub Class

Phenylpyrrolines

Direct Parent

Phenylpyrrolines

Alternative Parents

Substituents

3-phenylpyrroline
Alpha-amino acid
Alpha-amino acid or derivatives
Aniline or substituted anilines
Monocyclic benzene moiety
Benzenoid
Pyrrole
Amino acid or derivatives
Amino acid
Azacycle
Carboxylic acid derivative
Carboxylic acid
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Enamine
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Amine
Organic oxygen 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	0.33	ALOGPS
logP	-1.9	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	2.19	ChemAxon
pKa (Strongest Basic)	8.31	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	75.35 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	57.23 m³·mol⁻¹	ChemAxon
Polarizability	21.39 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA005917

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8211368

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10035803

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cain CC, Lee D, Waldo RH 3rd, Henry AT, Casida EJ Jr, Wani MC, Wall ME, Oberlies NH, Falkinham JO 3rd: Synergistic antimicrobial activity of metabolites produced by a nonobligate bacterial predator. Antimicrob Agents Chemother. 2003 Jul;47(7):2113-7. doi: 10.1128/aac.47.7.2113-2117.2003. [PubMed:12821455 ]

Showing NP-Card for Banegasine (NP0004645)

MOL for NP0004645 (Banegasine)

3D MOL for NP0004645 (Banegasine)

3D SDF for NP0004645 (Banegasine)

3D-SDF for NP0004645 (Banegasine)

PDB for NP0004645 (Banegasine)

3D PDB for NP0004645 (Banegasine)

SMILES for NP0004645 (Banegasine)

INCHI for NP0004645 (Banegasine)

Structure for NP0004645 (Banegasine)

3D Structure for NP0004645 (Banegasine)