NP-MRD: Showing NP-Card for Nagelamide C (NP0079211)

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Record Information

Version

2.0

Created at

2022-04-29 00:15:17 UTC

Updated at

2022-04-29 00:15:17 UTC

NP-MRD ID

NP0079211

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nagelamide C

Description

CHEMBL1162469 belongs to the class of organic compounds known as 2,4,5-trisubstituted imidazoles. These are imidazoles in which the imidazole ring is substituted at positions 2, 4, and 5. Nagelamide C is found in Agelas sp. Based on a literature review very few articles have been published on CHEMBL1162469.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202152D          

 38 41  0  0  0  0            999 V2000
    2.5330   -0.6552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2004   -1.1401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9455   -1.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1205   -1.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8655   -1.1401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6356   -2.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8151   -2.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3302   -3.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4903   -3.0872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9752   -3.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6397   -4.5083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7957   -3.6684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3478   -4.2815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1014   -3.9459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0152   -3.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2082   -2.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6283   -2.5734    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.8159   -4.3584    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.4304   -2.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2509   -2.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5864   -1.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4371   -0.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9522    0.3363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2576   -0.2449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6701    0.4695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4770    0.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0901    0.8500    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
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    2.5330    0.1698    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  1  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
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 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
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 15 17  1  0  0  0  0
 14 18  1  0  0  0  0
  3 19  1  0  0  0  0
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 20 21  1  0  0  0  0
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 32 36  1  0  0  0  0
 35 37  1  0  0  0  0
  1 38  1  0  0  0  0
M  END

     RDKit          3D

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   -4.6123    1.4378   -0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9560    1.1095   -1.3187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0650    1.6092   -0.5541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9790    1.9709    0.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2132    2.0317   -0.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9027    2.4746    0.6444 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -8.0502    1.7057   -1.4849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4394    1.6230   -2.7999 Br  0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7244   -5.4039    0.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
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  5  6  1  0
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 24 23  1  0
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 21 20  1  0
 38  2  1  0
 18 12  1  0
 20 19  1  0
 37 31  1  0
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 13 46  1  0
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 37 57  1  0
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 22 50  1  0
 20 48  1  0
M  END


  Mrv1652304292202152D          

 38 41  0  0  0  0            999 V2000
    2.5330   -0.6552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2004   -1.1401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2509   -2.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1015   -1.0848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9522    0.3363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0948   -3.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5073   -4.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9553   -4.6734    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5330    0.1698    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
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 27 28  2  0  0  0  0
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 27 31  1  0  0  0  0
 19 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
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  1 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0079211

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=NC=C(N1)C(=C\CNC(=O)C1=CC(Br)=C(Br)N1)\C1=C(/C=C/CNC(=O)C2=CC(Br)=C(Br)N2)N=C(N)N1

> <INCHI_IDENTIFIER>
InChI=1S/C22H20Br4N10O2/c23-10-6-13(32-17(10)25)19(37)29-4-1-2-12-16(36-22(28)34-12)9(15-8-31-21(27)35-15)3-5-30-20(38)14-7-11(24)18(26)33-14/h1-3,6-8,32-33H,4-5H2,(H,29,37)(H,30,38)(H3,27,31,35)(H3,28,34,36)/b2-1+,9-3-

> <INCHI_KEY>
HVSCSPHJFJDZCZ-BARZBYPCSA-N

> <FORMULA>
C22H20Br4N10O2

> <MOLECULAR_WEIGHT>
776.086

> <EXACT_MASS>
771.850422

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
61.22946388855576

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(2E)-3-{2-amino-5-[(1Z)-1-(2-amino-1H-imidazol-5-yl)-3-[(4,5-dibromo-1H-pyrrol-2-yl)formamido]prop-1-en-1-yl]-1H-imidazol-4-yl}prop-2-en-1-yl]-4,5-dibromo-1H-pyrrole-2-carboxamide

> <ALOGPS_LOGP>
4.05

> <JCHEM_LOGP>
2.2467180663333335

> <ALOGPS_LOGS>
-5.06

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
11.320928567207385

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.709333431939297

> <JCHEM_PKA_STRONGEST_BASIC>
12.15132874579336

> <JCHEM_POLAR_SURFACE_AREA>
199.17999999999998

> <JCHEM_REFRACTIVITY>
170.31599999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.69e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(2E)-3-{2-amino-5-[(1Z)-1-(2-amino-3H-imidazol-4-yl)-3-[(4,5-dibromo-1H-pyrrol-2-yl)formamido]prop-1-en-1-yl]-1H-imidazol-4-yl}prop-2-en-1-yl]-4,5-dibromo-1H-pyrrole-2-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       4.728  -1.223   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       5.974  -2.128   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.498  -3.593   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.958  -3.593   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       3.482  -2.128   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       3.053  -4.839   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.521  -4.678   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.616  -5.924   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.915  -5.763   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -1.820  -7.009   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.194  -8.415   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.352  -6.848   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -4.382  -7.992   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -5.789  -7.366   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.628  -5.834   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.122  -5.514   0.000  0.00  0.00           C+0
HETATM   17 Br   UNK     0      -6.773  -4.804   0.000  0.00  0.00          Br+0
HETATM   18 Br   UNK     0      -7.123  -8.136   0.000  0.00  0.00          Br+0
HETATM   19  C   UNK     0       6.403  -4.839   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.935  -4.678   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.561  -3.271   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       7.656  -2.025   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       8.283  -0.618   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.377   0.628   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.814  -0.457   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      10.584   0.876   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      12.090   0.556   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.251  -0.975   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.845  -1.602   0.000  0.00  0.00           C+0
HETATM   30 Br   UNK     0      13.585  -1.745   0.000  0.00  0.00          Br+0
HETATM   31 Br   UNK     0      13.235   1.587   0.000  0.00  0.00          Br+0
HETATM   32  C   UNK     0       5.777  -6.246   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.547  -7.579   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       5.517  -8.724   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       4.110  -8.097   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0       4.271  -6.566   0.000  0.00  0.00           N+0
HETATM   37  N   UNK     0       2.776  -8.867   0.000  0.00  0.00           N+0
HETATM   38  N   UNK     0       4.728   0.317   0.000  0.00  0.00           N+0
CONECT    1    2    5   38                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   12                                                       
CONECT   17   15                                                            
CONECT   18   14                                                            
CONECT   19    3   20   32                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   31                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28   25                                                       
CONECT   30   28                                                            
CONECT   31   27                                                            
CONECT   32   19   33   36                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35   32                                                       
CONECT   37   35                                                            
CONECT   38    1                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₀Br₄N₁₀O₂

Average Mass

776.0860 Da

Monoisotopic Mass

771.85042 Da

IUPAC Name

N-[(2E)-3-{2-amino-5-[(1Z)-1-(2-amino-1H-imidazol-5-yl)-3-[(4,5-dibromo-1H-pyrrol-2-yl)formamido]prop-1-en-1-yl]-1H-imidazol-4-yl}prop-2-en-1-yl]-4,5-dibromo-1H-pyrrole-2-carboxamide

Traditional Name

N-[(2E)-3-{2-amino-5-[(1Z)-1-(2-amino-3H-imidazol-4-yl)-3-[(4,5-dibromo-1H-pyrrol-2-yl)formamido]prop-1-en-1-yl]-1H-imidazol-4-yl}prop-2-en-1-yl]-4,5-dibromo-1H-pyrrole-2-carboxamide

CAS Registry Number

Not Available

SMILES

NC1=NC=C(N1)C(=C\CNC(=O)C1=CC(Br)=C(Br)N1)\C1=C(/C=C/CNC(=O)C2=CC(Br)=C(Br)N2)N=C(N)N1

InChI Identifier

InChI=1S/C22H20Br4N10O2/c23-10-6-13(32-17(10)25)19(37)29-4-1-2-12-16(36-22(28)34-12)9(15-8-31-21(27)35-15)3-5-30-20(38)14-7-11(24)18(26)33-14/h1-3,6-8,32-33H,4-5H2,(H,29,37)(H,30,38)(H3,27,31,35)(H3,28,34,36)/b2-1+,9-3-

InChI Key

HVSCSPHJFJDZCZ-BARZBYPCSA-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
Agelas sp.	Animalia	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,4,5-trisubstituted imidazoles. These are imidazoles in which the imidazole ring is substituted at positions 2, 4, and 5.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Imidazoles

Direct Parent

2,4,5-trisubstituted imidazoles

Alternative Parents

Substituents

2-heteroaryl carboxamide
2,4,5-trisubstituted-imidazole
Pyrrole-2-carboxylic acid or derivatives
Pyrrole-2-carboxamide
Aminoimidazole
Aryl bromide
Aryl halide
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Azacycle
Carboxylic acid derivative
Organobromide
Organohalogen compound
Amine
Primary amine
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	4.05	ALOGPS
logP	2.25	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	7.71	ChemAxon
pKa (Strongest Basic)	12.15	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	199.18 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	170.32 m³·mol⁻¹	ChemAxon
Polarizability	61.23 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00043746

Chemspider ID

9666015

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11491208

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Nagelamide C (NP0079211)

MOL for NP0079211 (Nagelamide C)

3D MOL for NP0079211 (Nagelamide C)

3D SDF for NP0079211 (Nagelamide C)

3D-SDF for NP0079211 (Nagelamide C)

PDB for NP0079211 (Nagelamide C)

3D PDB for NP0079211 (Nagelamide C)

SMILES for NP0079211 (Nagelamide C)

INCHI for NP0079211 (Nagelamide C)

Structure for NP0079211 (Nagelamide C)

3D Structure for NP0079211 (Nagelamide C)