NP-MRD: Showing NP-Card for Nagelamide L (NP0082051)

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Record Information

Version

2.0

Created at

2022-04-29 03:06:18 UTC

Updated at

2022-04-29 03:06:18 UTC

NP-MRD ID

NP0082051

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nagelamide L

Description

(1S,2S)-3-amino-1-{5-[(1E)-3-[(4,5-dibromo-1H-pyrrol-2-yl)formamido]prop-1-en-1-yl]-2-imino-2,3-dihydro-1H-imidazol-4-yl}-1-(2-imino-2,3-dihydro-1H-imidazol-4-yl)propan-2-yl 4,5-dibromo-1H-pyrrole-2-carboxylate 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 L is found in Agelas sp. Based on a literature review very few articles have been published on (1S,2S)-3-amino-1-{5-[(1E)-3-[(4,5-dibromo-1H-pyrrol-2-yl)formamido]prop-1-en-1-yl]-2-imino-2,3-dihydro-1H-imidazol-4-yl}-1-(2-imino-2,3-dihydro-1H-imidazol-4-yl)propan-2-yl 4,5-dibromo-1H-pyrrole-2-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292205062D          

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M  END

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M  END


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 32 33  1  0  0  0  0
  1 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
  1 37  1  0  0  0  0
 36 38  1  0  0  0  0
 35 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0082051

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC[C@@H](OC(=O)C1=CC(Br)=C(Br)N1)[C@@H](C1=CN=C(N)N1)C1=C(\C=C\CNC(=O)C2=CC(Br)=C(Br)N2)N=C(N)N1

> <INCHI_IDENTIFIER>
InChI=1S/C22H22Br4N10O3/c23-8-4-11(32-17(8)25)19(37)30-3-1-2-10-16(36-22(29)34-10)15(13-7-31-21(28)35-13)14(6-27)39-20(38)12-5-9(24)18(26)33-12/h1-2,4-5,7,14-15,32-33H,3,6,27H2,(H,30,37)(H3,28,31,35)(H3,29,34,36)/b2-1+/t14-,15-/m1/s1

> <INCHI_KEY>
BLRVIRVYVPYDEW-RIVGAVQESA-N

> <FORMULA>
C22H22Br4N10O3

> <MOLECULAR_WEIGHT>
794.101

> <EXACT_MASS>
789.860987

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
63.64891612193043

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.46

> <JCHEM_LOGP>
1.2348530094642398

> <ALOGPS_LOGS>
-4.81

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
3

> <JCHEM_PKA>
12.026348565348016

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.036385973629804

> <JCHEM_PKA_STRONGEST_BASIC>
9.485616105168134

> <JCHEM_POLAR_SURFACE_AREA>
222.4

> <JCHEM_REFRACTIVITY>
161.28489999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.23e-02 g/l

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

> <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       3.358  -8.189   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.692  -7.419   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.692  -5.879   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.025  -8.189   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.359  -7.419   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.693  -8.189   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.693  -9.729   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.939 -10.634   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       9.463 -12.099   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       7.923 -12.099   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       7.447 -10.634   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       7.018 -13.345   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      10.026  -7.419   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.187  -5.887   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      11.694  -5.567   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      12.464  -6.901   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      11.433  -8.045   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      13.995  -7.062   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       9.043  -4.857   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.363  -3.351   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.219  -2.320   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       8.539  -0.814   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       7.394   0.217   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.930  -0.259   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.715   1.723   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       6.684   2.867   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       7.454   4.201   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.960   3.881   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.121   2.349   0.000  0.00  0.00           C+0
HETATM   30 Br   UNK     0      10.105   4.911   0.000  0.00  0.00          Br+0
HETATM   31 Br   UNK     0       6.828   5.608   0.000  0.00  0.00          Br+0
HETATM   32  C   UNK     0       7.359  -5.879   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       6.025  -5.109   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       3.197  -9.721   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.691 -10.041   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.921  -8.707   0.000  0.00  0.00           C+0
HETATM   37  N   UNK     0       1.951  -7.563   0.000  0.00  0.00           N+0
HETATM   38 Br   UNK     0      -0.611  -8.546   0.000  0.00  0.00          Br+0
HETATM   39 Br   UNK     0       1.064 -11.448   0.000  0.00  0.00          Br+0
CONECT    1    2   34   37                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   32                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10    7                                                       
CONECT   12   10                                                            
CONECT   13    6   14   17                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16   13                                                       
CONECT   18   16                                                            
CONECT   19   14   20                                                       
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    5   33                                                       
CONECT   33   32                                                            
CONECT   34    1   35                                                       
CONECT   35   34   36   39                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36    1                                                       
CONECT   38   36                                                            
CONECT   39   35                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
(1S,2S)-3-Amino-1-{5-[(1E)-3-[(4,5-dibromo-1H-pyrrol-2-yl)formamido]prop-1-en-1-yl]-2-imino-2,3-dihydro-1H-imidazol-4-yl}-1-(2-imino-2,3-dihydro-1H-imidazol-4-yl)propan-2-yl 4,5-dibromo-1H-pyrrole-2-carboxylic acid	Generator

Chemical Formula

C₂₂H₂₂Br₄N₁₀O₃

Average Mass

794.1010 Da

Monoisotopic Mass

789.86099 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

NC[C@@H](OC(=O)C1=CC(Br)=C(Br)N1)[C@@H](C1=CN=C(N)N1)C1=C(\C=C\CNC(=O)C2=CC(Br)=C(Br)N2)N=C(N)N1

InChI Identifier

InChI=1S/C22H22Br4N10O3/c23-8-4-11(32-17(8)25)19(37)30-3-1-2-10-16(36-22(29)34-10)15(13-7-31-21(28)35-13)14(6-27)39-20(38)12-5-9(24)18(26)33-12/h1-2,4-5,7,14-15,32-33H,3,6,27H2,(H,30,37)(H3,28,31,35)(H3,29,34,36)/b2-1+/t14-,15-/m1/s1

InChI Key

BLRVIRVYVPYDEW-RIVGAVQESA-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-carboxamide
Pyrrole-2-carboxylic acid or derivatives
Aralkylamine
Aminoimidazole
Aryl bromide
Aryl halide
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organonitrogen compound
Organobromide
Organohalogen compound
Primary aliphatic amine
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Primary 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	3.46	ALOGPS
logP	1.23	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	9.04	ChemAxon
pKa (Strongest Basic)	9.49	ChemAxon
Physiological Charge	3	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	222.4 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	161.28 m³·mol⁻¹	ChemAxon
Polarizability	63.65 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

Not Available

Chemspider ID

27023625

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24899928

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Nagelamide L (NP0082051)

MOL for NP0082051 (Nagelamide L)

3D MOL for NP0082051 (Nagelamide L)

3D SDF for NP0082051 (Nagelamide L)

3D-SDF for NP0082051 (Nagelamide L)

PDB for NP0082051 (Nagelamide L)

3D PDB for NP0082051 (Nagelamide L)

SMILES for NP0082051 (Nagelamide L)

INCHI for NP0082051 (Nagelamide L)

Structure for NP0082051 (Nagelamide L)

3D Structure for NP0082051 (Nagelamide L)