NP-MRD: Showing NP-Card for 4-bromo-n-{[2-(2-imino-1,3-dihydroimidazol-4-yl)-5-oxo-6-{8-oxo-1h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-ylidene}-1h,2h,3h-[1,3]diazolo[1,2-a]imidazol-3-yl]methyl}-1h-pyrrole-2-carboxamide (NP0204371)

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Record Information

Version

2.0

Created at

2022-09-05 00:01:58 UTC

Updated at

2022-09-05 00:01:58 UTC

NP-MRD ID

NP0204371

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-bromo-n-{[2-(2-imino-1,3-dihydroimidazol-4-yl)-5-oxo-6-{8-oxo-1h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-ylidene}-1h,2h,3h-[1,3]diazolo[1,2-a]imidazol-3-yl]methyl}-1h-pyrrole-2-carboxamide

Description

4-Bromo-N-{[2-(2-imino-2,3-dihydro-1H-imidazol-4-yl)-5-oxo-6-{8-oxo-1H,4H,5H,6H,7H,8H-pyrrolo[2,3-c]azepin-4-ylidene}-1H,2H,3H,5H,6H-[1,3]diazolo[1,2-a]imidazol-3-yl]methyl}-1H-pyrrole-2-carboxamide belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 4-bromo-n-{[2-(2-imino-1,3-dihydroimidazol-4-yl)-5-oxo-6-{8-oxo-1h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-ylidene}-1h,2h,3h-[1,3]diazolo[1,2-a]imidazol-3-yl]methyl}-1h-pyrrole-2-carboxamide is found in Stylissa carteri. 4-Bromo-N-{[2-(2-imino-2,3-dihydro-1H-imidazol-4-yl)-5-oxo-6-{8-oxo-1H,4H,5H,6H,7H,8H-pyrrolo[2,3-c]azepin-4-ylidene}-1H,2H,3H,5H,6H-[1,3]diazolo[1,2-a]imidazol-3-yl]methyl}-1H-pyrrole-2-carboxamide is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251505252D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004251505252D          

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 31 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0204371

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=NC=C(N1)C1NC2=NC(C(=O)N2C1CNC(=O)C1=CC(Br)=CN1)=C1CCNC(=O)C2=C1C=CN2

> <INCHI_IDENTIFIER>
InChI=1S/C22H21BrN10O3/c23-9-5-12(27-6-9)18(34)28-8-14-17(13-7-29-21(24)30-13)32-22-31-16(20(36)33(14)22)11-2-4-26-19(35)15-10(11)1-3-25-15/h1,3,5-7,14,17,25,27H,2,4,8H2,(H,26,35)(H,28,34)(H,31,32)(H3,24,29,30)

> <INCHI_KEY>
RMUSSDXMUOCMGR-UHFFFAOYSA-N

> <FORMULA>
C22H21BrN10O3

> <MOLECULAR_WEIGHT>
553.381

> <EXACT_MASS>
552.098148

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
52.31908690667558

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-{[2-(2-amino-1H-imidazol-5-yl)-5-oxo-6-{8-oxo-1H,4H,5H,6H,7H,8H-pyrrolo[2,3-c]azepin-4-ylidene}-1H,2H,3H,5H,6H-imidazo[1,2-a]imidazolidin-3-yl]methyl}-4-bromo-1H-pyrrole-2-carboxamide

> <ALOGPS_LOGP>
1.17

> <JCHEM_LOGP>
-0.8773077199999991

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.123885907542999

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.019538420402476

> <JCHEM_PKA_STRONGEST_BASIC>
8.889186051096177

> <JCHEM_POLAR_SURFACE_AREA>
189.17999999999998

> <JCHEM_REFRACTIVITY>
134.053

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.83e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-{[2-(2-amino-3H-imidazol-4-yl)-5-oxo-6-{8-oxo-1H,5H,6H,7H-pyrrolo[2,3-c]azepin-4-ylidene}-1H,2H,3H-imidazo[1,2-a]imidazolidin-3-yl]methyl}-4-bromo-1H-pyrrole-2-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  N   UNK     0      -6.368  -7.480   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -5.122  -6.575   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -5.122  -5.035   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -3.657  -4.559   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.752  -5.805   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -3.657  -7.051   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -1.212  -5.805   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -0.307  -4.559   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.158  -5.035   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.623  -4.559   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       3.528  -5.805   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.068  -5.805   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.736  -4.418   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.237  -4.075   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       8.441  -5.035   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       8.441  -6.575   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.829  -7.243   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.237  -7.535   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       7.375  -9.069   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       5.959  -9.674   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.946  -8.515   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.736  -7.193   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.623  -7.051   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.099  -8.516   0.000  0.00  0.00           O+0
HETATM   25  N   UNK     0       1.158  -6.575   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      -0.307  -7.051   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.783  -8.516   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      -2.289  -8.836   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      -2.765 -10.301   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.734 -11.445   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -4.271 -10.621   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.897 -12.028   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.429 -11.867   0.000  0.00  0.00           C+0
HETATM   34 Br   UNK     0      -7.460 -13.011   0.000  0.00  0.00          Br+0
HETATM   35  C   UNK     0      -6.749 -10.360   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0      -5.416  -9.590   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    2                                                       
CONECT    7    5    8   26                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   25                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   23                                                  
CONECT   12   11   13   22                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   12   18                                                  
CONECT   23   11   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    9   26                                                  
CONECT   26   25    7   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   31                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₁BrN₁₀O₃

Average Mass

553.3810 Da

Monoisotopic Mass

552.09815 Da

IUPAC Name

N-{[2-(2-amino-1H-imidazol-5-yl)-5-oxo-6-{8-oxo-1H,4H,5H,6H,7H,8H-pyrrolo[2,3-c]azepin-4-ylidene}-1H,2H,3H,5H,6H-imidazo[1,2-a]imidazolidin-3-yl]methyl}-4-bromo-1H-pyrrole-2-carboxamide

Traditional Name

N-{[2-(2-amino-3H-imidazol-4-yl)-5-oxo-6-{8-oxo-1H,5H,6H,7H-pyrrolo[2,3-c]azepin-4-ylidene}-1H,2H,3H-imidazo[1,2-a]imidazolidin-3-yl]methyl}-4-bromo-1H-pyrrole-2-carboxamide

CAS Registry Number

Not Available

SMILES

NC1=NC=C(N1)C1NC2=NC(C(=O)N2C1CNC(=O)C1=CC(Br)=CN1)=C1CCNC(=O)C2=C1C=CN2

InChI Identifier

InChI=1S/C22H21BrN10O3/c23-9-5-12(27-6-9)18(34)28-8-14-17(13-7-29-21(24)30-13)32-22-31-16(20(36)33(14)22)11-2-4-26-19(35)15-10(11)1-3-25-15/h1,3,5-7,14,17,25,27H,2,4,8H2,(H,26,35)(H,28,34)(H,31,32)(H3,24,29,30)

InChI Key

RMUSSDXMUOCMGR-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
Axinella carteri	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Acylphloroglucinol derivative
Butyrophenone
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
Benzenetriol
Phloroglucinol derivative
Benzoyl
Aryl alkyl ketone
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Cyclic ketone
Enol
Polyol
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	1.17	ALOGPS
logP	-0.88	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	13.02	ChemAxon
pKa (Strongest Basic)	8.89	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	189.18 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	134.05 m³·mol⁻¹	ChemAxon
Polarizability	52.32 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-bromo-n-{[2-(2-imino-1,3-dihydroimidazol-4-yl)-5-oxo-6-{8-oxo-1h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-ylidene}-1h,2h,3h-[1,3]diazolo[1,2-a]imidazol-3-yl]methyl}-1h-pyrrole-2-carboxamide (NP0204371)

MOL for NP0204371 (4-bromo-n-{[2-(2-imino-1,3-dihydroimidazol-4-yl)-5-oxo-6-{8-oxo-1h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-ylidene}-1h,2h,3h-[1,3]diazolo[1,2-a]imidazol-3-yl]methyl}-1h-pyrrole-2-carboxamide)

3D MOL for NP0204371 (4-bromo-n-{[2-(2-imino-1,3-dihydroimidazol-4-yl)-5-oxo-6-{8-oxo-1h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-ylidene}-1h,2h,3h-[1,3]diazolo[1,2-a]imidazol-3-yl]methyl}-1h-pyrrole-2-carboxamide)

3D SDF for NP0204371 (4-bromo-n-{[2-(2-imino-1,3-dihydroimidazol-4-yl)-5-oxo-6-{8-oxo-1h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-ylidene}-1h,2h,3h-[1,3]diazolo[1,2-a]imidazol-3-yl]methyl}-1h-pyrrole-2-carboxamide)

3D-SDF for NP0204371 (4-bromo-n-{[2-(2-imino-1,3-dihydroimidazol-4-yl)-5-oxo-6-{8-oxo-1h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-ylidene}-1h,2h,3h-[1,3]diazolo[1,2-a]imidazol-3-yl]methyl}-1h-pyrrole-2-carboxamide)

PDB for NP0204371 (4-bromo-n-{[2-(2-imino-1,3-dihydroimidazol-4-yl)-5-oxo-6-{8-oxo-1h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-ylidene}-1h,2h,3h-[1,3]diazolo[1,2-a]imidazol-3-yl]methyl}-1h-pyrrole-2-carboxamide)

3D PDB for NP0204371 (4-bromo-n-{[2-(2-imino-1,3-dihydroimidazol-4-yl)-5-oxo-6-{8-oxo-1h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-ylidene}-1h,2h,3h-[1,3]diazolo[1,2-a]imidazol-3-yl]methyl}-1h-pyrrole-2-carboxamide)

SMILES for NP0204371 (4-bromo-n-{[2-(2-imino-1,3-dihydroimidazol-4-yl)-5-oxo-6-{8-oxo-1h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-ylidene}-1h,2h,3h-[1,3]diazolo[1,2-a]imidazol-3-yl]methyl}-1h-pyrrole-2-carboxamide)

INCHI for NP0204371 (4-bromo-n-{[2-(2-imino-1,3-dihydroimidazol-4-yl)-5-oxo-6-{8-oxo-1h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-ylidene}-1h,2h,3h-[1,3]diazolo[1,2-a]imidazol-3-yl]methyl}-1h-pyrrole-2-carboxamide)

Structure for NP0204371 (4-bromo-n-{[2-(2-imino-1,3-dihydroimidazol-4-yl)-5-oxo-6-{8-oxo-1h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-ylidene}-1h,2h,3h-[1,3]diazolo[1,2-a]imidazol-3-yl]methyl}-1h-pyrrole-2-carboxamide)

3D Structure for NP0204371 (4-bromo-n-{[2-(2-imino-1,3-dihydroimidazol-4-yl)-5-oxo-6-{8-oxo-1h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-ylidene}-1h,2h,3h-[1,3]diazolo[1,2-a]imidazol-3-yl]methyl}-1h-pyrrole-2-carboxamide)