NP-MRD: Showing NP-Card for 4-bromo-n-[(2s)-2-{4-[(4z)-8-hydroxy-1h,5h,6h-pyrrolo[2,3-c]azepin-4-ylidene]-2-imino-5-oxoimidazolidin-1-yl}-3-(2-imino-1,3-dihydroimidazol-4-yl)propyl]-1h-pyrrole-2-carboxamide (NP0240934)

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Record Information

Version

2.0

Created at

2022-09-07 00:52:28 UTC

Updated at

2022-09-07 00:52:29 UTC

NP-MRD ID

NP0240934

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-bromo-n-[(2s)-2-{4-[(4z)-8-hydroxy-1h,5h,6h-pyrrolo[2,3-c]azepin-4-ylidene]-2-imino-5-oxoimidazolidin-1-yl}-3-(2-imino-1,3-dihydroimidazol-4-yl)propyl]-1h-pyrrole-2-carboxamide

Description

4-Bromo-N-[(2S)-2-{4-[(4Z)-8-hydroxy-1H,4H,5H,6H-pyrrolo[2,3-c]azepin-4-ylidene]-2-imino-5-oxoimidazolidin-1-yl}-3-(2-imino-2,3-dihydro-1H-imidazol-4-yl)propyl]-1H-pyrrole-2-carboxamide belongs to the class of organic compounds known as pyrroloazepines. Pyrroloazepines are compounds containing a pyrroloazepine moiety, which is a bicyclic heterocycle which consists of a pyrrole ring fused to an azepine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Azepine is a 7-membered ring consisting of six carbon and one nitrogen atom. 4-bromo-n-[(2s)-2-{4-[(4z)-8-hydroxy-1h,5h,6h-pyrrolo[2,3-c]azepin-4-ylidene]-2-imino-5-oxoimidazolidin-1-yl}-3-(2-imino-1,3-dihydroimidazol-4-yl)propyl]-1h-pyrrole-2-carboxamide is found in Stylissa carteri. Based on a literature review very few articles have been published on 4-bromo-N-[(2S)-2-{4-[(4Z)-8-hydroxy-1H,4H,5H,6H-pyrrolo[2,3-c]azepin-4-ylidene]-2-imino-5-oxoimidazolidin-1-yl}-3-(2-imino-2,3-dihydro-1H-imidazol-4-yl)propyl]-1H-pyrrole-2-carboxamide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072202522D          

 36 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072202522D          

 36 40  0  0  1  0            999 V2000
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 34 36  1  0  0  0  0
 31 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0240934

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=NCC\C(=C2\NC(=N)N([C@H](CNC(=O)C3=CC(Br)=CN3)CC3=CNC(=N)N3)C2=O)C2=C1NC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C22H23BrN10O3/c23-10-5-15(28-7-10)18(34)29-9-12(6-11-8-30-21(24)31-11)33-20(36)17(32-22(33)25)14-2-4-27-19(35)16-13(14)1-3-26-16/h1,3,5,7-8,12,26,28H,2,4,6,9H2,(H2,25,32)(H,27,35)(H,29,34)(H3,24,30,31)/b17-14-/t12-/m0/s1

> <INCHI_KEY>
WOUYWOYRNOEAKO-SEQUMDBASA-N

> <FORMULA>
C22H23BrN10O3

> <MOLECULAR_WEIGHT>
555.397

> <EXACT_MASS>
554.113798

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
52.0980026019252

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-bromo-N-[(2S)-2-{4-[(4Z)-8-hydroxy-1H,4H,5H,6H-pyrrolo[2,3-c]azepin-4-ylidene]-2-imino-5-oxoimidazolidin-1-yl}-3-(2-imino-2,3-dihydro-1H-imidazol-4-yl)propyl]-1H-pyrrole-2-carboxamide

> <JCHEM_LOGP>
-0.48836700076070816

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
14.219019274721084

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.011430573355472

> <JCHEM_PKA_STRONGEST_BASIC>
7.547107485681816

> <JCHEM_POLAR_SURFACE_AREA>
197.36999999999998

> <JCHEM_REFRACTIVITY>
157.5566

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-bromo-N-[(2S)-2-{4-[(4Z)-8-hydroxy-1H,5H,6H-pyrrolo[2,3-c]azepin-4-ylidene]-2-imino-5-oxoimidazolidin-1-yl}-3-(2-imino-1,3-dihydroimidazol-4-yl)propyl]-1H-pyrrole-2-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  N   UNK     0       0.746 -10.193   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       1.906  -9.179   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.768  -7.646   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       3.184  -7.040   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.527  -5.539   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.028  -5.196   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.696  -3.809   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       5.028  -2.421   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       3.527  -2.079   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.184  -0.577   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.323  -3.039   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       0.858  -2.563   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -0.047  -3.809   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.858  -5.055   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.323  -4.579   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.197  -8.200   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.731  -8.062   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0       3.407  -9.522   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       4.013 -10.938   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.542 -11.122   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       6.147 -12.538   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       7.676 -12.722   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.600 -11.490   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.281 -14.138   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.782 -14.481   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.920 -16.015   0.000  0.00  0.00           C+0
HETATM   27 Br   UNK     0      11.242 -16.804   0.000  0.00  0.00          Br+0
HETATM   28  C   UNK     0       8.504 -16.620   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       7.491 -15.460   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       3.089 -12.170   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.694 -13.587   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.904 -14.909   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       3.917 -16.068   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       5.334 -15.463   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0       6.656 -16.253   0.000  0.00  0.00           N+0
HETATM   36  N   UNK     0       5.195 -13.929   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   11    5                                                  
CONECT   16    4   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    2   19                                                  
CONECT   19   18   20   30                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   24                                                       
CONECT   30   19   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   31                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₃BrN₁₀O₃

Average Mass

555.3970 Da

Monoisotopic Mass

554.11380 Da

IUPAC Name

4-bromo-N-[(2S)-2-{4-[(4Z)-8-hydroxy-1H,4H,5H,6H-pyrrolo[2,3-c]azepin-4-ylidene]-2-imino-5-oxoimidazolidin-1-yl}-3-(2-imino-2,3-dihydro-1H-imidazol-4-yl)propyl]-1H-pyrrole-2-carboxamide

Traditional Name

4-bromo-N-[(2S)-2-{4-[(4Z)-8-hydroxy-1H,5H,6H-pyrrolo[2,3-c]azepin-4-ylidene]-2-imino-5-oxoimidazolidin-1-yl}-3-(2-imino-1,3-dihydroimidazol-4-yl)propyl]-1H-pyrrole-2-carboxamide

CAS Registry Number

Not Available

SMILES

OC1=NCC\C(=C2\NC(=N)N([C@H](CNC(=O)C3=CC(Br)=CN3)CC3=CNC(=N)N3)C2=O)C2=C1NC=C2

InChI Identifier

InChI=1S/C22H23BrN10O3/c23-10-5-15(28-7-10)18(34)29-9-12(6-11-8-30-21(24)31-11)33-20(36)17(32-22(33)25)14-2-4-27-19(35)16-13(14)1-3-26-16/h1,3,5,7-8,12,26,28H,2,4,6,9H2,(H2,25,32)(H,27,35)(H,29,34)(H3,24,30,31)/b17-14-/t12-/m0/s1

InChI Key

WOUYWOYRNOEAKO-SEQUMDBASA-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 pyrroloazepines. Pyrroloazepines are compounds containing a pyrroloazepine moiety, which is a bicyclic heterocycle which consists of a pyrrole ring fused to an azepine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Azepine is a 7-membered ring consisting of six carbon and one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrroloazepines

Sub Class

Not Available

Direct Parent

Pyrroloazepines

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Pyrroloazepine
2-heteroaryl carboxamide
Pyrrole-2-carboxamide
Pyrrole-2-carboxylic acid or derivatives
Azepine
Aryl bromide
Aryl halide
Imidazolidinone
Substituted pyrrole
Azole
Imidazole
Imidazolidine
Heteroaromatic compound
Pyrrole
Cyclic carboximidic acid
Secondary carboxylic acid amide
Carboxamide group
Guanidine
Azacycle
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Organic 1,3-dipolar compound
Carboxylic acid derivative
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Imine
Organohalogen compound
Carbonyl group
Organic oxide
Organic nitrogen compound
Organobromide
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	-0.49	ChemAxon
pKa (Strongest Acidic)	9.01	ChemAxon
pKa (Strongest Basic)	7.55	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	197.37 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	157.56 m³·mol⁻¹	ChemAxon
Polarizability	52.1 Å³	ChemAxon
Number of Rings	5	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

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

163189474

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-[(2s)-2-{4-[(4z)-8-hydroxy-1h,5h,6h-pyrrolo[2,3-c]azepin-4-ylidene]-2-imino-5-oxoimidazolidin-1-yl}-3-(2-imino-1,3-dihydroimidazol-4-yl)propyl]-1h-pyrrole-2-carboxamide (NP0240934)

MOL for NP0240934 (4-bromo-n-[(2s)-2-{4-[(4z)-8-hydroxy-1h,5h,6h-pyrrolo[2,3-c]azepin-4-ylidene]-2-imino-5-oxoimidazolidin-1-yl}-3-(2-imino-1,3-dihydroimidazol-4-yl)propyl]-1h-pyrrole-2-carboxamide)

3D MOL for NP0240934 (4-bromo-n-[(2s)-2-{4-[(4z)-8-hydroxy-1h,5h,6h-pyrrolo[2,3-c]azepin-4-ylidene]-2-imino-5-oxoimidazolidin-1-yl}-3-(2-imino-1,3-dihydroimidazol-4-yl)propyl]-1h-pyrrole-2-carboxamide)

3D SDF for NP0240934 (4-bromo-n-[(2s)-2-{4-[(4z)-8-hydroxy-1h,5h,6h-pyrrolo[2,3-c]azepin-4-ylidene]-2-imino-5-oxoimidazolidin-1-yl}-3-(2-imino-1,3-dihydroimidazol-4-yl)propyl]-1h-pyrrole-2-carboxamide)

3D-SDF for NP0240934 (4-bromo-n-[(2s)-2-{4-[(4z)-8-hydroxy-1h,5h,6h-pyrrolo[2,3-c]azepin-4-ylidene]-2-imino-5-oxoimidazolidin-1-yl}-3-(2-imino-1,3-dihydroimidazol-4-yl)propyl]-1h-pyrrole-2-carboxamide)

PDB for NP0240934 (4-bromo-n-[(2s)-2-{4-[(4z)-8-hydroxy-1h,5h,6h-pyrrolo[2,3-c]azepin-4-ylidene]-2-imino-5-oxoimidazolidin-1-yl}-3-(2-imino-1,3-dihydroimidazol-4-yl)propyl]-1h-pyrrole-2-carboxamide)

3D PDB for NP0240934 (4-bromo-n-[(2s)-2-{4-[(4z)-8-hydroxy-1h,5h,6h-pyrrolo[2,3-c]azepin-4-ylidene]-2-imino-5-oxoimidazolidin-1-yl}-3-(2-imino-1,3-dihydroimidazol-4-yl)propyl]-1h-pyrrole-2-carboxamide)

SMILES for NP0240934 (4-bromo-n-[(2s)-2-{4-[(4z)-8-hydroxy-1h,5h,6h-pyrrolo[2,3-c]azepin-4-ylidene]-2-imino-5-oxoimidazolidin-1-yl}-3-(2-imino-1,3-dihydroimidazol-4-yl)propyl]-1h-pyrrole-2-carboxamide)

INCHI for NP0240934 (4-bromo-n-[(2s)-2-{4-[(4z)-8-hydroxy-1h,5h,6h-pyrrolo[2,3-c]azepin-4-ylidene]-2-imino-5-oxoimidazolidin-1-yl}-3-(2-imino-1,3-dihydroimidazol-4-yl)propyl]-1h-pyrrole-2-carboxamide)

Structure for NP0240934 (4-bromo-n-[(2s)-2-{4-[(4z)-8-hydroxy-1h,5h,6h-pyrrolo[2,3-c]azepin-4-ylidene]-2-imino-5-oxoimidazolidin-1-yl}-3-(2-imino-1,3-dihydroimidazol-4-yl)propyl]-1h-pyrrole-2-carboxamide)

3D Structure for NP0240934 (4-bromo-n-[(2s)-2-{4-[(4z)-8-hydroxy-1h,5h,6h-pyrrolo[2,3-c]azepin-4-ylidene]-2-imino-5-oxoimidazolidin-1-yl}-3-(2-imino-1,3-dihydroimidazol-4-yl)propyl]-1h-pyrrole-2-carboxamide)