NP-MRD: Showing NP-Card for 5-{2,3-dibromo-8-oxo-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-yl}-2-imino-3h-imidazol-4-one (NP0233260)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 14:47:46 UTC

Updated at

2022-09-06 14:47:46 UTC

NP-MRD ID

NP0233260

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-{2,3-dibromo-8-oxo-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-yl}-2-imino-3h-imidazol-4-one

Description

3-Bromohymenialdisine 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. 5-{2,3-dibromo-8-oxo-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-yl}-2-imino-3h-imidazol-4-one is found in Stylissa carteri. 5-{2,3-dibromo-8-oxo-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-yl}-2-imino-3h-imidazol-4-one was first documented in 2018 (PMID: 29353267). Based on a literature review very few articles have been published on 3-bromohymenialdisine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 31  0  0  0  0  0  0  0  0999 V2000
    4.6596    1.0875   -2.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5923    1.2719   -1.5549 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5410    0.9810   -0.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3601    0.3874   -1.3185 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4771    0.2061   -0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1262   -0.3928   -0.5821 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1070   -1.5894    0.3680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8546   -2.6581   -0.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2050   -2.3943    0.3266 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7502   -1.1383    0.6606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8121   -1.1242    1.3105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2211    0.1717    0.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8863    1.3418    0.5148 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1085    2.3841    0.1093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5505    4.2356    0.1392 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9145    1.8815   -0.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5234    2.9154   -1.0192 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9745    0.5154   -0.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0514    0.7111    0.8280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5114    0.7219    1.9503 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3612    1.1990    0.5419 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0341   -0.7702   -1.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1956   -1.2283    1.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1117   -2.0623    0.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5384   -3.6047    0.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8284   -2.8383   -1.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8291   -3.2409    0.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8475    1.4053    0.9051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0598    1.6251    1.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
 18 12  2  0
 12 13  1  0
 12 10  1  0
 10 11  2  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  3 21  1  0
 21 19  1  0
 19 20  2  0
 13 14  1  0
 19  5  1  0
  6 18  1  0
 13 28  1  0
  9 27  1  0
  8 25  1  0
  8 26  1  0
  7 23  1  0
  7 24  1  0
  6 22  1  6
  2  1  1  0
 21 29  1  0
M  END


  Mrv1652309062216472D          

 20 22  0  0  0  0            999 V2000
    1.8631    3.2144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4844    2.6716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4104    1.8499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690    1.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569   -0.9488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -1.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690   -1.9367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6130   -0.2055    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6680    1.2466    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7118    2.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5335    2.0730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2887    2.8552    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 11 17  2  0  0  0  0
  5 17  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  2 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0233260

> <DATABASE_NAME>
NP-MRD

> <SMILES>
BrC1=C(Br)C2=C(N1)C(=O)NCCC2C1=NC(=N)NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H9Br2N5O2/c12-5-4-3(6-10(20)18-11(14)17-6)1-2-15-9(19)7(4)16-8(5)13/h3,16H,1-2H2,(H,15,19)(H2,14,18,20)

> <INCHI_KEY>
XGURAOHYBRKUPL-UHFFFAOYSA-N

> <FORMULA>
C11H9Br2N5O2

> <MOLECULAR_WEIGHT>
403.034

> <EXACT_MASS>
400.912301

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
30.396624792562832

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{2,3-dibromo-8-oxo-1H,4H,5H,6H,7H,8H-pyrrolo[2,3-c]azepin-4-yl}-2-imino-2,5-dihydro-1H-imidazol-5-one

> <JCHEM_LOGP>
0.7882660043333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.660067530884035

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.282932758903533

> <JCHEM_PKA_STRONGEST_BASIC>
-0.24128320071053844

> <JCHEM_POLAR_SURFACE_AREA>
110.19999999999999

> <JCHEM_REFRACTIVITY>
88.88739999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-{2,3-dibromo-8-oxo-1H,4H,5H,6H,7H-pyrrolo[2,3-c]azepin-4-yl}-2-imino-3H-imidazol-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  N   UNK     0       3.478   6.000   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       4.637   4.987   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       4.499   3.453   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.916   2.848   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   1.347   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.760   1.004   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.428  -0.384   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       7.760  -1.771   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       6.258  -2.114   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.916  -3.615   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.054  -1.154   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       3.590  -1.629   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       2.684  -0.384   0.000  0.00  0.00           C+0
HETATM   14 Br   UNK     0       1.144  -0.384   0.000  0.00  0.00          Br+0
HETATM   15  C   UNK     0       3.590   0.862   0.000  0.00  0.00           C+0
HETATM   16 Br   UNK     0       3.114   2.327   0.000  0.00  0.00          Br+0
HETATM   17  C   UNK     0       5.054   0.386   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.929   4.008   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.463   3.870   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0       6.139   5.330   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6   17                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   11    5                                                  
CONECT   18    4   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    2                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₉Br₂N₅O₂

Average Mass

403.0340 Da

Monoisotopic Mass

400.91230 Da

IUPAC Name

4-{2,3-dibromo-8-oxo-1H,4H,5H,6H,7H,8H-pyrrolo[2,3-c]azepin-4-yl}-2-imino-2,5-dihydro-1H-imidazol-5-one

Traditional Name

5-{2,3-dibromo-8-oxo-1H,4H,5H,6H,7H-pyrrolo[2,3-c]azepin-4-yl}-2-imino-3H-imidazol-4-one

CAS Registry Number

Not Available

SMILES

BrC1=C(Br)C2=C(N1)C(=O)NCCC2C1=NC(=N)NC1=O

InChI Identifier

InChI=1S/C11H9Br2N5O2/c12-5-4-3(6-10(20)18-11(14)17-6)1-2-15-9(19)7(4)16-8(5)13/h3,16H,1-2H2,(H,15,19)(H2,14,18,20)

InChI Key

XGURAOHYBRKUPL-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 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

Pyrroloazepine
2-heteroaryl carboxamide
Azepine
Substituted pyrrole
Imidazolinone
Aryl halide
Aryl bromide
Heteroaromatic compound
Pyrrole
3-imidazoline
Secondary carboxylic acid amide
Lactam
Carboxamide group
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Imine
Carbonyl group
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	0.79	ChemAxon
pKa (Strongest Acidic)	9.28	ChemAxon
pKa (Strongest Basic)	-0.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	110.2 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	88.89 m³·mol⁻¹	ChemAxon
Polarizability	30.4 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00049340

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

145740525

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hamed ANE, Schmitz R, Bergermann A, Totzke F, Kubbutat M, Muller WEG, Youssef DTA, Bishr MM, Kamel MS, Edrada-Ebel R, Watjen W, Proksch P: Bioactive pyrrole alkaloids isolated from the Red Sea: marine sponge Stylissa carteri. Z Naturforsch C J Biosci. 2018 Apr 25;73(5-6):199-210. doi: 10.1515/znc-2017-0161. [PubMed:29353267 ]
LOTUS database [Link]

Showing NP-Card for 5-{2,3-dibromo-8-oxo-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-yl}-2-imino-3h-imidazol-4-one (NP0233260)

MOL for NP0233260 (5-{2,3-dibromo-8-oxo-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-yl}-2-imino-3h-imidazol-4-one)

3D MOL for NP0233260 (5-{2,3-dibromo-8-oxo-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-yl}-2-imino-3h-imidazol-4-one)

3D SDF for NP0233260 (5-{2,3-dibromo-8-oxo-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-yl}-2-imino-3h-imidazol-4-one)

3D-SDF for NP0233260 (5-{2,3-dibromo-8-oxo-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-yl}-2-imino-3h-imidazol-4-one)

PDB for NP0233260 (5-{2,3-dibromo-8-oxo-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-yl}-2-imino-3h-imidazol-4-one)

3D PDB for NP0233260 (5-{2,3-dibromo-8-oxo-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-yl}-2-imino-3h-imidazol-4-one)

SMILES for NP0233260 (5-{2,3-dibromo-8-oxo-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-yl}-2-imino-3h-imidazol-4-one)

INCHI for NP0233260 (5-{2,3-dibromo-8-oxo-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-yl}-2-imino-3h-imidazol-4-one)

Structure for NP0233260 (5-{2,3-dibromo-8-oxo-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-yl}-2-imino-3h-imidazol-4-one)

3D Structure for NP0233260 (5-{2,3-dibromo-8-oxo-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-4-yl}-2-imino-3h-imidazol-4-one)