NP-MRD: Showing NP-Card for 4,5-dibromo-n-{3-[(4z)-2,5-dihydroxyimidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide (NP0190239)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 06:52:43 UTC

Updated at

2022-09-04 06:52:44 UTC

NP-MRD ID

NP0190239

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5-dibromo-n-{3-[(4z)-2,5-dihydroxyimidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide

Description

N-[3-[(2,5-Dioxotetrahydro-1H-imidazol)-4-ylidene]propyl]-4,5-dibromo-1H-pyrrole-2-carboxamide belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4. 4,5-dibromo-n-{3-[(4z)-2,5-dihydroxyimidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide is found in Didiscus oxeatus. Based on a literature review very few articles have been published on N-[3-[(2,5-Dioxotetrahydro-1H-imidazol)-4-ylidene]propyl]-4,5-dibromo-1H-pyrrole-2-carboxamide.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
    1.6363   -1.1700   -1.5451 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9169   -0.7435   -0.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0936   -1.0530    0.7001 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958   -1.8628    0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1252   -1.2994   -0.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6184    0.0291    0.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8852    0.2130    0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9107   -0.7660    0.2515 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0278   -0.2032    0.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2859   -0.8336    0.6427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8023    1.1678    0.8881 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5695    1.4479    0.7463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9552    2.6603    0.9439 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1164    0.0816   -0.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5905    0.6417    0.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7399    1.3414    0.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8133    2.3147    1.9534 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.9646    1.2037   -0.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4474    1.9896   -1.5648 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.9798    0.4487   -1.1775 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3578   -0.6772    1.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5150   -2.1420    1.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2323   -2.8440    0.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9423   -2.0470   -0.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6830   -1.1964   -1.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9311    0.8546    0.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3128   -1.7889    0.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2329    3.5264    0.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0996    0.5199    1.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9047    0.1863   -2.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18 20  1  0
  7 12  1  0
 12 13  1  0
 12 11  2  0
 11  9  1  0
 20 14  1  0
 10 27  1  0
  6 26  1  0
  5 24  1  0
  5 25  1  0
  4 22  1  0
  4 23  1  0
  3 21  1  0
 15 29  1  0
 20 30  1  0
 13 28  1  0
M  END


  Mrv1652309042208522D          

 20 21  0  0  0  0            999 V2000
    1.1321   -2.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1321   -1.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8465   -1.2111    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5610   -1.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2755   -1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9899   -1.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7044   -1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7907   -0.3906    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5976   -0.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9332    0.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0101   -0.9336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4581   -1.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6296   -2.3536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4176   -1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3361   -1.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8881   -0.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7086   -1.0198    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4756   -0.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8112    0.5346    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.3314   -0.3906    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 14 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0190239

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=N\C(=C/CCNC(=O)C2=CC(Br)=C(Br)N2)C(O)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C11H10Br2N4O3/c12-5-4-7(15-8(5)13)9(18)14-3-1-2-6-10(19)17-11(20)16-6/h2,4,15H,1,3H2,(H,14,18)(H2,16,17,19,20)/b6-2-

> <INCHI_KEY>
HSXRXYKWRAQPTE-KXFIGUGUSA-N

> <FORMULA>
C11H10Br2N4O3

> <MOLECULAR_WEIGHT>
406.034

> <EXACT_MASS>
403.911966

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
31.922027551755235

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,5-dibromo-N-{3-[(4Z)-2,5-dihydroxy-4H-imidazol-4-ylidene]propyl}-1H-pyrrole-2-carboxamide

> <JCHEM_LOGP>
1.5261789886666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
6.216320576973869

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.278031732503955

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0609429345928607

> <JCHEM_POLAR_SURFACE_AREA>
110.07

> <JCHEM_REFRACTIVITY>
80.64130000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4,5-dibromo-N-{3-[(4Z)-2,5-dihydroxyimidazol-4-ylidene]propyl}-1H-pyrrole-2-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0       2.113  -4.571   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.113  -3.031   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       3.447  -2.261   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.781  -3.031   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.114  -2.261   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.448  -3.031   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.782  -2.261   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       8.943  -0.729   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      10.449  -0.409   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.075   0.998   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      11.219  -1.743   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      10.188  -2.887   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.509  -4.393   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.780  -2.261   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.627  -2.887   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.658  -1.743   0.000  0.00  0.00           C+0
HETATM   17 Br   UNK     0      -3.189  -1.904   0.000  0.00  0.00          Br+0
HETATM   18  C   UNK     0      -0.888  -0.409   0.000  0.00  0.00           C+0
HETATM   19 Br   UNK     0      -1.514   0.998   0.000  0.00  0.00          Br+0
HETATM   20  N   UNK     0       0.619  -0.729   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12                                                            
CONECT   14    2   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   14                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₀Br₂N₄O₃

Average Mass

406.0340 Da

Monoisotopic Mass

403.91197 Da

IUPAC Name

4,5-dibromo-N-{3-[(4Z)-2,5-dihydroxy-4H-imidazol-4-ylidene]propyl}-1H-pyrrole-2-carboxamide

Traditional Name

4,5-dibromo-N-{3-[(4Z)-2,5-dihydroxyimidazol-4-ylidene]propyl}-1H-pyrrole-2-carboxamide

CAS Registry Number

Not Available

SMILES

OC1=N\C(=C/CCNC(=O)C2=CC(Br)=C(Br)N2)C(O)=N1

InChI Identifier

InChI=1S/C11H10Br2N4O3/c12-5-4-7(15-8(5)13)9(18)14-3-1-2-6-10(19)17-11(20)16-6/h2,4,15H,1,3H2,(H,14,18)(H2,16,17,19,20)/b6-2-

InChI Key

HSXRXYKWRAQPTE-KXFIGUGUSA-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
Didiscus oxeatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolidines

Sub Class

Imidazolidines

Direct Parent

Hydantoins

Alternative Parents

Substituents

Hydantoin
Alpha-amino acid or derivatives
2-heteroaryl carboxamide
Pyrrole-2-carboxamide
Pyrrole-2-carboxylic acid or derivatives
5-monosubstituted hydantoin
Ureide
N-acyl urea
Aryl halide
Substituted pyrrole
Aryl bromide
Heteroaromatic compound
Pyrrole
Dicarboximide
Carboxamide group
Urea
Secondary carboxylic acid amide
Carbonic acid derivative
Azacycle
Carboxylic acid derivative
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organohalogen compound
Organobromide
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	1.53	ChemAxon
pKa (Strongest Acidic)	3.28	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	110.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	80.64 m³·mol⁻¹	ChemAxon
Polarizability	31.92 Å³	ChemAxon
Number of Rings	2	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

Not Available

Chemspider ID

555676

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

640319

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,5-dibromo-n-{3-[(4z)-2,5-dihydroxyimidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide (NP0190239)

MOL for NP0190239 (4,5-dibromo-n-{3-[(4z)-2,5-dihydroxyimidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide)

3D MOL for NP0190239 (4,5-dibromo-n-{3-[(4z)-2,5-dihydroxyimidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide)

3D SDF for NP0190239 (4,5-dibromo-n-{3-[(4z)-2,5-dihydroxyimidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide)

3D-SDF for NP0190239 (4,5-dibromo-n-{3-[(4z)-2,5-dihydroxyimidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide)

PDB for NP0190239 (4,5-dibromo-n-{3-[(4z)-2,5-dihydroxyimidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide)

3D PDB for NP0190239 (4,5-dibromo-n-{3-[(4z)-2,5-dihydroxyimidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide)

SMILES for NP0190239 (4,5-dibromo-n-{3-[(4z)-2,5-dihydroxyimidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide)

INCHI for NP0190239 (4,5-dibromo-n-{3-[(4z)-2,5-dihydroxyimidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide)

Structure for NP0190239 (4,5-dibromo-n-{3-[(4z)-2,5-dihydroxyimidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide)

3D Structure for NP0190239 (4,5-dibromo-n-{3-[(4z)-2,5-dihydroxyimidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide)