NP-MRD: Showing NP-Card for 4-bromo-n-[3-(2,5-dihydroxyimidazol-4-ylidene)-2-hydroxypropyl]-1h-pyrrole-2-carboxamide (NP0211680)

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Record Information

Version

2.0

Created at

2022-09-05 10:03:52 UTC

Updated at

2022-09-05 10:03:52 UTC

NP-MRD ID

NP0211680

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-bromo-n-[3-(2,5-dihydroxyimidazol-4-ylidene)-2-hydroxypropyl]-1h-pyrrole-2-carboxamide

Description

4-Bromo-N-[3-(2,5-dihydroxy-4H-imidazol-4-ylidene)-2-hydroxypropyl]-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-bromo-n-[3-(2,5-dihydroxyimidazol-4-ylidene)-2-hydroxypropyl]-1h-pyrrole-2-carboxamide is found in Axinella verrucosa. Based on a literature review very few articles have been published on 4-bromo-N-[3-(2,5-dihydroxy-4H-imidazol-4-ylidene)-2-hydroxypropyl]-1H-pyrrole-2-carboxamide.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
    2.0168    0.2715   -1.9733 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8742    0.5671   -0.7792 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6952    1.1053   -0.2592 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4690    1.3569   -1.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0419    0.0860   -1.5813 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2159   -0.6306   -2.4090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4015   -0.7331   -0.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5942   -0.5959    0.1680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6074    0.2751   -0.3080 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6538    0.1437    0.4678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8342    0.8480    0.2949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3464   -0.8148    1.4655 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1515   -1.2670    1.3201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4731   -2.2088    2.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9969    0.3409    0.1312 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2222   -0.1787   -0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0173   -0.2370    0.9310 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8127   -0.8690    1.0596 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.2422    0.2567    1.9593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0450    0.5911    1.4463 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6140    1.3573    0.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2356    1.8963   -0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429    2.0160   -1.9293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9961    0.3448   -2.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0882   -1.5387   -2.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6738   -1.3967    0.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0886    1.2905   -0.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8152   -3.1214    2.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5509   -0.5012   -1.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5643    0.3479    2.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2779    0.9977    2.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 20 15  1  0
 13  8  1  0
  6 25  1  0
  5 24  1  6
  4 22  1  0
  4 23  1  0
  3 21  1  0
 16 29  1  0
 19 30  1  0
 20 31  1  0
  7 26  1  0
 11 27  1  0
 14 28  1  0
M  END


  Mrv1652309052212032D          

 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
    3.2755   -0.3861    0.0000 O   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
    3.9899   -2.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6574   -2.9335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4024   -3.7181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8874   -4.3856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5774   -3.7181    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3225   -2.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5379   -2.6786    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
    0.3314   -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
  7  5  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0211680

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(CNC(=O)C1=CC(Br)=CN1)C=C1N=C(O)N=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H11BrN4O4/c12-5-1-7(13-3-5)9(18)14-4-6(17)2-8-10(19)16-11(20)15-8/h1-3,6,13,17H,4H2,(H,14,18)(H2,15,16,19,20)

> <INCHI_KEY>
ARVRQRRPZHARDM-UHFFFAOYSA-N

> <FORMULA>
C11H11BrN4O4

> <MOLECULAR_WEIGHT>
343.137

> <EXACT_MASS>
341.996368

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
28.984815224568266

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-bromo-N-[3-(2,5-dihydroxy-4H-imidazol-4-ylidene)-2-hydroxypropyl]-1H-pyrrole-2-carboxamide

> <JCHEM_LOGP>
0.13807472333333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
6.10828742530556

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1950254548674284

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0981788390672298

> <JCHEM_POLAR_SURFACE_AREA>
130.3

> <JCHEM_REFRACTIVITY>
74.444

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-bromo-N-[3-(2,5-dihydroxyimidazol-4-ylidene)-2-hydroxypropyl]-1H-pyrrole-2-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-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  O   UNK     0       6.114  -0.721   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.448  -3.031   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.448  -4.571   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       8.694  -5.476   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       8.218  -6.941   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.123  -8.186   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       6.678  -6.941   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       6.202  -5.476   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.737  -5.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.780  -2.261   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.627  -2.887   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.658  -1.743   0.000  0.00  0.00           C+0
HETATM   18 Br   UNK     0      -3.189  -1.904   0.000  0.00  0.00          Br+0
HETATM   19  C   UNK     0      -0.888  -0.409   0.000  0.00  0.00           C+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   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15    2   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₁BrN₄O₄

Average Mass

343.1370 Da

Monoisotopic Mass

341.99637 Da

IUPAC Name

4-bromo-N-[3-(2,5-dihydroxy-4H-imidazol-4-ylidene)-2-hydroxypropyl]-1H-pyrrole-2-carboxamide

Traditional Name

4-bromo-N-[3-(2,5-dihydroxyimidazol-4-ylidene)-2-hydroxypropyl]-1H-pyrrole-2-carboxamide

CAS Registry Number

Not Available

SMILES

OC(CNC(=O)C1=CC(Br)=CN1)C=C1N=C(O)N=C1O

InChI Identifier

InChI=1S/C11H11BrN4O4/c12-5-1-7(13-3-5)9(18)14-4-6(17)2-8-10(19)16-11(20)15-8/h1-3,6,13,17H,4H2,(H,14,18)(H2,15,16,19,20)

InChI Key

ARVRQRRPZHARDM-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 verrucosa	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
Aryl bromide
Substituted pyrrole
Heteroaromatic compound
Dicarboximide
Pyrrole
Carboxamide group
Urea
Secondary carboxylic acid amide
Carbonic acid derivative
Secondary alcohol
Carboxylic acid derivative
Azacycle
Organobromide
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Alcohol
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	0.14	ChemAxon
pKa (Strongest Acidic)	3.2	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	130.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	74.44 m³·mol⁻¹	ChemAxon
Polarizability	28.98 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

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

73838039

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-[3-(2,5-dihydroxyimidazol-4-ylidene)-2-hydroxypropyl]-1h-pyrrole-2-carboxamide (NP0211680)

MOL for NP0211680 (4-bromo-n-[3-(2,5-dihydroxyimidazol-4-ylidene)-2-hydroxypropyl]-1h-pyrrole-2-carboxamide)

3D MOL for NP0211680 (4-bromo-n-[3-(2,5-dihydroxyimidazol-4-ylidene)-2-hydroxypropyl]-1h-pyrrole-2-carboxamide)

3D SDF for NP0211680 (4-bromo-n-[3-(2,5-dihydroxyimidazol-4-ylidene)-2-hydroxypropyl]-1h-pyrrole-2-carboxamide)

3D-SDF for NP0211680 (4-bromo-n-[3-(2,5-dihydroxyimidazol-4-ylidene)-2-hydroxypropyl]-1h-pyrrole-2-carboxamide)

PDB for NP0211680 (4-bromo-n-[3-(2,5-dihydroxyimidazol-4-ylidene)-2-hydroxypropyl]-1h-pyrrole-2-carboxamide)

3D PDB for NP0211680 (4-bromo-n-[3-(2,5-dihydroxyimidazol-4-ylidene)-2-hydroxypropyl]-1h-pyrrole-2-carboxamide)

SMILES for NP0211680 (4-bromo-n-[3-(2,5-dihydroxyimidazol-4-ylidene)-2-hydroxypropyl]-1h-pyrrole-2-carboxamide)

INCHI for NP0211680 (4-bromo-n-[3-(2,5-dihydroxyimidazol-4-ylidene)-2-hydroxypropyl]-1h-pyrrole-2-carboxamide)

Structure for NP0211680 (4-bromo-n-[3-(2,5-dihydroxyimidazol-4-ylidene)-2-hydroxypropyl]-1h-pyrrole-2-carboxamide)

3D Structure for NP0211680 (4-bromo-n-[3-(2,5-dihydroxyimidazol-4-ylidene)-2-hydroxypropyl]-1h-pyrrole-2-carboxamide)