NP-MRD: Showing NP-Card for 4,5-dibromo-n-{3-[(4z)-5-hydroxy-2-imino-3h-imidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide (NP0210376)

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Record Information

Version

2.0

Created at

2022-09-05 08:09:23 UTC

Updated at

2022-09-05 08:09:23 UTC

NP-MRD ID

NP0210376

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

4,5-Dibromo-N-{3-[(5Z)-4-hydroxy-2-imino-2,5-dihydro-1H-imidazol-5-ylidene]propyl}-1H-pyrrole-2-carboxamide belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. 4,5-dibromo-n-{3-[(4z)-5-hydroxy-2-imino-3h-imidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide is found in Agelas clathrodes and Agelas dispar. Based on a literature review very few articles have been published on 4,5-dibromo-N-{3-[(5Z)-4-hydroxy-2-imino-2,5-dihydro-1H-imidazol-5-ylidene]propyl}-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
   -6.3678   -0.5519    2.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3332   -0.6594    2.2264 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8378   -0.2950    1.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4273    0.2337   -0.0630 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5778    0.4658   -0.9832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8596    0.9876   -2.2362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2482    0.0887   -0.4966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1286    0.1827   -1.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8349   -0.2306   -0.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0469    1.0221   -0.5627 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3437    0.7956   -0.0157 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2547   -0.1418   -0.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8881   -0.7943   -1.5722 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5776   -0.3571    0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5193   -1.2448   -0.4504 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6362   -1.1379    0.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2785   -2.0886    0.2824 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.3453   -0.1899    1.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4452    0.4328    2.7697 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.0968    0.2584    1.0793 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4263   -0.3886    0.8121 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5225    1.8831   -2.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1290    0.5701   -2.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9139   -0.6289    0.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4078   -1.0215   -1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0721    1.3569   -1.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5354    1.7899   -0.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6466    1.3360    0.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4664   -1.9136   -1.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6154    0.9751    1.6321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6825   -0.7346    1.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  3 21  1  0
 21  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 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  5  1  0
 20 14  1  0
  6 22  1  0
  2  1  1  0
 21 31  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 15 29  1  0
 20 30  1  0
M  END


  Mrv1652309052210092D          

 20 21  0  0  0  0            999 V2000
   -1.2707   -4.1539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9351   -3.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3476   -2.6857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7956   -2.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9671   -1.2657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0419   -2.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6725   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3870   -2.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8159   -2.4082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5304   -1.1707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2449   -2.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9986   -2.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5506   -2.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3711   -2.5995    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.1381   -3.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4736   -4.1539    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.3311   -3.2287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1282   -3.2287    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
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 13 19  1  0  0  0  0
  6 20  1  0  0  0  0
  2 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0210376

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=NC(=N)N\C1=C/CCNC(=O)C1=CC(Br)=C(Br)N1

> <INCHI_IDENTIFIER>
InChI=1S/C11H11Br2N5O2/c12-5-4-7(16-8(5)13)9(19)15-3-1-2-6-10(20)18-11(14)17-6/h2,4,16H,1,3H2,(H,15,19)(H3,14,17,18,20)/b6-2-

> <INCHI_KEY>
OZDXBLQPTGBKSW-KXFIGUGUSA-N

> <FORMULA>
C11H11Br2N5O2

> <MOLECULAR_WEIGHT>
405.05

> <EXACT_MASS>
402.927951

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
32.5273174105901

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-0.8145928303167872

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.150650456905982

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.5607938193320985

> <JCHEM_PKA_STRONGEST_BASIC>
16.85078323058267

> <JCHEM_POLAR_SURFACE_AREA>
113.35999999999999

> <JCHEM_REFRACTIVITY>
92.59160000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4,5-dibromo-N-{3-[(4Z)-5-hydroxy-2-imino-3H-imidazol-4-ylidene]propyl}-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  N   UNK     0      -2.372  -7.754   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -1.746  -6.347   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -2.516  -5.013   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.485  -3.869   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.805  -2.363   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.078  -4.495   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.255  -3.725   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.589  -4.495   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.923  -3.725   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       5.256  -4.495   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       6.590  -3.725   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.590  -2.185   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.924  -4.495   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.331  -3.869   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.361  -5.013   0.000  0.00  0.00           C+0
HETATM   16 Br   UNK     0      11.893  -4.852   0.000  0.00  0.00          Br+0
HETATM   17  C   UNK     0       9.591  -6.347   0.000  0.00  0.00           C+0
HETATM   18 Br   UNK     0      10.217  -7.754   0.000  0.00  0.00          Br+0
HETATM   19  N   UNK     0       8.085  -6.027   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0      -0.239  -6.027   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   13                                                       
CONECT   20    6    2                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₁Br₂N₅O₂

Average Mass

405.0500 Da

Monoisotopic Mass

402.92795 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC1=NC(=N)N\C1=C/CCNC(=O)C1=CC(Br)=C(Br)N1

InChI Identifier

InChI=1S/C11H11Br2N5O2/c12-5-4-7(16-8(5)13)9(19)15-3-1-2-6-10(20)18-11(14)17-6/h2,4,16H,1,3H2,(H,15,19)(H3,14,17,18,20)/b6-2-

InChI Key

OZDXBLQPTGBKSW-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
Agelas clathrodes	LOTUS Database	35616633
Agelas dispar	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
2-heteroaryl carboxamide
Pyrrole-2-carboxamide
Pyrrole-2-carboxylic acid or derivatives
Aryl bromide
Aryl halide
Imidazolinone
Substituted pyrrole
2-imidazoline
Heteroaromatic compound
Pyrrole
Carboxamide group
Guanidine
Secondary carboxylic acid amide
N-acylimine
Organic 1,3-dipolar compound
Organoheterocyclic compound
Azacycle
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Hydrocarbon derivative
Amine
Organic nitrogen compound
Carbonyl group
Organic oxide
Organic oxygen compound
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	-0.81	ChemAxon
pKa (Strongest Acidic)	-2.6	ChemAxon
pKa (Strongest Basic)	16.85	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	113.36 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	92.59 m³·mol⁻¹	ChemAxon
Polarizability	32.53 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

8245362

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10069822

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)-5-hydroxy-2-imino-3h-imidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide (NP0210376)

MOL for NP0210376 (4,5-dibromo-n-{3-[(4z)-5-hydroxy-2-imino-3h-imidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide)

3D MOL for NP0210376 (4,5-dibromo-n-{3-[(4z)-5-hydroxy-2-imino-3h-imidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide)

3D SDF for NP0210376 (4,5-dibromo-n-{3-[(4z)-5-hydroxy-2-imino-3h-imidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide)

3D-SDF for NP0210376 (4,5-dibromo-n-{3-[(4z)-5-hydroxy-2-imino-3h-imidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide)

PDB for NP0210376 (4,5-dibromo-n-{3-[(4z)-5-hydroxy-2-imino-3h-imidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide)

3D PDB for NP0210376 (4,5-dibromo-n-{3-[(4z)-5-hydroxy-2-imino-3h-imidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide)

SMILES for NP0210376 (4,5-dibromo-n-{3-[(4z)-5-hydroxy-2-imino-3h-imidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide)

INCHI for NP0210376 (4,5-dibromo-n-{3-[(4z)-5-hydroxy-2-imino-3h-imidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide)

Structure for NP0210376 (4,5-dibromo-n-{3-[(4z)-5-hydroxy-2-imino-3h-imidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide)

3D Structure for NP0210376 (4,5-dibromo-n-{3-[(4z)-5-hydroxy-2-imino-3h-imidazol-4-ylidene]propyl}-1h-pyrrole-2-carboxamide)