NP-MRD: Showing NP-Card for 4,5-dibromo-n-[(2-{[(4,5-dibromo-1h-pyrrol-2-yl)formamido]methyl}-3,4-bis(2-imino-1,3-dihydroimidazol-4-yl)cyclobutyl)methyl]-1h-pyrrole-2-carboxamide (NP0245769)

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Record Information

Version

2.0

Created at

2022-09-07 06:58:23 UTC

Updated at

2022-09-07 06:58:24 UTC

NP-MRD ID

NP0245769

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5-dibromo-n-[(2-{[(4,5-dibromo-1h-pyrrol-2-yl)formamido]methyl}-3,4-bis(2-imino-1,3-dihydroimidazol-4-yl)cyclobutyl)methyl]-1h-pyrrole-2-carboxamide

Description

Dibromosceptrin belongs to the class of organic compounds known as 2-heteroaryl carboxamides. 2-Heteroaryl carboxamides are compounds containing a heteroaromatic ring that carries a carboxamide group. 4,5-dibromo-n-[(2-{[(4,5-dibromo-1h-pyrrol-2-yl)formamido]methyl}-3,4-bis(2-imino-1,3-dihydroimidazol-4-yl)cyclobutyl)methyl]-1h-pyrrole-2-carboxamide is found in Agelas conifera. Dibromosceptrin is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191515392D          

 38 42  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004191515392D          

 38 42  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0245769

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=NC=C(N1)C1C(CNC(=O)C2=CC(Br)=C(Br)N2)C(CNC(=O)C2=CC(Br)=C(Br)N2)C1C1=CN=C(N)N1

> <INCHI_IDENTIFIER>
InChI=1S/C22H22Br4N10O2/c23-9-1-11(33-17(9)25)19(37)29-3-7-8(4-30-20(38)12-2-10(24)18(26)34-12)16(14-6-32-22(28)36-14)15(7)13-5-31-21(27)35-13/h1-2,5-8,15-16,33-34H,3-4H2,(H,29,37)(H,30,38)(H3,27,31,35)(H3,28,32,36)

> <INCHI_KEY>
HCZXBTALDGQIPO-UHFFFAOYSA-N

> <FORMULA>
C22H22Br4N10O2

> <MOLECULAR_WEIGHT>
778.102

> <EXACT_MASS>
773.866072

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
63.20731712551228

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-{[2,3-bis(2-amino-1H-imidazol-5-yl)-4-{[(4,5-dibromo-1H-pyrrol-2-yl)formamido]methyl}cyclobutyl]methyl}-4,5-dibromo-1H-pyrrole-2-carboxamide

> <ALOGPS_LOGP>
3.15

> <JCHEM_LOGP>
1.24208251

> <ALOGPS_LOGS>
-4.86

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
12.7894180200997

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.988652664202773

> <JCHEM_PKA_STRONGEST_BASIC>
9.274567569631136

> <JCHEM_POLAR_SURFACE_AREA>
199.17999999999995

> <JCHEM_REFRACTIVITY>
157.5292

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dibromosceptrin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  N   UNK     0       0.602   3.268   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       1.507   2.023   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       3.047   2.023   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       3.523   0.558   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.277  -0.347   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.031   0.558   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       2.277  -1.887   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.366  -2.976   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.906  -2.976   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       5.676  -1.642   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       7.216  -1.642   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.986  -2.976   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.986  -0.309   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.360   1.098   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.504   2.129   0.000  0.00  0.00           C+0
HETATM   16 Br   UNK     0       8.343   3.660   0.000  0.00  0.00          Br+0
HETATM   17  C   UNK     0       9.838   1.359   0.000  0.00  0.00           C+0
HETATM   18 Br   UNK     0      11.245   1.985   0.000  0.00  0.00          Br+0
HETATM   19  N   UNK     0       9.518  -0.148   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       2.277  -4.065   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.277  -5.605   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       0.943  -6.375   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       0.943  -7.915   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.277  -8.685   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.390  -8.685   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.551 -10.217   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.058 -10.537   0.000  0.00  0.00           C+0
HETATM   28 Br   UNK     0      -2.684 -11.944   0.000  0.00  0.00          Br+0
HETATM   29  C   UNK     0      -2.828  -9.203   0.000  0.00  0.00           C+0
HETATM   30 Br   UNK     0      -4.359  -9.042   0.000  0.00  0.00          Br+0
HETATM   31  N   UNK     0      -1.797  -8.059   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0       1.188  -2.976   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.352  -2.976   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.257  -4.222   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0      -2.722  -3.746   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0      -2.722  -2.206   0.000  0.00  0.00           C+0
HETATM   37  N   UNK     0      -3.968  -1.301   0.000  0.00  0.00           N+0
HETATM   38  N   UNK     0      -1.257  -1.730   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    2                                                       
CONECT    7    5    8   32                                                  
CONECT    8    7    9   20                                                  
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    8   21   32                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   25                                                       
CONECT   32   20    7   33                                                  
CONECT   33   32   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   33                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₂Br₄N₁₀O₂

Average Mass

778.1020 Da

Monoisotopic Mass

773.86607 Da

IUPAC Name

N-{[2,3-bis(2-amino-1H-imidazol-5-yl)-4-{[(4,5-dibromo-1H-pyrrol-2-yl)formamido]methyl}cyclobutyl]methyl}-4,5-dibromo-1H-pyrrole-2-carboxamide

Traditional Name

dibromosceptrin

CAS Registry Number

Not Available

SMILES

NC1=NC=C(N1)C1C(CNC(=O)C2=CC(Br)=C(Br)N2)C(CNC(=O)C2=CC(Br)=C(Br)N2)C1C1=CN=C(N)N1

InChI Identifier

InChI=1S/C22H22Br4N10O2/c23-9-1-11(33-17(9)25)19(37)29-3-7-8(4-30-20(38)12-2-10(24)18(26)34-12)16(14-6-32-22(28)36-14)15(7)13-5-31-21(27)35-13/h1-2,5-8,15-16,33-34H,3-4H2,(H,29,37)(H,30,38)(H3,27,31,35)(H3,28,32,36)

InChI Key

HCZXBTALDGQIPO-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
Agelas conifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-heteroaryl carboxamides. 2-Heteroaryl carboxamides are compounds containing a heteroaromatic ring that carries a carboxamide group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

2-heteroaryl carboxamides

Alternative Parents

Substituents

2-heteroaryl carboxamide
Pyrrole-2-carboxamide
Pyrrole-2-carboxylic acid or derivatives
Aminoimidazole
Aryl bromide
Aryl halide
Substituted pyrrole
Azole
Imidazole
Pyrrole
Heteroaromatic compound
Amino acid or derivatives
Secondary carboxylic acid amide
Organoheterocyclic compound
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Primary amine
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Amine
Organopnictogen compound
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	3.15	ALOGPS
logP	1.24	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	10.99	ChemAxon
pKa (Strongest Basic)	9.27	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	199.18 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	157.53 m³·mol⁻¹	ChemAxon
Polarizability	63.21 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

164038

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-[(2-{[(4,5-dibromo-1h-pyrrol-2-yl)formamido]methyl}-3,4-bis(2-imino-1,3-dihydroimidazol-4-yl)cyclobutyl)methyl]-1h-pyrrole-2-carboxamide (NP0245769)

MOL for NP0245769 (4,5-dibromo-n-[(2-{[(4,5-dibromo-1h-pyrrol-2-yl)formamido]methyl}-3,4-bis(2-imino-1,3-dihydroimidazol-4-yl)cyclobutyl)methyl]-1h-pyrrole-2-carboxamide)

3D MOL for NP0245769 (4,5-dibromo-n-[(2-{[(4,5-dibromo-1h-pyrrol-2-yl)formamido]methyl}-3,4-bis(2-imino-1,3-dihydroimidazol-4-yl)cyclobutyl)methyl]-1h-pyrrole-2-carboxamide)

3D SDF for NP0245769 (4,5-dibromo-n-[(2-{[(4,5-dibromo-1h-pyrrol-2-yl)formamido]methyl}-3,4-bis(2-imino-1,3-dihydroimidazol-4-yl)cyclobutyl)methyl]-1h-pyrrole-2-carboxamide)

3D-SDF for NP0245769 (4,5-dibromo-n-[(2-{[(4,5-dibromo-1h-pyrrol-2-yl)formamido]methyl}-3,4-bis(2-imino-1,3-dihydroimidazol-4-yl)cyclobutyl)methyl]-1h-pyrrole-2-carboxamide)

PDB for NP0245769 (4,5-dibromo-n-[(2-{[(4,5-dibromo-1h-pyrrol-2-yl)formamido]methyl}-3,4-bis(2-imino-1,3-dihydroimidazol-4-yl)cyclobutyl)methyl]-1h-pyrrole-2-carboxamide)

3D PDB for NP0245769 (4,5-dibromo-n-[(2-{[(4,5-dibromo-1h-pyrrol-2-yl)formamido]methyl}-3,4-bis(2-imino-1,3-dihydroimidazol-4-yl)cyclobutyl)methyl]-1h-pyrrole-2-carboxamide)

SMILES for NP0245769 (4,5-dibromo-n-[(2-{[(4,5-dibromo-1h-pyrrol-2-yl)formamido]methyl}-3,4-bis(2-imino-1,3-dihydroimidazol-4-yl)cyclobutyl)methyl]-1h-pyrrole-2-carboxamide)

INCHI for NP0245769 (4,5-dibromo-n-[(2-{[(4,5-dibromo-1h-pyrrol-2-yl)formamido]methyl}-3,4-bis(2-imino-1,3-dihydroimidazol-4-yl)cyclobutyl)methyl]-1h-pyrrole-2-carboxamide)

Structure for NP0245769 (4,5-dibromo-n-[(2-{[(4,5-dibromo-1h-pyrrol-2-yl)formamido]methyl}-3,4-bis(2-imino-1,3-dihydroimidazol-4-yl)cyclobutyl)methyl]-1h-pyrrole-2-carboxamide)

3D Structure for NP0245769 (4,5-dibromo-n-[(2-{[(4,5-dibromo-1h-pyrrol-2-yl)formamido]methyl}-3,4-bis(2-imino-1,3-dihydroimidazol-4-yl)cyclobutyl)methyl]-1h-pyrrole-2-carboxamide)