NP-MRD: Showing NP-Card for n-{[2,3-bis(2-imino-1,3-dihydroimidazol-4-yl)-4-[(1h-pyrrol-2-ylformamido)methyl]cyclobutyl]methyl}-4-bromo-1h-pyrrole-2-carboxamide (NP0314167)

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Record Information

Version

2.0

Created at

2022-09-11 12:07:48 UTC

Updated at

2022-09-11 12:07:49 UTC

NP-MRD ID

NP0314167

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Sceptrin dihydrochloride 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. n-{[2,3-bis(2-imino-1,3-dihydroimidazol-4-yl)-4-[(1h-pyrrol-2-ylformamido)methyl]cyclobutyl]methyl}-4-bromo-1h-pyrrole-2-carboxamide is found in Agelas conifera and Agelas nakamurai. Based on a literature review very few articles have been published on Sceptrin dihydrochloride.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112214072D          

 35 39  0  0  0  0            999 V2000
    0.3224    1.7510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8073    1.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6323    1.0835    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8873    0.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2198   -0.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2198   -1.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -1.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6282   -1.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0407   -0.8799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8657   -0.8799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2782   -1.5944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2782   -0.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9426    0.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5557    1.1403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2702    0.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0987   -0.0792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2198   -2.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2198   -3.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5054   -4.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2198   -4.6527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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M  END

     RDKit          3D

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    4.1296   -2.4668    0.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1537   -3.7815    0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4313   -4.0753   -0.3939 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0560   -5.7653   -0.9990 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.1558   -2.9227   -0.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3374   -1.9513    0.1728 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0235   -0.1475    0.3682 C   0  0  2  0  0  0  0  0  0  0  0  0
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    7.1890   -2.7712   -0.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309112214072D          

 35 39  0  0  0  0            999 V2000
    0.3224    1.7510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8073    1.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0314167

> <DATABASE_NAME>
NP-MRD

> <SMILES>
BrC1=CNC(=C1)C(=O)NCC1C(CNC(=O)C2=CC=CN2)C(C1C1=CNC(=N)N1)C1=CNC(=N)N1

> <INCHI_IDENTIFIER>
InChI=1S/C22H25BrN10O2/c23-10-4-14(27-5-10)20(35)29-7-12-11(6-28-19(34)13-2-1-3-26-13)17(15-8-30-21(24)32-15)18(12)16-9-31-22(25)33-16/h1-5,8-9,11-12,17-18,26-27H,6-7H2,(H,28,34)(H,29,35)(H3,24,30,32)(H3,25,31,33)

> <INCHI_KEY>
OHXDZYOSEDUXGN-UHFFFAOYSA-N

> <FORMULA>
C22H25BrN10O2

> <MOLECULAR_WEIGHT>
541.414

> <EXACT_MASS>
540.134533

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
52.7187673560468

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-0.8698239333333322

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
15.066334581747693

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.18079112104666

> <JCHEM_PKA_STRONGEST_BASIC>
7.99778840162359

> <JCHEM_POLAR_SURFACE_AREA>
185.6

> <JCHEM_REFRACTIVITY>
155.69580000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
N-{[2,3-bis(2-imino-1,3-dihydroimidazol-4-yl)-4-[(1H-pyrrol-2-ylformamido)methyl]cyclobutyl]methyl}-4-bromo-1H-pyrrole-2-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         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  C   UNK     0       2.277  -1.887   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.366  -2.976   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.906  -2.976   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       5.676  -1.642   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       7.216  -1.642   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.986  -2.976   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.986  -0.309   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.360   1.098   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.504   2.129   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.838   1.359   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       9.518  -0.148   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       2.277  -4.065   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.277  -5.605   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       0.943  -6.375   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       0.943  -7.915   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.277  -8.685   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.390  -8.685   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.551 -10.217   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.058 -10.537   0.000  0.00  0.00           C+0
HETATM   25 Br   UNK     0      -2.684 -11.944   0.000  0.00  0.00          Br+0
HETATM   26  C   UNK     0      -2.828  -9.203   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      -1.797  -8.059   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       1.188  -2.976   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.352  -2.976   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.257  -4.222   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0      -2.722  -3.746   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0      -2.722  -2.206   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0      -3.968  -1.301   0.000  0.00  0.00           N+0
HETATM   34  N   UNK     0      -1.257  -1.730   0.000  0.00  0.00           N+0
HETATM   35  N   UNK     0       1.031   0.558   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   35                                                  
CONECT    6    5    7   28                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
CONECT   17    7   18   28                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   22                                                       
CONECT   28   17    6   29                                                  
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   29                                                       
CONECT   35    5    2                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₅BrN₁₀O₂

Average Mass

541.4140 Da

Monoisotopic Mass

540.13453 Da

IUPAC Name

N-{[2,3-bis(2-imino-2,3-dihydro-1H-imidazol-4-yl)-4-{[(1H-pyrrol-2-yl)formamido]methyl}cyclobutyl]methyl}-4-bromo-1H-pyrrole-2-carboxamide

Traditional Name

N-{[2,3-bis(2-imino-1,3-dihydroimidazol-4-yl)-4-[(1H-pyrrol-2-ylformamido)methyl]cyclobutyl]methyl}-4-bromo-1H-pyrrole-2-carboxamide

CAS Registry Number

Not Available

SMILES

BrC1=CNC(=C1)C(=O)NCC1C(CNC(=O)C2=CC=CN2)C(C1C1=CNC(=N)N1)C1=CNC(=N)N1

InChI Identifier

InChI=1S/C22H25BrN10O2/c23-10-4-14(27-5-10)20(35)29-7-12-11(6-28-19(34)13-2-1-3-26-13)17(15-8-30-21(24)32-15)18(12)16-9-31-22(25)33-16/h1-5,8-9,11-12,17-18,26-27H,6-7H2,(H,28,34)(H,29,35)(H3,24,30,32)(H3,25,31,33)

InChI Key

OHXDZYOSEDUXGN-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
Agelas nakamurai	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
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Amine
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	-0.87	ChemAxon
pKa (Strongest Acidic)	14.18	ChemAxon
pKa (Strongest Basic)	8	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	185.6 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	155.7 m³·mol⁻¹	ChemAxon
Polarizability	52.72 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

28592507

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14840689

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-{[2,3-bis(2-imino-1,3-dihydroimidazol-4-yl)-4-[(1h-pyrrol-2-ylformamido)methyl]cyclobutyl]methyl}-4-bromo-1h-pyrrole-2-carboxamide (NP0314167)

MOL for NP0314167 (n-{[2,3-bis(2-imino-1,3-dihydroimidazol-4-yl)-4-[(1h-pyrrol-2-ylformamido)methyl]cyclobutyl]methyl}-4-bromo-1h-pyrrole-2-carboxamide)

3D MOL for NP0314167 (n-{[2,3-bis(2-imino-1,3-dihydroimidazol-4-yl)-4-[(1h-pyrrol-2-ylformamido)methyl]cyclobutyl]methyl}-4-bromo-1h-pyrrole-2-carboxamide)

3D SDF for NP0314167 (n-{[2,3-bis(2-imino-1,3-dihydroimidazol-4-yl)-4-[(1h-pyrrol-2-ylformamido)methyl]cyclobutyl]methyl}-4-bromo-1h-pyrrole-2-carboxamide)

3D-SDF for NP0314167 (n-{[2,3-bis(2-imino-1,3-dihydroimidazol-4-yl)-4-[(1h-pyrrol-2-ylformamido)methyl]cyclobutyl]methyl}-4-bromo-1h-pyrrole-2-carboxamide)

PDB for NP0314167 (n-{[2,3-bis(2-imino-1,3-dihydroimidazol-4-yl)-4-[(1h-pyrrol-2-ylformamido)methyl]cyclobutyl]methyl}-4-bromo-1h-pyrrole-2-carboxamide)

3D PDB for NP0314167 (n-{[2,3-bis(2-imino-1,3-dihydroimidazol-4-yl)-4-[(1h-pyrrol-2-ylformamido)methyl]cyclobutyl]methyl}-4-bromo-1h-pyrrole-2-carboxamide)

SMILES for NP0314167 (n-{[2,3-bis(2-imino-1,3-dihydroimidazol-4-yl)-4-[(1h-pyrrol-2-ylformamido)methyl]cyclobutyl]methyl}-4-bromo-1h-pyrrole-2-carboxamide)

INCHI for NP0314167 (n-{[2,3-bis(2-imino-1,3-dihydroimidazol-4-yl)-4-[(1h-pyrrol-2-ylformamido)methyl]cyclobutyl]methyl}-4-bromo-1h-pyrrole-2-carboxamide)

Structure for NP0314167 (n-{[2,3-bis(2-imino-1,3-dihydroimidazol-4-yl)-4-[(1h-pyrrol-2-ylformamido)methyl]cyclobutyl]methyl}-4-bromo-1h-pyrrole-2-carboxamide)

3D Structure for NP0314167 (n-{[2,3-bis(2-imino-1,3-dihydroimidazol-4-yl)-4-[(1h-pyrrol-2-ylformamido)methyl]cyclobutyl]methyl}-4-bromo-1h-pyrrole-2-carboxamide)