NP-MRD: Showing NP-Card for 3-bromo-4-(2-imino-1,3-dihydroimidazol-4-yl)-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-8-ol (NP0160111)

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Record Information

Version

2.0

Created at

2022-09-02 17:59:43 UTC

Updated at

2022-09-02 17:59:43 UTC

NP-MRD ID

NP0160111

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-bromo-4-(2-imino-1,3-dihydroimidazol-4-yl)-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-8-ol

Description

3-Bromo-4-(2-imino-2,3-dihydro-1H-imidazol-4-yl)-1H,4H,5H,6H-pyrrolo[2,3-c]azepin-8-ol belongs to the class of organic compounds known as pyrroloazepines. Pyrroloazepines are compounds containing a pyrroloazepine moiety, which is a bicyclic heterocycle which consists of a pyrrole ring fused to an azepine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Azepine is a 7-membered ring consisting of six carbon and one nitrogen atom. 3-bromo-4-(2-imino-1,3-dihydroimidazol-4-yl)-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-8-ol is found in Stylissa carteri. 3-Bromo-4-(2-imino-2,3-dihydro-1H-imidazol-4-yl)-1H,4H,5H,6H-pyrrolo[2,3-c]azepin-8-ol is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
    4.1879    0.9687    1.3793 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1815    0.8430    0.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9923    0.2587    0.5582 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2561    0.2992   -0.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0983   -0.2683   -0.7452 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0605   -1.6471   -0.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0649   -2.5917   -0.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3626   -2.4736   -0.0564 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8092   -1.3300    0.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7584   -1.4790    1.4627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3483    0.0620    0.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9852    1.1304    0.9754 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2949    2.2502    0.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1235    1.9020    0.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211    3.1360   -0.5678 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1636    0.5324   -0.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0629    0.9581   -1.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2040    1.2674   -0.8873 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7969    0.1670    1.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3484    1.8695    1.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2927   -0.3342   -1.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -2.0733   -0.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2543   -1.4936    0.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2143   -2.3302   -1.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7219   -3.6295   -0.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0082   -3.2703   -0.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9170    1.0644    1.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5633    3.2713    0.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7922    1.1698   -2.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0515    1.7704   -1.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4 17  2  0
 17 18  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 16  2  0
 16 14  1  0
 14 15  1  0
 14 13  2  0
 13 12  1  0
 18  2  1  0
 16  5  1  0
 12 11  1  0
  1 19  1  0
  1 20  1  0
 17 29  1  0
 18 30  1  0
  5 21  1  6
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
 13 28  1  0
 12 27  1  0
M  END


  Mrv1533004161507492D          

 18 20  0  0  0  0            999 V2000
    3.6129    3.6138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2887    2.8552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7118    2.1470    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690    1.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4104    1.8499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4844    2.6716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569   -0.9488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -1.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690   -1.9367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6680    1.2466    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  4  7  1  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  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  7 18  1  0  0  0  0
 13 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0160111

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=NC(=CN1)C1CCNC(=O)C2=C1C(Br)=CN2

> <INCHI_IDENTIFIER>
InChI=1S/C11H12BrN5O/c12-6-3-15-9-8(6)5(1-2-14-10(9)18)7-4-16-11(13)17-7/h3-5,15H,1-2H2,(H,14,18)(H3,13,16,17)

> <INCHI_KEY>
GUEAIKUGJDAITI-UHFFFAOYSA-N

> <FORMULA>
C11H12BrN5O

> <MOLECULAR_WEIGHT>
310.155

> <EXACT_MASS>
309.022523

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
26.776388374765382

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(2-amino-1H-imidazol-4-yl)-3-bromo-1H,4H,5H,6H,7H,8H-pyrrolo[2,3-c]azepin-8-one

> <ALOGPS_LOGP>
1.17

> <JCHEM_LOGP>
0.5882174496666663

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.961496852042519

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.37530441557871

> <JCHEM_PKA_STRONGEST_BASIC>
8.782001241035246

> <JCHEM_POLAR_SURFACE_AREA>
99.58999999999997

> <JCHEM_REFRACTIVITY>
71.577

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.43e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(2-amino-1H-imidazol-4-yl)-3-bromo-1H,4H,5H,6H,7H-pyrrolo[2,3-c]azepin-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  N   UNK     0       6.744   6.746   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       6.139   5.330   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       6.929   4.008   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.916   2.848   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.499   3.453   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       4.637   4.987   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       6.258   1.347   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.760   1.004   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.428  -0.384   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       7.760  -1.771   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       6.258  -2.114   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.916  -3.615   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.054  -1.154   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       3.590  -1.629   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       2.684  -0.384   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.590   0.862   0.000  0.00  0.00           C+0
HETATM   17 Br   UNK     0       3.114   2.327   0.000  0.00  0.00          Br+0
HETATM   18  C   UNK     0       5.054   0.386   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    2                                                       
CONECT    7    4    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    7   13                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₂BrN₅O

Average Mass

310.1550 Da

Monoisotopic Mass

309.02252 Da

IUPAC Name

4-(2-amino-1H-imidazol-4-yl)-3-bromo-1H,4H,5H,6H,7H,8H-pyrrolo[2,3-c]azepin-8-one

Traditional Name

4-(2-amino-1H-imidazol-4-yl)-3-bromo-1H,4H,5H,6H,7H-pyrrolo[2,3-c]azepin-8-one

CAS Registry Number

Not Available

SMILES

NC1=NC(=CN1)C1CCNC(=O)C2=C1C(Br)=CN2

InChI Identifier

InChI=1S/C11H12BrN5O/c12-6-3-15-9-8(6)5(1-2-14-10(9)18)7-4-16-11(13)17-7/h3-5,15H,1-2H2,(H,14,18)(H3,13,16,17)

InChI Key

GUEAIKUGJDAITI-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 carteri	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloazepines. Pyrroloazepines are compounds containing a pyrroloazepine moiety, which is a bicyclic heterocycle which consists of a pyrrole ring fused to an azepine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Azepine is a 7-membered ring consisting of six carbon and one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrroloazepines

Sub Class

Not Available

Direct Parent

Pyrroloazepines

Alternative Parents

Substituents

Pyrroloazepine
2-heteroaryl carboxamide
Azepine
Aminoimidazole
Aryl bromide
Aryl halide
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Azole
Imidazole
Amino acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Lactam
Azacycle
Carboxylic acid derivative
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Primary amine
Amine
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organobromide
Organohalogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	1.17	ALOGPS
logP	0.59	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	13.38	ChemAxon
pKa (Strongest Basic)	8.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.59 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.58 m³·mol⁻¹	ChemAxon
Polarizability	26.78 Å³	ChemAxon
Number of Rings	3	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

9926678

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-bromo-4-(2-imino-1,3-dihydroimidazol-4-yl)-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-8-ol (NP0160111)

MOL for NP0160111 (3-bromo-4-(2-imino-1,3-dihydroimidazol-4-yl)-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-8-ol)

3D MOL for NP0160111 (3-bromo-4-(2-imino-1,3-dihydroimidazol-4-yl)-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-8-ol)

3D SDF for NP0160111 (3-bromo-4-(2-imino-1,3-dihydroimidazol-4-yl)-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-8-ol)

3D-SDF for NP0160111 (3-bromo-4-(2-imino-1,3-dihydroimidazol-4-yl)-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-8-ol)

PDB for NP0160111 (3-bromo-4-(2-imino-1,3-dihydroimidazol-4-yl)-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-8-ol)

3D PDB for NP0160111 (3-bromo-4-(2-imino-1,3-dihydroimidazol-4-yl)-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-8-ol)

SMILES for NP0160111 (3-bromo-4-(2-imino-1,3-dihydroimidazol-4-yl)-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-8-ol)

INCHI for NP0160111 (3-bromo-4-(2-imino-1,3-dihydroimidazol-4-yl)-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-8-ol)

Structure for NP0160111 (3-bromo-4-(2-imino-1,3-dihydroimidazol-4-yl)-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-8-ol)

3D Structure for NP0160111 (3-bromo-4-(2-imino-1,3-dihydroimidazol-4-yl)-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-8-ol)