NP-MRD: Showing NP-Card for 7-bromo-1,8a-dihydroxy-4-[(2-imino-1,3-dihydroimidazol-4-yl)methylidene]-3h-pyrrolo[1,2-a]pyrazin-6-one (NP0193990)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 11:34:00 UTC

Updated at

2022-09-04 11:34:00 UTC

NP-MRD ID

NP0193990

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-bromo-1,8a-dihydroxy-4-[(2-imino-1,3-dihydroimidazol-4-yl)methylidene]-3h-pyrrolo[1,2-a]pyrazin-6-one

Description

7-Bromo-1,8a-dihydroxy-4-[(2-imino-2,3-dihydro-1H-imidazol-4-yl)methylidene]-3H,4H,6H,8aH-pyrrolo[1,2-a]pyrazin-6-one belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms. 7-Bromo-1,8a-dihydroxy-4-[(2-imino-2,3-dihydro-1H-imidazol-4-yl)methylidene]-3H,4H,6H,8aH-pyrrolo[1,2-a]pyrazin-6-one 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
    5.2173    0.5687   -0.4541 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0898   -0.3085   -0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1388   -1.5482    0.2579 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8830   -2.0308    0.2756 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0012   -1.0733   -0.2405 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5750   -1.1955   -0.4028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2764   -0.2233   -0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1382    1.1302    0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8967    1.6329    1.2084 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2424    1.6593    0.7373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1013    2.3976    1.2312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5714    0.7451   -0.3926 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3945    1.4197   -1.6063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9152    0.1931   -0.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8978   -1.1165   -0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4137   -2.2675   -0.5112 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.5124   -1.5427   -0.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0639   -2.7390   -0.5129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6856   -0.4123   -0.3319 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8057   -0.0267   -0.5525 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3652    1.3938    0.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9094    0.4050   -1.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5425   -2.9989    0.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1808   -2.1354   -0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0649    1.0390    0.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3504    1.8085   -0.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6769    1.9654    2.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2630    1.6069   -2.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8698    0.7702   -0.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5187    0.8831   -0.9677 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  5  2  0
  5 20  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
 20  2  1  0
 19  7  1  0
 19 12  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
 20 30  1  0
  6 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 13 28  1  0
 14 29  1  0
M  END


  Mrv1533004171512102D          

 20 22  0  0  0  0            999 V2000
    5.2222    4.2207    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8866    3.4670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2991    2.7525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7471    2.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4782   -0.8205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0796    3.2955    0.0000 N   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
  6  5  1  4  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  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  7 19  1  0  0  0  0
 12 19  1  0  0  0  0
  5 20  1  0  0  0  0
  2 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0193990

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=NC=C(N1)C=C1CNC(=O)C2(O)C=C(Br)C(=O)N12

> <INCHI_IDENTIFIER>
InChI=1S/C11H10BrN5O3/c12-7-2-11(20)9(19)14-4-6(17(11)8(7)18)1-5-3-15-10(13)16-5/h1-3,20H,4H2,(H,14,19)(H3,13,15,16)

> <INCHI_KEY>
XKFVLOVEQBJMER-UHFFFAOYSA-N

> <FORMULA>
C11H10BrN5O3

> <MOLECULAR_WEIGHT>
340.137

> <EXACT_MASS>
338.996702

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
27.518767371972423

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(2-amino-1H-imidazol-5-yl)methylidene]-7-bromo-8a-hydroxy-1H,2H,3H,4H,6H,8aH-pyrrolo[1,2-a]piperazine-1,6-dione

> <ALOGPS_LOGP>
-0.43

> <JCHEM_LOGP>
-1.4620775374337458

> <ALOGPS_LOGS>
-2.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
11.904283252217661

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.337698255907704

> <JCHEM_PKA_STRONGEST_BASIC>
8.830767005474424

> <JCHEM_POLAR_SURFACE_AREA>
124.34

> <JCHEM_REFRACTIVITY>
75.36260000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.77e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(2-amino-3H-imidazol-4-yl)methylidene]-7-bromo-8a-hydroxy-2H,3H-pyrrolo[1,2-a]piperazine-1,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  N   UNK     0       9.748   7.879   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       9.122   6.472   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       9.892   5.138   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       8.861   3.994   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       7.454   0.000   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.626  -1.532   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   16 Br   UNK     0       0.877   0.770   0.000  0.00  0.00          Br+0
HETATM   17  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.846   3.481   0.000  0.00  0.00           O+0
HETATM   19  N   UNK     0       4.787   1.540   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       7.615   6.152   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   20                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   19                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    7   12                                                  
CONECT   20    5    2                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₀BrN₅O₃

Average Mass

340.1370 Da

Monoisotopic Mass

338.99670 Da

IUPAC Name

4-[(2-amino-1H-imidazol-5-yl)methylidene]-7-bromo-8a-hydroxy-1H,2H,3H,4H,6H,8aH-pyrrolo[1,2-a]piperazine-1,6-dione

Traditional Name

4-[(2-amino-3H-imidazol-4-yl)methylidene]-7-bromo-8a-hydroxy-2H,3H-pyrrolo[1,2-a]piperazine-1,6-dione

CAS Registry Number

Not Available

SMILES

NC1=NC=C(N1)C=C1CNC(=O)C2(O)C=C(Br)C(=O)N12

InChI Identifier

InChI=1S/C11H10BrN5O3/c12-7-2-11(20)9(19)14-4-6(17(11)8(7)18)1-5-3-15-10(13)16-5/h1-3,20H,4H2,(H,14,19)(H3,13,15,16)

InChI Key

XKFVLOVEQBJMER-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Imidazoles

Direct Parent

Imidazoles

Alternative Parents

Substituents

Imidazole
Pyrroline
Heteroaromatic compound
Tertiary carboxylic acid amide
Cyclic carboximidic acid
Carboxamide group
Lactam
Alkanolamine
Carboxylic acid derivative
Azacycle
Vinyl bromide
Vinyl halide
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Bromoalkene
Haloalkene
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Organohalogen compound
Organobromide
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	-0.43	ALOGPS
logP	-1.5	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	10.34	ChemAxon
pKa (Strongest Basic)	8.83	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.34 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.36 m³·mol⁻¹	ChemAxon
Polarizability	27.52 Å³	ChemAxon
Number of Rings	3	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

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

73236920

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-bromo-1,8a-dihydroxy-4-[(2-imino-1,3-dihydroimidazol-4-yl)methylidene]-3h-pyrrolo[1,2-a]pyrazin-6-one (NP0193990)

MOL for NP0193990 (7-bromo-1,8a-dihydroxy-4-[(2-imino-1,3-dihydroimidazol-4-yl)methylidene]-3h-pyrrolo[1,2-a]pyrazin-6-one)

3D MOL for NP0193990 (7-bromo-1,8a-dihydroxy-4-[(2-imino-1,3-dihydroimidazol-4-yl)methylidene]-3h-pyrrolo[1,2-a]pyrazin-6-one)

3D SDF for NP0193990 (7-bromo-1,8a-dihydroxy-4-[(2-imino-1,3-dihydroimidazol-4-yl)methylidene]-3h-pyrrolo[1,2-a]pyrazin-6-one)

3D-SDF for NP0193990 (7-bromo-1,8a-dihydroxy-4-[(2-imino-1,3-dihydroimidazol-4-yl)methylidene]-3h-pyrrolo[1,2-a]pyrazin-6-one)

PDB for NP0193990 (7-bromo-1,8a-dihydroxy-4-[(2-imino-1,3-dihydroimidazol-4-yl)methylidene]-3h-pyrrolo[1,2-a]pyrazin-6-one)

3D PDB for NP0193990 (7-bromo-1,8a-dihydroxy-4-[(2-imino-1,3-dihydroimidazol-4-yl)methylidene]-3h-pyrrolo[1,2-a]pyrazin-6-one)

SMILES for NP0193990 (7-bromo-1,8a-dihydroxy-4-[(2-imino-1,3-dihydroimidazol-4-yl)methylidene]-3h-pyrrolo[1,2-a]pyrazin-6-one)

INCHI for NP0193990 (7-bromo-1,8a-dihydroxy-4-[(2-imino-1,3-dihydroimidazol-4-yl)methylidene]-3h-pyrrolo[1,2-a]pyrazin-6-one)

Structure for NP0193990 (7-bromo-1,8a-dihydroxy-4-[(2-imino-1,3-dihydroimidazol-4-yl)methylidene]-3h-pyrrolo[1,2-a]pyrazin-6-one)

3D Structure for NP0193990 (7-bromo-1,8a-dihydroxy-4-[(2-imino-1,3-dihydroimidazol-4-yl)methylidene]-3h-pyrrolo[1,2-a]pyrazin-6-one)