NP-MRD: Showing NP-Card for 6,7-dibromo-4-hydroxy-2h,3h,4h-pyrrolo[1,2-a]pyrazin-1-one (NP0229922)

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Record Information

Version

2.0

Created at

2022-09-06 10:11:42 UTC

Updated at

2022-09-06 10:11:43 UTC

NP-MRD ID

NP0229922

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,7-dibromo-4-hydroxy-2h,3h,4h-pyrrolo[1,2-a]pyrazin-1-one

Description

6,7-Dibromo-4-hydroxy-1H,2H,3H,4H-pyrrolo[1,2-a]pyrazin-1-one 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. 6,7-dibromo-4-hydroxy-2h,3h,4h-pyrrolo[1,2-a]pyrazin-1-one is found in Agelas cervicornis. 6,7-Dibromo-4-hydroxy-1H,2H,3H,4H-pyrrolo[1,2-a]pyrazin-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191523162D          

 13 14  0  0  0  0            999 V2000
    3.2789    2.0625    0.0000 O   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
    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 Br  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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  2 13  1  0  0  0  0
  7 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0229922

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CNC(=O)C2=CC(Br)=C(Br)N12

> <INCHI_IDENTIFIER>
InChI=1S/C7H6Br2N2O2/c8-3-1-4-7(13)10-2-5(12)11(4)6(3)9/h1,5,12H,2H2,(H,10,13)

> <INCHI_KEY>
NUVAABCZBKHWMX-UHFFFAOYSA-N

> <FORMULA>
C7H6Br2N2O2

> <MOLECULAR_WEIGHT>
309.945

> <EXACT_MASS>
307.879603

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
21.254886497491803

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6,7-dibromo-4-hydroxy-1H,2H,3H,4H-pyrrolo[1,2-a]pyrazin-1-one

> <ALOGPS_LOGP>
0.78

> <JCHEM_LOGP>
0.9732353366666666

> <ALOGPS_LOGS>
-2.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.809078512932249

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.655250074334706

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6580104594738105

> <JCHEM_POLAR_SURFACE_AREA>
54.26

> <JCHEM_REFRACTIVITY>
53.6546

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.81e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,7-dibromo-4-hydroxy-2H,3H,4H-pyrrolo[1,2-a]pyrazin-1-one

> <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  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       7.454   0.000   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   10 Br   UNK     0       0.877   0.770   0.000  0.00  0.00          Br+0
HETATM   11  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   12 Br   UNK     0       2.846   3.481   0.000  0.00  0.00          Br+0
HETATM   13  N   UNK     0       4.787   1.540   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol

Synonyms

Value	Source
(+/-)-longamide	ChEMBL

Chemical Formula

C₇H₆Br₂N₂O₂

Average Mass

309.9450 Da

Monoisotopic Mass

307.87960 Da

IUPAC Name

6,7-dibromo-4-hydroxy-1H,2H,3H,4H-pyrrolo[1,2-a]pyrazin-1-one

Traditional Name

6,7-dibromo-4-hydroxy-2H,3H,4H-pyrrolo[1,2-a]pyrazin-1-one

CAS Registry Number

Not Available

SMILES

OC1CNC(=O)C2=CC(Br)=C(Br)N12

InChI Identifier

InChI=1S/C7H6Br2N2O2/c8-3-1-4-7(13)10-2-5(12)11(4)6(3)9/h1,5,12H,2H2,(H,10,13)

InChI Key

NUVAABCZBKHWMX-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 cervicornis	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
Aryl bromide
Aryl halide
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Lactam
Secondary carboxylic acid amide
Alkanolamine
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	0.78	ALOGPS
logP	0.97	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	12.66	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	54.26 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	53.65 m³·mol⁻¹	ChemAxon
Polarizability	21.25 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

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

10902963

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6,7-dibromo-4-hydroxy-2h,3h,4h-pyrrolo[1,2-a]pyrazin-1-one (NP0229922)

MOL for NP0229922 (6,7-dibromo-4-hydroxy-2h,3h,4h-pyrrolo[1,2-a]pyrazin-1-one)

3D MOL for NP0229922 (6,7-dibromo-4-hydroxy-2h,3h,4h-pyrrolo[1,2-a]pyrazin-1-one)

3D SDF for NP0229922 (6,7-dibromo-4-hydroxy-2h,3h,4h-pyrrolo[1,2-a]pyrazin-1-one)

3D-SDF for NP0229922 (6,7-dibromo-4-hydroxy-2h,3h,4h-pyrrolo[1,2-a]pyrazin-1-one)

PDB for NP0229922 (6,7-dibromo-4-hydroxy-2h,3h,4h-pyrrolo[1,2-a]pyrazin-1-one)

3D PDB for NP0229922 (6,7-dibromo-4-hydroxy-2h,3h,4h-pyrrolo[1,2-a]pyrazin-1-one)

SMILES for NP0229922 (6,7-dibromo-4-hydroxy-2h,3h,4h-pyrrolo[1,2-a]pyrazin-1-one)

INCHI for NP0229922 (6,7-dibromo-4-hydroxy-2h,3h,4h-pyrrolo[1,2-a]pyrazin-1-one)

Structure for NP0229922 (6,7-dibromo-4-hydroxy-2h,3h,4h-pyrrolo[1,2-a]pyrazin-1-one)

3D Structure for NP0229922 (6,7-dibromo-4-hydroxy-2h,3h,4h-pyrrolo[1,2-a]pyrazin-1-one)