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Showing NP-Card for 3,6-bis(6-bromo-1h-indol-3-yl)-5,6-dihydro-1h-pyrazin-2-one (NP0222591)

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Record Information
Version2.0
Created at2022-09-06 00:27:54 UTC
Updated at2022-09-06 00:27:54 UTC
NP-MRD IDNP0222591
Secondary Accession NumbersNone
Natural Product Identification
Common Name3,6-bis(6-bromo-1h-indol-3-yl)-5,6-dihydro-1h-pyrazin-2-one
DescriptionHamacanthin A belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Hamacanthin A is a moderately basic compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0222591 (3,6-bis(6-bromo-1h-indol-3-yl)-5,6-dihydro-1h-pyrazin-2-one)


  Mrv1533004161505182D          

 27 31  0  0  0  0            999 V2000
   -2.8091   -5.9963    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0946   -5.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0946   -4.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3801   -4.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6657   -4.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1190   -4.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -5.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1190   -5.8387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6657   -5.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3801   -5.9963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -2.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428   -2.5916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -3.5477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    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
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
  2 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 11 17  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 18 27  1  0  0  0  0
 21 27  1  0  0  0  0
M  END
Download

3D MOL for NP0222591 (3,6-bis(6-bromo-1h-indol-3-yl)-5,6-dihydro-1h-pyrazin-2-one)

Download
3D SDF for NP0222591 (3,6-bis(6-bromo-1h-indol-3-yl)-5,6-dihydro-1h-pyrazin-2-one)

  Mrv1533004161505182D          

 27 31  0  0  0  0            999 V2000
   -2.8091   -5.9963    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0946   -5.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0946   -4.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3801   -4.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6657   -4.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1190   -4.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -5.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1190   -5.8387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6657   -5.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3801   -5.9963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -2.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428   -2.5916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -3.5477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    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
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
  2 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 11 17  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 18 27  1  0  0  0  0
 21 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222591

> <DATABASE_NAME>
NP-MRD

> <SMILES>
BrC1=CC=C2C(NC=C2C2CN=C(C3=CNC4=CC(Br)=CC=C34)C(=O)N2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H14Br2N4O/c21-10-1-3-12-14(7-23-16(12)5-10)18-9-25-19(20(27)26-18)15-8-24-17-6-11(22)2-4-13(15)17/h1-8,18,23-24H,9H2,(H,26,27)

> <INCHI_KEY>
LJVUNJVGWMVCQH-UHFFFAOYSA-N

> <FORMULA>
C20H14Br2N4O

> <MOLECULAR_WEIGHT>
486.167

> <EXACT_MASS>
483.953437

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
43.61066383360782

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,6-bis(6-bromo-1H-indol-3-yl)-1,2,5,6-tetrahydropyrazin-2-one

> <ALOGPS_LOGP>
4.40

> <JCHEM_LOGP>
4.491302991333333

> <ALOGPS_LOGS>
-5.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.521158693615835

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.935870644305655

> <JCHEM_PKA_STRONGEST_BASIC>
2.1570962044348616

> <JCHEM_POLAR_SURFACE_AREA>
73.03999999999999

> <JCHEM_REFRACTIVITY>
111.66080000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.59e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,6-bis(6-bromo-1H-indol-3-yl)-5,6-dihydro-1H-pyrazin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0222591 (3,6-bis(6-bromo-1h-indol-3-yl)-5,6-dihydro-1h-pyrazin-2-one)
Download
PDB for NP0222591 (3,6-bis(6-bromo-1h-indol-3-yl)-5,6-dihydro-1h-pyrazin-2-one)
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 Br   UNK     0      -5.244 -11.193   0.000  0.00  0.00          Br+0
HETATM    2  C   UNK     0      -3.910 -10.423   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.910  -8.883   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.576  -8.113   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.243  -8.883   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.222  -8.407   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.127  -9.653   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.222 -10.899   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -1.243 -10.423   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.576 -11.193   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.698  -6.943   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       0.143  -4.334   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.680  -5.158   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.187  -4.838   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       2.204  -6.622   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   24 Br   UNK     0       7.591   0.237   0.000  0.00  0.00          Br+0
HETATM   25  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5   10                                                  
CONECT   10    9    2                                                       
CONECT   11    6   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   11                                                       
CONECT   18   14   19   27                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   18   21                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

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3D PDB for NP0222591 (3,6-bis(6-bromo-1h-indol-3-yl)-5,6-dihydro-1h-pyrazin-2-one)
Download
SMILES for NP0222591 (3,6-bis(6-bromo-1h-indol-3-yl)-5,6-dihydro-1h-pyrazin-2-one)
BrC1=CC=C2C(NC=C2C2CN=C(C3=CNC4=CC(Br)=CC=C34)C(=O)N2)=C1
Download
INCHI for NP0222591 (3,6-bis(6-bromo-1h-indol-3-yl)-5,6-dihydro-1h-pyrazin-2-one)
InChI=1S/C20H14Br2N4O/c21-10-1-3-12-14(7-23-16(12)5-10)18-9-25-19(20(27)26-18)15-8-24-17-6-11(22)2-4-13(15)17/h1-8,18,23-24H,9H2,(H,26,27)
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View in JSmol
Synonyms
ValueSource
Hamacanthine aMeSH
Chemical FormulaC20H14Br2N4O
Average Mass486.1670 Da
Monoisotopic Mass483.95344 Da
IUPAC Name3,6-bis(6-bromo-1H-indol-3-yl)-1,2,5,6-tetrahydropyrazin-2-one
Traditional Name3,6-bis(6-bromo-1H-indol-3-yl)-5,6-dihydro-1H-pyrazin-2-one
CAS Registry NumberNot Available
SMILES
BrC1=CC=C2C(NC=C2C2CN=C(C3=CNC4=CC(Br)=CC=C34)C(=O)N2)=C1
InChI Identifier
InChI=1S/C20H14Br2N4O/c21-10-1-3-12-14(7-23-16(12)5-10)18-9-25-19(20(27)26-18)15-8-24-17-6-11(22)2-4-13(15)17/h1-8,18,23-24H,9H2,(H,26,27)
InChI KeyLJVUNJVGWMVCQH-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIndoles and derivatives  
Sub ClassIndoles  
Direct Parent3-alkylindoles  
Alternative Parents
Substituents
  • 3-alkylindole
    • 

  • Aryl bromide
    • 

  • Aryl halide
    • 

  • Substituted pyrrole
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Pyrrole
    • 

  • Carboxamide group
    • 

  • Ketimine
    • 

  • Lactam
    • 

  • Secondary carboxylic acid amide
    • 

  • Carboxylic acid derivative
    • 

  • Azacycle
    • 

  • Organic 1,3-dipolar compound
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Organonitrogen compound
    • 

  • Organobromide
    • 

  • Organohalogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Imine
    • 

  • Organopnictogen compound
    • 

  • Organooxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.4ALOGPS
logP4.49ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)10.94ChemAxon
pKa (Strongest Basic)2.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area73.04 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity111.66 m³·mol⁻¹ChemAxon
Polarizability43.61 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound461371  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]