NP-MRD: Showing NP-Card for 10-[5-(6-bromo-1h-indol-3-yl)-6-oxo-1h-pyrazin-2-yl]-1-hydroxy-4-imino-7-methyl-3,5,12-triazatetracyclo[6.6.1.0²,⁶.0⁹,¹³]pentadeca-2(6),9(13),10-trien-14-one (NP0209683)

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Record Information

Version

2.0

Created at

2022-09-05 07:11:27 UTC

Updated at

2022-09-05 07:11:27 UTC

NP-MRD ID

NP0209683

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-[5-(6-bromo-1h-indol-3-yl)-6-oxo-1h-pyrazin-2-yl]-1-hydroxy-4-imino-7-methyl-3,5,12-triazatetracyclo[6.6.1.0²,⁶.0⁹,¹³]pentadeca-2(6),9(13),10-trien-14-one

Description

10-[5-(6-Bromo-1H-indol-3-yl)-6-oxo-1,6-dihydropyrazin-2-yl]-1-hydroxy-4-imino-7-methyl-3,5,12-triazatetracyclo[6.6.1.0²,⁶.0⁹,¹³]Pentadeca-2(6),9(13),10-trien-14-one belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. 10-[5-(6-Bromo-1H-indol-3-yl)-6-oxo-1,6-dihydropyrazin-2-yl]-1-hydroxy-4-imino-7-methyl-3,5,12-triazatetracyclo[6.6.1.0²,⁶.0⁹,¹³]Pentadeca-2(6),9(13),10-trien-14-one is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241502022D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004241502022D          

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M  END
> <DATABASE_ID>
NP0209683

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2CC(O)(C3=C1N=C(N)N3)C(=O)C1=C2C(=CN1)C1=CN=C(C2=CNC3=CC(Br)=CC=C23)C(=O)N1

> <INCHI_IDENTIFIER>
InChI=1S/C25H20BrN7O3/c1-9-12-5-25(36,21-18(9)32-24(27)33-21)22(34)20-17(12)14(7-29-20)16-8-30-19(23(35)31-16)13-6-28-15-4-10(26)2-3-11(13)15/h2-4,6-9,12,28-29,36H,5H2,1H3,(H,31,35)(H3,27,32,33)

> <INCHI_KEY>
DCPFQRFLBCNBTP-UHFFFAOYSA-N

> <FORMULA>
C25H20BrN7O3

> <MOLECULAR_WEIGHT>
546.385

> <EXACT_MASS>
545.081101

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
52.82538264331727

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-amino-10-[5-(6-bromo-1H-indol-3-yl)-6-oxo-1,6-dihydropyrazin-2-yl]-1-hydroxy-7-methyl-3,5,12-triazatetracyclo[6.6.1.0²,⁶.0⁹,¹³]pentadeca-2(6),4,9(13),10-tetraen-14-one

> <ALOGPS_LOGP>
3.20

> <JCHEM_LOGP>
1.5776739463839247

> <ALOGPS_LOGS>
-4.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
11.865010693419952

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.069198714354586

> <JCHEM_PKA_STRONGEST_BASIC>
8.364115385113239

> <JCHEM_POLAR_SURFACE_AREA>
165.03999999999996

> <JCHEM_REFRACTIVITY>
137.04720000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-amino-10-[5-(6-bromo-1H-indol-3-yl)-6-oxo-1H-pyrazin-2-yl]-1-hydroxy-7-methyl-3,5,12-triazatetracyclo[6.6.1.0²,⁶.0⁹,¹³]pentadeca-2(6),4,9(13),10-tetraen-14-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       1.354  -0.448   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.944   0.975   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.484   0.975   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.249   2.641   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.944   4.693   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.354   6.116   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.484   4.693   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.073   6.116   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.573   3.604   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       6.037   4.080   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       6.943   2.834   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.037   1.588   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.513   0.123   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.020  -0.197   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       8.496  -1.661   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       7.465  -2.806   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.959  -2.486   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.928  -3.630   0.000  0.00  0.00           O+0
HETATM   19  N   UNK     0       5.483  -1.021   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       7.941  -4.271   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.406  -4.746   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       9.406  -6.286   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       7.941  -6.762   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.315  -8.169   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.783  -8.330   0.000  0.00  0.00           C+0
HETATM   26 Br   UNK     0       5.157  -9.737   0.000  0.00  0.00          Br+0
HETATM   27  C   UNK     0       4.878  -7.084   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.504  -5.677   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.036  -5.516   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.573   2.064   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.855   3.604   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0      -0.610   4.080   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0      -1.515   2.834   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      -3.055   2.834   0.000  0.00  0.00           N+0
HETATM   35  N   UNK     0      -0.610   1.588   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0       0.855   2.064   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4   30                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7   31                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   30                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   30                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   13                                                       
CONECT   20   16   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   20   23                                                  
CONECT   30   12    3    9                                                  
CONECT   31    5   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35    2   31                                                  
MASTER        0    0    0    0    0    0    0    0   36    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₀BrN₇O₃

Average Mass

546.3850 Da

Monoisotopic Mass

545.08110 Da

IUPAC Name

4-amino-10-[5-(6-bromo-1H-indol-3-yl)-6-oxo-1,6-dihydropyrazin-2-yl]-1-hydroxy-7-methyl-3,5,12-triazatetracyclo[6.6.1.0²,⁶.0⁹,¹³]pentadeca-2(6),4,9(13),10-tetraen-14-one

Traditional Name

4-amino-10-[5-(6-bromo-1H-indol-3-yl)-6-oxo-1H-pyrazin-2-yl]-1-hydroxy-7-methyl-3,5,12-triazatetracyclo[6.6.1.0²,⁶.0⁹,¹³]pentadeca-2(6),4,9(13),10-tetraen-14-one

CAS Registry Number

Not Available

SMILES

CC1C2CC(O)(C3=C1N=C(N)N3)C(=O)C1=C2C(=CN1)C1=CN=C(C2=CNC3=CC(Br)=CC=C23)C(=O)N1

InChI Identifier

InChI=1S/C25H20BrN7O3/c1-9-12-5-25(36,21-18(9)32-24(27)33-21)22(34)20-17(12)14(7-29-20)16-8-30-19(23(35)31-16)13-6-28-15-4-10(26)2-3-11(13)15/h2-4,6-9,12,28-29,36H,5H2,1H3,(H,31,35)(H3,27,32,33)

InChI Key

DCPFQRFLBCNBTP-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 indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

Indoles

Alternative Parents

Substituents

Indole
Aryl alkyl ketone
Aryl ketone
Aminoimidazole
Aryl bromide
Aryl halide
Pyrazine
Substituted pyrrole
Benzenoid
Azole
Imidazole
Heteroaromatic compound
Pyrrole
Tertiary alcohol
Lactam
Ketone
Azacycle
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Hydrocarbon derivative
Amine
Alcohol
Organic oxide
Primary amine
Organic nitrogen compound
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	3.2	ALOGPS
logP	1.58	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	10.07	ChemAxon
pKa (Strongest Basic)	8.36	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	165.04 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	137.05 m³·mol⁻¹	ChemAxon
Polarizability	52.83 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

9872177

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10-[5-(6-bromo-1h-indol-3-yl)-6-oxo-1h-pyrazin-2-yl]-1-hydroxy-4-imino-7-methyl-3,5,12-triazatetracyclo[6.6.1.0²,⁶.0⁹,¹³]pentadeca-2(6),9(13),10-trien-14-one (NP0209683)

MOL for NP0209683 (10-[5-(6-bromo-1h-indol-3-yl)-6-oxo-1h-pyrazin-2-yl]-1-hydroxy-4-imino-7-methyl-3,5,12-triazatetracyclo[6.6.1.0²,⁶.0⁹,¹³]pentadeca-2(6),9(13),10-trien-14-one)

3D MOL for NP0209683 (10-[5-(6-bromo-1h-indol-3-yl)-6-oxo-1h-pyrazin-2-yl]-1-hydroxy-4-imino-7-methyl-3,5,12-triazatetracyclo[6.6.1.0²,⁶.0⁹,¹³]pentadeca-2(6),9(13),10-trien-14-one)

3D SDF for NP0209683 (10-[5-(6-bromo-1h-indol-3-yl)-6-oxo-1h-pyrazin-2-yl]-1-hydroxy-4-imino-7-methyl-3,5,12-triazatetracyclo[6.6.1.0²,⁶.0⁹,¹³]pentadeca-2(6),9(13),10-trien-14-one)

3D-SDF for NP0209683 (10-[5-(6-bromo-1h-indol-3-yl)-6-oxo-1h-pyrazin-2-yl]-1-hydroxy-4-imino-7-methyl-3,5,12-triazatetracyclo[6.6.1.0²,⁶.0⁹,¹³]pentadeca-2(6),9(13),10-trien-14-one)

PDB for NP0209683 (10-[5-(6-bromo-1h-indol-3-yl)-6-oxo-1h-pyrazin-2-yl]-1-hydroxy-4-imino-7-methyl-3,5,12-triazatetracyclo[6.6.1.0²,⁶.0⁹,¹³]pentadeca-2(6),9(13),10-trien-14-one)

3D PDB for NP0209683 (10-[5-(6-bromo-1h-indol-3-yl)-6-oxo-1h-pyrazin-2-yl]-1-hydroxy-4-imino-7-methyl-3,5,12-triazatetracyclo[6.6.1.0²,⁶.0⁹,¹³]pentadeca-2(6),9(13),10-trien-14-one)

SMILES for NP0209683 (10-[5-(6-bromo-1h-indol-3-yl)-6-oxo-1h-pyrazin-2-yl]-1-hydroxy-4-imino-7-methyl-3,5,12-triazatetracyclo[6.6.1.0²,⁶.0⁹,¹³]pentadeca-2(6),9(13),10-trien-14-one)

INCHI for NP0209683 (10-[5-(6-bromo-1h-indol-3-yl)-6-oxo-1h-pyrazin-2-yl]-1-hydroxy-4-imino-7-methyl-3,5,12-triazatetracyclo[6.6.1.0²,⁶.0⁹,¹³]pentadeca-2(6),9(13),10-trien-14-one)

Structure for NP0209683 (10-[5-(6-bromo-1h-indol-3-yl)-6-oxo-1h-pyrazin-2-yl]-1-hydroxy-4-imino-7-methyl-3,5,12-triazatetracyclo[6.6.1.0²,⁶.0⁹,¹³]pentadeca-2(6),9(13),10-trien-14-one)

3D Structure for NP0209683 (10-[5-(6-bromo-1h-indol-3-yl)-6-oxo-1h-pyrazin-2-yl]-1-hydroxy-4-imino-7-methyl-3,5,12-triazatetracyclo[6.6.1.0²,⁶.0⁹,¹³]pentadeca-2(6),9(13),10-trien-14-one)