NP-MRD: Showing NP-Card for 6-(6-bromo-1h-indol-3-yl)-11-hydroxy-2,9-diimino-12-(1h-indol-3-yl)-1,3-dimethyl-1,3,8,10-tetraazadispiro[4.1.4⁷.1⁵]dodec-10-en-4-one (NP0280457)

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Record Information

Version

2.0

Created at

2022-09-09 06:15:54 UTC

Updated at

2022-09-09 06:15:54 UTC

NP-MRD ID

NP0280457

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-(6-bromo-1h-indol-3-yl)-11-hydroxy-2,9-diimino-12-(1h-indol-3-yl)-1,3-dimethyl-1,3,8,10-tetraazadispiro[4.1.4⁷.1⁵]dodec-10-en-4-one

Description

6-(6-Bromo-1H-indol-3-yl)-11-hydroxy-2,9-diimino-12-(1H-indol-3-yl)-1,3-dimethyl-1,3,8,10-tetraazadispiro[4.1.4⁷.1⁵]Dodec-10-en-4-one belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. 6-(6-Bromo-1H-indol-3-yl)-11-hydroxy-2,9-diimino-12-(1H-indol-3-yl)-1,3-dimethyl-1,3,8,10-tetraazadispiro[4.1.4⁷.1⁵]Dodec-10-en-4-one is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171520272D          

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M  END

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M  END


  Mrv1533004171520272D          

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M  END
> <DATABASE_ID>
NP0280457

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=N)N(C)C2(C(C3=CNC4=CC=CC=C34)C3(NC(N)=NC3=O)C2C2=CNC3=CC(Br)=CC=C23)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H23BrN8O2/c1-34-22(37)26(35(2)24(34)29)19(15-10-30-17-6-4-3-5-13(15)17)25(21(36)32-23(28)33-25)20(26)16-11-31-18-9-12(27)7-8-14(16)18/h3-11,19-20,29-31H,1-2H3,(H3,28,32,33,36)

> <INCHI_KEY>
ZGQPAKMMZIVWLH-UHFFFAOYSA-N

> <FORMULA>
C26H23BrN8O2

> <MOLECULAR_WEIGHT>
559.428

> <EXACT_MASS>
558.112735

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
53.736845344562035

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-6-(6-bromo-1H-indol-3-yl)-9-imino-12-(1H-indol-3-yl)-8,10-dimethyl-1,3,8,10-tetraazadispiro[4.1.4⁷.1⁵]dodec-2-ene-4,11-dione

> <ALOGPS_LOGP>
3.11

> <JCHEM_LOGP>
1.9830272713333335

> <ALOGPS_LOGS>
-4.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.253500063705683

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.609666524984

> <JCHEM_PKA_STRONGEST_BASIC>
4.412494893289914

> <JCHEM_POLAR_SURFACE_AREA>
146.46

> <JCHEM_REFRACTIVITY>
150.7662

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.87e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-6-(6-bromo-1H-indol-3-yl)-9-imino-12-(1H-indol-3-yl)-8,10-dimethyl-1,3,8,10-tetraazadispiro[4.1.4⁷.1⁵]dodec-2-ene-4,11-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  C   UNK     0       7.330  -0.052   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       5.865  -0.527   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.390  -1.992   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       6.295  -3.238   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       3.850  -1.992   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       2.944  -3.238   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.374  -0.527   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.002  -1.227   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.526  -2.691   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.431  -3.937   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.526  -5.183   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       0.061  -4.707   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.273  -5.477   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.606  -4.707   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.606  -3.167   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.273  -2.397   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.061  -3.167   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.302   0.146   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       0.057  -0.760   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      -1.189   0.146   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      -0.713   1.610   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       0.827   1.610   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.732   2.856   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0      -2.654  -0.330   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       2.675   0.845   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.150   2.309   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.245   3.555   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       3.150   4.801   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       4.615   4.325   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.949   5.095   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.282   4.325   0.000  0.00  0.00           C+0
HETATM   32 Br   UNK     0       8.616   5.095   0.000  0.00  0.00          Br+0
HETATM   33  C   UNK     0       7.282   2.785   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.949   2.015   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.615   2.785   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.620   0.378   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.620   1.918   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   25   36                                             
CONECT    8    7    9   18                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    9   12                                                  
CONECT   18    8   19   22   25                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   18   23                                                  
CONECT   23   22                                                            
CONECT   24   20                                                            
CONECT   25   18    7   26                                                  
CONECT   26   25   27   35                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   26   29                                                  
CONECT   36    7    2   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₃BrN₈O₂

Average Mass

559.4280 Da

Monoisotopic Mass

558.11274 Da

IUPAC Name

2-amino-6-(6-bromo-1H-indol-3-yl)-9-imino-12-(1H-indol-3-yl)-8,10-dimethyl-1,3,8,10-tetraazadispiro[4.1.4⁷.1⁵]dodec-2-ene-4,11-dione

Traditional Name

2-amino-6-(6-bromo-1H-indol-3-yl)-9-imino-12-(1H-indol-3-yl)-8,10-dimethyl-1,3,8,10-tetraazadispiro[4.1.4⁷.1⁵]dodec-2-ene-4,11-dione

CAS Registry Number

Not Available

SMILES

CN1C(=N)N(C)C2(C(C3=CNC4=CC=CC=C34)C3(NC(N)=NC3=O)C2C2=CNC3=CC(Br)=CC=C23)C1=O

InChI Identifier

InChI=1S/C26H23BrN8O2/c1-34-22(37)26(35(2)24(34)29)19(15-10-30-17-6-4-3-5-13(15)17)25(21(36)32-23(28)33-25)20(26)16-11-31-18-9-12(27)7-8-14(16)18/h3-11,19-20,29-31H,1-2H3,(H3,28,32,33,36)

InChI Key

ZGQPAKMMZIVWLH-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 alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
3-alkylindole
Indole
Indole or derivatives
Aryl bromide
Aryl halide
Imidazolidinone
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Imidazolidine
3-imidazoline
Pyrrole
Guanidine
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Organic oxide
Imine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organohalogen compound
Organobromide
Organonitrogen compound
Organooxygen 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	3.11	ALOGPS
logP	1.98	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	15.61	ChemAxon
pKa (Strongest Basic)	4.41	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	146.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	150.77 m³·mol⁻¹	ChemAxon
Polarizability	53.74 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	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

75167616

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-(6-bromo-1h-indol-3-yl)-11-hydroxy-2,9-diimino-12-(1h-indol-3-yl)-1,3-dimethyl-1,3,8,10-tetraazadispiro[4.1.4⁷.1⁵]dodec-10-en-4-one (NP0280457)

MOL for NP0280457 (6-(6-bromo-1h-indol-3-yl)-11-hydroxy-2,9-diimino-12-(1h-indol-3-yl)-1,3-dimethyl-1,3,8,10-tetraazadispiro[4.1.4⁷.1⁵]dodec-10-en-4-one)

3D MOL for NP0280457 (6-(6-bromo-1h-indol-3-yl)-11-hydroxy-2,9-diimino-12-(1h-indol-3-yl)-1,3-dimethyl-1,3,8,10-tetraazadispiro[4.1.4⁷.1⁵]dodec-10-en-4-one)

3D SDF for NP0280457 (6-(6-bromo-1h-indol-3-yl)-11-hydroxy-2,9-diimino-12-(1h-indol-3-yl)-1,3-dimethyl-1,3,8,10-tetraazadispiro[4.1.4⁷.1⁵]dodec-10-en-4-one)

3D-SDF for NP0280457 (6-(6-bromo-1h-indol-3-yl)-11-hydroxy-2,9-diimino-12-(1h-indol-3-yl)-1,3-dimethyl-1,3,8,10-tetraazadispiro[4.1.4⁷.1⁵]dodec-10-en-4-one)

PDB for NP0280457 (6-(6-bromo-1h-indol-3-yl)-11-hydroxy-2,9-diimino-12-(1h-indol-3-yl)-1,3-dimethyl-1,3,8,10-tetraazadispiro[4.1.4⁷.1⁵]dodec-10-en-4-one)

3D PDB for NP0280457 (6-(6-bromo-1h-indol-3-yl)-11-hydroxy-2,9-diimino-12-(1h-indol-3-yl)-1,3-dimethyl-1,3,8,10-tetraazadispiro[4.1.4⁷.1⁵]dodec-10-en-4-one)

SMILES for NP0280457 (6-(6-bromo-1h-indol-3-yl)-11-hydroxy-2,9-diimino-12-(1h-indol-3-yl)-1,3-dimethyl-1,3,8,10-tetraazadispiro[4.1.4⁷.1⁵]dodec-10-en-4-one)

INCHI for NP0280457 (6-(6-bromo-1h-indol-3-yl)-11-hydroxy-2,9-diimino-12-(1h-indol-3-yl)-1,3-dimethyl-1,3,8,10-tetraazadispiro[4.1.4⁷.1⁵]dodec-10-en-4-one)

Structure for NP0280457 (6-(6-bromo-1h-indol-3-yl)-11-hydroxy-2,9-diimino-12-(1h-indol-3-yl)-1,3-dimethyl-1,3,8,10-tetraazadispiro[4.1.4⁷.1⁵]dodec-10-en-4-one)

3D Structure for NP0280457 (6-(6-bromo-1h-indol-3-yl)-11-hydroxy-2,9-diimino-12-(1h-indol-3-yl)-1,3-dimethyl-1,3,8,10-tetraazadispiro[4.1.4⁷.1⁵]dodec-10-en-4-one)