NP-MRD: Showing NP-Card for 2'-(6-bromo-1h-indol-3-yl)-2''-imino-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'h-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,5,5''-trione (NP0244543)

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Record Information

Version

2.0

Created at

2022-09-07 05:21:48 UTC

Updated at

2022-09-07 05:21:48 UTC

NP-MRD ID

NP0244543

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2'-(6-bromo-1h-indol-3-yl)-2''-imino-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'h-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,5,5''-trione

Description

2'-(6-Bromo-1H-indol-3-yl)-2''-imino-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'H-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,5,5''-trione belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. 2'-(6-bromo-1h-indol-3-yl)-2''-imino-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'h-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,5,5''-trione is found in Tubastraea coccinea. 2'-(6-Bromo-1H-indol-3-yl)-2''-imino-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'H-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,5,5''-trione is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161503282D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004161503282D          

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  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 17  1  0  0  0  0
 12 17  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 20 29  1  0  0  0  0
 23 29  1  0  0  0  0
 18 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 18 36  1  0  0  0  0
 36 37  2  0  0  0  0
  7 38  1  0  0  0  0
  2 38  1  0  0  0  0
 38 39  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0244543

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=N)N(C)C2(CC3=C(NC4=CC=CC=C34)C3(C2C2=CNC4=CC(Br)=CC=C24)N(C)C(=O)N(C)C3=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H26BrN7O3/c1-33-23(37)27(35(3)25(33)30)12-17-15-7-5-6-8-19(15)32-22(17)28(24(38)34(2)26(39)36(28)4)21(27)18-13-31-20-11-14(29)9-10-16(18)20/h5-11,13,21,30-32H,12H2,1-4H3

> <INCHI_KEY>
WILDJHDKEXXKQZ-UHFFFAOYSA-N

> <FORMULA>
C28H26BrN7O3

> <MOLECULAR_WEIGHT>
588.466

> <EXACT_MASS>
587.128051

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
57.21134954234609

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2'-(6-bromo-1H-indol-3-yl)-2''-imino-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'H-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,5,5''-trione

> <ALOGPS_LOGP>
3.83

> <JCHEM_LOGP>
2.884354965000001

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.05866496741892

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.452296051728997

> <JCHEM_PKA_STRONGEST_BASIC>
4.486094684624108

> <JCHEM_POLAR_SURFACE_AREA>
119.6

> <JCHEM_REFRACTIVITY>
158.97230000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2'-(6-bromo-1H-indol-3-yl)-2''-imino-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'H-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,5,5''-trione

> <JCHEM_VEBER_RULE>
0

$$$$

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  C   UNK     0      11.190  -0.780   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       9.813  -1.654   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       9.528  -3.168   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      11.177  -3.898   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       8.001  -3.364   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.639  -4.559   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.342  -1.972   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.832  -0.519   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.319  -0.234   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.315  -1.402   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       2.894  -0.808   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       3.020   0.727   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.963   1.847   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.405   3.322   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.903   3.677   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.960   2.557   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.518   1.082   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.825  -2.855   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.338  -3.140   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.861  -4.316   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.972  -5.860   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       6.905  -7.084   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       8.359  -6.575   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.710  -7.314   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.025  -6.513   0.000  0.00  0.00           C+0
HETATM   26 Br   UNK     0      12.377  -7.252   0.000  0.00  0.00          Br+0
HETATM   27  C   UNK     0      10.990  -4.973   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.639  -4.235   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.323  -5.035   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       5.180  -4.353   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0       6.610  -5.225   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.864  -5.154   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.928  -6.512   0.000  0.00  0.00           O+0
HETATM   34  N   UNK     0       2.696  -4.150   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       1.121  -4.589   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.290  -2.729   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       1.920  -1.941   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       8.462  -0.915   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       9.182   0.562   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   38                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   19   38                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11   18                                                  
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   10   19   30   36                                             
CONECT   19   18    7   20                                                  
CONECT   20   19   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   18   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   18   37                                                  
CONECT   37   36                                                            
CONECT   38    7    2   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₆BrN₇O₃

Average Mass

588.4660 Da

Monoisotopic Mass

587.12805 Da

IUPAC Name

2'-(6-bromo-1H-indol-3-yl)-2''-imino-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'H-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,5,5''-trione

Traditional Name

2'-(6-bromo-1H-indol-3-yl)-2''-imino-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'H-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,5,5''-trione

CAS Registry Number

Not Available

SMILES

CN1C(=N)N(C)C2(CC3=C(NC4=CC=CC=C34)C3(C2C2=CNC4=CC(Br)=CC=C24)N(C)C(=O)N(C)C3=O)C1=O

InChI Identifier

InChI=1S/C28H26BrN7O3/c1-33-23(37)27(35(3)25(33)30)12-17-15-7-5-6-8-19(15)32-22(17)28(24(38)34(2)26(39)36(28)4)21(27)18-13-31-20-11-14(29)9-10-16(18)20/h5-11,13,21,30-32H,12H2,1-4H3

InChI Key

WILDJHDKEXXKQZ-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
Tubastraea aurea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
Hydantoin
Alpha-amino acid or derivatives
3-alkylindole
Indole
Ureide
N-acyl urea
Aryl bromide
Aryl halide
Benzenoid
Imidazolidinone
Substituted pyrrole
Dicarboximide
Heteroaromatic compound
Imidazolidine
Pyrrole
Guanidine
Urea
Carbonic acid derivative
Carboximidamide
Azacycle
Carboxylic acid derivative
Organonitrogen compound
Organooxygen compound
Imine
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
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	3.83	ALOGPS
logP	2.88	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	15.45	ChemAxon
pKa (Strongest Basic)	4.49	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	119.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	158.97 m³·mol⁻¹	ChemAxon
Polarizability	57.21 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2'-(6-bromo-1h-indol-3-yl)-2''-imino-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'h-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,5,5''-trione (NP0244543)

MOL for NP0244543 (2'-(6-bromo-1h-indol-3-yl)-2''-imino-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'h-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,5,5''-trione)

3D MOL for NP0244543 (2'-(6-bromo-1h-indol-3-yl)-2''-imino-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'h-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,5,5''-trione)

3D SDF for NP0244543 (2'-(6-bromo-1h-indol-3-yl)-2''-imino-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'h-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,5,5''-trione)

3D-SDF for NP0244543 (2'-(6-bromo-1h-indol-3-yl)-2''-imino-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'h-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,5,5''-trione)

PDB for NP0244543 (2'-(6-bromo-1h-indol-3-yl)-2''-imino-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'h-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,5,5''-trione)

3D PDB for NP0244543 (2'-(6-bromo-1h-indol-3-yl)-2''-imino-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'h-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,5,5''-trione)

SMILES for NP0244543 (2'-(6-bromo-1h-indol-3-yl)-2''-imino-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'h-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,5,5''-trione)

INCHI for NP0244543 (2'-(6-bromo-1h-indol-3-yl)-2''-imino-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'h-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,5,5''-trione)

Structure for NP0244543 (2'-(6-bromo-1h-indol-3-yl)-2''-imino-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'h-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,5,5''-trione)

3D Structure for NP0244543 (2'-(6-bromo-1h-indol-3-yl)-2''-imino-1,1'',3,3''-tetramethyl-4',9'-dihydro-2'h-dispiro[imidazolidine-4,1'-carbazole-3',4''-imidazolidine]-2,5,5''-trione)