NP-MRD: Showing NP-Card for 2,2',3,4',5,5'-hexabromo-1'h-1,3'-biindole (NP0147192)

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Record Information

Version

2.0

Created at

2022-09-02 02:45:01 UTC

Updated at

2022-09-02 02:45:01 UTC

NP-MRD ID

NP0147192

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,2',3,4',5,5'-hexabromo-1'h-1,3'-biindole

Description

SCHEMBL17866744 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. SCHEMBL17866744 is an extremely weak acidic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 33  0  0  0  0  0  0  0  0999 V2000
    5.9772    0.6169   -1.5630 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.2171    0.2503   -0.8803 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1747   -0.0516   -1.7311 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9022   -0.3207   -1.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6648   -0.2834    0.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7008    0.0176    0.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9858    0.2878    0.4749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1540   -0.0248    2.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1071    0.3076    3.8136 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.8246   -0.3459    2.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4479   -0.5480    3.4876 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.5135   -0.5064    0.7708 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7515   -0.8415    0.2017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1964   -2.0629   -0.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2023   -3.6865   -0.2326 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4510   -1.9406   -0.7107 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8420   -0.6586   -0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0069    0.0327   -0.8670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1625    1.3816   -0.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1016    2.0621   -0.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2051    3.9348    0.3344 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.9383    1.3920    0.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4859    2.3532    1.0332 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8040    0.0570   -0.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3987   -0.0712   -2.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0973   -0.5553   -1.9767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7766    0.5203    1.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0286   -2.6978   -1.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8075   -0.5390   -1.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0629    1.9202   -0.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 10  1  0
 10 11  1  0
 10  8  2  0
  8  9  1  0
  8  6  1  0
  6  7  2  0
  7  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
 13 24  1  0
 24 22  2  0
 22 23  1  0
 22 20  1  0
 20 21  1  0
 20 19  2  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
 16 14  1  0
  5 12  1  0
 17 24  1  0
  5  6  1  0
  7 27  1  0
  3 25  1  0
  4 26  1  0
 19 30  1  0
 18 29  1  0
 16 28  1  0
M  END


  Mrv1533004241503032D          

 24 27  0  0  0  0            999 V2000
   -2.0443   -3.6424    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.3298   -3.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3298   -2.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6153   -1.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -2.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -3.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6153   -3.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -3.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -4.2695    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.3687   -2.8174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937   -2.8174    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    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
   -0.1712   -0.6979    0.0000 Br  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
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 Br  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
    2.6378   -2.3479    0.0000 Br  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
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  5 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
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 13 24  1  0  0  0  0
 17 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0147192

> <DATABASE_NAME>
NP-MRD

> <SMILES>
BrC1=C(N2C(Br)=C(Br)C3=CC(Br)=CC=C23)C2=C(Br)C(Br)=CC=C2N1

> <INCHI_IDENTIFIER>
InChI=1S/C16H6Br6N2/c17-6-1-4-10-7(5-6)12(19)16(22)24(10)14-11-9(23-15(14)21)3-2-8(18)13(11)20/h1-5,23H

> <INCHI_KEY>
DMXOQZLSFLIYAF-UHFFFAOYSA-N

> <FORMULA>
C16H6Br6N2

> <MOLECULAR_WEIGHT>
705.662

> <EXACT_MASS>
699.563126

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
45.92263424034005

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3,5-tribromo-1-(2,4,5-tribromo-1H-indol-3-yl)-1H-indole

> <ALOGPS_LOGP>
7.22

> <JCHEM_LOGP>
8.065631054333332

> <ALOGPS_LOGS>
-6.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.710598478696578

> <JCHEM_POLAR_SURFACE_AREA>
20.72

> <JCHEM_REFRACTIVITY>
128.52540000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.10e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3,5-tribromo-1-(2,4,5-tribromo-1H-indol-3-yl)indole

> <JCHEM_VEBER_RULE>
1

$$$$

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 Br   UNK     0      -3.816  -6.799   0.000  0.00  0.00          Br+0
HETATM    2  C   UNK     0      -2.482  -6.029   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.482  -4.489   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.149  -3.719   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.185  -4.489   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.185  -6.029   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.149  -6.799   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.650  -6.505   0.000  0.00  0.00           C+0
HETATM    9 Br   UNK     0       2.126  -7.970   0.000  0.00  0.00          Br+0
HETATM   10  C   UNK     0       2.555  -5.259   0.000  0.00  0.00           C+0
HETATM   11 Br   UNK     0       4.095  -5.259   0.000  0.00  0.00          Br+0
HETATM   12  N   UNK     0       1.650  -4.013   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   15 Br   UNK     0      -0.320  -1.303   0.000  0.00  0.00          Br+0
HETATM   16  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   21 Br   UNK     0       7.591  -2.843   0.000  0.00  0.00          Br+0
HETATM   22  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   23 Br   UNK     0       4.924  -4.383   0.000  0.00  0.00          Br+0
HETATM   24  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5   13                                                  
CONECT   13   12   14   24                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   13   17                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₆Br₆N₂

Average Mass

705.6620 Da

Monoisotopic Mass

699.56313 Da

IUPAC Name

2,3,5-tribromo-1-(2,4,5-tribromo-1H-indol-3-yl)-1H-indole

Traditional Name

2,3,5-tribromo-1-(2,4,5-tribromo-1H-indol-3-yl)indole

CAS Registry Number

Not Available

SMILES

BrC1=C(N2C(Br)=C(Br)C3=CC(Br)=CC=C23)C2=C(Br)C(Br)=CC=C2N1

InChI Identifier

InChI=1S/C16H6Br6N2/c17-6-1-4-10-7(5-6)12(19)16(22)24(10)14-11-9(23-15(14)21)3-2-8(18)13(11)20/h1-5,23H

InChI Key

DMXOQZLSFLIYAF-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
Benzenoid
Substituted pyrrole
Aryl halide
Aryl bromide
Heteroaromatic compound
Pyrrole
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Organobromide
Organohalogen 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	7.22	ALOGPS
logP	8.07	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	15.71	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.72 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	128.53 m³·mol⁻¹	ChemAxon
Polarizability	45.92 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

21674193

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,2',3,4',5,5'-hexabromo-1'h-1,3'-biindole (NP0147192)

MOL for NP0147192 (2,2',3,4',5,5'-hexabromo-1'h-1,3'-biindole)

3D MOL for NP0147192 (2,2',3,4',5,5'-hexabromo-1'h-1,3'-biindole)

3D SDF for NP0147192 (2,2',3,4',5,5'-hexabromo-1'h-1,3'-biindole)

3D-SDF for NP0147192 (2,2',3,4',5,5'-hexabromo-1'h-1,3'-biindole)

PDB for NP0147192 (2,2',3,4',5,5'-hexabromo-1'h-1,3'-biindole)

3D PDB for NP0147192 (2,2',3,4',5,5'-hexabromo-1'h-1,3'-biindole)

SMILES for NP0147192 (2,2',3,4',5,5'-hexabromo-1'h-1,3'-biindole)

INCHI for NP0147192 (2,2',3,4',5,5'-hexabromo-1'h-1,3'-biindole)

Structure for NP0147192 (2,2',3,4',5,5'-hexabromo-1'h-1,3'-biindole)

3D Structure for NP0147192 (2,2',3,4',5,5'-hexabromo-1'h-1,3'-biindole)