NP-MRD: Showing NP-Card for 6,8-dibromo-1-ethyl-9h-pyrido[3,4-b]indole (NP0233112)

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Record Information

Version

2.0

Created at

2022-09-06 14:36:02 UTC

Updated at

2022-09-06 14:36:02 UTC

NP-MRD ID

NP0233112

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,8-dibromo-1-ethyl-9h-pyrido[3,4-b]indole

Description

6,8-Dibromo-1-ethyl-9H-pyrido[3,4-b]indole belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole. 6,8-dibromo-1-ethyl-9h-pyrido[3,4-b]indole is found in Aglaophenia pluma. 6,8-Dibromo-1-ethyl-9H-pyrido[3,4-b]indole is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241502232D          

 17 19  0  0  0  0            999 V2000
   -0.0953   -3.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7117   -3.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9666   -2.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4146   -2.1447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6695   -1.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4765   -1.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0285   -1.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8535   -1.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4056   -1.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125   -1.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7646   -0.7470    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.4675   -2.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9154   -2.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1704   -3.5424    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.1085   -2.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4410   -3.0712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7736   -2.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  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
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  8 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  3 17  1  0  0  0  0
  7 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0233112

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1=NC=CC2=C1NC1=C2C=C(Br)C=C1Br

> <INCHI_IDENTIFIER>
InChI=1S/C13H10Br2N2/c1-2-11-13-8(3-4-16-11)9-5-7(14)6-10(15)12(9)17-13/h3-6,17H,2H2,1H3

> <INCHI_KEY>
ZKHUMPXYARQUSA-UHFFFAOYSA-N

> <FORMULA>
C13H10Br2N2

> <MOLECULAR_WEIGHT>
354.045

> <EXACT_MASS>
351.921074

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
29.323197998646954

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,8-dibromo-1-ethyl-9H-pyrido[3,4-b]indole

> <ALOGPS_LOGP>
5.04

> <JCHEM_LOGP>
4.2426245289999995

> <ALOGPS_LOGS>
-5.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.697455615350975

> <JCHEM_PKA_STRONGEST_BASIC>
5.79832928121358

> <JCHEM_POLAR_SURFACE_AREA>
28.68

> <JCHEM_REFRACTIVITY>
75.77930000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.06e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,8-dibromo-1-ethyl-9H-pyrido[3,4-b]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  C   UNK     0      -0.178  -6.933   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.328  -6.612   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.804  -5.148   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       0.774  -4.003   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.250  -2.539   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.756  -2.219   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.787  -3.363   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.327  -3.363   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.357  -2.219   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.863  -2.539   0.000  0.00  0.00           C+0
HETATM   11 Br   UNK     0       8.894  -1.394   0.000  0.00  0.00          Br+0
HETATM   12  C   UNK     0       8.339  -4.003   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.309  -5.148   0.000  0.00  0.00           C+0
HETATM   14 Br   UNK     0       7.785  -6.612   0.000  0.00  0.00          Br+0
HETATM   15  C   UNK     0       5.802  -4.828   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       4.557  -5.733   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       3.311  -4.828   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   17                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    8   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16    3    7                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₀Br₂N₂

Average Mass

354.0450 Da

Monoisotopic Mass

351.92107 Da

IUPAC Name

6,8-dibromo-1-ethyl-9H-pyrido[3,4-b]indole

Traditional Name

6,8-dibromo-1-ethyl-9H-pyrido[3,4-b]indole

CAS Registry Number

Not Available

SMILES

CCC1=NC=CC2=C1NC1=C2C=C(Br)C=C1Br

InChI Identifier

InChI=1S/C13H10Br2N2/c1-2-11-13-8(3-4-16-11)9-5-7(14)6-10(15)12(9)17-13/h3-6,17H,2H2,1H3

InChI Key

ZKHUMPXYARQUSA-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
Aglaophenia pluma	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Harmala alkaloids

Sub Class

Not Available

Direct Parent

Harmala alkaloids

Alternative Parents

Substituents

Harman
Beta-carboline
Pyridoindole
Indole
Indole or derivatives
Aryl bromide
Aryl halide
Pyridine
Benzenoid
Heteroaromatic compound
Pyrrole
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Organobromide
Organohalogen compound
Hydrocarbon derivative
Organic nitrogen 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	5.04	ALOGPS
logP	4.24	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	12.7	ChemAxon
pKa (Strongest Basic)	5.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	28.68 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.78 m³·mol⁻¹	ChemAxon
Polarizability	29.32 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

13942346

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6,8-dibromo-1-ethyl-9h-pyrido[3,4-b]indole (NP0233112)

MOL for NP0233112 (6,8-dibromo-1-ethyl-9h-pyrido[3,4-b]indole)

3D MOL for NP0233112 (6,8-dibromo-1-ethyl-9h-pyrido[3,4-b]indole)

3D SDF for NP0233112 (6,8-dibromo-1-ethyl-9h-pyrido[3,4-b]indole)

3D-SDF for NP0233112 (6,8-dibromo-1-ethyl-9h-pyrido[3,4-b]indole)

PDB for NP0233112 (6,8-dibromo-1-ethyl-9h-pyrido[3,4-b]indole)

3D PDB for NP0233112 (6,8-dibromo-1-ethyl-9h-pyrido[3,4-b]indole)

SMILES for NP0233112 (6,8-dibromo-1-ethyl-9h-pyrido[3,4-b]indole)

INCHI for NP0233112 (6,8-dibromo-1-ethyl-9h-pyrido[3,4-b]indole)

Structure for NP0233112 (6,8-dibromo-1-ethyl-9h-pyrido[3,4-b]indole)

3D Structure for NP0233112 (6,8-dibromo-1-ethyl-9h-pyrido[3,4-b]indole)