NP-MRD: Showing NP-Card for 1-{7-bromo-9h-pyrido[3,4-b]indol-1-yl}-2-phenylethanone (NP0226554)

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Record Information

Version

2.0

Created at

2022-09-06 05:38:08 UTC

Updated at

2022-09-06 05:38:08 UTC

NP-MRD ID

NP0226554

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-{7-bromo-9h-pyrido[3,4-b]indol-1-yl}-2-phenylethanone

Description

1-{7-Bromo-9H-pyrido[3,4-b]indol-1-yl}-2-phenylethan-1-one 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. 1-{7-Bromo-9H-pyrido[3,4-b]indol-1-yl}-2-phenylethan-1-one is a moderately basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004191522342D          

 23 26  0  0  0  0            999 V2000
    4.7674    0.0694    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046   -1.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6024   -1.3283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7566   -1.7698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5017   -2.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0537   -3.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7988   -3.9522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0082   -4.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5602   -3.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3053   -2.7260    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
  2  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  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
  5 14  1  0  0  0  0
  9 14  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  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  2  0  0  0  0
 18 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226554

> <DATABASE_NAME>
NP-MRD

> <SMILES>
BrC1=CC2=C(C=C1)C1=C(N2)C(=NC=C1)C(=O)CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H13BrN2O/c20-13-6-7-14-15-8-9-21-19(18(15)22-16(14)11-13)17(23)10-12-4-2-1-3-5-12/h1-9,11,22H,10H2

> <INCHI_KEY>
LXFYFAZNYYSTME-UHFFFAOYSA-N

> <FORMULA>
C19H13BrN2O

> <MOLECULAR_WEIGHT>
365.23

> <EXACT_MASS>
364.021126

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
35.52542648362926

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-{7-bromo-9H-pyrido[3,4-b]indol-1-yl}-2-phenylethan-1-one

> <ALOGPS_LOGP>
4.56

> <JCHEM_LOGP>
4.419803551666666

> <ALOGPS_LOGS>
-5.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.015350006110307

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.680833693126083

> <JCHEM_PKA_STRONGEST_BASIC>
2.9155588577522837

> <JCHEM_POLAR_SURFACE_AREA>
45.75

> <JCHEM_REFRACTIVITY>
93.69080000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.72e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-{7-bromo-9H-pyrido[3,4-b]indol-1-yl}-2-phenylethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1 Br   UNK     0       8.899   0.130   0.000  0.00  0.00          Br+0
HETATM    2  C   UNK     0       7.393   0.450   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.917   1.914   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.410   2.235   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.380   1.090   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.856  -0.374   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.362  -0.695   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       3.610  -1.280   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -0.173   0.450   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.382  -2.159   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.124  -2.479   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.412  -3.304   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.936  -4.768   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.967  -5.913   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.491  -7.377   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.015  -7.698   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.046  -6.553   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.570  -5.089   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   14                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    5    9                                                  
CONECT   15   10   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₃BrN₂O

Average Mass

365.2300 Da

Monoisotopic Mass

364.02113 Da

IUPAC Name

1-{7-bromo-9H-pyrido[3,4-b]indol-1-yl}-2-phenylethan-1-one

Traditional Name

1-{7-bromo-9H-pyrido[3,4-b]indol-1-yl}-2-phenylethanone

CAS Registry Number

Not Available

SMILES

BrC1=CC2=C(C=C1)C1=C(N2)C(=NC=C1)C(=O)CC1=CC=CC=C1

InChI Identifier

InChI=1S/C19H13BrN2O/c20-13-6-7-14-15-8-9-21-19(18(15)22-16(14)11-13)17(23)10-12-4-2-1-3-5-12/h1-9,11,22H,10H2

InChI Key

LXFYFAZNYYSTME-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 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 ketone
Aryl alkyl ketone
Aryl bromide
Aryl halide
Monocyclic benzene moiety
Pyridine
Benzenoid
Heteroaromatic compound
Pyrrole
Vinylogous amide
Ketone
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	4.56	ALOGPS
logP	4.42	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	11.68	ChemAxon
pKa (Strongest Basic)	2.92	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	45.75 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	93.69 m³·mol⁻¹	ChemAxon
Polarizability	35.53 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

23425843

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-{7-bromo-9h-pyrido[3,4-b]indol-1-yl}-2-phenylethanone (NP0226554)

MOL for NP0226554 (1-{7-bromo-9h-pyrido[3,4-b]indol-1-yl}-2-phenylethanone)

3D MOL for NP0226554 (1-{7-bromo-9h-pyrido[3,4-b]indol-1-yl}-2-phenylethanone)

3D SDF for NP0226554 (1-{7-bromo-9h-pyrido[3,4-b]indol-1-yl}-2-phenylethanone)

3D-SDF for NP0226554 (1-{7-bromo-9h-pyrido[3,4-b]indol-1-yl}-2-phenylethanone)

PDB for NP0226554 (1-{7-bromo-9h-pyrido[3,4-b]indol-1-yl}-2-phenylethanone)

3D PDB for NP0226554 (1-{7-bromo-9h-pyrido[3,4-b]indol-1-yl}-2-phenylethanone)

SMILES for NP0226554 (1-{7-bromo-9h-pyrido[3,4-b]indol-1-yl}-2-phenylethanone)

INCHI for NP0226554 (1-{7-bromo-9h-pyrido[3,4-b]indol-1-yl}-2-phenylethanone)

Structure for NP0226554 (1-{7-bromo-9h-pyrido[3,4-b]indol-1-yl}-2-phenylethanone)

3D Structure for NP0226554 (1-{7-bromo-9h-pyrido[3,4-b]indol-1-yl}-2-phenylethanone)