NP-MRD: Showing NP-Card for 9-acetyl-7-bromopyrido[3,4-b]indol-6-yl acetate (NP0144003)

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Record Information

Version

2.0

Created at

2022-09-01 22:52:38 UTC

Updated at

2022-09-01 22:52:38 UTC

NP-MRD ID

NP0144003

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-acetyl-7-bromopyrido[3,4-b]indol-6-yl acetate

Description

9-Acetyl-7-bromo-9H-pyrido[3,4-b]indol-6-yl acetate belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. Based on a literature review very few articles have been published on 9-acetyl-7-bromo-9H-pyrido[3,4-b]indol-6-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
    5.6426   -0.0945   -0.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1712   -0.2156   -0.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5797   -0.4983   -1.6390 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4062   -0.0351    0.5694 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0336   -0.1716    0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1895    0.8803    0.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1776    0.7226    0.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2327    1.5659   -0.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2440    2.9164   -0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4524    3.5367   -0.6563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5909    2.8340   -0.6015 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6188    1.4967   -0.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4180    0.8735   -0.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1161   -0.4317    0.2031 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0802   -1.4507    0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8020   -2.8654    0.6534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3137   -1.1244    0.1708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7594   -0.5224    0.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0838   -1.5684    0.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4781   -1.3975    0.6982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5893   -2.8870    1.1012 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.9776    0.2362    0.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9656    0.6738   -1.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0856   -1.0944   -0.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6055    1.8638    0.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3234    3.5025   -0.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4415    4.6098   -0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5905    1.0062   -0.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2004   -3.3636   -0.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3579   -2.9755    1.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7724   -3.4608    0.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3166   -2.5616    0.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 18 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 14 13  1  0
 13  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 20  5  1  0
 12 13  1  0
  8  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
 19 32  1  0
 16 29  1  0
 16 30  1  0
 16 31  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
M  END


  Mrv1652309022200522D          

 21 23  0  0  0  0            999 V2000
   -1.2415   -0.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6895   -0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9444   -1.7031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1175   -0.7470    0.0000 O   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
    4.4675   -2.1447    0.0000 N   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
    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
    2.4410   -3.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7266   -4.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1555   -4.3087    0.0000 O   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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3924   -2.3162    0.0000 Br  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
  2  4  1  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
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  8 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 14 18  1  0  0  0  0
  7 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  5 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0144003

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1=CC2=C(C=C1Br)N(C(C)=O)C1=C2C=CN=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H11BrN2O3/c1-8(19)18-13-6-12(16)15(21-9(2)20)5-11(13)10-3-4-17-7-14(10)18/h3-7H,1-2H3

> <INCHI_KEY>
WAQMAUZBBFONMB-UHFFFAOYSA-N

> <FORMULA>
C15H11BrN2O3

> <MOLECULAR_WEIGHT>
347.168

> <EXACT_MASS>
345.995305

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
30.91860910725272

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-acetyl-7-bromo-9H-pyrido[3,4-b]indol-6-yl acetate

> <ALOGPS_LOGP>
3.33

> <JCHEM_LOGP>
1.5690359713333333

> <ALOGPS_LOGS>
-4.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.893447380916065

> <JCHEM_PKA_STRONGEST_BASIC>
4.366539326455376

> <JCHEM_POLAR_SURFACE_AREA>
61.19

> <JCHEM_REFRACTIVITY>
79.3408

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-acetyl-7-bromopyrido[3,4-b]indol-6-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.317  -0.570   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.287  -1.715   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.763  -3.179   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.219  -1.394   0.000  0.00  0.00           O+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  N   UNK     0       8.339  -4.003   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       7.309  -5.148   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.802  -4.828   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       4.557  -5.733   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       4.557  -7.273   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.223  -8.043   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.890  -8.043   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.311  -4.828   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.804  -5.148   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.774  -4.003   0.000  0.00  0.00           C+0
HETATM   21 Br   UNK     0      -0.732  -4.324   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   20                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   18                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   14    7   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    5   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
9-Acetyl-7-bromo-9H-pyrido[3,4-b]indol-6-yl acetic acid	Generator

Chemical Formula

C₁₅H₁₁BrN₂O₃

Average Mass

347.1680 Da

Monoisotopic Mass

345.99530 Da

IUPAC Name

9-acetyl-7-bromo-9H-pyrido[3,4-b]indol-6-yl acetate

Traditional Name

9-acetyl-7-bromopyrido[3,4-b]indol-6-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1=CC2=C(C=C1Br)N(C(C)=O)C1=C2C=CN=C1

InChI Identifier

InChI=1S/C15H11BrN2O3/c1-8(19)18-13-6-12(16)15(21-9(2)20)5-11(13)10-3-4-17-7-14(10)18/h3-7H,1-2H3

InChI Key

WAQMAUZBBFONMB-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 beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Beta carbolines

Alternative Parents

Substituents

Beta-carboline
Indole
Aryl bromide
Aryl halide
Pyridine
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Acetamide
Pyrrole
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Azacycle
Organobromide
Organohalogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen 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	3.33	ALOGPS
logP	1.57	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	19.89	ChemAxon
pKa (Strongest Basic)	4.37	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.19 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.34 m³·mol⁻¹	ChemAxon
Polarizability	30.92 Å³	ChemAxon
Number of Rings	3	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

10355733

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23247394

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9-acetyl-7-bromopyrido[3,4-b]indol-6-yl acetate (NP0144003)

MOL for NP0144003 (9-acetyl-7-bromopyrido[3,4-b]indol-6-yl acetate)

3D MOL for NP0144003 (9-acetyl-7-bromopyrido[3,4-b]indol-6-yl acetate)

3D SDF for NP0144003 (9-acetyl-7-bromopyrido[3,4-b]indol-6-yl acetate)

3D-SDF for NP0144003 (9-acetyl-7-bromopyrido[3,4-b]indol-6-yl acetate)

PDB for NP0144003 (9-acetyl-7-bromopyrido[3,4-b]indol-6-yl acetate)

3D PDB for NP0144003 (9-acetyl-7-bromopyrido[3,4-b]indol-6-yl acetate)

SMILES for NP0144003 (9-acetyl-7-bromopyrido[3,4-b]indol-6-yl acetate)

INCHI for NP0144003 (9-acetyl-7-bromopyrido[3,4-b]indol-6-yl acetate)

Structure for NP0144003 (9-acetyl-7-bromopyrido[3,4-b]indol-6-yl acetate)

3D Structure for NP0144003 (9-acetyl-7-bromopyrido[3,4-b]indol-6-yl acetate)