NP-MRD: Showing NP-Card for 1-acetyl-beta-carboline (NP0036253)

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Record Information

Version

2.0

Created at

2021-06-20 19:28:30 UTC

Updated at

2021-06-30 00:07:49 UTC

NP-MRD ID

NP0036253

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-acetyl-beta-carboline

Provided By

JEOL Database JEOL Logo

Description

1-{9H-pyrido[3,4-b]indol-1-yl}ethan-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-acetyl-beta-carboline is found in Ailanthus triphysa, Eremogone kansuensis, Ligusticum sinense, Marinactinospora thermotolerans, Ophiocordyceps sinensis, Picrasma quassioides, Rauvolfia serpentina, Streptomyces kasugaensis and Tedania ignis. 1-acetyl-beta-carboline was first documented in 2011 (Huang, H., et al.). Based on a literature review very few articles have been published on 1-{9H-pyrido[3,4-b]indol-1-yl}ethan-1-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121283D          

 26 28  0  0  0  0            999 V2000
   -3.2284   -3.5473    2.1770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7859   -2.2683    1.6143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9345   -2.1876    1.1776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8950   -1.0846    1.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6337   -1.2083    2.0901 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8237   -0.1269    2.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1791    1.1253    1.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4801    1.2620    1.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3128    0.1466    1.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5184    0.5287    0.5593 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4926    1.8528    0.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4868    2.6468   -0.3889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1747    3.9832   -0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9187    4.5018   -0.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9357    3.6935    0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2249    2.3415    0.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9926   -4.3286    2.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9531   -3.4089    3.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3640   -3.8713    1.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1711   -0.2952    2.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4810    1.9536    1.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3072   -0.0994    0.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4666    2.2457   -0.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9257    4.6269   -1.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6981    5.5445   -0.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9600    4.1084    0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
 16  8  1  0  0  0  0
  5  4  2  0  0  0  0
 16 11  2  0  0  0  0
  4  9  1  0  0  0  0
 11 12  1  0  0  0  0
  8  9  2  0  0  0  0
 12 13  2  0  0  0  0
  7  6  2  0  0  0  0
 13 14  1  0  0  0  0
  8  7  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  6  5  1  0  0  0  0
  4  2  1  0  0  0  0
  9 10  1  0  0  0  0
  2  1  1  0  0  0  0
 10 11  1  0  0  0  0
  2  3  2  0  0  0  0
  7 21  1  0  0  0  0
  6 20  1  0  0  0  0
 10 22  1  0  0  0  0
 12 23  1  0  0  0  0
 13 24  1  0  0  0  0
 14 25  1  0  0  0  0
 15 26  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
M  END


  Mrv1652306202121283D          

 26 28  0  0  0  0            999 V2000
   -3.2284   -3.5473    2.1770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7859   -2.2683    1.6143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9345   -2.1876    1.1776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8950   -1.0846    1.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6337   -1.2083    2.0901 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8237   -0.1269    2.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1791    1.1253    1.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4801    1.2620    1.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3128    0.1466    1.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5184    0.5287    0.5593 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4926    1.8528    0.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4868    2.6468   -0.3889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1747    3.9832   -0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9187    4.5018   -0.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9357    3.6935    0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2249    2.3415    0.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9926   -4.3286    2.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9531   -3.4089    3.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3640   -3.8713    1.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1711   -0.2952    2.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4810    1.9536    1.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3072   -0.0994    0.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4666    2.2457   -0.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9257    4.6269   -1.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6981    5.5445   -0.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9600    4.1084    0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
 16  8  1  0  0  0  0
  5  4  2  0  0  0  0
 16 11  2  0  0  0  0
  4  9  1  0  0  0  0
 11 12  1  0  0  0  0
  8  9  2  0  0  0  0
 12 13  2  0  0  0  0
  7  6  2  0  0  0  0
 13 14  1  0  0  0  0
  8  7  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  6  5  1  0  0  0  0
  4  2  1  0  0  0  0
  9 10  1  0  0  0  0
  2  1  1  0  0  0  0
 10 11  1  0  0  0  0
  2  3  2  0  0  0  0
  7 21  1  0  0  0  0
  6 20  1  0  0  0  0
 10 22  1  0  0  0  0
 12 23  1  0  0  0  0
 13 24  1  0  0  0  0
 14 25  1  0  0  0  0
 15 26  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036253

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C2=C(C([H])=C([H])C([H])=C2[H])C2=C1C(=NC([H])=C2[H])C(=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C13H10N2O/c1-8(16)12-13-10(6-7-14-12)9-4-2-3-5-11(9)15-13/h2-7,15H,1H3

> <INCHI_KEY>
NXZSUJKPVSDFNF-UHFFFAOYSA-N

> <FORMULA>
C13H10N2O

> <MOLECULAR_WEIGHT>
210.236

> <EXACT_MASS>
210.07931295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
22.672139298131547

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-{9H-pyrido[3,4-b]indol-1-yl}ethan-1-one

> <ALOGPS_LOGP>
2.53

> <JCHEM_LOGP>
1.8167111066666668

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.592157335795747

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.99659223639316

> <JCHEM_PKA_STRONGEST_BASIC>
3.0069891266368245

> <JCHEM_POLAR_SURFACE_AREA>
45.75

> <JCHEM_REFRACTIVITY>
61.3461

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-acetyl-β-carboline

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.228  -3.547   2.177  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.786  -2.268   1.614  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.934  -2.188   1.178  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.895  -1.085   1.601  0.00  0.00           C+0
HETATM    5  N   UNK     0      -1.634  -1.208   2.090  0.00  0.00           N+0
HETATM    6  C   UNK     0      -0.824  -0.127   2.076  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.179   1.125   1.594  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.480   1.262   1.086  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.313   0.147   1.102  0.00  0.00           C+0
HETATM   10  N   UNK     0      -4.518   0.529   0.559  0.00  0.00           N+0
HETATM   11  C   UNK     0      -4.493   1.853   0.194  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.487   2.647  -0.389  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.175   3.983  -0.654  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.919   4.502  -0.349  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.936   3.693   0.234  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.225   2.341   0.513  0.00  0.00           C+0
HETATM   17  H   UNK     0      -3.993  -4.329   2.123  0.00  0.00           H+0
HETATM   18  H   UNK     0      -2.953  -3.409   3.226  0.00  0.00           H+0
HETATM   19  H   UNK     0      -2.364  -3.871   1.591  0.00  0.00           H+0
HETATM   20  H   UNK     0       0.171  -0.295   2.482  0.00  0.00           H+0
HETATM   21  H   UNK     0      -0.481   1.954   1.611  0.00  0.00           H+0
HETATM   22  H   UNK     0      -5.307  -0.099   0.453  0.00  0.00           H+0
HETATM   23  H   UNK     0      -6.467   2.246  -0.629  0.00  0.00           H+0
HETATM   24  H   UNK     0      -5.926   4.627  -1.107  0.00  0.00           H+0
HETATM   25  H   UNK     0      -3.698   5.545  -0.564  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.960   4.108   0.469  0.00  0.00           H+0
CONECT    1    2   17   18   19                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    9    2                                                  
CONECT    5    4    6                                                       
CONECT    6    7    5   20                                                  
CONECT    7    6    8   21                                                  
CONECT    8   16    9    7                                                  
CONECT    9    4    8   10                                                  
CONECT   10    9   11   22                                                  
CONECT   11   16   12   10                                                  
CONECT   12   11   13   23                                                  
CONECT   13   12   14   24                                                  
CONECT   14   13   15   25                                                  
CONECT   15   14   16   26                                                  
CONECT   16    8   11   15                                                  
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    6                                                            
CONECT   21    7                                                            
CONECT   22   10                                                            
CONECT   23   12                                                            
CONECT   24   13                                                            
CONECT   25   14                                                            
CONECT   26   15                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
1-Acetyl-b-carboline	Generator
1-Acetyl-β-carboline	Generator

Chemical Formula

C₁₃H₁₀N₂O

Average Mass

210.2360 Da

Monoisotopic Mass

210.07931 Da

IUPAC Name

1-{9H-pyrido[3,4-b]indol-1-yl}ethan-1-one

Traditional Name

1-acetyl-β-carboline

CAS Registry Number

Not Available

SMILES

[H]N1C2=C(C([H])=C([H])C([H])=C2[H])C2=C1C(=NC([H])=C2[H])C(=O)C([H])([H])[H]

InChI Identifier

InChI=1S/C13H10N2O/c1-8(16)12-13-10(6-7-14-12)9-4-2-3-5-11(9)15-13/h2-7,15H,1H3

InChI Key

NXZSUJKPVSDFNF-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ailanthus triphysus	LOTUS Database	35616633
Arenaria kansuensis	LOTUS Database	35616633
Ligusticum sinense	LOTUS Database	35616633
Marinactinospora thermotolerans	JEOL database	Huang, H., et al, J. Nat. Prod. 74, 2122 (2011)
Ophiocordyceps sinensis	LOTUS Database	35616633
Picrasma quassioides	LOTUS Database	35616633
Rauvolfia serpentina	LOTUS Database	35616633
Sedum sarmentosum	KNApSAcK Database	22123792
Streptomyces kasugaensis	LOTUS Database	35616633
Tedania ignis	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 alkyl ketone
Aryl ketone
Pyridine
Benzenoid
Heteroaromatic compound
Pyrrole
Vinylogous amide
Ketone
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

harmala alkaloid (CHEBI:69598 )

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	2.53	ALOGPS
logP	1.82	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	12	ChemAxon
pKa (Strongest Basic)	3.01	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	1	ChemAxon
Refractivity	61.35 m³·mol⁻¹	ChemAxon
Polarizability	22.67 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

C00029415

Chemspider ID

554156

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

Huang, H., et al. (2011). Huang, H., et al, J. Nat. Prod. 74, 2122 (2011). J. Nat. Prod..

Showing NP-Card for 1-acetyl-beta-carboline (NP0036253)

MOL for NP0036253 (1-acetyl-beta-carboline)

3D MOL for NP0036253 (1-acetyl-beta-carboline)

3D SDF for NP0036253 (1-acetyl-beta-carboline)

3D-SDF for NP0036253 (1-acetyl-beta-carboline)

PDB for NP0036253 (1-acetyl-beta-carboline)

3D PDB for NP0036253 (1-acetyl-beta-carboline)

SMILES for NP0036253 (1-acetyl-beta-carboline)

INCHI for NP0036253 (1-acetyl-beta-carboline)

Structure for NP0036253 (1-acetyl-beta-carboline)

3D Structure for NP0036253 (1-acetyl-beta-carboline)