NP-MRD: Showing NP-Card for Koumine N-oxide (NP0140486)

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Record Information

Version

2.0

Created at

2022-06-29 21:36:47 UTC

Updated at

2022-06-29 21:36:47 UTC

NP-MRD ID

NP0140486

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Koumine N-oxide

Description

Koumine N-oxide belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Koumine N-oxide is found in Gelsemium elegans. Based on a literature review very few articles have been published on Koumine N-oxide.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 46 51  0  0  0  0  0  0  0  0999 V2000
   -0.2097    2.4629   -2.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0932    1.1908   -1.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4846    0.4056   -0.7364 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3320    1.3497    0.0926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9912    0.6680    1.1854 N   0  0  1  0  0  4  0  0  0  0  0  0
   -1.6989    1.3200    2.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3507    0.6818    1.0610 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.6067   -0.7298    1.2017 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1278   -0.8625    1.3118 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5445   -0.3153    0.0608 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0599   -1.4821   -0.7061 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3396   -1.4827   -0.7787 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8264   -0.3246   -0.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1447    0.0546    0.0269 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4503    1.2154    0.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4277    1.9757    1.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1183    1.5817    1.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7710    0.4116    0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0893   -2.4843   -1.2625 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8218   -1.6514   -2.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4830   -0.6215   -1.2862 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1223   -1.3035   -0.1232 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9124   -2.8037   -0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5473   -3.0938   -0.2236 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2348    2.9978   -2.9072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8961    3.0366   -1.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7913    0.6970   -2.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1533    1.6956   -0.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8010    2.2523    0.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8994    2.0658    2.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5691    1.8798    2.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4049    0.5684    3.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1328   -1.2553    2.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2648   -1.8447    1.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1946   -0.1750    2.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9663   -0.5449   -0.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4948    1.5516    0.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7027    2.8891    1.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3564    2.1929    1.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5760   -3.2175   -1.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5614   -2.2327   -2.6916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1583   -1.1197   -2.8623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2042   -0.0488   -1.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2059   -1.1169   -0.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4387   -3.1971   -1.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3332   -3.2372    0.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  7  1  6
  5  4  1  0
  4  3  1  0
  3  2  1  6
  2  1  2  3
  3 21  1  0
 21 20  1  0
 20 19  1  0
 19 24  1  0
 24 23  1  0
 23 22  1  0
 22  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  8  5  1  0
 10 18  1  1
 10  3  1  0
 18 13  1  0
 22 21  1  0
 11 19  1  0
  6 30  1  0
  6 31  1  0
  6 32  1  0
  4 28  1  0
  4 29  1  0
  2 27  1  0
  1 25  1  0
  1 26  1  0
 21 43  1  6
 20 41  1  0
 20 42  1  0
 19 40  1  6
 23 45  1  0
 23 46  1  0
 22 44  1  6
  8 33  1  1
  9 34  1  0
  9 35  1  0
 14 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
M  CHG  2   5   1   7  -1
M  END


  Mrv1652306292223362D          

 24 29  0  0  0  0            999 V2000
    4.8373    1.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3220    0.4661    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    5.0329    0.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8655   -0.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6979   -0.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3449   -1.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0029   -2.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2032   -2.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6480   -2.6654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9203   -2.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0970   -2.2995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6395   -1.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0053   -0.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8286   -0.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2861   -1.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1014   -1.1277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5388   -0.4613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4044   -0.3730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0160   -1.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9010   -1.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8715   -2.2926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0183    0.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0740    1.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4892    0.9656    0.0000 O   0  5  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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  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
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
  8 16  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  7 21  1  0  0  0  0
  4 22  1  0  0  0  0
 22 23  2  0  0  0  0
  2 24  1  0  0  0  0
M  CHG  2   2   1  24  -1
M  END
> <DATABASE_ID>
NP0140486

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[N+]1([O-])CC2(C=C)C3CC4OCC3C1CC21C4=NC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H22N2O2/c1-3-19-11-22(2,23)16-9-20(19)13-6-4-5-7-15(13)21-18(20)17-8-14(19)12(16)10-24-17/h3-7,12,14,16-17H,1,8-11H2,2H3

> <INCHI_KEY>
OISZCFMVBRTVHR-UHFFFAOYSA-N

> <FORMULA>
C20H22N2O2

> <MOLECULAR_WEIGHT>
322.408

> <EXACT_MASS>
322.168127956

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
34.60691525924151

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15-ethenyl-13-methyl-19-oxa-3,13-diazahexacyclo[14.3.1.0^{2,10}.0^{4,9}.0^{10,15}.0^{12,17}]icosa-2,4,6,8-tetraen-13-ium-13-olate

> <ALOGPS_LOGP>
0.37

> <JCHEM_LOGP>
1.6009676476666674

> <ALOGPS_LOGS>
-5.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.716363204004746

> <JCHEM_POLAR_SURFACE_AREA>
44.65

> <JCHEM_REFRACTIVITY>
94.35990000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-ethenyl-13-methyl-19-oxa-3,13-diazahexacyclo[14.3.1.0^{2,10}.0^{4,9}.0^{10,15}.0^{12,17}]icosa-2,4,6,8-tetraen-13-ium-13-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       9.030   2.353   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       8.068   0.870   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       9.395   0.635   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.082  -0.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.636  -1.322   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.977  -2.934   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.339  -4.365   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.846  -3.759   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       6.810  -4.975   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       5.451  -4.194   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.914  -4.292   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.060  -3.011   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.743  -1.631   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.280  -1.532   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.134  -2.813   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.656  -2.105   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.606  -0.861   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.221  -0.696   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.363  -1.903   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.015  -2.668   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.960  -4.280   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.501   0.188   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.605   1.982   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.513   1.802   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3   18   24                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   16   22                                             
CONECT    5    4    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   21                                                  
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15    8    4   17                                             
CONECT   17   16   18                                                       
CONECT   18   17    2   19                                                  
CONECT   19   18    5   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    7                                                       
CONECT   22    4   23                                                       
CONECT   23   22                                                            
CONECT   24    2                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂N₂O₂

Average Mass

322.4080 Da

Monoisotopic Mass

322.16813 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[N+]1([O-])CC2(C=C)C3CC4OCC3C1CC21C4=NC2=CC=CC=C12

InChI Identifier

InChI=1S/C20H22N2O2/c1-3-19-11-22(2,23)16-9-20(19)13-6-4-5-7-15(13)21-18(20)17-8-14(19)12(16)10-24-17/h3-7,12,14,16-17H,1,8-11H2,2H3

InChI Key

OISZCFMVBRTVHR-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
Gelsemium elegans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Oxane
Piperidine
Benzenoid
Trialkyl amine oxide
Ketimine
N-oxide
Dialkyl ether
Ether
Oxacycle
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Trisubstituted n-oxide
Organic nitrogen compound
Organic oxygen compound
Organic salt
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Imine
Organopnictogen compound
Organic cation
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

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

4477309

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318847

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Koumine N-oxide (NP0140486)

MOL for NP0140486 (Koumine N-oxide)

3D MOL for NP0140486 (Koumine N-oxide)

3D SDF for NP0140486 (Koumine N-oxide)

3D-SDF for NP0140486 (Koumine N-oxide)

PDB for NP0140486 (Koumine N-oxide)

3D PDB for NP0140486 (Koumine N-oxide)

SMILES for NP0140486 (Koumine N-oxide)

INCHI for NP0140486 (Koumine N-oxide)

Structure for NP0140486 (Koumine N-oxide)

3D Structure for NP0140486 (Koumine N-oxide)