NP-MRD: Showing NP-Card for (12s)-12-ethyl-9-hydroxy-8,16-diazatetracyclo[10.6.1.0²,⁷.0¹⁶,¹⁹]nonadeca-1(19),2,4,6,8,17-hexaen-15-one (NP0260397)

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Record Information

Version

2.0

Created at

2022-09-08 02:33:19 UTC

Updated at

2022-09-08 02:33:19 UTC

NP-MRD ID

NP0260397

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(12s)-12-ethyl-9-hydroxy-8,16-diazatetracyclo[10.6.1.0²,⁷.0¹⁶,¹⁹]nonadeca-1(19),2,4,6,8,17-hexaen-15-one

Description

Rhazinicine belongs to the class of organic compounds known as benzenoids. These are aromatic compounds containing one or more benzene rings. (12s)-12-ethyl-9-hydroxy-8,16-diazatetracyclo[10.6.1.0²,⁷.0¹⁶,¹⁹]nonadeca-1(19),2,4,6,8,17-hexaen-15-one is found in Kopsia singapurensis. (12s)-12-ethyl-9-hydroxy-8,16-diazatetracyclo[10.6.1.0²,⁷.0¹⁶,¹⁹]nonadeca-1(19),2,4,6,8,17-hexaen-15-one was first documented in 2007 (PMID: 17939738). Based on a literature review a small amount of articles have been published on rhazinicine (PMID: 23647487) (PMID: 26125941) (PMID: 23744784) (PMID: 18338359).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 46  0  0  0  0  0  0  0  0999 V2000
   -2.7027   -1.7854   -0.7329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8587   -0.5458   -0.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0953   -0.1255    0.2986 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1567    0.1695    1.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2672    1.0241    0.8462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6515    2.1279    0.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4309    2.9834   -0.4261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2370    2.2017   -0.0989 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5029    3.2853   -0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7979    2.8803   -0.3738 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8750    1.4878   -0.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4048    1.1198    0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1467    0.7896   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1420    1.4404    0.7486 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4041    0.9493    0.9295 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7471   -0.2370    0.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8399   -0.8946   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5185   -0.4110   -0.6158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6748   -1.1825   -1.4054 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7083   -1.9711   -1.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -2.5742   -2.3926 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1300   -2.3345    0.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2675   -1.2090    0.9139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7193   -2.0876    0.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7994   -1.6019   -0.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4475   -2.6089   -1.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6435    0.2544   -1.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2950   -0.5020   -1.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6142    0.7614    2.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4949   -0.7557    1.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7465    1.5081    1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0574    0.4911    0.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8804    4.3110   -0.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6155    3.5947   -0.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9504    2.4022    1.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1541    1.4574    1.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7580   -0.6485    0.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1915   -1.8326   -0.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1906   -3.5772   -2.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6178   -3.1369   -0.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9911   -2.8400    0.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7198   -1.6697    1.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6649   -0.7078    1.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 12  3  1  0
 18 13  1  0
 23  3  1  0
 12  8  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  9 33  1  0
 10 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
 23 42  1  0
 23 43  1  0
M  END


  Mrv1652309082204332D          

 23 26  0  0  1  0            999 V2000
    1.8692   -2.4044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5255   -1.6544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0031   -0.9818    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2845   -1.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7984   -0.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1326    0.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6465    0.9641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9530    0.3852    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4367    1.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2218    0.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2232   -0.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4391   -0.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9887   -0.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4246    0.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2492    0.3403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6378   -0.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2018   -1.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3773   -1.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2072   -1.8678    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5580   -2.3768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8143   -3.1610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7334   -2.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1194   -1.7985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  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  2  0  0  0  0
  6  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
  8 12  1  0  0  0  0
  3 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 19 18  1  4  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0260397

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@]12CCC(=O)N3C=CC(=C13)C1=CC=CC=C1N=C(O)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C19H20N2O2/c1-2-19-10-7-16(22)20-15-6-4-3-5-13(15)14-9-12-21(18(14)19)17(23)8-11-19/h3-6,9,12H,2,7-8,10-11H2,1H3,(H,20,22)/t19-/m0/s1

> <INCHI_KEY>
TXWKUWXSHGUINF-IBGZPJMESA-N

> <FORMULA>
C19H20N2O2

> <MOLECULAR_WEIGHT>
308.381

> <EXACT_MASS>
308.152477892

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
33.42197894231087

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(12S)-12-ethyl-9-hydroxy-8,16-diazatetracyclo[10.6.1.0^{2,7}.0^{16,19}]nonadeca-1(19),2,4,6,8,17-hexaen-15-one

> <JCHEM_LOGP>
3.4794400556666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.636915774670839

> <JCHEM_PKA_STRONGEST_BASIC>
0.924781504763385

> <JCHEM_POLAR_SURFACE_AREA>
54.59

> <JCHEM_REFRACTIVITY>
90.4332

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(12S)-12-ethyl-9-hydroxy-8,16-diazatetracyclo[10.6.1.0^{2,7}.0^{16,19}]nonadeca-1(19),2,4,6,8,17-hexaen-15-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       3.489  -4.488   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.848  -3.088   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.739  -1.833   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.398  -2.097   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.490  -0.853   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.114   0.555   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.207   1.800   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       3.646   0.719   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       4.548   1.967   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.014   1.493   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.017  -0.047   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.553  -0.525   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.446  -0.621   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.259   0.686   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.798   0.635   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.524  -0.723   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.710  -2.031   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.171  -1.980   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       7.853  -3.486   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       6.642  -4.437   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.120  -5.901   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.102  -4.386   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.956  -3.357   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   12   23                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11    8    3                                                  
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22    3                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₀N₂O₂

Average Mass

308.3810 Da

Monoisotopic Mass

308.15248 Da

IUPAC Name

(12S)-12-ethyl-9-hydroxy-8,16-diazatetracyclo[10.6.1.0^{2,7}.0^{16,19}]nonadeca-1(19),2,4,6,8,17-hexaen-15-one

Traditional Name

(12S)-12-ethyl-9-hydroxy-8,16-diazatetracyclo[10.6.1.0^{2,7}.0^{16,19}]nonadeca-1(19),2,4,6,8,17-hexaen-15-one

CAS Registry Number

Not Available

SMILES

CC[C@]12CCC(=O)N3C=CC(=C13)C1=CC=CC=C1N=C(O)CC2

InChI Identifier

InChI=1S/C19H20N2O2/c1-2-19-10-7-16(22)20-15-6-4-3-5-13(15)14-9-12-21(18(14)19)17(23)8-11-19/h3-6,9,12H,2,7-8,10-11H2,1H3,(H,20,22)/t19-/m0/s1

InChI Key

TXWKUWXSHGUINF-IBGZPJMESA-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
Kopsia singapurensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzenoids. These are aromatic compounds containing one or more benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Not Available

Sub Class

Not Available

Direct Parent

Benzenoids

Alternative Parents

Substituents

Benzenoid
Pyrrole
Heteroaromatic compound
Carboxamide group
Lactam
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organopnictogen compound
Hydrocarbon derivative
Organic oxide
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	3.48	ChemAxon
pKa (Strongest Acidic)	5.64	ChemAxon
pKa (Strongest Basic)	0.92	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.59 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	90.43 m³·mol⁻¹	ChemAxon
Polarizability	33.42 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

555342

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

639955

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gan CY, Low YY, Thomas NF, Kam TS: Rhazinilam-Leuconolam-Leuconoxine Alkaloids from Leuconotis griffithii. J Nat Prod. 2013 May 24;76(5):957-64. doi: 10.1021/np400214y. Epub 2013 May 6. [PubMed:23647487 ]
Lim JL, Sim KS, Yong KT, Loong BJ, Ting KN, Lim SH, Low YY, Kam TS: Biologically active vallesamine, strychnan, and rhazinilam alkaloids from Alstonia: Pneumatophorine, a nor-secovallesamine with unusual incorporation of a 3-ethylpyridine moiety. Phytochemistry. 2015 Sep;117:317-324. doi: 10.1016/j.phytochem.2015.06.024. Epub 2015 Jun 27. [PubMed:26125941 ]
Sugimoto K, Toyoshima K, Nonaka S, Kotaki K, Ueda H, Tokuyama H: Protecting-group-free total synthesis of (-)-rhazinilam and (-)-rhazinicine using a gold-catalyzed cascade cyclization. Angew Chem Int Ed Engl. 2013 Jul 8;52(28):7168-71. doi: 10.1002/anie.201303067. Epub 2013 Jun 6. [PubMed:23744784 ]
Beck EM, Hatley R, Gaunt MJ: Synthesis of rhazinicine by a metal-catalyzed C-H bond functionalization strategy. Angew Chem Int Ed Engl. 2008;47(16):3004-7. doi: 10.1002/anie.200705005. [PubMed:18338359 ]
Subramaniam G, Hiraku O, Hayashi M, Koyano T, Komiyama K, Kam TS: Biologically active aspidofractinine, rhazinilam, akuammiline, and vincorine alkaloids from Kopsia. J Nat Prod. 2007 Nov;70(11):1783-9. doi: 10.1021/np0703747. Epub 2007 Oct 17. [PubMed:17939738 ]
LOTUS database [Link]

Showing NP-Card for (12s)-12-ethyl-9-hydroxy-8,16-diazatetracyclo[10.6.1.0²,⁷.0¹⁶,¹⁹]nonadeca-1(19),2,4,6,8,17-hexaen-15-one (NP0260397)

MOL for NP0260397 ((12s)-12-ethyl-9-hydroxy-8,16-diazatetracyclo[10.6.1.0²,⁷.0¹⁶,¹⁹]nonadeca-1(19),2,4,6,8,17-hexaen-15-one)

3D MOL for NP0260397 ((12s)-12-ethyl-9-hydroxy-8,16-diazatetracyclo[10.6.1.0²,⁷.0¹⁶,¹⁹]nonadeca-1(19),2,4,6,8,17-hexaen-15-one)

3D SDF for NP0260397 ((12s)-12-ethyl-9-hydroxy-8,16-diazatetracyclo[10.6.1.0²,⁷.0¹⁶,¹⁹]nonadeca-1(19),2,4,6,8,17-hexaen-15-one)

3D-SDF for NP0260397 ((12s)-12-ethyl-9-hydroxy-8,16-diazatetracyclo[10.6.1.0²,⁷.0¹⁶,¹⁹]nonadeca-1(19),2,4,6,8,17-hexaen-15-one)

PDB for NP0260397 ((12s)-12-ethyl-9-hydroxy-8,16-diazatetracyclo[10.6.1.0²,⁷.0¹⁶,¹⁹]nonadeca-1(19),2,4,6,8,17-hexaen-15-one)

3D PDB for NP0260397 ((12s)-12-ethyl-9-hydroxy-8,16-diazatetracyclo[10.6.1.0²,⁷.0¹⁶,¹⁹]nonadeca-1(19),2,4,6,8,17-hexaen-15-one)

SMILES for NP0260397 ((12s)-12-ethyl-9-hydroxy-8,16-diazatetracyclo[10.6.1.0²,⁷.0¹⁶,¹⁹]nonadeca-1(19),2,4,6,8,17-hexaen-15-one)

INCHI for NP0260397 ((12s)-12-ethyl-9-hydroxy-8,16-diazatetracyclo[10.6.1.0²,⁷.0¹⁶,¹⁹]nonadeca-1(19),2,4,6,8,17-hexaen-15-one)

Structure for NP0260397 ((12s)-12-ethyl-9-hydroxy-8,16-diazatetracyclo[10.6.1.0²,⁷.0¹⁶,¹⁹]nonadeca-1(19),2,4,6,8,17-hexaen-15-one)

3D Structure for NP0260397 ((12s)-12-ethyl-9-hydroxy-8,16-diazatetracyclo[10.6.1.0²,⁷.0¹⁶,¹⁹]nonadeca-1(19),2,4,6,8,17-hexaen-15-one)