NP-MRD: Showing NP-Card for 3,14-dehydroleuconolam (NP0043406)

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Record Information

Version

1.0

Created at

2021-06-21 00:49:26 UTC

Updated at

2021-06-30 00:19:04 UTC

NP-MRD ID

NP0043406

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,14-dehydroleuconolam

Provided By

JEOL Database JEOL Logo

Description

(12S,19S)-12-ethyl-9,19-dihydroxy-8,16-diazatetracyclo[10.6.1.0²,⁷.0¹⁶,¹⁹]Nonadeca-1(18),2,4,6,8,14-hexaen-17-one belongs to the class of organic compounds known as rhazinilam alkaloids. These are alkaloids with a structure based on the rhazinilam skeleton, a tetracyclic compound with a complex tetracyclic carbon skeleton containing pyrrole ring embedded in its indolizine core. 3,14-dehydroleuconolam is found in Leuconotis grif f ithii. It was first documented in 2002 (PMID: 33651529). Based on a literature review a significant number of articles have been published on (12S,19S)-12-ethyl-9,19-dihydroxy-8,16-diazatetracyclo[10.6.1.0²,⁷.0¹⁶,¹⁹]Nonadeca-1(18),2,4,6,8,14-hexaen-17-one (PMID: 33079503) (PMID: 26389513) (PMID: 26389498) (PMID: 26389454).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102493D          

 44 47  0  0  0  0            999 V2000
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    0.2952   -1.0081    1.2808 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3549   -2.1103    0.3774 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4811   -3.4015    1.2743 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6520   -4.6851    0.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3654   -4.7855   -0.7880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1478   -3.7130   -1.4677 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2353   -3.6388   -2.8472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0341   -4.5087   -3.6754 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5634   -2.2492   -3.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7631    1.5361   -1.7994 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9240    2.4694   -2.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6350    2.1026   -2.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0814   -0.2157   -2.2173 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9443   -0.2959   -0.7041 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7859   -1.7046   -0.1249 C   0  0  1  0  0  0  0  0  0  0  0  0
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 16 15  2  0  0  0  0
 17 18  1  0  0  0  0
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 22  3  1  0  0  0  0
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 22 43  1  0  0  0  0
 10 34  1  0  0  0  0
  2 28  1  0  0  0  0
  2 29  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
  5 32  1  0  0  0  0
  6 33  1  0  0  0  0
 24 44  1  0  0  0  0
M  END

     RDKit          3D

 44 47  0  0  0  0  0  0  0  0999 V2000
   -0.5373   -0.5627    2.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2952   -1.0081    1.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3549   -2.1103    0.3774 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4811   -3.4015    1.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6520   -4.6851    0.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3654   -4.7855   -0.7880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1478   -3.7130   -1.4677 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2353   -3.6388   -2.8472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0341   -4.5087   -3.6754 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5634   -2.2492   -3.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0369   -0.1630   -1.9981 C   0  0  0  0  0  0  0  0  0  0  0  0
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 22  3  1  0
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M  END


  Mrv1652306212102493D          

 44 47  0  0  0  0            999 V2000
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    0.2952   -1.0081    1.2808 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.4811   -3.4015    1.2743 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6520   -4.6851    0.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
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  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
  5 32  1  0  0  0  0
  6 33  1  0  0  0  0
 24 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043406

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]12N3C([H])=C([H])C([H])([H])[C@]1(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])C(=O)N([H])C1=C(C([H])=C([H])C([H])=C1[H])C2=C([H])C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H20N2O3/c1-2-18-9-5-11-21-17(23)12-14(19(18,21)24)13-6-3-4-7-15(13)20-16(22)8-10-18/h3-7,11-12,24H,2,8-10H2,1H3,(H,20,22)/t18-,19-/m1/s1

> <INCHI_KEY>
FEJHJZLLIABPMH-RTBURBONSA-N

> <FORMULA>
C19H20N2O3

> <MOLECULAR_WEIGHT>
324.38

> <EXACT_MASS>
324.147392512

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
33.746570091906136

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(12S,19S)-12-ethyl-19-hydroxy-8,16-diazatetracyclo[10.6.1.0^{2,7}.0^{16,19}]nonadeca-1(18),2(7),3,5,14-pentaene-9,17-dione

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
2.2636184876666667

> <ALOGPS_LOGS>
-3.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.528132357041262

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.973771542372024

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4327445415201514

> <JCHEM_POLAR_SURFACE_AREA>
69.64

> <JCHEM_REFRACTIVITY>
92.4009

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(12S,19S)-12-ethyl-19-hydroxy-8,16-diazatetracyclo[10.6.1.0^{2,7}.0^{16,19}]nonadeca-1(18),2(7),3,5,14-pentaene-9,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 44 47  0  0  0  0  0  0  0  0999 V2000
   -0.5373   -0.5627    2.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2952   -1.0081    1.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3549   -2.1103    0.3774 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4811   -3.4015    1.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6520   -4.6851    0.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3654   -4.7855   -0.7880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1478   -3.7130   -1.4677 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2353   -3.6388   -2.8472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0341   -4.5087   -3.6754 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5634   -2.2492   -3.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7048   -1.5901   -2.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0369   -0.1630   -1.9981 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3287    0.2227   -1.6123 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7631    1.5361   -1.7994 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9240    2.4694   -2.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6350    2.1026   -2.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1693    0.8079   -2.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1561    0.5179   -2.9141 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0814   -0.2157   -2.2173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0675   -0.6712   -2.7958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9443   -0.2959   -0.7041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7859   -1.7046   -0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5787   -2.4892   -0.8213 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8994   -2.7401   -0.3452 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0097    0.2000    3.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7394   -1.3919    3.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4901   -0.1223    2.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433   -0.1189    0.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2560   -1.3713    1.6683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3336   -3.2972    1.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4086   -3.5180    1.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0552   -5.5432    1.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5609   -5.6887   -1.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6342   -1.8859   -4.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0239   -0.5078   -1.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7701    1.8205   -1.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738    3.4853   -2.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0130    2.8481   -3.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4954    0.8862   -3.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9000    0.1034   -0.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2079    0.4169   -0.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1652   -2.4442   -0.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4682   -1.7670    0.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9826   -3.7081   -0.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 17  2  0
 16 15  2  0
 17 18  1  0
  8 10  1  0
 10 11  2  0
 15 14  1  0
 19 20  2  0
 18 19  1  0
  3  2  1  1
 14 13  2  0
  2  1  1  0
 23  3  1  0
 13 12  1  0
 11 12  1  0
 17 16  1  0
 19 21  1  0
 21 22  1  0
 23  7  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
 22  3  1  0
  8  9  2  0
 11 23  1  0
 23 24  1  1
 18 39  1  0
 16 38  1  0
 15 37  1  0
 14 36  1  0
 13 35  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
 10 34  1  0
  2 28  1  0
  2 29  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
 24 44  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.537  -0.563   2.480  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.295  -1.008   1.281  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.355  -2.110   0.377  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.481  -3.401   1.274  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.652  -4.685   0.513  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.365  -4.785  -0.788  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.148  -3.713  -1.468  0.00  0.00           N+0
HETATM    8  C   UNK     0       0.235  -3.639  -2.847  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.034  -4.509  -3.675  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.563  -2.249  -3.178  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.705  -1.590  -2.016  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.037  -0.163  -1.998  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.329   0.223  -1.612  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.763   1.536  -1.799  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.924   2.469  -2.404  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.635   2.103  -2.791  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.169   0.808  -2.543  0.00  0.00           C+0
HETATM   18  N   UNK     0      -1.156   0.518  -2.914  0.00  0.00           N+0
HETATM   19  C   UNK     0      -2.081  -0.216  -2.217  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.067  -0.671  -2.796  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.944  -0.296  -0.704  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.786  -1.705  -0.125  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.579  -2.489  -0.821  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.899  -2.740  -0.345  0.00  0.00           O+0
HETATM   25  H   UNK     0       0.010   0.200   3.045  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.739  -1.392   3.164  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.490  -0.122   2.175  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.543  -0.119   0.697  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.256  -1.371   1.668  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.334  -3.297   1.957  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.409  -3.518   1.907  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.055  -5.543   1.044  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.561  -5.689  -1.362  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.634  -1.886  -4.187  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.024  -0.508  -1.201  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.770   1.821  -1.503  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.274   3.485  -2.571  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.013   2.848  -3.245  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.495   0.886  -3.795  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.900   0.103  -0.333  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.208   0.417  -0.333  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.165  -2.444  -0.840  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.468  -1.767   0.734  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.983  -3.708  -0.392  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    3    1   28   29                                             
CONECT    3    2   23    4   22                                             
CONECT    4    3    5   30   31                                             
CONECT    5    4    6   32                                                  
CONECT    6    5    7   33                                                  
CONECT    7   23    6    8                                                  
CONECT    8   10    7    9                                                  
CONECT    9    8                                                            
CONECT   10    8   11   34                                                  
CONECT   11   10   12   23                                                  
CONECT   12   17   13   11                                                  
CONECT   13   14   12   35                                                  
CONECT   14   15   13   36                                                  
CONECT   15   16   14   37                                                  
CONECT   16   15   17   38                                                  
CONECT   17   12   18   16                                                  
CONECT   18   17   19   39                                                  
CONECT   19   20   18   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   40   41                                             
CONECT   22   21    3   42   43                                             
CONECT   23    3    7   11   24                                             
CONECT   24   23   44                                                       
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    2                                                            
CONECT   29    2                                                            
CONECT   30    4                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
CONECT   33    6                                                            
CONECT   34   10                                                            
CONECT   35   13                                                            
CONECT   36   14                                                            
CONECT   37   15                                                            
CONECT   38   16                                                            
CONECT   39   18                                                            
CONECT   40   21                                                            
CONECT   41   21                                                            
CONECT   42   22                                                            
CONECT   43   22                                                            
CONECT   44   24                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   94    0
END

RDKit          3D

44 47  0  0  0  0  0  0  0  0999 V2000
   -0.5373   -0.5627    2.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2952   -1.0081    1.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3549   -2.1103    0.3774 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4811   -3.4015    1.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6520   -4.6851    0.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3654   -4.7855   -0.7880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1478   -3.7130   -1.4677 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2353   -3.6388   -2.8472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0341   -4.5087   -3.6754 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5634   -2.2492   -3.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7048   -1.5901   -2.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0369   -0.1630   -1.9981 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3287    0.2227   -1.6123 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7631    1.5361   -1.7994 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9240    2.4694   -2.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6350    2.1026   -2.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1693    0.8079   -2.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1561    0.5179   -2.9141 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0814   -0.2157   -2.2173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0675   -0.6712   -2.7958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9443   -0.2959   -0.7041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7859   -1.7046   -0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5787   -2.4892   -0.8213 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8994   -2.7401   -0.3452 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0097    0.2000    3.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7394   -1.3919    3.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4901   -0.1223    2.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433   -0.1189    0.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2560   -1.3713    1.6683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3336   -3.2972    1.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4086   -3.5180    1.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0552   -5.5432    1.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5609   -5.6887   -1.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6342   -1.8859   -4.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0239   -0.5078   -1.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7701    1.8205   -1.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738    3.4853   -2.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0130    2.8481   -3.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4954    0.8862   -3.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9000    0.1034   -0.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2079    0.4169   -0.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1652   -2.4442   -0.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4682   -1.7670    0.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9826   -3.7081   -0.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 17  2  0
 16 15  2  0
 17 18  1  0
  8 10  1  0
 10 11  2  0
 15 14  1  0
 19 20  2  0
 18 19  1  0
  3  2  1  1
 14 13  2  0
  2  1  1  0
 23  3  1  0
 13 12  1  0
 11 12  1  0
 17 16  1  0
 19 21  1  0
 21 22  1  0
 23  7  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
 22  3  1  0
  8  9  2  0
 11 23  1  0
 23 24  1  1
 18 39  1  0
 16 38  1  0
 15 37  1  0
 14 36  1  0
 13 35  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
 10 34  1  0
  2 28  1  0
  2 29  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
 24 44  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₁₉H₂₀N₂O₃

Average Mass

324.3800 Da

Monoisotopic Mass

324.14739 Da

IUPAC Name

(12S,19S)-12-ethyl-19-hydroxy-8,16-diazatetracyclo[10.6.1.0^{2,7}.0^{16,19}]nonadeca-1(18),2(7),3,5,14-pentaene-9,17-dione

Traditional Name

(12S,19S)-12-ethyl-19-hydroxy-8,16-diazatetracyclo[10.6.1.0^{2,7}.0^{16,19}]nonadeca-1(18),2(7),3,5,14-pentaene-9,17-dione

CAS Registry Number

Not Available

SMILES

[H]O[C@@]12N3C([H])=C([H])C([H])([H])[C@]1(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])C(=O)N([H])C1=C(C([H])=C([H])C([H])=C1[H])C2=C([H])C3=O

InChI Identifier

InChI=1S/C19H20N2O3/c1-2-18-9-5-11-21-17(23)12-14(19(18,21)24)13-6-3-4-7-15(13)20-16(22)8-10-18/h3-7,11-12,24H,2,8-10H2,1H3,(H,20,22)/t18-,19-/m1/s1

InChI Key

FEJHJZLLIABPMH-RTBURBONSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, 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, 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, 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

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Leuconotis grif f ithii	JEOL database	Gan, C. -Y., et al, J. Nat. Prod. 76, 957 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as rhazinilam alkaloids. These are alkaloids with a structure based on the rhazinilam skeleton, a tetracyclic compound with a complex tetracyclic carbon skeleton containing pyrrole ring embedded in its indolizine core.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Rhazinilam alkaloids

Sub Class

Not Available

Direct Parent

Rhazinilam alkaloids

Alternative Parents

Substituents

Rhazinilam skeleton
Tetrahydropyridine
Benzenoid
Pyrroline
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Alkanolamine
Azacycle
Organoheterocyclic compound
Organic oxide
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
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	1.91	ALOGPS
logP	2.26	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	11.97	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.64 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	92.4 m³·mol⁻¹	ChemAxon
Polarizability	33.75 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

71714597

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Curcumin (Curcuma, Turmeric) and Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:33651529 ]
Authors unspecified: Cancer Therapy Interactions With Foods and Dietary Supplements (PDQ(R)): Health Professional Version. 2002. [PubMed:33079503 ]
Authors unspecified: Planning the Transition to End-of-Life Care in Advanced Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:26389513 ]
Authors unspecified: Childhood Central Nervous System Germ Cell Tumors Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389498 ]
Authors unspecified: Childhood Acute Myeloid Leukemia/Other Myeloid Malignancies Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389454 ]
Gan, C. -Y., et al. (2013). Gan, C. -Y., et al, J. Nat. Prod. 76, 957 (2013). J. Nat. Prod..

Showing NP-Card for 3,14-dehydroleuconolam (NP0043406)

MOL for NP0043406 (3,14-dehydroleuconolam)

3D MOL for NP0043406 (3,14-dehydroleuconolam)

3D SDF for NP0043406 (3,14-dehydroleuconolam)

3D-SDF for NP0043406 (3,14-dehydroleuconolam)

PDB for NP0043406 (3,14-dehydroleuconolam)

3D PDB for NP0043406 (3,14-dehydroleuconolam)

SMILES for NP0043406 (3,14-dehydroleuconolam)

INCHI for NP0043406 (3,14-dehydroleuconolam)

Structure for NP0043406 (3,14-dehydroleuconolam)

3D Structure for NP0043406 (3,14-dehydroleuconolam)