NP-MRD: Showing NP-Card for Leuconodine B (NP0043919)

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Record Information

Version

2.0

Created at

2021-06-22 17:29:09 UTC

Updated at

2021-06-22 17:29:09 UTC

NP-MRD ID

NP0043919

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Leuconodine B

Description

(8R,15R,19R)-15-ethyl-8-hydroxy-1,11-diazapentacyclo[9.7.1.0²,⁷.0⁸,¹⁹.0¹⁵,¹⁹]Nonadeca-2,4,6-triene-10,18-dione 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. Leuconodine B is found in Leuconotis griffithii. Based on a literature review very few articles have been published on (8R,15R,19R)-15-ethyl-8-hydroxy-1,11-diazapentacyclo[9.7.1.0²,⁷.0⁸,¹⁹.0¹⁵,¹⁹]Nonadeca-2,4,6-triene-10,18-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

NP0043919
     RDKit          3D

 46 50  0  0  0  0  0  0  0  0999 V2000
   -0.7982    1.4731    2.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7792    0.5993    1.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4461    0.1492   -0.0394 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6548   -0.6437   -0.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5279   -2.1285   -0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4401   -2.3051   -1.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2313   -1.7410   -1.0866 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1042   -2.2010   -1.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7587   -2.6056   -2.1606 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6287   -2.1097    0.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7519   -0.9312    0.7915 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2147   -1.4473    1.9387 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8230    0.0827    0.9926 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7754    0.2833    1.9498 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7261    1.2662    1.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6908    2.0403    0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7468    1.8674   -0.3115 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7831    0.8530   -0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6578    0.5202   -0.9363 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1825    1.0405   -2.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9578    1.2820   -3.0838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3004    1.2877   -2.3296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6600    1.4569   -0.8521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1710   -0.5172   -0.2718 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3517    2.2814    2.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1969    2.1102    1.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2073    0.9744    2.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7351    1.1931    1.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1032   -0.2770    2.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5655   -0.3203    0.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9633   -0.3787   -1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2315   -2.6068    0.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4567   -2.5464   -0.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667   -3.3359   -1.8953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7837   -1.7014   -2.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6740   -1.8829    0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3660   -3.0537    0.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8164   -1.2383    2.6934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7710   -0.3493    2.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4590    1.4063    2.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4561    2.8244    0.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7298    2.4767   -1.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4512    2.3021   -2.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8469    0.5902   -2.8938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7151    1.7026   -0.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9899    2.2577   -0.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  1
 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  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 24 19  1  6
 23  3  1  0
 24  3  1  0
 24  7  1  0
 24 11  1  0
 18 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
 10 36  1  0
 10 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 22 43  1  0
 22 44  1  0
 23 45  1  0
 23 46  1  0
M  END


  Mrv1652306222119292D          

 24 28  0  0  1  0            999 V2000
    0.6705    0.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4962    0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6056    0.6119    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9344    0.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583    0.3481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0156    1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7796    1.6066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9529    2.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4453    3.1025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7840    2.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1697    1.7111    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7178    2.4050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9074    1.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6511    1.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3322    1.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2697    0.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5260    0.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8448    0.4770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0564    0.2594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4711   -0.5095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -1.2818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6188   -0.3447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6645    0.5865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5769    1.1715    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  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
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  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
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  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
 24 19  1  1  0  0  0
  3 24  1  0  0  0  0
  7 24  1  0  0  0  0
 11 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043919

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]12CCCN3C(=O)C[C@@]4(O)C5=CC=CC=C5N(C(=O)CC1)[C@@]234

> <INCHI_IDENTIFIER>
InChI=1S/C19H22N2O3/c1-2-17-9-5-11-20-16(23)12-18(24)13-6-3-4-7-14(13)21(19(17,18)20)15(22)8-10-17/h3-4,6-7,24H,2,5,8-12H2,1H3/t17-,18-,19-/m1/s1

> <INCHI_KEY>
LZUIMMLDZPLMRH-GUDVDZBRSA-N

> <FORMULA>
C19H22N2O3

> <MOLECULAR_WEIGHT>
326.396

> <EXACT_MASS>
326.163042576

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
33.97802478596759

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(8R,15R,19R)-15-ethyl-8-hydroxy-1,11-diazapentacyclo[9.7.1.0^{2,7}.0^{8,19}.0^{15,19}]nonadeca-2,4,6-triene-10,18-dione

> <ALOGPS_LOGP>
1.29

> <JCHEM_LOGP>
1.6938987366666665

> <ALOGPS_LOGS>
-1.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.569630034215116

> <JCHEM_PKA_STRONGEST_BASIC>
-1.7869412871694261

> <JCHEM_POLAR_SURFACE_AREA>
60.85000000000001

> <JCHEM_REFRACTIVITY>
87.55579999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(8R,15R,19R)-15-ethyl-8-hydroxy-1,11-diazapentacyclo[9.7.1.0^{2,7}.0^{8,19}.0^{15,19}]nonadeca-2,4,6-triene-10,18-dione

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043919
     RDKit          3D

 46 50  0  0  0  0  0  0  0  0999 V2000
   -0.7982    1.4731    2.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7792    0.5993    1.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4461    0.1492   -0.0394 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6548   -0.6437   -0.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5279   -2.1285   -0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4401   -2.3051   -1.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2313   -1.7410   -1.0866 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1042   -2.2010   -1.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7587   -2.6056   -2.1606 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6287   -2.1097    0.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7519   -0.9312    0.7915 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2147   -1.4473    1.9387 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8230    0.0827    0.9926 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7754    0.2833    1.9498 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7261    1.2662    1.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6908    2.0403    0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7468    1.8674   -0.3115 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7831    0.8530   -0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6578    0.5202   -0.9363 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1825    1.0405   -2.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9578    1.2820   -3.0838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3004    1.2877   -2.3296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6600    1.4569   -0.8521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1710   -0.5172   -0.2718 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3517    2.2814    2.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1969    2.1102    1.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2073    0.9744    2.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7351    1.1931    1.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1032   -0.2770    2.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5655   -0.3203    0.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9633   -0.3787   -1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2315   -2.6068    0.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4567   -2.5464   -0.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667   -3.3359   -1.8953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7837   -1.7014   -2.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6740   -1.8829    0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3660   -3.0537    0.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8164   -1.2383    2.6934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7710   -0.3493    2.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4590    1.4063    2.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4561    2.8244    0.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7298    2.4767   -1.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4512    2.3021   -2.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8469    0.5902   -2.8938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7151    1.7026   -0.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9899    2.2577   -0.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  1
 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  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 24 19  1  6
 23  3  1  0
 24  3  1  0
 24  7  1  0
 24 11  1  0
 18 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
 10 36  1  0
 10 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 22 43  1  0
 22 44  1  0
 23 45  1  0
 23 46  1  0
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0       2.045   1.457   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.811   1.057   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.864   1.142   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.611   0.146   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.976   0.650   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.896   2.218   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.322   2.999   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.645   4.485   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   5.765   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.197   4.603   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.917   3.194   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.965   4.473   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.294   2.426   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.682   3.093   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.954   2.224   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.837   0.688   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.448   0.021   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.177   0.890   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       5.705   0.484   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       4.613  -0.951   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.391  -2.409   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.022  -0.643   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.107   1.095   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.810   2.187   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23   24                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   24                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13   24                                             
CONECT   12   11                                                            
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   24                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22    3                                                       
CONECT   24   19    3    7   11                                             
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

COMPND    NP0043919
HETATM    1  C1  UNL     1      -0.798   1.473   2.055  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.779   0.599   1.371  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.446   0.149  -0.039  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.655  -0.644  -0.470  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.528  -2.128  -0.511  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.440  -2.305  -1.603  1.00  0.00           C  
HETATM    7  N1  UNL     1      -0.231  -1.741  -1.087  1.00  0.00           N  
HETATM    8  C7  UNL     1       1.104  -2.201  -1.169  1.00  0.00           C  
HETATM    9  O1  UNL     1       1.759  -2.606  -2.161  1.00  0.00           O  
HETATM   10  C8  UNL     1       1.629  -2.110   0.250  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.752  -0.931   0.791  1.00  0.00           C  
HETATM   12  O2  UNL     1       0.215  -1.447   1.939  1.00  0.00           O  
HETATM   13  C10 UNL     1       1.823   0.083   0.993  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.775   0.283   1.950  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.726   1.266   1.804  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.691   2.040   0.669  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.747   1.867  -0.312  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.783   0.853  -0.134  1.00  0.00           C  
HETATM   19  N2  UNL     1       0.658   0.520  -0.936  1.00  0.00           N  
HETATM   20  C16 UNL     1       0.183   1.041  -2.175  1.00  0.00           C  
HETATM   21  O3  UNL     1       0.958   1.282  -3.084  1.00  0.00           O  
HETATM   22  C17 UNL     1      -1.300   1.288  -2.330  1.00  0.00           C  
HETATM   23  C18 UNL     1      -1.660   1.457  -0.852  1.00  0.00           C  
HETATM   24  C19 UNL     1      -0.171  -0.517  -0.272  1.00  0.00           C  
HETATM   25  H1  UNL     1      -1.352   2.281   2.678  1.00  0.00           H  
HETATM   26  H2  UNL     1      -0.197   2.110   1.390  1.00  0.00           H  
HETATM   27  H3  UNL     1      -0.207   0.974   2.843  1.00  0.00           H  
HETATM   28  H4  UNL     1      -2.735   1.193   1.278  1.00  0.00           H  
HETATM   29  H5  UNL     1      -2.103  -0.277   2.002  1.00  0.00           H  
HETATM   30  H6  UNL     1      -3.565  -0.320   0.113  1.00  0.00           H  
HETATM   31  H7  UNL     1      -2.963  -0.379  -1.542  1.00  0.00           H  
HETATM   32  H8  UNL     1      -2.232  -2.607   0.416  1.00  0.00           H  
HETATM   33  H9  UNL     1      -3.457  -2.546  -0.927  1.00  0.00           H  
HETATM   34  H10 UNL     1      -1.467  -3.336  -1.895  1.00  0.00           H  
HETATM   35  H11 UNL     1      -1.784  -1.701  -2.456  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.674  -1.883   0.173  1.00  0.00           H  
HETATM   37  H13 UNL     1       1.366  -3.054   0.718  1.00  0.00           H  
HETATM   38  H14 UNL     1       0.816  -1.238   2.693  1.00  0.00           H  
HETATM   39  H15 UNL     1       2.771  -0.349   2.834  1.00  0.00           H  
HETATM   40  H16 UNL     1       4.459   1.406   2.561  1.00  0.00           H  
HETATM   41  H17 UNL     1       4.456   2.824   0.558  1.00  0.00           H  
HETATM   42  H18 UNL     1       2.730   2.477  -1.191  1.00  0.00           H  
HETATM   43  H19 UNL     1      -1.451   2.302  -2.770  1.00  0.00           H  
HETATM   44  H20 UNL     1      -1.847   0.590  -2.894  1.00  0.00           H  
HETATM   45  H21 UNL     1      -2.715   1.703  -0.797  1.00  0.00           H  
HETATM   46  H22 UNL     1      -0.990   2.258  -0.475  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   23   24
CONECT    4    5   30   31
CONECT    5    6   32   33
CONECT    6    7   34   35
CONECT    7    8   24
CONECT    8    9    9   10
CONECT   10   11   36   37
CONECT   11   12   13   24
CONECT   12   38
CONECT   13   14   14   18
CONECT   14   15   39
CONECT   15   16   16   40
CONECT   16   17   41
CONECT   17   18   18   42
CONECT   18   19
CONECT   19   20   24
CONECT   20   21   21   22
CONECT   22   23   43   44
CONECT   23   45   46
END

NP0043919
     RDKit          3D

46 50  0  0  0  0  0  0  0  0999 V2000
   -0.7982    1.4731    2.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7792    0.5993    1.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4461    0.1492   -0.0394 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6548   -0.6437   -0.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5279   -2.1285   -0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4401   -2.3051   -1.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2313   -1.7410   -1.0866 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1042   -2.2010   -1.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7587   -2.6056   -2.1606 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6287   -2.1097    0.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7519   -0.9312    0.7915 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2147   -1.4473    1.9387 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8230    0.0827    0.9926 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7754    0.2833    1.9498 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7261    1.2662    1.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6908    2.0403    0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7468    1.8674   -0.3115 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7831    0.8530   -0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6578    0.5202   -0.9363 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1825    1.0405   -2.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9578    1.2820   -3.0838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3004    1.2877   -2.3296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6600    1.4569   -0.8521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1710   -0.5172   -0.2718 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3517    2.2814    2.6785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1969    2.1102    1.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2073    0.9744    2.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7351    1.1931    1.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1032   -0.2770    2.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5655   -0.3203    0.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9633   -0.3787   -1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2315   -2.6068    0.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4567   -2.5464   -0.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667   -3.3359   -1.8953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7837   -1.7014   -2.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6740   -1.8829    0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3660   -3.0537    0.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8164   -1.2383    2.6934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7710   -0.3493    2.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4590    1.4063    2.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4561    2.8244    0.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7298    2.4767   -1.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4512    2.3021   -2.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8469    0.5902   -2.8938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7151    1.7026   -0.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9899    2.2577   -0.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  1
 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  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 24 19  1  6
 23  3  1  0
 24  3  1  0
 24  7  1  0
 24 11  1  0
 18 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
 10 36  1  0
 10 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 22 43  1  0
 22 44  1  0
 23 45  1  0
 23 46  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂N₂O₃

Average Mass

326.3960 Da

Monoisotopic Mass

326.16304 Da

IUPAC Name

(8R,15R,19R)-15-ethyl-8-hydroxy-1,11-diazapentacyclo[9.7.1.0^{2,7}.0^{8,19}.0^{15,19}]nonadeca-2,4,6-triene-10,18-dione

Traditional Name

(8R,15R,19R)-15-ethyl-8-hydroxy-1,11-diazapentacyclo[9.7.1.0^{2,7}.0^{8,19}.0^{15,19}]nonadeca-2,4,6-triene-10,18-dione

CAS Registry Number

Not Available

SMILES

CC[C@@]12CCCN3C(=O)C[C@@]4(O)C5=CC=CC=C5N(C(=O)CC1)[C@@]234

InChI Identifier

InChI=1S/C19H22N2O3/c1-2-17-9-5-11-20-16(23)12-18(24)13-6-3-4-7-14(13)21(19(17,18)20)15(22)8-10-17/h3-4,6-7,24H,2,5,8-12H2,1H3/t17-,18-,19-/m1/s1

InChI Key

LZUIMMLDZPLMRH-GUDVDZBRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Leuconotis griffithii	Linigton's dataset	23647487

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
Pyrroloindole
Diazanaphthalene
Azaspirodecane
Naphthyridine
Indole
Indole or derivatives
Indolizidine
Delta-lactam
Piperidinone
Piperidine
Pyrrolidone
2-pyrrolidone
Benzenoid
N-alkylpyrrolidine
Tertiary carboxylic acid amide
Pyrrolidine
Pyrrole
Tertiary alcohol
Carboxamide group
Lactam
Organoheterocyclic compound
Carboxylic acid derivative
Azacycle
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Organooxygen 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	1.29	ALOGPS
logP	1.69	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	12.57	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.85 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	87.56 m³·mol⁻¹	ChemAxon
Polarizability	33.98 Å³	ChemAxon
Number of Rings	5	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

57592404

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

134949937

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Leuconodine B (NP0043919)

MOL for NP0043919 (Leuconodine B )

3D MOL for NP0043919 (Leuconodine B )

3D SDF for NP0043919 (Leuconodine B )

3D-SDF for NP0043919 (Leuconodine B )

PDB for NP0043919 (Leuconodine B )

3D PDB for NP0043919 (Leuconodine B )

SMILES for NP0043919 (Leuconodine B )

INCHI for NP0043919 (Leuconodine B )

Structure for NP0043919 (Leuconodine B )

3D Structure for NP0043919 (Leuconodine B )