NP-MRD: Showing NP-Card for Lyconadin A (NP0025513)

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Record Information

Version

1.0

Created at

2021-06-19 17:37:10 UTC

Updated at

2021-06-29 23:50:31 UTC

NP-MRD ID

NP0025513

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lyconadin A

Provided By

JEOL Database JEOL Logo

Description

Lyconadin A is found in Lycopodium Complanatum. It was first documented in 2013 (PMID: 23843911). Based on a literature review a significant number of articles have been published on (+)-Lyconadin A (PMID: 25152067) (PMID: 24596132) (PMID: 23449194) (PMID: 23330605).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119373D          

 39 43  0  0  0  0            999 V2000
    3.7466    0.5803    0.6296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3430    0.0734    0.3044 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2846    0.7650    1.1711 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1538    0.6259    0.6409 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2944    1.1327   -0.7890 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8000    1.1544   -1.1957 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5672   -0.1626   -0.8859 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0745   -0.7607    0.4519 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5853   -0.7919    0.4859 N   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0377   -1.2470   -0.8640 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0593   -1.7930   -1.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7327   -2.8123   -2.7123 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5951   -3.3151   -3.6576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2893   -4.2253   -4.4187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9412   -2.6819   -3.7149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2478   -1.6834   -2.8727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2741   -1.2239   -1.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5285    0.0489   -1.5024 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0255    0.2336   -1.1878 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9785    0.4260    1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8448    1.6496    0.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4978    0.0456    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3307   -0.9969    0.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5152    1.8365    1.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3408    0.3700    2.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7996    1.1811    1.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1353    2.1313   -0.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2826    1.9632   -0.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8931    1.4125   -2.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6447    0.0313   -0.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4559   -1.7812    0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4703   -0.1869    1.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7353   -2.0039   -0.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1816   -3.2448   -2.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6312   -3.0672   -4.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2252   -1.2142   -2.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3908    0.1058   -2.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6099   -0.4978   -1.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3400    1.2259   -1.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0  0  0  0
 12 11  1  0  0  0  0
  5  6  1  0  0  0  0
  2  3  1  0  0  0  0
  4  9  1  0  0  0  0
 11 17  2  0  0  0  0
 18 10  1  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  0  0  0  0
 16 15  2  0  0  0  0
 13 14  2  0  0  0  0
 17  7  1  0  0  0  0
  6  7  1  0  0  0  0
 15 13  1  0  0  0  0
  9  8  1  0  0  0  0
  7  8  1  0  0  0  0
 17 16  1  0  0  0  0
  2  1  1  0  0  0  0
 13 12  1  0  0  0  0
  4 26  1  1  0  0  0
  2 19  1  0  0  0  0
  5 27  1  1  0  0  0
  3  4  1  0  0  0  0
 18 37  1  6  0  0  0
  4  5  1  0  0  0  0
  7 30  1  1  0  0  0
  5 18  1  0  0  0  0
 10 33  1  1  0  0  0
 16 36  1  0  0  0  0
 15 35  1  0  0  0  0
 12 34  1  0  0  0  0
  2 23  1  1  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
 19 38  1  0  0  0  0
 19 39  1  0  0  0  0
  6 28  1  0  0  0  0
  6 29  1  0  0  0  0
  8 31  1  0  0  0  0
  8 32  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
M  END

     RDKit          3D

 39 43  0  0  0  0  0  0  0  0999 V2000
    3.7466    0.5803    0.6296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3430    0.0734    0.3044 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2846    0.7650    1.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1538    0.6259    0.6409 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2944    1.1327   -0.7890 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8000    1.1544   -1.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5672   -0.1626   -0.8859 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0745   -0.7607    0.4519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5853   -0.7919    0.4859 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0377   -1.2470   -0.8640 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0593   -1.7930   -1.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7327   -2.8123   -2.7123 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5951   -3.3151   -3.6576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2893   -4.2253   -4.4187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9412   -2.6819   -3.7149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2478   -1.6834   -2.8727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2741   -1.2239   -1.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5285    0.0489   -1.5024 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0255    0.2336   -1.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9785    0.4260    1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8448    1.6496    0.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4978    0.0456    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3307   -0.9969    0.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5152    1.8365    1.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3408    0.3700    2.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7996    1.1811    1.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1353    2.1313   -0.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2826    1.9632   -0.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8931    1.4125   -2.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6447    0.0313   -0.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4559   -1.7812    0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4703   -0.1869    1.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7353   -2.0039   -0.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1816   -3.2448   -2.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6312   -3.0672   -4.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2252   -1.2142   -2.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3908    0.1058   -2.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6099   -0.4978   -1.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3400    1.2259   -1.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0
 12 11  1  0
  5  6  1  0
  2  3  1  0
  4  9  1  0
 11 17  2  0
 18 10  1  0
 10  9  1  0
 10 11  1  0
 16 15  2  0
 13 14  2  0
 17  7  1  0
  6  7  1  0
 15 13  1  0
  9  8  1  0
  7  8  1  0
 17 16  1  0
  2  1  1  0
 13 12  1  0
  4 26  1  1
  2 19  1  0
  5 27  1  1
  3  4  1  0
 18 37  1  6
  4  5  1  0
  7 30  1  1
  5 18  1  0
 10 33  1  1
 16 36  1  0
 15 35  1  0
 12 34  1  0
  2 23  1  1
  3 24  1  0
  3 25  1  0
 19 38  1  0
 19 39  1  0
  6 28  1  0
  6 29  1  0
  8 31  1  0
  8 32  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
M  END


  Mrv1652306192119373D          

 39 43  0  0  0  0            999 V2000
    3.7466    0.5803    0.6296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3430    0.0734    0.3044 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2846    0.7650    1.1711 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1538    0.6259    0.6409 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2944    1.1327   -0.7890 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8000    1.1544   -1.1957 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5672   -0.1626   -0.8859 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0745   -0.7607    0.4519 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5853   -0.7919    0.4859 N   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0377   -1.2470   -0.8640 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0593   -1.7930   -1.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7327   -2.8123   -2.7123 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5951   -3.3151   -3.6576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2893   -4.2253   -4.4187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9412   -2.6819   -3.7149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2478   -1.6834   -2.8727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2741   -1.2239   -1.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5285    0.0489   -1.5024 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0255    0.2336   -1.1878 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9785    0.4260    1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8448    1.6496    0.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4978    0.0456    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3307   -0.9969    0.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5152    1.8365    1.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3408    0.3700    2.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7996    1.1811    1.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1353    2.1313   -0.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2826    1.9632   -0.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8931    1.4125   -2.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6447    0.0313   -0.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4559   -1.7812    0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4703   -0.1869    1.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7353   -2.0039   -0.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1816   -3.2448   -2.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6312   -3.0672   -4.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2252   -1.2142   -2.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3908    0.1058   -2.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6099   -0.4978   -1.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3400    1.2259   -1.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0  0  0  0
 12 11  1  0  0  0  0
  5  6  1  0  0  0  0
  2  3  1  0  0  0  0
  4  9  1  0  0  0  0
 11 17  2  0  0  0  0
 18 10  1  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  0  0  0  0
 16 15  2  0  0  0  0
 13 14  2  0  0  0  0
 17  7  1  0  0  0  0
  6  7  1  0  0  0  0
 15 13  1  0  0  0  0
  9  8  1  0  0  0  0
  7  8  1  0  0  0  0
 17 16  1  0  0  0  0
  2  1  1  0  0  0  0
 13 12  1  0  0  0  0
  4 26  1  1  0  0  0
  2 19  1  0  0  0  0
  5 27  1  1  0  0  0
  3  4  1  0  0  0  0
 18 37  1  6  0  0  0
  4  5  1  0  0  0  0
  7 30  1  1  0  0  0
  5 18  1  0  0  0  0
 10 33  1  1  0  0  0
 16 36  1  0  0  0  0
 15 35  1  0  0  0  0
 12 34  1  0  0  0  0
  2 23  1  1  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
 19 38  1  0  0  0  0
 19 39  1  0  0  0  0
  6 28  1  0  0  0  0
  6 29  1  0  0  0  0
  8 31  1  0  0  0  0
  8 32  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025513

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C(=O)C([H])=C([H])C2=C1[C@]1([H])N3C([H])([H])[C@@]2([H])C([H])([H])[C@@]2([H])[C@]3([H])C([H])([H])[C@]([H])(C([H])([H])[H])C([H])([H])[C@@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H20N2O/c1-8-4-12-11-6-9-7-18(13(11)5-8)16(12)15-10(9)2-3-14(19)17-15/h2-3,8-9,11-13,16H,4-7H2,1H3,(H,17,19)/t8-,9-,11-,12-,13+,16-/m1/s1

> <INCHI_KEY>
RGTBQDIMBCXYGD-JJAUGWOVSA-N

> <FORMULA>
C16H20N2O

> <MOLECULAR_WEIGHT>
256.349

> <EXACT_MASS>
256.157563272

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
28.586469650198758

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,9S,11R,12R,14R,16S)-14-methyl-1,4-diazapentacyclo[7.7.1.0^{2,12}.0^{3,8}.0^{11,16}]heptadeca-3(8),6-dien-5-one

> <ALOGPS_LOGP>
1.68

> <JCHEM_LOGP>
0.7414627324127752

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.241698500686317

> <JCHEM_PKA_STRONGEST_BASIC>
9.7601820005595

> <JCHEM_POLAR_SURFACE_AREA>
32.34

> <JCHEM_REFRACTIVITY>
75.5973

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,9S,11R,12R,14R,16S)-14-methyl-1,4-diazapentacyclo[7.7.1.0^{2,12}.0^{3,8}.0^{11,16}]heptadeca-3(8),6-dien-5-one

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 39 43  0  0  0  0  0  0  0  0999 V2000
    3.7466    0.5803    0.6296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3430    0.0734    0.3044 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2846    0.7650    1.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1538    0.6259    0.6409 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2944    1.1327   -0.7890 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8000    1.1544   -1.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5672   -0.1626   -0.8859 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0745   -0.7607    0.4519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5853   -0.7919    0.4859 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0377   -1.2470   -0.8640 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0593   -1.7930   -1.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7327   -2.8123   -2.7123 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5951   -3.3151   -3.6576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2893   -4.2253   -4.4187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9412   -2.6819   -3.7149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2478   -1.6834   -2.8727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2741   -1.2239   -1.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5285    0.0489   -1.5024 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0255    0.2336   -1.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9785    0.4260    1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8448    1.6496    0.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4978    0.0456    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3307   -0.9969    0.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5152    1.8365    1.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3408    0.3700    2.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7996    1.1811    1.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1353    2.1313   -0.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2826    1.9632   -0.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8931    1.4125   -2.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6447    0.0313   -0.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4559   -1.7812    0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4703   -0.1869    1.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7353   -2.0039   -0.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1816   -3.2448   -2.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6312   -3.0672   -4.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2252   -1.2142   -2.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3908    0.1058   -2.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6099   -0.4978   -1.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3400    1.2259   -1.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0
 12 11  1  0
  5  6  1  0
  2  3  1  0
  4  9  1  0
 11 17  2  0
 18 10  1  0
 10  9  1  0
 10 11  1  0
 16 15  2  0
 13 14  2  0
 17  7  1  0
  6  7  1  0
 15 13  1  0
  9  8  1  0
  7  8  1  0
 17 16  1  0
  2  1  1  0
 13 12  1  0
  4 26  1  1
  2 19  1  0
  5 27  1  1
  3  4  1  0
 18 37  1  6
  4  5  1  0
  7 30  1  1
  5 18  1  0
 10 33  1  1
 16 36  1  0
 15 35  1  0
 12 34  1  0
  2 23  1  1
  3 24  1  0
  3 25  1  0
 19 38  1  0
 19 39  1  0
  6 28  1  0
  6 29  1  0
  8 31  1  0
  8 32  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       3.747   0.580   0.630  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.343   0.073   0.304  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.285   0.765   1.171  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.154   0.626   0.641  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.294   1.133  -0.789  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.800   1.154  -1.196  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.567  -0.163  -0.886  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.075  -0.761   0.452  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.585  -0.792   0.486  0.00  0.00           N+0
HETATM   10  C   UNK     0      -0.038  -1.247  -0.864  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.059  -1.793  -1.851  0.00  0.00           C+0
HETATM   12  N   UNK     0      -0.733  -2.812  -2.712  0.00  0.00           N+0
HETATM   13  C   UNK     0      -1.595  -3.315  -3.658  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.289  -4.225  -4.419  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.941  -2.682  -3.715  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.248  -1.683  -2.873  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.274  -1.224  -1.913  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.529   0.049  -1.502  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.026   0.234  -1.188  0.00  0.00           C+0
HETATM   20  H   UNK     0       3.978   0.426   1.689  0.00  0.00           H+0
HETATM   21  H   UNK     0       3.845   1.650   0.414  0.00  0.00           H+0
HETATM   22  H   UNK     0       4.498   0.046   0.039  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.331  -0.997   0.548  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.515   1.837   1.241  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.341   0.370   2.193  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.800   1.181   1.334  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.135   2.131  -0.926  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.283   1.963  -0.631  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.893   1.413  -2.258  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.645   0.031  -0.832  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.456  -1.781   0.595  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.470  -0.187   1.300  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.735  -2.004  -0.691  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.182  -3.245  -2.675  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.631  -3.067  -4.453  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.225  -1.214  -2.902  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.391   0.106  -2.589  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.610  -0.498  -1.760  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.340   1.226  -1.536  0.00  0.00           H+0
CONECT    1    2   20   21   22                                             
CONECT    2    3    1   19   23                                             
CONECT    3    2    4   24   25                                             
CONECT    4    9   26    3    5                                             
CONECT    5    6   27    4   18                                             
CONECT    6    5    7   28   29                                             
CONECT    7   17    6    8   30                                             
CONECT    8    9    7   31   32                                             
CONECT    9    4   10    8                                                  
CONECT   10   18    9   11   33                                             
CONECT   11   12   17   10                                                  
CONECT   12   11   13   34                                                  
CONECT   13   14   15   12                                                  
CONECT   14   13                                                            
CONECT   15   16   13   35                                                  
CONECT   16   15   17   36                                                  
CONECT   17   11    7   16                                                  
CONECT   18   19   10   37    5                                             
CONECT   19   18    2   38   39                                             
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    2                                                            
CONECT   24    3                                                            
CONECT   25    3                                                            
CONECT   26    4                                                            
CONECT   27    5                                                            
CONECT   28    6                                                            
CONECT   29    6                                                            
CONECT   30    7                                                            
CONECT   31    8                                                            
CONECT   32    8                                                            
CONECT   33   10                                                            
CONECT   34   12                                                            
CONECT   35   15                                                            
CONECT   36   16                                                            
CONECT   37   18                                                            
CONECT   38   19                                                            
CONECT   39   19                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

RDKit          3D

39 43  0  0  0  0  0  0  0  0999 V2000
    3.7466    0.5803    0.6296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3430    0.0734    0.3044 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2846    0.7650    1.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1538    0.6259    0.6409 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2944    1.1327   -0.7890 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8000    1.1544   -1.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5672   -0.1626   -0.8859 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0745   -0.7607    0.4519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5853   -0.7919    0.4859 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0377   -1.2470   -0.8640 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0593   -1.7930   -1.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7327   -2.8123   -2.7123 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5951   -3.3151   -3.6576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2893   -4.2253   -4.4187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9412   -2.6819   -3.7149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2478   -1.6834   -2.8727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2741   -1.2239   -1.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5285    0.0489   -1.5024 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0255    0.2336   -1.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9785    0.4260    1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8448    1.6496    0.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4978    0.0456    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3307   -0.9969    0.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5152    1.8365    1.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3408    0.3700    2.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7996    1.1811    1.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1353    2.1313   -0.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2826    1.9632   -0.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8931    1.4125   -2.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6447    0.0313   -0.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4559   -1.7812    0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4703   -0.1869    1.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7353   -2.0039   -0.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1816   -3.2448   -2.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6312   -3.0672   -4.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2252   -1.2142   -2.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3908    0.1058   -2.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6099   -0.4978   -1.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3400    1.2259   -1.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0
 12 11  1  0
  5  6  1  0
  2  3  1  0
  4  9  1  0
 11 17  2  0
 18 10  1  0
 10  9  1  0
 10 11  1  0
 16 15  2  0
 13 14  2  0
 17  7  1  0
  6  7  1  0
 15 13  1  0
  9  8  1  0
  7  8  1  0
 17 16  1  0
  2  1  1  0
 13 12  1  0
  4 26  1  1
  2 19  1  0
  5 27  1  1
  3  4  1  0
 18 37  1  6
  4  5  1  0
  7 30  1  1
  5 18  1  0
 10 33  1  1
 16 36  1  0
 15 35  1  0
 12 34  1  0
  2 23  1  1
  3 24  1  0
  3 25  1  0
 19 38  1  0
 19 39  1  0
  6 28  1  0
  6 29  1  0
  8 31  1  0
  8 32  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₀N₂O

Average Mass

256.3490 Da

Monoisotopic Mass

256.15756 Da

IUPAC Name

(2R,9S,11R,12R,14R,16S)-14-methyl-1,4-diazapentacyclo[7.7.1.0^{2,12}.0^{3,8}.0^{11,16}]heptadeca-3(8),6-dien-5-one

Traditional Name

(2R,9S,11R,12R,14R,16S)-14-methyl-1,4-diazapentacyclo[7.7.1.0^{2,12}.0^{3,8}.0^{11,16}]heptadeca-3(8),6-dien-5-one

CAS Registry Number

Not Available

SMILES

[H]N1C(=O)C([H])=C([H])C2=C1[C@]1([H])N3C([H])([H])[C@@]2([H])C([H])([H])[C@@]2([H])[C@]3([H])C([H])([H])[C@]([H])(C([H])([H])[H])C([H])([H])[C@@]12[H]

InChI Identifier

InChI=1S/C16H20N2O/c1-8-4-12-11-6-9-7-18(13(11)5-8)16(12)15-10(9)2-3-14(19)17-15/h2-3,8-9,11-13,16H,4-7H2,1H3,(H,17,19)/t8-,9-,11-,12-,13+,16-/m1/s1

InChI Key

RGTBQDIMBCXYGD-JJAUGWOVSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD at 300K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD at 300K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD at 300K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD at 300K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD at 300K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD at 300K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD at 300K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD at 300K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD at 300K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD at 300K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD at 300K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD at 300K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD at 300K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD at 300K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD at 300K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD at 300K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD at 300K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD at 300K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD at 300K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD at 300K, 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
Diphasiastrum complanatum	JEOL database	Kobayahi, J., et al, J. Org. Chem. 66, 5901 (2001)

Chemical Taxonomy

Classification

Not classified

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	1.68	ALOGPS
logP	0.74	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	11.24	ChemAxon
pKa (Strongest Basic)	9.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.34 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	75.6 m³·mol⁻¹	ChemAxon
Polarizability	28.59 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

8236533

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10060981

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lee AS, Liau BB, Shair MD: A unified strategy for the synthesis of 7-membered-ring-containing Lycopodium alkaloids. J Am Chem Soc. 2014 Sep 24;136(38):13442-52. doi: 10.1021/ja507740u. Epub 2014 Sep 12. [PubMed:25152067 ]
Yang Y, Haskins CW, Zhang W, Low PL, Dai M: Divergent total syntheses of lyconadins A and C. Angew Chem Int Ed Engl. 2014 Apr 7;53(15):3922-5. doi: 10.1002/anie.201400416. Epub 2014 Mar 5. [PubMed:24596132 ]
Loertscher BM, Zhang Y, Castle SL: Exploration of an epoxidation-ring-opening strategy for the synthesis of lyconadin A and discovery of an unexpected Payne rearrangement. Beilstein J Org Chem. 2013 Jun 18;9:1179-84. doi: 10.3762/bjoc.9.132. Print 2013. [PubMed:23843911 ]
Yokoshima S: Synthesis of natural products with polycyclic systems. Chem Pharm Bull (Tokyo). 2013;61(3):251-7. doi: 10.1248/cpb.c12-01031. [PubMed:23449194 ]
Nishimura T, Unni AK, Yokoshima S, Fukuyama T: Total syntheses of lyconadins A-C. J Am Chem Soc. 2013 Feb 27;135(8):3243-7. doi: 10.1021/ja312065m. Epub 2013 Feb 12. [PubMed:23330605 ]
Kobayahi, J., et al. (2001). Kobayahi, J., et al, J. Org. Chem. 66, 5901 (2001). J. Org. Chem..

Showing NP-Card for Lyconadin A (NP0025513)

MOL for NP0025513 (Lyconadin A)

3D MOL for NP0025513 (Lyconadin A)

3D SDF for NP0025513 (Lyconadin A)

3D-SDF for NP0025513 (Lyconadin A)

PDB for NP0025513 (Lyconadin A)

3D PDB for NP0025513 (Lyconadin A)

SMILES for NP0025513 (Lyconadin A)

INCHI for NP0025513 (Lyconadin A)

Structure for NP0025513 (Lyconadin A)

3D Structure for NP0025513 (Lyconadin A)