NP-MRD: Showing NP-Card for lycopodine (NP0042389)

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Record Information

Version

2.0

Created at

2021-06-21 00:04:00 UTC

Updated at

2021-06-30 00:17:26 UTC

NP-MRD ID

NP0042389

Secondary Accession Numbers

None

Natural Product Identification

Common Name

lycopodine

Provided By

JEOL Database JEOL Logo

Description

lycopodine is found in Austrolycopodium magellanicum, Dendrolycopodium obscurum, Diphasiastrum alpinum, Diphasiastrum thyoides, Diphasiastrum tristachyum, Huperzia lucidula, Palhinhaea cernua, Phlegmariurus filiformis, Phlegmariurus phlegmaria, Phlegmariurus varius and Pseudodiphasium volubile. lycopodine was first documented in 2019 (PMID: 30928888). Based on a literature review a small amount of articles have been published on lycopodine (PMID: 33804083) (PMID: 32941036) (PMID: 32914364) (PMID: 32009077).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102043D          

 43 46  0  0  0  0            999 V2000
    2.3998   -0.9426    1.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1505   -1.1717    0.1983 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3843   -0.6708   -1.2332 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1013   -0.6106   -2.0835 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4285   -2.0118   -2.4102 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0444   -2.6969   -1.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8744   -3.9009   -1.0152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9740   -1.8569   -0.3473 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4232   -2.5771    0.9278 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3971   -1.7038    1.7155 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8804   -0.2754    1.9149 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3879    0.3749    0.6838 N   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5192    0.8164   -0.1510 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0761    1.5243   -1.4285 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1205    0.6576   -2.2365 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9380    0.2580   -1.3493 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3740   -0.4530   -0.0355 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0797   -0.5157    0.8548 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6346    0.1237    1.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2676   -1.4459    0.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2567   -1.3411    2.0634 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4398    1.2031   -1.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2658   -1.0371    1.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0  0  0  0
 14 15  1  0  0  0  0
 13 12  1  0  0  0  0
  8  9  1  0  0  0  0
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  3  2  1  0  0  0  0
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  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
M  END

     RDKit          3D

 43 46  0  0  0  0  0  0  0  0999 V2000
    2.3998   -0.9426    1.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1505   -1.1717    0.1983 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3843   -0.6708   -1.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1013   -0.6106   -2.0835 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4285   -2.0118   -2.4102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0444   -2.6969   -1.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8744   -3.9009   -1.0152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9740   -1.8569   -0.3473 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4232   -2.5771    0.9278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3971   -1.7038    1.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8804   -0.2754    1.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3879    0.3749    0.6838 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5192    0.8164   -0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0761    1.5243   -1.4285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1205    0.6576   -2.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9380    0.2580   -1.3493 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3740   -0.4530   -0.0355 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0797   -0.5157    0.8548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6346    0.1237    1.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2676   -1.4459    0.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9970   -2.2557    0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1320   -1.3033   -1.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8181    0.3378   -1.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3660   -0.1257   -3.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1978   -1.9610   -3.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3825   -2.6407   -2.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8708   -1.7472   -0.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9136   -3.5256    0.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5616   -2.8411    1.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3592   -1.6762    1.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5922   -2.1626    2.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0811   -0.2839    2.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1346    1.5216    0.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1741   -0.0200   -0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6535   -0.2159   -2.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1911    0.5129    1.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2658   -1.0371    1.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 14 15  1  0
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  8  9  1  0
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  6  7  2  0
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  1 21  1  0
M  END


  Mrv1652306212102043D          

 43 46  0  0  0  0            999 V2000
    2.3998   -0.9426    1.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1505   -1.1717    0.1983 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3843   -0.6708   -1.2332 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1013   -0.6106   -2.0835 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4285   -2.0118   -2.4102 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0444   -2.6969   -1.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8744   -3.9009   -1.0152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9740   -1.8569   -0.3473 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4232   -2.5771    0.9278 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3971   -1.7038    1.7155 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8804   -0.2754    1.9149 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3879    0.3749    0.6838 N   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5192    0.8164   -0.1510 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0761    1.5243   -1.4285 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1205    0.6576   -2.2365 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9380    0.2580   -1.3493 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3740   -0.4530   -0.0355 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0797   -0.5157    0.8548 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6346    0.1237    1.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2676   -1.4459    0.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2567   -1.3411    2.0634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9970   -2.2557    0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1320   -1.3033   -1.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8181    0.3378   -1.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3592   -1.6762    1.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6535   -0.2159   -2.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7636    1.2218   -3.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4398    1.2031   -1.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1911    0.5129    1.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2658   -1.0371    1.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0  0  0  0
 14 15  1  0  0  0  0
 13 12  1  0  0  0  0
  8  9  1  0  0  0  0
 17 12  1  0  0  0  0
 12 11  1  0  0  0  0
 11 10  1  0  0  0  0
 10  9  1  0  0  0  0
 16  4  1  0  0  0  0
  4  3  1  0  0  0  0
  8  6  1  0  0  0  0
 16 41  1  1  0  0  0
  6  5  1  0  0  0  0
 17 18  1  1  0  0  0
  5  4  1  0  0  0  0
 18  2  1  0  0  0  0
  3  2  1  0  0  0  0
  8 17  1  0  0  0  0
  2  1  1  0  0  0  0
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  6  7  2  0  0  0  0
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 15 40  1  0  0  0  0
  5 26  1  0  0  0  0
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  4 25  1  6  0  0  0
 11 33  1  0  0  0  0
 11 34  1  0  0  0  0
 10 31  1  0  0  0  0
 10 32  1  0  0  0  0
  9 29  1  0  0  0  0
  9 30  1  0  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
 18 42  1  0  0  0  0
 18 43  1  0  0  0  0
  2 22  1  6  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042389

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])([H])[C@]1([H])C([H])([H])[C@@]2([H])C([H])([H])C(=O)[C@@]3([H])C([H])([H])C([H])([H])C([H])([H])N4C([H])([H])C([H])([H])C([H])([H])[C@@]2([H])[C@]34C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H25NO/c1-11-8-12-9-15(18)14-5-3-7-17-6-2-4-13(12)16(14,17)10-11/h11-14H,2-10H2,1H3/t11-,12+,13-,14-,16-/m1/s1

> <INCHI_KEY>
BCZFSDNVXODRAJ-JTTNIQEDSA-N

> <FORMULA>
C16H25NO

> <MOLECULAR_WEIGHT>
247.382

> <EXACT_MASS>
247.193614429

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
28.62622765685512

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,10S,13S,15R)-15-methyl-6-azatetracyclo[8.6.0.0^{1,6}.0^{2,13}]hexadecan-11-one

> <ALOGPS_LOGP>
3.09

> <JCHEM_LOGP>
2.7295717539999993

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.178061710449693

> <JCHEM_PKA_STRONGEST_BASIC>
10.249772886051124

> <JCHEM_POLAR_SURFACE_AREA>
20.310000000000002

> <JCHEM_REFRACTIVITY>
72.7318

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.86e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,10S,13S,15R)-15-methyl-6-azatetracyclo[8.6.0.0^{1,6}.0^{2,13}]hexadecan-11-one

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 43 46  0  0  0  0  0  0  0  0999 V2000
    2.3998   -0.9426    1.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1505   -1.1717    0.1983 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3843   -0.6708   -1.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1013   -0.6106   -2.0835 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4285   -2.0118   -2.4102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0444   -2.6969   -1.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8744   -3.9009   -1.0152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9740   -1.8569   -0.3473 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4232   -2.5771    0.9278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3971   -1.7038    1.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8804   -0.2754    1.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3879    0.3749    0.6838 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5192    0.8164   -0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0761    1.5243   -1.4285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1205    0.6576   -2.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9380    0.2580   -1.3493 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3740   -0.4530   -0.0355 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0797   -0.5157    0.8548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6346    0.1237    1.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2676   -1.4459    0.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2567   -1.3411    2.0634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9970   -2.2557    0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1320   -1.3033   -1.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8181    0.3378   -1.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3660   -0.1257   -3.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1978   -1.9610   -3.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3825   -2.6407   -2.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8708   -1.7472   -0.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9136   -3.5256    0.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5616   -2.8411    1.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3592   -1.6762    1.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5922   -2.1626    2.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0811   -0.2839    2.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6708    0.3344    2.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1346    1.5216    0.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1741   -0.0200   -0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5879    2.4735   -1.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9534    1.7726   -2.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6535   -0.2159   -2.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7636    1.2218   -3.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4398    1.2031   -1.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1911    0.5129    1.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2658   -1.0371    1.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 14 15  1  0
 13 12  1  0
  8  9  1  0
 17 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
 16  4  1  0
  4  3  1  0
  8  6  1  0
 16 41  1  1
  6  5  1  0
 17 18  1  1
  5  4  1  0
 18  2  1  0
  3  2  1  0
  8 17  1  0
  2  1  1  0
 16 15  1  0
  8 28  1  6
 16 17  1  0
  6  7  2  0
 14 37  1  0
 14 38  1  0
 13 35  1  0
 13 36  1  0
 15 39  1  0
 15 40  1  0
  5 26  1  0
  5 27  1  0
  4 25  1  6
 11 33  1  0
 11 34  1  0
 10 31  1  0
 10 32  1  0
  9 29  1  0
  9 30  1  0
  3 23  1  0
  3 24  1  0
 18 42  1  0
 18 43  1  0
  2 22  1  6
  1 19  1  0
  1 20  1  0
  1 21  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       2.400  -0.943   1.053  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.151  -1.172   0.198  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.384  -0.671  -1.233  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.101  -0.611  -2.083  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.429  -2.012  -2.410  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.044  -2.697  -1.208  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.874  -3.901  -1.015  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.974  -1.857  -0.347  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.423  -2.577   0.928  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.397  -1.704   1.716  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.880  -0.275   1.915  0.00  0.00           C+0
HETATM   12  N   UNK     0      -2.388   0.375   0.684  0.00  0.00           N+0
HETATM   13  C   UNK     0      -3.519   0.816  -0.151  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.076   1.524  -1.429  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.120   0.658  -2.236  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.938   0.258  -1.349  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.374  -0.453  -0.036  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.080  -0.516   0.855  0.00  0.00           C+0
HETATM   19  H   UNK     0       2.635   0.124   1.140  0.00  0.00           H+0
HETATM   20  H   UNK     0       3.268  -1.446   0.614  0.00  0.00           H+0
HETATM   21  H   UNK     0       2.257  -1.341   2.063  0.00  0.00           H+0
HETATM   22  H   UNK     0       0.997  -2.256   0.173  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.132  -1.303  -1.728  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.818   0.338  -1.196  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.366  -0.126  -3.032  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.198  -1.961  -3.188  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.383  -2.641  -2.795  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.871  -1.747  -0.972  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.914  -3.526   0.676  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.562  -2.841   1.552  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.359  -1.676   1.190  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.592  -2.163   2.692  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.081  -0.284   2.665  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.671   0.334   2.371  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.135   1.522   0.422  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.174  -0.020  -0.421  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.588   2.474  -1.173  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.953   1.773  -2.037  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.654  -0.216  -2.626  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.764   1.222  -3.106  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.440   1.203  -1.079  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.191   0.513   1.137  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.266  -1.037   1.800  0.00  0.00           H+0
CONECT    1    2   19   20   21                                             
CONECT    2   18    3    1   22                                             
CONECT    3    4    2   23   24                                             
CONECT    4   16    3    5   25                                             
CONECT    5    6    4   26   27                                             
CONECT    6    8    5    7                                                  
CONECT    7    6                                                            
CONECT    8    9    6   17   28                                             
CONECT    9    8   10   29   30                                             
CONECT   10   11    9   31   32                                             
CONECT   11   12   10   33   34                                             
CONECT   12   13   17   11                                                  
CONECT   13   14   12   35   36                                             
CONECT   14   13   15   37   38                                             
CONECT   15   14   16   39   40                                             
CONECT   16    4   41   15   17                                             
CONECT   17   12   18    8   16                                             
CONECT   18   17    2   42   43                                             
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    2                                                            
CONECT   23    3                                                            
CONECT   24    3                                                            
CONECT   25    4                                                            
CONECT   26    5                                                            
CONECT   27    5                                                            
CONECT   28    8                                                            
CONECT   29    9                                                            
CONECT   30    9                                                            
CONECT   31   10                                                            
CONECT   32   10                                                            
CONECT   33   11                                                            
CONECT   34   11                                                            
CONECT   35   13                                                            
CONECT   36   13                                                            
CONECT   37   14                                                            
CONECT   38   14                                                            
CONECT   39   15                                                            
CONECT   40   15                                                            
CONECT   41   16                                                            
CONECT   42   18                                                            
CONECT   43   18                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   92    0
END

RDKit          3D

43 46  0  0  0  0  0  0  0  0999 V2000
    2.3998   -0.9426    1.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1505   -1.1717    0.1983 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3843   -0.6708   -1.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1013   -0.6106   -2.0835 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4285   -2.0118   -2.4102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0444   -2.6969   -1.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8744   -3.9009   -1.0152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9740   -1.8569   -0.3473 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4232   -2.5771    0.9278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3971   -1.7038    1.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8804   -0.2754    1.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3879    0.3749    0.6838 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5192    0.8164   -0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0761    1.5243   -1.4285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1205    0.6576   -2.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9380    0.2580   -1.3493 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3740   -0.4530   -0.0355 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0797   -0.5157    0.8548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6346    0.1237    1.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2676   -1.4459    0.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2567   -1.3411    2.0634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9970   -2.2557    0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1320   -1.3033   -1.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8181    0.3378   -1.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3660   -0.1257   -3.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1978   -1.9610   -3.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3825   -2.6407   -2.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8708   -1.7472   -0.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9136   -3.5256    0.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5616   -2.8411    1.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3592   -1.6762    1.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5922   -2.1626    2.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0811   -0.2839    2.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6708    0.3344    2.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1346    1.5216    0.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1741   -0.0200   -0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5879    2.4735   -1.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9534    1.7726   -2.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6535   -0.2159   -2.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7636    1.2218   -3.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4398    1.2031   -1.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1911    0.5129    1.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2658   -1.0371    1.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 14 15  1  0
 13 12  1  0
  8  9  1  0
 17 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
 16  4  1  0
  4  3  1  0
  8  6  1  0
 16 41  1  1
  6  5  1  0
 17 18  1  1
  5  4  1  0
 18  2  1  0
  3  2  1  0
  8 17  1  0
  2  1  1  0
 16 15  1  0
  8 28  1  6
 16 17  1  0
  6  7  2  0
 14 37  1  0
 14 38  1  0
 13 35  1  0
 13 36  1  0
 15 39  1  0
 15 40  1  0
  5 26  1  0
  5 27  1  0
  4 25  1  6
 11 33  1  0
 11 34  1  0
 10 31  1  0
 10 32  1  0
  9 29  1  0
  9 30  1  0
  3 23  1  0
  3 24  1  0
 18 42  1  0
 18 43  1  0
  2 22  1  6
  1 19  1  0
  1 20  1  0
  1 21  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
(16R)-Methyllycopodan-5-one	MeSH

Chemical Formula

C₁₆H₂₅NO

Average Mass

247.3820 Da

Monoisotopic Mass

247.19361 Da

IUPAC Name

(1R,2R,10S,13S,15R)-15-methyl-6-azatetracyclo[8.6.0.0^{1,6}.0^{2,13}]hexadecan-11-one

Traditional Name

(1R,2R,10S,13S,15R)-15-methyl-6-azatetracyclo[8.6.0.0^{1,6}.0^{2,13}]hexadecan-11-one

CAS Registry Number

Not Available

SMILES

[H]C([H])([H])[C@]1([H])C([H])([H])[C@@]2([H])C([H])([H])C(=O)[C@@]3([H])C([H])([H])C([H])([H])C([H])([H])N4C([H])([H])C([H])([H])C([H])([H])[C@@]2([H])[C@]34C1([H])[H]

InChI Identifier

InChI=1S/C16H25NO/c1-11-8-12-9-15(18)14-5-3-7-17-6-2-4-13(12)16(14,17)10-11/h11-14H,2-10H2,1H3/t11-,12+,13-,14-,16-/m1/s1

InChI Key

BCZFSDNVXODRAJ-JTTNIQEDSA-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, 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
Austrolycopodium magellanicum	LOTUS Database	35616633
Dendrolycopodium obscurum	LOTUS Database	35616633
Diphasiastrum alpinum	JEOL database	Halldorsdottir, E. S., et al, Phytochem. Lett. 6, 355 (2013)
Diphasiastrum thyoides	LOTUS Database	35616633
Diphasiastrum tristachyum	LOTUS Database	35616633
Huperzia lucidula	LOTUS Database	35616633
Huperzia miyoshiana	KNApSAcK Database	22123792
Huperzia selago	KNApSAcK Database	22123792
Huperzia serrata	KNApSAcK Database	22123792
Lycopodium alopecuroides	KNApSAcK Database	22123792
Lycopodium annotinum	KNApSAcK Database	22123792
Lycopodium carolinum	KNApSAcK Database	22123792
Lycopodium cernuum	KNApSAcK Database	22123792
Lycopodium clavatum	KNApSAcK Database	22123792
Lycopodium complanatum	KNApSAcK Database	22123792
Lycopodium contiguum	KNApSAcK Database	22123792
Lycopodium densum	KNApSAcK Database	22123792
Lycopodium deuterodensum	KNApSAcK Database	22123792
Lycopodium erythraeum	KNApSAcK Database	22123792
Lycopodium fastigiatum	KNApSAcK Database	22123792
Lycopodium flabelliforme	KNApSAcK Database	22123792
Lycopodium inundatum	KNApSAcK Database	22123792
Lycopodium issleri	KNApSAcK Database	22123792
Lycopodium japonicum	KNApSAcK Database	22123792
Lycopodium lucidulum	KNApSAcK Database	22123792
Lycopodium lucidum Michx.	KNApSAcK Database	22123792
Lycopodium magellanicum	KNApSAcK Database	22123792
Lycopodium obscurum	KNApSAcK Database	22123792
Lycopodium paniculatum	KNApSAcK Database	22123792
Lycopodium phlegmaria	KNApSAcK Database	22123792
Lycopodium serratum	KNApSAcK Database	22123792
Lycopodium stichense	KNApSAcK Database	22123792
Lycopodium thyoides	KNApSAcK Database	22123792
Lycopodium tristachyum	KNApSAcK Database	22123792
Lycopodium verticillatum	KNApSAcK Database	22123792
Lycopodium volubile	KNApSAcK Database	22123792
Palhinhaea cernua	LOTUS Database	35616633
Phlegmariurus filiformis	LOTUS Database	35616633
Phlegmariurus phlegmaria	LOTUS Database	35616633
Phlegmariurus varius	LOTUS Database	35616633
Pseudodiphasium volubile	LOTUS Database	35616633

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	3.09	ALOGPS
logP	2.73	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	19.18	ChemAxon
pKa (Strongest Basic)	10.25	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	20.31 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	72.73 m³·mol⁻¹	ChemAxon
Polarizability	28.63 Å³	ChemAxon
Number of Rings	4	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

C00001948

Chemspider ID

10194155

KEGG Compound ID

C09883

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

6597

Good Scents ID

Not Available

References

General References

Dymek A, Widelski J, Wojtanowski KK, Ploszaj P, Zhuravchak R, Mroczek T: Optimization of Pressurized Liquid Extraction of Lycopodiaceae Alkaloids Obtained from Two Lycopodium Species. Molecules. 2021 Mar 15;26(6). pii: molecules26061626. doi: 10.3390/molecules26061626. [PubMed:33804083 ]
Zhu X, Xia D, Zhou Z, Xie S, Shi Z, Chen G, Wang L, Pan K: Lycosquarrines A-R, Lycopodium Alkaloids from Phlegmariurus squarrosus. J Nat Prod. 2020 Oct 23;83(10):2831-2843. doi: 10.1021/acs.jnatprod.9b00815. Epub 2020 Sep 17. [PubMed:32941036 ]
Yang Z, Yin Q, Ma J, Yang C, Sheng Y, Song L, Pang T, Zhuang P, Guo H, Zhang Y: Screen the Effective Components of Lycopodii herba on Rheumatoid Arthritis with the Aid of Spectrum-Effect Relationship and Uncover its Potential Mechanism. Inflammation. 2020 Dec;43(6):2087-2097. doi: 10.1007/s10753-020-01276-z. [PubMed:32914364 ]
Takayama H: Total Syntheses of Lycopodium and Monoterpenoid Indole Alkaloids Based on Biosynthesis-Inspired Strategies. Chem Pharm Bull (Tokyo). 2020;68(2):103-116. doi: 10.1248/cpb.c19-00872. [PubMed:32009077 ]
Xiong J, Meng WJ, Zhang HY, Zou Y, Wang WX, Wang XY, Yang QL, Osman EEA, Hu JF: Lycofargesiines A-F, further Lycopodium alkaloids from the club moss Huperzia fargesii. Phytochemistry. 2019 Jun;162:183-192. doi: 10.1016/j.phytochem.2019.03.015. Epub 2019 Mar 29. [PubMed:30928888 ]
Halldorsdottir, E. S., et al. (2013). Halldorsdottir, E. S., et al, Phytochem. Lett. 6, 355 (2013). Phytochem..

Showing NP-Card for lycopodine (NP0042389)

MOL for NP0042389 (lycopodine)

3D MOL for NP0042389 (lycopodine)

3D SDF for NP0042389 (lycopodine)

3D-SDF for NP0042389 (lycopodine)

PDB for NP0042389 (lycopodine)

3D PDB for NP0042389 (lycopodine)

SMILES for NP0042389 (lycopodine)

INCHI for NP0042389 (lycopodine)

Structure for NP0042389 (lycopodine)

3D Structure for NP0042389 (lycopodine)