NP-MRD: Showing NP-Card for lycojaponicumin A (NP0041464)

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Record Information

Version

2.0

Created at

2021-06-20 23:22:21 UTC

Updated at

2021-06-30 00:15:59 UTC

NP-MRD ID

NP0041464

Secondary Accession Numbers

None

Natural Product Identification

Common Name

lycojaponicumin A

Provided By

JEOL Database JEOL Logo

Description

Lycojaponicumin A belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom. lycojaponicumin A is found in Lycopodium japonicum. lycojaponicumin A was first documented in 2020 (PMID: 32803967). Based on a literature review very few articles have been published on Lycojaponicumin A (PMID: 32330061).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101223D          

 42 46  0  0  0  0            999 V2000
   -1.9203    1.1505   -2.9081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0168    1.1261   -1.6718 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5245    2.4504   -1.4773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8120    0.6928   -0.4427 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8850    0.5818    0.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0896    1.2426    1.7603 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2848   -0.3907    0.6164 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1773   -1.8538    0.6497 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0727   -2.6493    1.0298 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9142   -1.7180    1.9127 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8702   -1.9704    3.3752 N   0  0  2  0  0  0  0  0  0  0  0  0
    0.5070   -2.0991    3.9220 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0891   -0.6999    3.8214 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0437    0.0834    3.1768 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1470   -0.5919    3.8307 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3496   -0.2955    1.7329 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3656    0.6619    1.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3572    1.0995    1.6905 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0101    1.0580   -0.2896 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0636   -0.0715   -0.6856 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1862    0.2016   -1.9164 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3694    1.5073   -3.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7588    1.8420   -2.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3263    0.1587   -3.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2792    3.0578   -1.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5842    1.4325   -0.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3050   -0.2739   -0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9704   -2.0035    1.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5800   -2.1942   -0.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6407   -2.8984    0.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8296   -3.6058    1.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9643   -1.7863    1.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0984   -2.8583    3.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5702   -2.4044    4.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2784   -0.3162    4.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0318   -0.6799    3.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0512    1.1524    3.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9003    1.0787   -0.9233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5405    2.0424   -0.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7037   -0.9234   -0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1838   -0.7655   -2.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8204    0.6169   -2.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  1  0  0  0
 16 17  1  6  0  0  0
 21  2  1  0  0  0  0
 17 19  1  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  0  0  0  0
 20 19  1  0  0  0  0
  5  6  2  0  0  0  0
 20  7  1  0  0  0  0
  2  3  1  1  0  0  0
  7  8  1  0  0  0  0
 16 14  1  0  0  0  0
  8  9  1  0  0  0  0
 14 15  1  0  0  0  0
 10  9  1  0  0  0  0
 15 11  1  0  0  0  0
 10 11  1  0  0  0  0
 10 16  1  0  0  0  0
 11 12  1  0  0  0  0
 16  7  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  0  0  0  0
 20 21  1  0  0  0  0
 17 18  2  0  0  0  0
  2  1  1  0  0  0  0
 19 38  1  0  0  0  0
 19 39  1  0  0  0  0
 20 40  1  6  0  0  0
  8 28  1  0  0  0  0
  8 29  1  0  0  0  0
  9 30  1  0  0  0  0
  9 31  1  0  0  0  0
 10 32  1  6  0  0  0
 21 41  1  0  0  0  0
 21 42  1  0  0  0  0
  4 26  1  0  0  0  0
  4 27  1  0  0  0  0
  3 25  1  0  0  0  0
 14 37  1  6  0  0  0
 12 33  1  0  0  0  0
 12 34  1  0  0  0  0
 13 35  1  0  0  0  0
 13 36  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
M  END

     RDKit          3D

 42 46  0  0  0  0  0  0  0  0999 V2000
   -1.9203    1.1505   -2.9081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0168    1.1261   -1.6718 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5245    2.4504   -1.4773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8120    0.6928   -0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8850    0.5818    0.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0896    1.2426    1.7603 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2848   -0.3907    0.6164 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1773   -1.8538    0.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0727   -2.6493    1.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9142   -1.7180    1.9127 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8702   -1.9704    3.3752 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5070   -2.0991    3.9220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0891   -0.6999    3.8214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0437    0.0834    3.1768 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1470   -0.5919    3.8307 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3496   -0.2955    1.7329 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3656    0.6619    1.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3572    1.0995    1.6905 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0101    1.0580   -0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0636   -0.0715   -0.6856 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1862    0.2016   -1.9164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3694    1.5073   -3.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7588    1.8420   -2.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3263    0.1587   -3.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2792    3.0578   -1.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5842    1.4325   -0.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3050   -0.2739   -0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9704   -2.0035    1.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5800   -2.1942   -0.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6407   -2.8984    0.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8296   -3.6058    1.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9643   -1.7863    1.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0984   -2.8583    3.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5702   -2.4044    4.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2784   -0.3162    4.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0318   -0.6799    3.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0512    1.1524    3.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9003    1.0787   -0.9233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5405    2.0424   -0.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7037   -0.9234   -0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1838   -0.7655   -2.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8204    0.6169   -2.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  1
 16 17  1  6
 21  2  1  0
 17 19  1  0
  2  4  1  0
  5  4  1  0
 20 19  1  0
  5  6  2  0
 20  7  1  0
  2  3  1  1
  7  8  1  0
 16 14  1  0
  8  9  1  0
 14 15  1  0
 10  9  1  0
 15 11  1  0
 10 11  1  0
 10 16  1  0
 11 12  1  0
 16  7  1  0
 12 13  1  0
 14 13  1  0
 20 21  1  0
 17 18  2  0
  2  1  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  6
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  6
 21 41  1  0
 21 42  1  0
  4 26  1  0
  4 27  1  0
  3 25  1  0
 14 37  1  6
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
M  END


  Mrv1652306212101223D          

 42 46  0  0  0  0            999 V2000
   -1.9203    1.1505   -2.9081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0168    1.1261   -1.6718 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5245    2.4504   -1.4773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8120    0.6928   -0.4427 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8850    0.5818    0.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0896    1.2426    1.7603 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2848   -0.3907    0.6164 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1773   -1.8538    0.6497 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0727   -2.6493    1.0298 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9142   -1.7180    1.9127 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8702   -1.9704    3.3752 N   0  0  2  0  0  0  0  0  0  0  0  0
    0.5070   -2.0991    3.9220 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0891   -0.6999    3.8214 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0437    0.0834    3.1768 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1470   -0.5919    3.8307 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3496   -0.2955    1.7329 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3656    0.6619    1.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3572    1.0995    1.6905 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0101    1.0580   -0.2896 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0636   -0.0715   -0.6856 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1862    0.2016   -1.9164 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3694    1.5073   -3.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7588    1.8420   -2.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3263    0.1587   -3.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2792    3.0578   -1.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5842    1.4325   -0.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3050   -0.2739   -0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9704   -2.0035    1.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5800   -2.1942   -0.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6407   -2.8984    0.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8296   -3.6058    1.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9643   -1.7863    1.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0984   -2.8583    3.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5702   -2.4044    4.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2784   -0.3162    4.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0318   -0.6799    3.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0512    1.1524    3.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9003    1.0787   -0.9233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5405    2.0424   -0.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7037   -0.9234   -0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1838   -0.7655   -2.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8204    0.6169   -2.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  1  0  0  0
 16 17  1  6  0  0  0
 21  2  1  0  0  0  0
 17 19  1  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  0  0  0  0
 20 19  1  0  0  0  0
  5  6  2  0  0  0  0
 20  7  1  0  0  0  0
  2  3  1  1  0  0  0
  7  8  1  0  0  0  0
 16 14  1  0  0  0  0
  8  9  1  0  0  0  0
 14 15  1  0  0  0  0
 10  9  1  0  0  0  0
 15 11  1  0  0  0  0
 10 11  1  0  0  0  0
 10 16  1  0  0  0  0
 11 12  1  0  0  0  0
 16  7  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  0  0  0  0
 20 21  1  0  0  0  0
 17 18  2  0  0  0  0
  2  1  1  0  0  0  0
 19 38  1  0  0  0  0
 19 39  1  0  0  0  0
 20 40  1  6  0  0  0
  8 28  1  0  0  0  0
  8 29  1  0  0  0  0
  9 30  1  0  0  0  0
  9 31  1  0  0  0  0
 10 32  1  6  0  0  0
 21 41  1  0  0  0  0
 21 42  1  0  0  0  0
  4 26  1  0  0  0  0
  4 27  1  0  0  0  0
  3 25  1  0  0  0  0
 14 37  1  6  0  0  0
 12 33  1  0  0  0  0
 12 34  1  0  0  0  0
 13 35  1  0  0  0  0
 13 36  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0041464

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1(C([H])([H])[H])C([H])([H])C(=O)[C@]23C([H])([H])C([H])([H])[C@]4([H])N5O[C@]([H])(C([H])([H])C5([H])[H])[C@]24C(=O)C([H])([H])[C@]3([H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H21NO4/c1-14(20)7-9-6-11(18)16-10(17-5-3-13(16)21-17)2-4-15(9,16)12(19)8-14/h9-10,13,20H,2-8H2,1H3/t9-,10+,13-,14+,15-,16+/m1/s1

> <INCHI_KEY>
WGVQKABRYXBLGW-WUZBVLBZSA-N

> <FORMULA>
C16H21NO4

> <MOLECULAR_WEIGHT>
291.347

> <EXACT_MASS>
291.14705816

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
29.513468544648077

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,5S,7S,10S,13S)-7-hydroxy-7-methyl-17-oxa-14-azapentacyclo[12.2.1.0^{2,10}.0^{2,13}.0^{5,10}]heptadecane-3,9-dione

> <ALOGPS_LOGP>
0.35

> <JCHEM_LOGP>
0.08245619466666582

> <ALOGPS_LOGS>
-0.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.68547013532755

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.858207082818051

> <JCHEM_PKA_STRONGEST_BASIC>
0.5898771871486834

> <JCHEM_POLAR_SURFACE_AREA>
66.84

> <JCHEM_REFRACTIVITY>
73.6142

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.12e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5S,7S,10S,13S)-7-hydroxy-7-methyl-17-oxa-14-azapentacyclo[12.2.1.0^{2,10}.0^{2,13}.0^{5,10}]heptadecane-3,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 42 46  0  0  0  0  0  0  0  0999 V2000
   -1.9203    1.1505   -2.9081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0168    1.1261   -1.6718 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5245    2.4504   -1.4773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8120    0.6928   -0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8850    0.5818    0.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0896    1.2426    1.7603 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2848   -0.3907    0.6164 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1773   -1.8538    0.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0727   -2.6493    1.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9142   -1.7180    1.9127 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8702   -1.9704    3.3752 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5070   -2.0991    3.9220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0891   -0.6999    3.8214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0437    0.0834    3.1768 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1470   -0.5919    3.8307 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3496   -0.2955    1.7329 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3656    0.6619    1.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3572    1.0995    1.6905 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0101    1.0580   -0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0636   -0.0715   -0.6856 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1862    0.2016   -1.9164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3694    1.5073   -3.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7588    1.8420   -2.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3263    0.1587   -3.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2792    3.0578   -1.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5842    1.4325   -0.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3050   -0.2739   -0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9704   -2.0035    1.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5800   -2.1942   -0.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6407   -2.8984    0.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8296   -3.6058    1.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9643   -1.7863    1.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0984   -2.8583    3.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5702   -2.4044    4.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2784   -0.3162    4.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0318   -0.6799    3.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0512    1.1524    3.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9003    1.0787   -0.9233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5405    2.0424   -0.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7037   -0.9234   -0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1838   -0.7655   -2.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8204    0.6169   -2.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  1
 16 17  1  6
 21  2  1  0
 17 19  1  0
  2  4  1  0
  5  4  1  0
 20 19  1  0
  5  6  2  0
 20  7  1  0
  2  3  1  1
  7  8  1  0
 16 14  1  0
  8  9  1  0
 14 15  1  0
 10  9  1  0
 15 11  1  0
 10 11  1  0
 10 16  1  0
 11 12  1  0
 16  7  1  0
 12 13  1  0
 14 13  1  0
 20 21  1  0
 17 18  2  0
  2  1  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  6
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  6
 21 41  1  0
 21 42  1  0
  4 26  1  0
  4 27  1  0
  3 25  1  0
 14 37  1  6
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
  1 22  1  0
  1 23  1  0
  1 24  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      -1.920   1.151  -2.908  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.017   1.126  -1.672  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.525   2.450  -1.477  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.812   0.693  -0.443  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.885   0.582   0.745  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.090   1.243   1.760  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.285  -0.391   0.616  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.177  -1.854   0.650  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.073  -2.649   1.030  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.914  -1.718   1.913  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.870  -1.970   3.375  0.00  0.00           N+0
HETATM   12  C   UNK     0       0.507  -2.099   3.922  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.089  -0.700   3.821  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.044   0.083   3.177  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.147  -0.592   3.831  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.350  -0.296   1.733  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.366   0.662   1.121  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.357   1.099   1.690  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.010   1.058  -0.290  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.064  -0.072  -0.686  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.186   0.202  -1.916  0.00  0.00           C+0
HETATM   22  H   UNK     0      -1.369   1.507  -3.786  0.00  0.00           H+0
HETATM   23  H   UNK     0      -2.759   1.842  -2.766  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.326   0.159  -3.132  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.279   3.058  -1.368  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.584   1.433  -0.200  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.305  -0.274  -0.591  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.970  -2.003   1.389  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.580  -2.194  -0.310  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.641  -2.898   0.125  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.830  -3.606   1.503  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.964  -1.786   1.602  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.098  -2.858   3.420  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.570  -2.404   4.973  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.278  -0.316   4.831  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.032  -0.680   3.274  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.051   1.152   3.404  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.900   1.079  -0.923  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.541   2.042  -0.261  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.704  -0.923  -0.956  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.184  -0.766  -2.283  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.820   0.617  -2.711  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2   21    4    3    1                                             
CONECT    3    2   25                                                       
CONECT    4    2    5   26   27                                             
CONECT    5    7    4    6                                                  
CONECT    6    5                                                            
CONECT    7    5   20    8   16                                             
CONECT    8    7    9   28   29                                             
CONECT    9    8   10   30   31                                             
CONECT   10    9   11   16   32                                             
CONECT   11   15   10   12                                                  
CONECT   12   11   13   33   34                                             
CONECT   13   12   14   35   36                                             
CONECT   14   16   15   13   37                                             
CONECT   15   14   11                                                       
CONECT   16   17   14   10    7                                             
CONECT   17   16   19   18                                                  
CONECT   18   17                                                            
CONECT   19   17   20   38   39                                             
CONECT   20   19    7   21   40                                             
CONECT   21    2   20   41   42                                             
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    3                                                            
CONECT   26    4                                                            
CONECT   27    4                                                            
CONECT   28    8                                                            
CONECT   29    8                                                            
CONECT   30    9                                                            
CONECT   31    9                                                            
CONECT   32   10                                                            
CONECT   33   12                                                            
CONECT   34   12                                                            
CONECT   35   13                                                            
CONECT   36   13                                                            
CONECT   37   14                                                            
CONECT   38   19                                                            
CONECT   39   19                                                            
CONECT   40   20                                                            
CONECT   41   21                                                            
CONECT   42   21                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

RDKit          3D

42 46  0  0  0  0  0  0  0  0999 V2000
   -1.9203    1.1505   -2.9081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0168    1.1261   -1.6718 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5245    2.4504   -1.4773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8120    0.6928   -0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8850    0.5818    0.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0896    1.2426    1.7603 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2848   -0.3907    0.6164 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1773   -1.8538    0.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0727   -2.6493    1.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9142   -1.7180    1.9127 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8702   -1.9704    3.3752 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5070   -2.0991    3.9220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0891   -0.6999    3.8214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0437    0.0834    3.1768 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1470   -0.5919    3.8307 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3496   -0.2955    1.7329 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3656    0.6619    1.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3572    1.0995    1.6905 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0101    1.0580   -0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0636   -0.0715   -0.6856 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1862    0.2016   -1.9164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3694    1.5073   -3.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7588    1.8420   -2.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3263    0.1587   -3.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2792    3.0578   -1.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5842    1.4325   -0.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3050   -0.2739   -0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9704   -2.0035    1.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5800   -2.1942   -0.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6407   -2.8984    0.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8296   -3.6058    1.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9643   -1.7863    1.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0984   -2.8583    3.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5702   -2.4044    4.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2784   -0.3162    4.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0318   -0.6799    3.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0512    1.1524    3.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9003    1.0787   -0.9233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5405    2.0424   -0.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7037   -0.9234   -0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1838   -0.7655   -2.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8204    0.6169   -2.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  1
 16 17  1  6
 21  2  1  0
 17 19  1  0
  2  4  1  0
  5  4  1  0
 20 19  1  0
  5  6  2  0
 20  7  1  0
  2  3  1  1
  7  8  1  0
 16 14  1  0
  8  9  1  0
 14 15  1  0
 10  9  1  0
 15 11  1  0
 10 11  1  0
 10 16  1  0
 11 12  1  0
 16  7  1  0
 12 13  1  0
 14 13  1  0
 20 21  1  0
 17 18  2  0
  2  1  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  6
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  6
 21 41  1  0
 21 42  1  0
  4 26  1  0
  4 27  1  0
  3 25  1  0
 14 37  1  6
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₁NO₄

Average Mass

291.3470 Da

Monoisotopic Mass

291.14706 Da

IUPAC Name

(1R,2S,5S,7S,10S,13S)-7-hydroxy-7-methyl-17-oxa-14-azapentacyclo[12.2.1.0^{2,10}.0^{2,13}.0^{5,10}]heptadecane-3,9-dione

Traditional Name

(1R,2S,5S,7S,10S,13S)-7-hydroxy-7-methyl-17-oxa-14-azapentacyclo[12.2.1.0^{2,10}.0^{2,13}.0^{5,10}]heptadecane-3,9-dione

CAS Registry Number

Not Available

SMILES

[H]O[C@]1(C([H])([H])[H])C([H])([H])C(=O)[C@]23C([H])([H])C([H])([H])[C@]4([H])N5O[C@]([H])(C([H])([H])C5([H])[H])[C@]24C(=O)C([H])([H])[C@]3([H])C1([H])[H]

InChI Identifier

InChI=1S/C16H21NO4/c1-14(20)7-9-6-11(18)16-10(17-5-3-13(16)21-17)2-4-15(9,16)12(19)8-14/h9-10,13,20H,2-8H2,1H3/t9-,10+,13-,14+,15-,16+/m1/s1

InChI Key

WGVQKABRYXBLGW-WUZBVLBZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, 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
Lycopodium japonicum	JEOL database	Wang, X.-J., et al, Org. Lett. 14, 2614 (2012)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaspirodecane derivatives

Sub Class

Not Available

Direct Parent

Azaspirodecane derivatives

Alternative Parents

Substituents

Azaspirodecane
Piperidine
Cyclic alcohol
Isoxazolidine
Tertiary alcohol
Ketone
Oxacycle
Azacycle
N-organohydroxylamine
Organic nitrogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.35	ALOGPS
logP	0.082	ChemAxon
logS	-0.85	ALOGPS
pKa (Strongest Acidic)	14.86	ChemAxon
pKa (Strongest Basic)	0.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.84 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	73.61 m³·mol⁻¹	ChemAxon
Polarizability	29.51 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

60145017

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shao H, Wang YP, Fang K, Zhao YM, Tu YQ: Total Synthesis of Sieboldine A. J Org Chem. 2020 Sep 18;85(18):11968-11974. doi: 10.1021/acs.joc.0c01660. Epub 2020 Sep 2. [PubMed:32803967 ]
Shao H, Fang K, Wang YP, Zhang XM, Ding TM, Zhang SY, Chen ZM, Tu YQ: Total Synthesis of Fawcettimine-Type Alkaloid, Lycojaponicumin A. Org Lett. 2020 May 15;22(10):3775-3779. doi: 10.1021/acs.orglett.0c00961. Epub 2020 Apr 24. [PubMed:32330061 ]
Wang, X.-J., et al. (2012). Wang, X.-J., et al, Org. Lett. 14, 2614 (2012). Org. Lett..

Showing NP-Card for lycojaponicumin A (NP0041464)

MOL for NP0041464 (lycojaponicumin A)

3D MOL for NP0041464 (lycojaponicumin A)

3D SDF for NP0041464 (lycojaponicumin A)

3D-SDF for NP0041464 (lycojaponicumin A)

PDB for NP0041464 (lycojaponicumin A)

3D PDB for NP0041464 (lycojaponicumin A)

SMILES for NP0041464 (lycojaponicumin A)

INCHI for NP0041464 (lycojaponicumin A)

Structure for NP0041464 (lycojaponicumin A)

3D Structure for NP0041464 (lycojaponicumin A)