NP-MRD: Showing NP-Card for Huperserratinine (NP0069953)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 15:14:55 UTC

Updated at

2022-04-28 15:14:55 UTC

NP-MRD ID

NP0069953

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Huperserratinine

Description

(1R,4S,5S,6S,8R,9S)-8-hydroxy-6-methyl-2-oxo-13-azatetracyclo[7.7.0.0¹,¹³.0⁴,⁹]Hexadecan-5-yl 2-(4-methoxyphenyl)acetate 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. Huperserratinine is found in Huperzia serrata . Based on a literature review very few articles have been published on (1R,4S,5S,6S,8R,9S)-8-hydroxy-6-methyl-2-oxo-13-azatetracyclo[7.7.0.0¹,¹³.0⁴,⁹]Hexadecan-5-yl 2-(4-methoxyphenyl)acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282217142D          

 31 35  0  0  1  0            999 V2000
    0.2554   -1.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0759   -1.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4114   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9265    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1060    0.3263    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1206   -0.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2295    1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3835    1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0980    1.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8517    1.5550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0500    1.1662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5350    0.4987    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1994   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3789   -0.3412    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0434   -1.0949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3554    0.5850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3856    1.9199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2061    2.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5416    2.7598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6910    1.3386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5115    1.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9964    0.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8169    0.8437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1524    1.5974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6675    2.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8470    2.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9729    1.6836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4578    1.0162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4114    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1960    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1960    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  6  0  0  0
 12 16  1  6  0  0  0
 11 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
  4 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  3 31  1  0  0  0  0
M  END

     RDKit          3D

 64 68  0  0  0  0  0  0  0  0999 V2000
    7.4334    3.3209    0.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3623    2.0864   -0.0566 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3062    1.2295    0.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3608    1.5567    1.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3307    0.7043    1.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1889   -0.5179    0.9056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0877   -1.4603    1.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9477   -1.1605    0.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9815   -0.2387   -0.5417 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7524   -1.8713    0.3562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3425   -1.6239   -0.4664 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8222   -2.8277   -1.2321 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1903   -3.8888   -0.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0807   -2.4447   -1.9615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4224   -0.9790   -1.8322 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7078   -0.8370   -2.4081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5550   -0.5311   -0.4011 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9165   -0.9563    0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3481   -0.2816    1.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1572    1.1925    1.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2650    1.7013    0.3651 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5541    2.9064   -0.3014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3907    3.0704   -1.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1011    1.6174   -1.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3021    0.9404   -0.2648 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9951    1.0768    0.4551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1377    1.9277    0.3791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9282   -0.1097    1.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4868   -1.1891    0.4305 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1320   -0.8536   -0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1675   -0.0039   -0.3579 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4836    3.8894    0.4335 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3122    3.9090    0.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4784    3.1536    1.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4480    2.5117    1.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5939    0.9708    2.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4132   -2.5049    1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8104   -1.2670    2.2935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1657   -0.7726   -1.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1093   -3.2082   -1.9661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9027   -4.8962   -0.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6595   -3.6790    0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2916   -3.9042   -0.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9702   -3.0183   -1.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0417   -2.6644   -3.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7308   -0.3932   -2.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6700   -1.2481   -3.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6422   -0.6370   -0.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9448   -2.0495    0.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8427   -0.7324    2.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4299   -0.5257    1.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1668    1.6814    1.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8594    1.5208    2.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5275    2.9610   -0.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4729    3.7487    0.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6579    3.6638   -2.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5186    3.4559   -0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8302    1.3257   -2.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0493    1.5823   -1.9494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5664    0.0240    2.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0760   -0.3495    1.6977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8685   -2.0366    1.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0368   -1.8262   -0.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9185   -0.2406   -1.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 29  1  0
 29 28  1  0
 28 26  1  0
 26 27  2  0
 25 26  1  0
 25 24  1  6
 24 23  1  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 17 18  1  1
 17 15  1  0
 15 16  1  0
 15 14  1  0
 14 12  1  0
 12 13  1  0
  6 30  1  0
 30 31  2  0
 31  3  1  0
 12 11  1  0
 17 29  1  0
 21 25  1  0
 17 25  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  5 36  1  0
  7 37  1  0
  7 38  1  0
 11 39  1  6
 29 62  1  1
 28 60  1  0
 28 61  1  0
 24 58  1  0
 24 59  1  0
 23 56  1  0
 23 57  1  0
 22 54  1  0
 22 55  1  0
 20 52  1  0
 20 53  1  0
 19 50  1  0
 19 51  1  0
 18 48  1  0
 18 49  1  0
 15 46  1  6
 16 47  1  0
 14 44  1  0
 14 45  1  0
 12 40  1  6
 13 41  1  0
 13 42  1  0
 13 43  1  0
 30 63  1  0
 31 64  1  0
M  END


  Mrv1652304282217142D          

 31 35  0  0  1  0            999 V2000
    0.2554   -1.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0759   -1.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4114   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9265    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1060    0.3263    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1206   -0.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2295    1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3835    1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0980    1.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8517    1.5550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0500    1.1662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5350    0.4987    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1994   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3789   -0.3412    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0434   -1.0949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3554    0.5850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3856    1.9199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2061    2.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5416    2.7598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6910    1.3386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5115    1.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9964    0.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8169    0.8437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1524    1.5974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6675    2.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8470    2.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9729    1.6836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4578    1.0162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4114    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1960    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1960    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  6  0  0  0
 12 16  1  6  0  0  0
 11 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
  4 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  3 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0069953

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(CC(=O)O[C@@H]2[C@H]3CC(=O)[C@]45CCCN4CCC[C@]35[C@H](O)C[C@@H]2C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H33NO5/c1-16-13-20(27)24-9-3-11-26-12-4-10-25(24,26)21(28)15-19(24)23(16)31-22(29)14-17-5-7-18(30-2)8-6-17/h5-8,16,19-20,23,27H,3-4,9-15H2,1-2H3/t16-,19+,20+,23-,24+,25-/m0/s1

> <INCHI_KEY>
WGOOPTFIDGLATG-VGGXNRKWSA-N

> <FORMULA>
C25H33NO5

> <MOLECULAR_WEIGHT>
427.541

> <EXACT_MASS>
427.235873167

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
46.862211039338334

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4S,5S,6S,8R,9S)-8-hydroxy-6-methyl-2-oxo-13-azatetracyclo[7.7.0.0^{1,13}.0^{4,9}]hexadecan-5-yl 2-(4-methoxyphenyl)acetate

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
2.732692519999998

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.291350015848796

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.580592687575379

> <JCHEM_PKA_STRONGEST_BASIC>
8.804967163802829

> <JCHEM_POLAR_SURFACE_AREA>
76.07000000000001

> <JCHEM_REFRACTIVITY>
115.97479999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,5S,6S,8R,9S)-8-hydroxy-6-methyl-2-oxo-13-azatetracyclo[7.7.0.0^{1,13}.0^{4,9}]hexadecan-5-yl (4-methoxyphenyl)acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       0.477  -2.044   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.008  -1.883   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.635  -0.476   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.729   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.198   0.609   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.225  -0.876   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.428   2.016   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.716   3.046   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.050   2.276   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.456   2.903   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.960   2.177   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.865   0.931   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.239  -0.476   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.707  -0.637   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.081  -2.044   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.397   1.092   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.586   3.584   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.118   3.745   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.744   5.152   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -5.023   2.499   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.555   2.660   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -7.460   1.414   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -8.991   1.575   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -9.618   2.982   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -8.713   4.228   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -7.181   4.067   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0     -11.149   3.143   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0     -12.055   1.897   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.635   2.016   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.099   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.099   0.000   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5    9   29                                             
CONECT    5    4    6    7   14                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9                                                            
CONECT   11    7   12   17                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13    5   15                                                  
CONECT   15   14                                                            
CONECT   16   12                                                            
CONECT   17   11   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
CONECT   27   24   28                                                       
CONECT   28   27                                                            
CONECT   29    4   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30    3                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
(1R,4S,5S,6S,8R,9S)-8-Hydroxy-6-methyl-2-oxo-13-azatetracyclo[7.7.0.0,.0,]hexadecan-5-yl 2-(4-methoxyphenyl)acetic acid	Generator

Chemical Formula

C₂₅H₃₃NO₅

Average Mass

427.5410 Da

Monoisotopic Mass

427.23587 Da

IUPAC Name

(1R,4S,5S,6S,8R,9S)-8-hydroxy-6-methyl-2-oxo-13-azatetracyclo[7.7.0.0^{1,13}.0^{4,9}]hexadecan-5-yl 2-(4-methoxyphenyl)acetate

Traditional Name

(1R,4S,5S,6S,8R,9S)-8-hydroxy-6-methyl-2-oxo-13-azatetracyclo[7.7.0.0^{1,13}.0^{4,9}]hexadecan-5-yl (4-methoxyphenyl)acetate

CAS Registry Number

Not Available

SMILES

COC1=CC=C(CC(=O)O[C@@H]2[C@H]3CC(=O)[C@]45CCCN4CCC[C@]35[C@H](O)C[C@@H]2C)C=C1

InChI Identifier

InChI=1S/C25H33NO5/c1-16-13-20(27)24-9-3-11-26-12-4-10-25(24,26)21(28)15-19(24)23(16)31-22(29)14-17-5-7-18(30-2)8-6-17/h5-8,16,19-20,23,27H,3-4,9-15H2,1-2H3/t16-,19+,20+,23-,24+,25-/m0/s1

InChI Key

WGOOPTFIDGLATG-VGGXNRKWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Huperzia serrata	Plant	KNApSAcK

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
Indolizidine
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
Alkyl aryl ether
Benzenoid
N-alkylpyrrolidine
Piperidine
Monocyclic benzene moiety
Pyrrolidine
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Ketone
Carboxylic acid ester
Amino acid or derivatives
Azacycle
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.36	ALOGPS
logP	2.73	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	14.58	ChemAxon
pKa (Strongest Basic)	8.8	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	115.97 m³·mol⁻¹	ChemAxon
Polarizability	46.86 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

163053145

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Huperserratinine (NP0069953)

MOL for NP0069953 (Huperserratinine)

3D MOL for NP0069953 (Huperserratinine)

3D SDF for NP0069953 (Huperserratinine)

3D-SDF for NP0069953 (Huperserratinine)

PDB for NP0069953 (Huperserratinine)

3D PDB for NP0069953 (Huperserratinine)

SMILES for NP0069953 (Huperserratinine)

INCHI for NP0069953 (Huperserratinine)

Structure for NP0069953 (Huperserratinine)

3D Structure for NP0069953 (Huperserratinine)