NP-MRD: Showing NP-Card for methyl (1'r,3r,5's,6s,11's,12's)-6-ethyl-6-methoxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate (NP0319729)

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Record Information

Version

2.0

Created at

2022-09-11 20:54:46 UTC

Updated at

2022-09-11 20:54:47 UTC

NP-MRD ID

NP0319729

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1'r,3r,5's,6s,11's,12's)-6-ethyl-6-methoxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate

Description

Yuzurine 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. methyl (1'r,3r,5's,6s,11's,12's)-6-ethyl-6-methoxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate is found in Daphniphyllum macropodum and Daphniphyllum oldhamii. It was first documented in 2002 (PMID: 31593387). Based on a literature review a significant number of articles have been published on Yuzurine (PMID: 17887722) (PMID: 22642560) (PMID: 21355269) (PMID: 19554242).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112222542D          

 29 33  0  0  1  0            999 V2000
    1.0851   -2.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8090   -2.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8283   -1.6841    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6372   -1.8463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9012   -2.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0127   -1.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4973   -1.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7975   -0.3957    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6130   -0.2715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1390   -1.0318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4281    0.2916    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0557    0.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8852    0.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3301    0.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9683   -0.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5524   -1.3118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2841   -0.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1435   -0.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1324   -2.0414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4809   -2.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3027   -2.8614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0074   -3.4648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3559   -4.2126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3134   -1.8953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1451   -1.0559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3102   -1.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4241   -0.9289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1638   -1.2942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3397   -0.0853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  6  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  3 10  1  0  0  0  0
  8 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
 14 15  2  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 24  1  0  0  0  0
 25 24  1  6  0  0  0
 15 25  1  0  0  0  0
  8 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 11 29  1  1  0  0  0
M  END

     RDKit          3D

 66 70  0  0  0  0  0  0  0  0999 V2000
    4.2675    3.3540   -0.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4224    2.4893   -1.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2927    1.1059   -0.4196 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6331    0.6905   -0.2919 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7768   -0.5936    0.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6278    1.2340    0.9029 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6107    0.1946    1.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7721   -0.2512    0.0512 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2355    0.5625   -1.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5934    0.3137   -1.3031 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0496   -1.6944   -0.2025 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7151   -2.2119   -1.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7498   -2.5315   -1.7617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6272   -1.3403   -1.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4247   -0.3169   -0.8892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730    0.8494   -1.4315 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4217    0.1961   -1.8589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8641   -1.0858   -2.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1894    1.7952   -0.3071 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4604    1.9913    0.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0100    3.1226    0.3219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1459    1.0289    1.0930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3792    1.3292    1.7168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0633    1.3721    0.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7047   -0.0284    0.3317 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0947   -0.9533    1.4792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9330   -2.3449    1.0895 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3516   -3.1581    2.2176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4426   -2.6217    0.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7977    3.4977    0.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4134    4.3230   -0.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2702    2.9095   -0.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4738    3.0070   -1.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0079    2.3847   -2.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8913   -0.7748    0.2085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3241   -0.8065    1.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4292   -1.2765   -0.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1983    2.2520    1.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4343    1.1605    1.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0255   -0.6860    1.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9107    0.6647    1.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0336    1.6221   -0.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6474    0.3589   -2.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1677   -1.8270   -0.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0658   -1.6030   -2.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2480   -3.2014   -1.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8316   -2.9313   -2.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1048   -3.3350   -1.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6218    1.2045   -2.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0236    0.7618   -2.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0481   -0.1626   -1.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6083   -1.8982   -2.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6398   -0.9218   -3.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8564    2.7815   -0.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3564    2.3446    2.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6422    0.5656    2.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1672    1.4024    0.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5259    1.4161    1.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2276    2.0709    0.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1816   -0.8062    1.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5835   -0.7010    2.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4596   -3.1101    2.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9795   -4.2009    2.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9398   -2.7363    3.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5618   -3.6546    0.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0506   -2.5917    1.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  6  1  0
  6  7  1  0
  8  7  1  1
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 29  1  0
 29 27  1  0
 27 28  1  0
 27 26  1  0
 25 26  1  1
 25 24  1  0
 24 19  1  0
 19 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
 14 13  1  0
 13 12  1  0
 14 15  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
  3  4  1  1
  4  5  1  0
 10  3  1  0
 12 11  1  0
 25  8  1  0
 15 25  1  0
 15 16  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  9 42  1  0
  9 43  1  0
 11 44  1  1
 29 65  1  0
 29 66  1  0
 28 62  1  0
 28 63  1  0
 28 64  1  0
 26 60  1  0
 26 61  1  0
 24 58  1  0
 24 59  1  0
 19 54  1  6
 16 49  1  6
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 13 47  1  0
 13 48  1  0
 12 45  1  0
 12 46  1  0
 23 55  1  0
 23 56  1  0
 23 57  1  0
  5 35  1  0
  5 36  1  0
  5 37  1  0
M  END


  Mrv1652309112222542D          

 29 33  0  0  1  0            999 V2000
    1.0851   -2.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8090   -2.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8283   -1.6841    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6372   -1.8463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9012   -2.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0127   -1.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4973   -1.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7975   -0.3957    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6130   -0.2715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1390   -1.0318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4281    0.2916    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0557    0.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8852    0.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3301    0.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9683   -0.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5524   -1.3118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2841   -0.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1435   -0.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1324   -2.0414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4809   -2.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3027   -2.8614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0074   -3.4648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3559   -4.2126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3134   -1.8953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1451   -1.0559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3102   -1.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4241   -0.9289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1638   -1.2942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3397   -0.0853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  6  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  3 10  1  0  0  0  0
  8 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
 14 15  2  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 24  1  0  0  0  0
 25 24  1  6  0  0  0
 15 25  1  0  0  0  0
  8 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 11 29  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0319729

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@]1(CC[C@@]2(CO1)[C@H]1CN(C)C[C@@]22C[C@@H]([C@@H]3CCC(CC1)=C23)C(=O)OC)OC

> <INCHI_IDENTIFIER>
InChI=1S/C24H37NO4/c1-5-24(28-4)11-10-22(15-29-24)17-8-6-16-7-9-18-19(21(26)27-3)12-23(22,20(16)18)14-25(2)13-17/h17-19H,5-15H2,1-4H3/t17-,18+,19+,22-,23-,24+/m1/s1

> <INCHI_KEY>
PHYQKWIULCXYSF-CUDJPDNHSA-N

> <FORMULA>
C24H37NO4

> <MOLECULAR_WEIGHT>
403.563

> <EXACT_MASS>
403.272258675

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
46.27257200859407

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1'R,3R,5'S,6S,11'S,12'S)-6-ethyl-6-methoxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1^{1,5}.0^{11,14}]pentadecan]-8'(14')-ene-12'-carboxylate

> <JCHEM_LOGP>
2.7270632343333325

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.086378606445985

> <JCHEM_POLAR_SURFACE_AREA>
48.00000000000001

> <JCHEM_REFRACTIVITY>
112.90709999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1'R,3R,5'S,6S,11'S,12'S)-6-ethyl-6-methoxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1^{1,5}.0^{11,14}]pentadecan]-8'(14')-ene-12'-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       2.026  -5.422   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.377  -4.683   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.413  -3.144   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.923  -3.446   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.416  -4.905   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.890  -3.376   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.928  -2.173   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.489  -0.739   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.011  -0.507   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.993  -1.926   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.799   0.544   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.971   1.649   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.519   1.404   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.350   0.088   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.674  -1.359   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.764  -2.449   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.130  -1.673   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.868  -0.141   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.981  -3.811   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.631  -5.206   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.165  -5.341   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.747  -6.468   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.398  -7.864   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.452  -3.538   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.138  -1.971   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.579  -2.581   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      -0.792  -1.734   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      -2.172  -2.416   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.634  -0.159   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    6   10                                             
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   11   25                                             
CONECT    9    8   10                                                       
CONECT   10    9    3                                                       
CONECT   11    8   12   29                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16   25                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   14                                                       
CONECT   19   16   20   24                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22                                                            
CONECT   24   19   25                                                       
CONECT   25   24   15    8   26                                             
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   11                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₇NO₄

Average Mass

403.5630 Da

Monoisotopic Mass

403.27226 Da

IUPAC Name

methyl (1'R,3R,5'S,6S,11'S,12'S)-6-ethyl-6-methoxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1^{1,5}.0^{11,14}]pentadecan]-8'(14')-ene-12'-carboxylate

Traditional Name

methyl (1'R,3R,5'S,6S,11'S,12'S)-6-ethyl-6-methoxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1^{1,5}.0^{11,14}]pentadecan]-8'(14')-ene-12'-carboxylate

CAS Registry Number

Not Available

SMILES

CC[C@]1(CC[C@@]2(CO1)[C@H]1CN(C)C[C@@]22C[C@@H]([C@@H]3CCC(CC1)=C23)C(=O)OC)OC

InChI Identifier

InChI=1S/C24H37NO4/c1-5-24(28-4)11-10-22(15-29-24)17-8-6-16-7-9-18-19(21(26)27-3)12-23(22,20(16)18)14-25(2)13-17/h17-19H,5-15H2,1-4H3/t17-,18+,19+,22-,23-,24+/m1/s1

InChI Key

PHYQKWIULCXYSF-CUDJPDNHSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Daphniphyllum macropodum	LOTUS Database	35616633
Daphniphyllum oldhamii	LOTUS Database	35616633

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
Ketal
Oxane
Piperidine
Methyl ester
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Acetal
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Azacycle
Organonitrogen compound
Amine
Organopnictogen compound
Carbonyl group
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen 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	2.73	ChemAxon
pKa (Strongest Basic)	10.09	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	48 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	112.91 m³·mol⁻¹	ChemAxon
Polarizability	46.27 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

C00040722

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

102267541

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mu SZ, Li CS, He HP, Di YT, Wang Y, Wang YH, Zhang Z, Lu Y, Zhang L, Hao XJ: Daphnipaxianines A-D, alkaloids from Daphniphyllum paxianum. J Nat Prod. 2007 Oct;70(10):1628-31. doi: 10.1021/np070342j. Epub 2007 Sep 22. [PubMed:17887722 ]
Authors unspecified: Childhood Esophageal Cancer Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:31593387 ]
Cao M, Zhang Y, He H, Li S, Huang S, Chen D, Tang G, Li S, Di Y, Hao X: Daphmacromines A-J, alkaloids from Daphniphyllum macropodum. J Nat Prod. 2012 Jun 22;75(6):1076-82. doi: 10.1021/np200960z. Epub 2012 May 29. [PubMed:22642560 ]
He T, Mu S, Hao X, Zhou Y, Zhang J, Huang L, Yan C: [Alkaloids of Daphniphyllum angustifolium]. Zhongguo Zhong Yao Za Zhi. 2010 Nov;35(22):2999-3001. [PubMed:21355269 ]
Kobayashi J, Kubota T: The Daphniphyllum alkaloids. Nat Prod Rep. 2009 Jul;26(7):936-62. doi: 10.1039/b813006j. Epub 2009 May 8. [PubMed:19554242 ]
LOTUS database [Link]

Showing NP-Card for methyl (1'r,3r,5's,6s,11's,12's)-6-ethyl-6-methoxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate (NP0319729)

MOL for NP0319729 (methyl (1'r,3r,5's,6s,11's,12's)-6-ethyl-6-methoxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate)

3D MOL for NP0319729 (methyl (1'r,3r,5's,6s,11's,12's)-6-ethyl-6-methoxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate)

3D SDF for NP0319729 (methyl (1'r,3r,5's,6s,11's,12's)-6-ethyl-6-methoxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate)

3D-SDF for NP0319729 (methyl (1'r,3r,5's,6s,11's,12's)-6-ethyl-6-methoxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate)

PDB for NP0319729 (methyl (1'r,3r,5's,6s,11's,12's)-6-ethyl-6-methoxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate)

3D PDB for NP0319729 (methyl (1'r,3r,5's,6s,11's,12's)-6-ethyl-6-methoxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate)

SMILES for NP0319729 (methyl (1'r,3r,5's,6s,11's,12's)-6-ethyl-6-methoxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate)

INCHI for NP0319729 (methyl (1'r,3r,5's,6s,11's,12's)-6-ethyl-6-methoxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate)

Structure for NP0319729 (methyl (1'r,3r,5's,6s,11's,12's)-6-ethyl-6-methoxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate)

3D Structure for NP0319729 (methyl (1'r,3r,5's,6s,11's,12's)-6-ethyl-6-methoxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate)