NP-MRD: Showing NP-Card for oxystemoninine (NP0033860)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-06-20 17:45:29 UTC

Updated at

2021-06-30 00:03:53 UTC

NP-MRD ID

NP0033860

Secondary Accession Numbers

None

Natural Product Identification

Common Name

oxystemoninine

Provided By

JEOL Database JEOL Logo

Description

(2R)-1,3',3abeta,4,4',5,6,8,9,10,10aalpha,10balpha-Dodecahydro-1alpha-ethyl-3'alpha-hydroxy-4'beta-methyl-8alpha-(tetrahydro-4alpha-methyl-5-oxofuran-2alpha-yl)spiro[2H-furo[3,2-c]pyrrolo[1,2-a]azepine-2,2'(5'H)-furan]-5'-one belongs to the class of organic compounds known as stichoneurine-type alkaloids. These are stemona alkaloids with a structure that typically contains a 3-methyloxolan-2-one and a 5-propyloxolan-2-one moieties that are attached to the characteristic pyrrolo[1,2-a]azepine skeleton at the C3 and C9 position, respectively. oxystemoninine is found in Stemona tuberosa. oxystemoninine was first documented in 2008 ( Lin, L. -G., et al.). Based on a literature review very few articles have been published on (2R)-1,3',3abeta,4,4',5,6,8,9,10,10aalpha,10balpha-Dodecahydro-1alpha-ethyl-3'alpha-hydroxy-4'beta-methyl-8alpha-(tetrahydro-4alpha-methyl-5-oxofuran-2alpha-yl)spiro[2H-furo[3,2-c]pyrrolo[1,2-a]azepine-2,2'(5'H)-furan]-5'-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202119453D          

 62 66  0  0  0  0            999 V2000
    1.7413    0.6017    5.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2015   -0.1809    3.9984 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0045    0.4476    3.2695 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4447   -0.4619    2.1037 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4822   -0.4533    0.8760 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8806    0.9434    0.3771 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1312    0.7501   -1.1062 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0566   -0.2667   -1.4832 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2734   -0.9372   -2.8525 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4752   -1.8566   -2.9634 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7325   -1.8524   -4.4569 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1787   -2.1478   -4.8059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3153   -0.4525   -4.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6321    0.1492   -5.8395 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4848    0.0550   -3.8671 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0555   -1.1762   -0.3296 N   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0235   -2.1461   -0.2402 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4407   -1.5893   -0.0935 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7858   -1.0841    1.3000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8663    0.0032    1.8408 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3946    0.4139    3.1108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3199    0.5980    4.0550 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4192   -0.4030    5.0626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0977    0.0971    6.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3984   -0.5673    7.1084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4467    1.5472    5.9397 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9391    1.6920    5.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5816    1.9404    4.7549 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4003    2.5883    5.2214 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6486    0.1205    5.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0236    0.6326    6.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0064    1.6226    4.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0250   -0.2933    3.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9544   -1.1952    4.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799    1.4317    2.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4858   -1.4920    2.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116   -0.9510    1.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0729    1.6716    0.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7713    1.3268    0.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1455    0.3679   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320    1.6901   -1.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8867    0.2939   -1.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6384   -1.4843   -3.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2753   -2.8592   -2.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3433   -1.4579   -2.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0597   -2.5518   -4.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8567   -1.4016   -4.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4749   -3.1347   -4.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3243   -2.1324   -5.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0026   -2.7630   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8168   -2.8556    0.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6341   -0.8030   -0.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1455   -2.3953   -0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8043   -1.9293    2.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8167   -0.7062    1.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9010    0.8805    1.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1573    2.0985    6.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5118    1.3838    6.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1950    2.7331    5.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2774    1.0703    4.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0853    2.6497    4.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6604    3.4382    5.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
 16  8  1  0  0  0  0
  8  7  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
 17 18  1  0  0  0  0
  8  9  1  0  0  0  0
  9 15  1  0  0  0  0
 19 18  1  0  0  0  0
 20  4  1  0  0  0  0
 26 24  1  0  0  0  0
 24 23  1  0  0  0  0
 15 13  1  0  0  0  0
 13 11  1  0  0  0  0
 11 10  1  0  0  0  0
 10  9  1  0  0  0  0
 22 23  1  1  0  0  0
 13 14  2  0  0  0  0
  4  5  1  0  0  0  0
 24 25  2  0  0  0  0
  4  3  1  0  0  0  0
 26 27  1  0  0  0  0
  3 22  1  0  0  0  0
  4 36  1  1  0  0  0
 22 21  1  0  0  0  0
  9 43  1  6  0  0  0
 21 20  1  0  0  0  0
 20 56  1  6  0  0  0
  5 16  1  0  0  0  0
 11 12  1  0  0  0  0
 22 28  1  0  0  0  0
  5 37  1  1  0  0  0
 16 17  1  0  0  0  0
 28 29  1  0  0  0  0
  3  2  1  0  0  0  0
 20 19  1  0  0  0  0
  2  1  1  0  0  0  0
 28 26  1  0  0  0  0
  8 42  1  6  0  0  0
 28 61  1  6  0  0  0
 26 57  1  1  0  0  0
 17 50  1  0  0  0  0
 17 51  1  0  0  0  0
 19 54  1  0  0  0  0
 19 55  1  0  0  0  0
 18 52  1  0  0  0  0
 18 53  1  0  0  0  0
  3 35  1  6  0  0  0
  7 40  1  0  0  0  0
  7 41  1  0  0  0  0
  6 38  1  0  0  0  0
  6 39  1  0  0  0  0
 11 46  1  6  0  0  0
 10 44  1  0  0  0  0
 10 45  1  0  0  0  0
 27 58  1  0  0  0  0
 27 59  1  0  0  0  0
 27 60  1  0  0  0  0
 12 47  1  0  0  0  0
 12 48  1  0  0  0  0
 12 49  1  0  0  0  0
 29 62  1  0  0  0  0
  2 33  1  0  0  0  0
  2 34  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
M  END

     RDKit          3D

 62 66  0  0  0  0  0  0  0  0999 V2000
    1.7413    0.6017    5.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2015   -0.1809    3.9984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0045    0.4476    3.2695 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4447   -0.4619    2.1037 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4822   -0.4533    0.8760 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8806    0.9434    0.3771 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1312    0.7501   -1.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0566   -0.2667   -1.4832 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2734   -0.9372   -2.8525 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4752   -1.8566   -2.9634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7325   -1.8524   -4.4569 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1787   -2.1478   -4.8059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3153   -0.4525   -4.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6321    0.1492   -5.8395 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4848    0.0550   -3.8671 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0555   -1.1762   -0.3296 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0235   -2.1461   -0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4407   -1.5893   -0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7858   -1.0841    1.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8663    0.0032    1.8408 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3946    0.4139    3.1108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3199    0.5980    4.0550 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4192   -0.4030    5.0626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0977    0.0971    6.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3984   -0.5673    7.1084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4467    1.5472    5.9397 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9391    1.6920    5.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5816    1.9404    4.7549 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4003    2.5883    5.2214 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6486    0.1205    5.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0236    0.6326    6.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0064    1.6226    4.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0250   -0.2933    3.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9544   -1.1952    4.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799    1.4317    2.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4858   -1.4920    2.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116   -0.9510    1.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0729    1.6716    0.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7713    1.3268    0.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1455    0.3679   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320    1.6901   -1.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8867    0.2939   -1.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6384   -1.4843   -3.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2753   -2.8592   -2.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3433   -1.4579   -2.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0597   -2.5518   -4.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8567   -1.4016   -4.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4749   -3.1347   -4.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3243   -2.1324   -5.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0026   -2.7630   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8168   -2.8556    0.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6341   -0.8030   -0.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1455   -2.3953   -0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8043   -1.9293    2.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8167   -0.7062    1.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9010    0.8805    1.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1573    2.0985    6.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5118    1.3838    6.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1950    2.7331    5.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2774    1.0703    4.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0853    2.6497    4.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6604    3.4382    5.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
 16  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
 17 18  1  0
  8  9  1  0
  9 15  1  0
 19 18  1  0
 20  4  1  0
 26 24  1  0
 24 23  1  0
 15 13  1  0
 13 11  1  0
 11 10  1  0
 10  9  1  0
 22 23  1  1
 13 14  2  0
  4  5  1  0
 24 25  2  0
  4  3  1  0
 26 27  1  0
  3 22  1  0
  4 36  1  1
 22 21  1  0
  9 43  1  6
 21 20  1  0
 20 56  1  6
  5 16  1  0
 11 12  1  0
 22 28  1  0
  5 37  1  1
 16 17  1  0
 28 29  1  0
  3  2  1  0
 20 19  1  0
  2  1  1  0
 28 26  1  0
  8 42  1  6
 28 61  1  6
 26 57  1  1
 17 50  1  0
 17 51  1  0
 19 54  1  0
 19 55  1  0
 18 52  1  0
 18 53  1  0
  3 35  1  6
  7 40  1  0
  7 41  1  0
  6 38  1  0
  6 39  1  0
 11 46  1  6
 10 44  1  0
 10 45  1  0
 27 58  1  0
 27 59  1  0
 27 60  1  0
 12 47  1  0
 12 48  1  0
 12 49  1  0
 29 62  1  0
  2 33  1  0
  2 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
M  END


  Mrv1652306202119453D          

 62 66  0  0  0  0            999 V2000
    1.7413    0.6017    5.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2015   -0.1809    3.9984 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0045    0.4476    3.2695 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4447   -0.4619    2.1037 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4822   -0.4533    0.8760 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8806    0.9434    0.3771 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1312    0.7501   -1.1062 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0566   -0.2667   -1.4832 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2734   -0.9372   -2.8525 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4752   -1.8566   -2.9634 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7325   -1.8524   -4.4569 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1787   -2.1478   -4.8059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3153   -0.4525   -4.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6321    0.1492   -5.8395 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4848    0.0550   -3.8671 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0555   -1.1762   -0.3296 N   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0235   -2.1461   -0.2402 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4407   -1.5893   -0.0935 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7858   -1.0841    1.3000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8663    0.0032    1.8408 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3946    0.4139    3.1108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3199    0.5980    4.0550 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4192   -0.4030    5.0626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0977    0.0971    6.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3984   -0.5673    7.1084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4467    1.5472    5.9397 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9391    1.6920    5.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5816    1.9404    4.7549 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4003    2.5883    5.2214 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6486    0.1205    5.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0236    0.6326    6.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0064    1.6226    4.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0250   -0.2933    3.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9544   -1.1952    4.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799    1.4317    2.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4858   -1.4920    2.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116   -0.9510    1.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0729    1.6716    0.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7713    1.3268    0.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1455    0.3679   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320    1.6901   -1.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8867    0.2939   -1.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6384   -1.4843   -3.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2753   -2.8592   -2.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3433   -1.4579   -2.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0597   -2.5518   -4.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8567   -1.4016   -4.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4749   -3.1347   -4.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3243   -2.1324   -5.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0026   -2.7630   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8168   -2.8556    0.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6341   -0.8030   -0.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1455   -2.3953   -0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8043   -1.9293    2.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8167   -0.7062    1.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9010    0.8805    1.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1573    2.0985    6.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5118    1.3838    6.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1950    2.7331    5.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2774    1.0703    4.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0853    2.6497    4.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6604    3.4382    5.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
 16  8  1  0  0  0  0
  8  7  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
 17 18  1  0  0  0  0
  8  9  1  0  0  0  0
  9 15  1  0  0  0  0
 19 18  1  0  0  0  0
 20  4  1  0  0  0  0
 26 24  1  0  0  0  0
 24 23  1  0  0  0  0
 15 13  1  0  0  0  0
 13 11  1  0  0  0  0
 11 10  1  0  0  0  0
 10  9  1  0  0  0  0
 22 23  1  1  0  0  0
 13 14  2  0  0  0  0
  4  5  1  0  0  0  0
 24 25  2  0  0  0  0
  4  3  1  0  0  0  0
 26 27  1  0  0  0  0
  3 22  1  0  0  0  0
  4 36  1  1  0  0  0
 22 21  1  0  0  0  0
  9 43  1  6  0  0  0
 21 20  1  0  0  0  0
 20 56  1  6  0  0  0
  5 16  1  0  0  0  0
 11 12  1  0  0  0  0
 22 28  1  0  0  0  0
  5 37  1  1  0  0  0
 16 17  1  0  0  0  0
 28 29  1  0  0  0  0
  3  2  1  0  0  0  0
 20 19  1  0  0  0  0
  2  1  1  0  0  0  0
 28 26  1  0  0  0  0
  8 42  1  6  0  0  0
 28 61  1  6  0  0  0
 26 57  1  1  0  0  0
 17 50  1  0  0  0  0
 17 51  1  0  0  0  0
 19 54  1  0  0  0  0
 19 55  1  0  0  0  0
 18 52  1  0  0  0  0
 18 53  1  0  0  0  0
  3 35  1  6  0  0  0
  7 40  1  0  0  0  0
  7 41  1  0  0  0  0
  6 38  1  0  0  0  0
  6 39  1  0  0  0  0
 11 46  1  6  0  0  0
 10 44  1  0  0  0  0
 10 45  1  0  0  0  0
 27 58  1  0  0  0  0
 27 59  1  0  0  0  0
 27 60  1  0  0  0  0
 12 47  1  0  0  0  0
 12 48  1  0  0  0  0
 12 49  1  0  0  0  0
 29 62  1  0  0  0  0
  2 33  1  0  0  0  0
  2 34  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0033860

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])[C@]([H])(C(=O)O[C@@]11O[C@]2([H])C([H])([H])C([H])([H])C([H])([H])N3[C@@]([H])(C([H])([H])C([H])([H])[C@@]3([H])[C@@]2([H])[C@]1([H])C([H])([H])C([H])([H])[H])[C@@]1([H])OC(=O)[C@@]([H])(C([H])([H])[H])C1([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H33NO6/c1-4-13-18-15-8-7-14(17-10-11(2)20(25)27-17)23(15)9-5-6-16(18)28-22(13)19(24)12(3)21(26)29-22/h11-19,24H,4-10H2,1-3H3/t11-,12+,13-,14-,15-,16+,17-,18+,19+,22+/m0/s1

> <INCHI_KEY>
BSPUHYSQEMPWMI-NYENQNTGSA-N

> <FORMULA>
C22H33NO6

> <MOLECULAR_WEIGHT>
407.507

> <EXACT_MASS>
407.230787787

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
44.452304748678536

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,2R,2'R,3R,3'S,4R,6'R,11'S)-3'-ethyl-3-hydroxy-4-methyl-11'-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-5'-oxa-10'-azaspiro[oxolane-2,4'-tricyclo[8.3.0.0^{2,6}]tridecane]-5-one

> <ALOGPS_LOGP>
2.14

> <JCHEM_LOGP>
2.520282942873117

> <ALOGPS_LOGS>
-2.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.777780230127984

> <JCHEM_PKA_STRONGEST_BASIC>
11.073818860286169

> <JCHEM_POLAR_SURFACE_AREA>
85.3

> <JCHEM_REFRACTIVITY>
103.3523

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2R,2'R,3R,3'S,4R,6'R,11'S)-3'-ethyl-3-hydroxy-4-methyl-11'-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-5'-oxa-10'-azaspiro[oxolane-2,4'-tricyclo[8.3.0.0^{2,6}]tridecane]-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 62 66  0  0  0  0  0  0  0  0999 V2000
    1.7413    0.6017    5.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2015   -0.1809    3.9984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0045    0.4476    3.2695 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4447   -0.4619    2.1037 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4822   -0.4533    0.8760 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8806    0.9434    0.3771 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1312    0.7501   -1.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0566   -0.2667   -1.4832 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2734   -0.9372   -2.8525 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4752   -1.8566   -2.9634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7325   -1.8524   -4.4569 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1787   -2.1478   -4.8059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3153   -0.4525   -4.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6321    0.1492   -5.8395 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4848    0.0550   -3.8671 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0555   -1.1762   -0.3296 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0235   -2.1461   -0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4407   -1.5893   -0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7858   -1.0841    1.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8663    0.0032    1.8408 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3946    0.4139    3.1108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3199    0.5980    4.0550 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4192   -0.4030    5.0626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0977    0.0971    6.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3984   -0.5673    7.1084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4467    1.5472    5.9397 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9391    1.6920    5.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5816    1.9404    4.7549 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4003    2.5883    5.2214 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6486    0.1205    5.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0236    0.6326    6.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0064    1.6226    4.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0250   -0.2933    3.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9544   -1.1952    4.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799    1.4317    2.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4858   -1.4920    2.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116   -0.9510    1.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0729    1.6716    0.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7713    1.3268    0.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1455    0.3679   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320    1.6901   -1.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8867    0.2939   -1.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6384   -1.4843   -3.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2753   -2.8592   -2.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3433   -1.4579   -2.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0597   -2.5518   -4.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8567   -1.4016   -4.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4749   -3.1347   -4.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3243   -2.1324   -5.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0026   -2.7630   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8168   -2.8556    0.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6341   -0.8030   -0.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1455   -2.3953   -0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8043   -1.9293    2.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8167   -0.7062    1.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9010    0.8805    1.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1573    2.0985    6.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5118    1.3838    6.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1950    2.7331    5.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2774    1.0703    4.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0853    2.6497    4.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6604    3.4382    5.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
 16  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
 17 18  1  0
  8  9  1  0
  9 15  1  0
 19 18  1  0
 20  4  1  0
 26 24  1  0
 24 23  1  0
 15 13  1  0
 13 11  1  0
 11 10  1  0
 10  9  1  0
 22 23  1  1
 13 14  2  0
  4  5  1  0
 24 25  2  0
  4  3  1  0
 26 27  1  0
  3 22  1  0
  4 36  1  1
 22 21  1  0
  9 43  1  6
 21 20  1  0
 20 56  1  6
  5 16  1  0
 11 12  1  0
 22 28  1  0
  5 37  1  1
 16 17  1  0
 28 29  1  0
  3  2  1  0
 20 19  1  0
  2  1  1  0
 28 26  1  0
  8 42  1  6
 28 61  1  6
 26 57  1  1
 17 50  1  0
 17 51  1  0
 19 54  1  0
 19 55  1  0
 18 52  1  0
 18 53  1  0
  3 35  1  6
  7 40  1  0
  7 41  1  0
  6 38  1  0
  6 39  1  0
 11 46  1  6
 10 44  1  0
 10 45  1  0
 27 58  1  0
 27 59  1  0
 27 60  1  0
 12 47  1  0
 12 48  1  0
 12 49  1  0
 29 62  1  0
  2 33  1  0
  2 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       1.741   0.602   5.181  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.202  -0.181   3.998  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.005   0.448   3.269  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.445  -0.462   2.104  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.482  -0.453   0.876  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.881   0.943   0.377  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.131   0.750  -1.106  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.057  -0.267  -1.483  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.273  -0.937  -2.853  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.475  -1.857  -2.963  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.732  -1.852  -4.457  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.179  -2.148  -4.806  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.315  -0.453  -4.827  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.632   0.149  -5.840  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.485   0.055  -3.867  0.00  0.00           O+0
HETATM   16  N   UNK     0       0.056  -1.176  -0.330  0.00  0.00           N+0
HETATM   17  C   UNK     0      -1.024  -2.146  -0.240  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.441  -1.589  -0.094  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.786  -1.084   1.300  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.866   0.003   1.841  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.395   0.414   3.111  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.320   0.598   4.055  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.419  -0.403   5.063  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.098   0.097   6.127  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.398  -0.567   7.108  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.447   1.547   5.940  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.939   1.692   5.682  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.582   1.940   4.755  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.400   2.588   5.221  0.00  0.00           O+0
HETATM   30  H   UNK     0       2.649   0.121   5.562  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.024   0.633   6.005  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.006   1.623   4.891  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.025  -0.293   3.283  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.954  -1.195   4.335  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.280   1.432   2.878  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.486  -1.492   2.488  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.412  -0.951   1.183  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.073   1.672   0.509  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.771   1.327   0.885  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.146   0.368  -1.262  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.032   1.690  -1.658  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.887   0.294  -1.530  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.638  -1.484  -3.127  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.275  -2.859  -2.573  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.343  -1.458  -2.428  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.060  -2.552  -4.967  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.857  -1.402  -4.377  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.475  -3.135  -4.436  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.324  -2.132  -5.891  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.003  -2.763  -1.147  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.817  -2.856   0.571  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.634  -0.803  -0.831  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.146  -2.395  -0.336  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.804  -1.929   2.002  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.817  -0.706   1.292  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.901   0.881   1.186  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.157   2.099   6.841  0.00  0.00           H+0
HETATM   58  H   UNK     0      -4.512   1.384   6.563  0.00  0.00           H+0
HETATM   59  H   UNK     0      -4.195   2.733   5.460  0.00  0.00           H+0
HETATM   60  H   UNK     0      -4.277   1.070   4.846  0.00  0.00           H+0
HETATM   61  H   UNK     0      -2.085   2.650   4.088  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.660   3.438   5.620  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    3    1   33   34                                             
CONECT    3    4   22    2   35                                             
CONECT    4   20    5    3   36                                             
CONECT    5    6    4   16   37                                             
CONECT    6    7    5   38   39                                             
CONECT    7    8    6   40   41                                             
CONECT    8   16    7    9   42                                             
CONECT    9    8   15   10   43                                             
CONECT   10   11    9   44   45                                             
CONECT   11   13   10   12   46                                             
CONECT   12   11   47   48   49                                             
CONECT   13   15   11   14                                                  
CONECT   14   13                                                            
CONECT   15    9   13                                                       
CONECT   16    8    5   17                                                  
CONECT   17   18   16   50   51                                             
CONECT   18   17   19   52   53                                             
CONECT   19   18   20   54   55                                             
CONECT   20    4   21   56   19                                             
CONECT   21   22   20                                                       
CONECT   22   23    3   21   28                                             
CONECT   23   24   22                                                       
CONECT   24   26   23   25                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28   57                                             
CONECT   27   26   58   59   60                                             
CONECT   28   22   29   26   61                                             
CONECT   29   28   62                                                       
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    2                                                            
CONECT   34    2                                                            
CONECT   35    3                                                            
CONECT   36    4                                                            
CONECT   37    5                                                            
CONECT   38    6                                                            
CONECT   39    6                                                            
CONECT   40    7                                                            
CONECT   41    7                                                            
CONECT   42    8                                                            
CONECT   43    9                                                            
CONECT   44   10                                                            
CONECT   45   10                                                            
CONECT   46   11                                                            
CONECT   47   12                                                            
CONECT   48   12                                                            
CONECT   49   12                                                            
CONECT   50   17                                                            
CONECT   51   17                                                            
CONECT   52   18                                                            
CONECT   53   18                                                            
CONECT   54   19                                                            
CONECT   55   19                                                            
CONECT   56   20                                                            
CONECT   57   26                                                            
CONECT   58   27                                                            
CONECT   59   27                                                            
CONECT   60   27                                                            
CONECT   61   28                                                            
CONECT   62   29                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  132    0
END

RDKit          3D

62 66  0  0  0  0  0  0  0  0999 V2000
    1.7413    0.6017    5.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2015   -0.1809    3.9984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0045    0.4476    3.2695 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4447   -0.4619    2.1037 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4822   -0.4533    0.8760 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8806    0.9434    0.3771 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1312    0.7501   -1.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0566   -0.2667   -1.4832 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2734   -0.9372   -2.8525 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4752   -1.8566   -2.9634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7325   -1.8524   -4.4569 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1787   -2.1478   -4.8059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3153   -0.4525   -4.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6321    0.1492   -5.8395 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4848    0.0550   -3.8671 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0555   -1.1762   -0.3296 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0235   -2.1461   -0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4407   -1.5893   -0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7858   -1.0841    1.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8663    0.0032    1.8408 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3946    0.4139    3.1108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3199    0.5980    4.0550 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4192   -0.4030    5.0626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0977    0.0971    6.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3984   -0.5673    7.1084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4467    1.5472    5.9397 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9391    1.6920    5.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5816    1.9404    4.7549 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4003    2.5883    5.2214 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6486    0.1205    5.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0236    0.6326    6.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0064    1.6226    4.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0250   -0.2933    3.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9544   -1.1952    4.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799    1.4317    2.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4858   -1.4920    2.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116   -0.9510    1.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0729    1.6716    0.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7713    1.3268    0.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1455    0.3679   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320    1.6901   -1.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8867    0.2939   -1.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6384   -1.4843   -3.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2753   -2.8592   -2.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3433   -1.4579   -2.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0597   -2.5518   -4.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8567   -1.4016   -4.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4749   -3.1347   -4.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3243   -2.1324   -5.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0026   -2.7630   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8168   -2.8556    0.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6341   -0.8030   -0.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1455   -2.3953   -0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8043   -1.9293    2.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8167   -0.7062    1.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9010    0.8805    1.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1573    2.0985    6.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5118    1.3838    6.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1950    2.7331    5.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2774    1.0703    4.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0853    2.6497    4.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6604    3.4382    5.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
 16  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
 17 18  1  0
  8  9  1  0
  9 15  1  0
 19 18  1  0
 20  4  1  0
 26 24  1  0
 24 23  1  0
 15 13  1  0
 13 11  1  0
 11 10  1  0
 10  9  1  0
 22 23  1  1
 13 14  2  0
  4  5  1  0
 24 25  2  0
  4  3  1  0
 26 27  1  0
  3 22  1  0
  4 36  1  1
 22 21  1  0
  9 43  1  6
 21 20  1  0
 20 56  1  6
  5 16  1  0
 11 12  1  0
 22 28  1  0
  5 37  1  1
 16 17  1  0
 28 29  1  0
  3  2  1  0
 20 19  1  0
  2  1  1  0
 28 26  1  0
  8 42  1  6
 28 61  1  6
 26 57  1  1
 17 50  1  0
 17 51  1  0
 19 54  1  0
 19 55  1  0
 18 52  1  0
 18 53  1  0
  3 35  1  6
  7 40  1  0
  7 41  1  0
  6 38  1  0
  6 39  1  0
 11 46  1  6
 10 44  1  0
 10 45  1  0
 27 58  1  0
 27 59  1  0
 27 60  1  0
 12 47  1  0
 12 48  1  0
 12 49  1  0
 29 62  1  0
  2 33  1  0
  2 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
M  END

View in JSmol

Synonyms

Value	Source
(2R)-1,3',3Abeta,4,4',5,6,8,9,10,10aalpha,10balpha-dodecahydro-1a-ethyl-3'a-hydroxy-4'b-methyl-8a-(tetrahydro-4a-methyl-5-oxofuran-2a-yl)spiro[2H-furo[3,2-c]pyrrolo[1,2-a]azepine-2,2'(5'H)-furan]-5'-one	Generator
(2R)-1,3',3Abeta,4,4',5,6,8,9,10,10aalpha,10balpha-dodecahydro-1α-ethyl-3'α-hydroxy-4'β-methyl-8α-(tetrahydro-4α-methyl-5-oxofuran-2α-yl)spiro[2H-furo[3,2-c]pyrrolo[1,2-a]azepine-2,2'(5'H)-furan]-5'-one	Generator

Chemical Formula

C₂₂H₃₃NO₆

Average Mass

407.5070 Da

Monoisotopic Mass

407.23079 Da

IUPAC Name

(1'S,2R,2'R,3R,3'S,4R,6'R,11'S)-3'-ethyl-3-hydroxy-4-methyl-11'-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-5'-oxa-10'-azaspiro[oxolane-2,4'-tricyclo[8.3.0.0^{2,6}]tridecane]-5-one

Traditional Name

(1'S,2R,2'R,3R,3'S,4R,6'R,11'S)-3'-ethyl-3-hydroxy-4-methyl-11'-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-5'-oxa-10'-azaspiro[oxolane-2,4'-tricyclo[8.3.0.0^{2,6}]tridecane]-5-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])[C@]([H])(C(=O)O[C@@]11O[C@]2([H])C([H])([H])C([H])([H])C([H])([H])N3[C@@]([H])(C([H])([H])C([H])([H])[C@@]3([H])[C@@]2([H])[C@]1([H])C([H])([H])C([H])([H])[H])[C@@]1([H])OC(=O)[C@@]([H])(C([H])([H])[H])C1([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H33NO6/c1-4-13-18-15-8-7-14(17-10-11(2)20(25)27-17)23(15)9-5-6-16(18)28-22(13)19(24)12(3)21(26)29-22/h11-19,24H,4-10H2,1-3H3/t11-,12+,13-,14-,15-,16+,17-,18+,19+,22+/m0/s1

InChI Key

BSPUHYSQEMPWMI-NYENQNTGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Stemona tuberosa	JEOL database	Lin, L. -G., et al, J. Nat. Prod. 71, 1107 (2008)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stichoneurine-type alkaloids. These are stemona alkaloids with a structure that typically contains a 3-methyloxolan-2-one and a 5-propyloxolan-2-one moieties that are attached to the characteristic pyrrolo[1,2-a]azepine skeleton at the C3 and C9 position, respectively.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Stemona alkaloids

Sub Class

Stemoamide-type alkaloids

Direct Parent

Stichoneurine-type alkaloids

Alternative Parents

Substituents

Stichoneurine-type alkaloid
Azepane
Ketal
Dicarboxylic acid or derivatives
Gamma butyrolactone
N-alkylpyrrolidine
Oxolane
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Lactone
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Carbonyl group
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Amine
Organic nitrogen 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	2.14	ALOGPS
logP	2.52	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	12.78	ChemAxon
pKa (Strongest Basic)	11.07	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	85.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	103.35 m³·mol⁻¹	ChemAxon
Polarizability	44.45 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

102193180

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lin, L. -G., et al. (2008). Lin, L. -G., et al, J. Nat. Prod. 71, 1107 (2008). J. Nat. Prod..

Showing NP-Card for oxystemoninine (NP0033860)

MOL for NP0033860 (oxystemoninine)

3D MOL for NP0033860 (oxystemoninine)

3D SDF for NP0033860 (oxystemoninine)

3D-SDF for NP0033860 (oxystemoninine)

PDB for NP0033860 (oxystemoninine)

3D PDB for NP0033860 (oxystemoninine)

SMILES for NP0033860 (oxystemoninine)

INCHI for NP0033860 (oxystemoninine)

Structure for NP0033860 (oxystemoninine)

3D Structure for NP0033860 (oxystemoninine)