NP-MRD: Showing NP-Card for [(2r,3r,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-4-oxo-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate (NP0267236)

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Record Information

Version

2.0

Created at

2022-09-08 11:57:09 UTC

Updated at

2022-09-08 11:57:09 UTC

NP-MRD ID

NP0267236

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3r,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-4-oxo-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate

Description

[(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-{[(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyl-9-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-5-yl]oxy}oxan-2-yl]methyl acetate belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. [(2r,3r,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-4-oxo-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate is found in Gynura japonica. Based on a literature review very few articles have been published on [(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-{[(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyl-9-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-5-yl]oxy}oxan-2-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082213572D          

 54 58  0  0  1  0            999 V2000
   -0.5116   -1.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3056   -1.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165   -2.1509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4338   -2.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7337   -0.1885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2974   -2.2757    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1095   -2.1305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6413   -2.7612    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4534   -2.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7337   -1.8401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5458   -1.6949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8261   -0.9189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0777   -2.3256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3610   -3.5371    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.8928   -4.1678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7049   -4.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9852   -3.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2368   -4.6533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5489   -3.6824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2686   -4.4583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8004   -5.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6125   -4.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5201   -5.8649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0171   -3.0516    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2049   -3.1969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9246   -3.9728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4565   -4.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1125   -4.1180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1102   -2.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4211   -3.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7071   -2.6894    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  6  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  6  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 33 38  1  0  0  0  0
 20 38  1  0  0  0  0
 38 39  1  1  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 18 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 16 45  1  0  0  0  0
 45 46  1  1  0  0  0
 45 47  1  0  0  0  0
 12 47  1  0  0  0  0
 47 48  1  1  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 11 50  1  0  0  0  0
  8 50  1  0  0  0  0
 50 51  1  1  0  0  0
  3 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  1  0  0  0  0
M  END

     RDKit          3D

118122  0  0  0  0  0  0  0  0999 V2000
   10.2591   -0.8770   -1.1115 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2805   -1.1945    0.3639 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8610   -1.1747    0.9373 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3219    0.1984    0.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2281    0.3726   -0.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7135    1.7150   -0.2763 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0174    2.0935   -1.7146 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3550    2.0479    0.1606 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0787    3.4918   -0.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6690    3.5010   -0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0847    2.3210   -0.1982 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8397    1.7242   -0.7037 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8768    2.7124   -1.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1438    3.8845   -1.3713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5000    2.1730   -1.3551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8760    1.1198   -0.6625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2764    0.6035   -0.8937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0230    0.3240    0.3687 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9059   -0.7234    0.0769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2456   -0.3322    0.0318 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0315   -1.0157    0.9082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3726   -0.8836    0.5873 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.2598   -1.3611    1.7260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9928   -0.5921    2.8662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1708    0.7674    2.9888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8646    1.5298    4.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6103    1.4361    2.0250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7461   -1.6665   -0.6852 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.6983   -0.9896   -1.4597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9309   -1.5527   -1.8037 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9211   -0.8144   -2.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1410   -2.7129   -1.3742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4867   -1.8103   -1.5028 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7192   -2.8175   -0.8703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2365   -3.9485   -1.4678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4458   -4.9211   -0.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4891   -4.1242   -2.6937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7814   -0.4522   -1.3824 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7473    0.5208   -1.7028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6800    1.4018   -2.7446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7331    2.4147   -3.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6720    1.3527   -3.4940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1591   -0.0709    1.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8304    0.5769    1.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0281    0.4177    0.3131 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0697   -1.0616   -0.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3237    0.9056    0.4619 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3409   -0.1933    0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7490    0.2268    0.7524 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1952    1.2379   -0.2598 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2278    0.6483   -1.6187 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8640   -1.5209    2.3985 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4415   -2.8945    2.6509 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.4795    0.2218   -1.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1001   -1.4086   -1.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
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   10.9535   -0.4847    0.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7306   -2.2058    0.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2823   -1.9172    0.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8333    1.0411    1.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8154   -0.5527   -0.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3862    2.4163    0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4607    1.2599   -2.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7494    2.9276   -1.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1278    2.4411   -2.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3603    2.0277    1.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8248    3.9089   -0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0165    4.1526    0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6983    3.5232   -1.9211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417    4.4406   -0.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9998    2.5279    0.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0072    1.0383   -1.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1902    2.6212   -2.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8371    1.3443   -1.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2140   -0.3135   -1.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5983    1.2715    0.5773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2784    0.7467    0.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6135    0.1774    0.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.3060   -1.1723    1.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3334    2.4796    4.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3182    0.9142    4.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
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  -11.1014   -1.4195   -3.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6296   -2.0951   -2.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8463   -5.5792   -1.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7468   -4.3834   -0.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
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 54118  1  0
M  END


  Mrv1652309082213572D          

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 52 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0267236

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](\C=C\[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@@]1(C)CC[C@@H](CC1=CC3=O)O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C43H64O11/c1-11-29(23(2)3)13-12-24(4)32-14-15-33-37-34(17-19-43(32,33)10)42(9)18-16-31(20-30(42)21-35(37)48)53-41-40(52-28(8)47)39(51-27(7)46)38(50-26(6)45)36(54-41)22-49-25(5)44/h12-13,21,23-24,29,31-34,36-41H,11,14-20,22H2,1-10H3/b13-12+/t24-,29-,31+,32-,33+,34+,36-,37+,38-,39+,40-,41-,42+,43-/m1/s1

> <INCHI_KEY>
BNXCGNXMUCWRST-GOJKELCZSA-N

> <FORMULA>
C43H64O11

> <MOLECULAR_WEIGHT>
756.974

> <EXACT_MASS>
756.444862881

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
118

> <JCHEM_AVERAGE_POLARIZABILITY>
86.49754090995481

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-{[(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyl-9-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxy}oxan-2-yl]methyl acetate

> <JCHEM_LOGP>
6.912715733999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.295545498505565

> <JCHEM_PKA_STRONGEST_BASIC>
-4.036271608336224

> <JCHEM_POLAR_SURFACE_AREA>
140.73000000000002

> <JCHEM_REFRACTIVITY>
200.54600000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-{[(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyl-9-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxy}oxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.955  -2.378   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.571  -2.589   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.151  -4.015   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.676  -4.226   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.836  -0.352   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      17.355  -4.248   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      18.871  -3.977   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      19.864  -5.154   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.380  -4.883   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      21.903  -3.435   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      23.419  -3.164   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      23.942  -1.715   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      24.412  -4.341   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      19.341  -6.603   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      20.333  -7.780   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      21.849  -7.509   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      22.372  -6.061   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      22.842  -8.686   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      17.825  -6.874   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      17.301  -8.322   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      18.294  -9.499   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      19.810  -9.228   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      17.771 -10.948   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      16.832  -5.696   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      15.316  -5.967   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      14.793  -7.416   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      15.785  -8.593   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      13.277  -7.687   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       0.206  -5.231   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       0.786  -6.657   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -1.320  -5.020   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   52                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   50                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   50                                                  
CONECT   12   11   13   47                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   45                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   43                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   38                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   22   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   33   20   39                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
CONECT   43   18   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   16   46   47                                             
CONECT   46   45                                                            
CONECT   47   45   12   48                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   11    8   51                                             
CONECT   51   50                                                            
CONECT   52    3   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  116    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3R,4S,5R,6R)-3,4,5-Tris(acetyloxy)-6-{[(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyl-9-oxotetracyclo[8.7.0.0,.0,]heptadec-7-en-5-yl]oxy}oxan-2-yl]methyl acetic acid	Generator

Chemical Formula

C₄₃H₆₄O₁₁

Average Mass

756.9740 Da

Monoisotopic Mass

756.44486 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC[C@H](\C=C\[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@@]1(C)CC[C@@H](CC1=CC3=O)O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O)C(C)C

InChI Identifier

InChI=1S/C43H64O11/c1-11-29(23(2)3)13-12-24(4)32-14-15-33-37-34(17-19-43(32,33)10)42(9)18-16-31(20-30(42)21-35(37)48)53-41-40(52-28(8)47)39(51-27(7)46)38(50-26(6)45)36(54-41)22-49-25(5)44/h12-13,21,23-24,29,31-34,36-41H,11,14-20,22H2,1-10H3/b13-12+/t24-,29-,31+,32-,33+,34+,36-,37+,38-,39+,40-,41-,42+,43-/m1/s1

InChI Key

BNXCGNXMUCWRST-GOJKELCZSA-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
Gynura japonica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

C24-propyl-sterol-skeleton
Stigmastane-skeleton
Triterpenoid
Steroidal glycoside
Oxosteroid
7-oxosteroid
Delta-5-steroid
Tetracarboxylic acid or derivatives
Glycosyl compound
O-glycosyl compound
Cyclohexenone
Monosaccharide
Oxane
Carboxylic acid ester
Ketone
Oxacycle
Acetal
Organoheterocyclic compound
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen 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

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

162887757

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3r,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-4-oxo-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate (NP0267236)

MOL for NP0267236 ([(2r,3r,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-4-oxo-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

3D MOL for NP0267236 ([(2r,3r,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-4-oxo-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

3D SDF for NP0267236 ([(2r,3r,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-4-oxo-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

3D-SDF for NP0267236 ([(2r,3r,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-4-oxo-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

PDB for NP0267236 ([(2r,3r,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-4-oxo-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

3D PDB for NP0267236 ([(2r,3r,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-4-oxo-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

SMILES for NP0267236 ([(2r,3r,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-4-oxo-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

INCHI for NP0267236 ([(2r,3r,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-4-oxo-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

Structure for NP0267236 ([(2r,3r,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-4-oxo-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

3D Structure for NP0267236 ([(2r,3r,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-4-oxo-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)