NP-MRD: Showing NP-Card for (1s,3r,5s,7r,9s,10s,12r,14r,15s,18r,19r,22s,23r)-10,22-dihydroxy-14-(hydroxymethyl)-7,18-dimethyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-9-yl acetate (NP0215609)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 15:17:01 UTC

Updated at

2022-09-05 15:17:01 UTC

NP-MRD ID

NP0215609

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3r,5s,7r,9s,10s,12r,14r,15s,18r,19r,22s,23r)-10,22-dihydroxy-14-(hydroxymethyl)-7,18-dimethyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-9-yl acetate

Description

(1S,3R,5S,7R,9S,10S,12R,14R,15S,18R,19R,22S,23R)-10,22-dihydroxy-14-(hydroxymethyl)-7,18-dimethyl-19-(5-oxo-2,5-dihydrofuran-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]Pentacosan-9-yl acetate belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety. (1s,3r,5s,7r,9s,10s,12r,14r,15s,18r,19r,22s,23r)-10,22-dihydroxy-14-(hydroxymethyl)-7,18-dimethyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-9-yl acetate is found in Asclepias curassavica. Based on a literature review very few articles have been published on (1S,3R,5S,7R,9S,10S,12R,14R,15S,18R,19R,22S,23R)-10,22-dihydroxy-14-(hydroxymethyl)-7,18-dimethyl-19-(5-oxo-2,5-dihydrofuran-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]Pentacosan-9-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052217172D          

 41 47  0  0  1  0            999 V2000
   -4.4299    2.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5893    1.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3700    1.0700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9680    0.7939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1274   -0.0155    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9081   -0.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0675   -1.0917    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8483   -1.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4462   -1.6345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6655   -1.3678    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0442   -1.9106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2635   -1.6439    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6422   -2.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8615   -1.9200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2402   -2.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5405   -2.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6999   -1.3867    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0786   -0.8439    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2380   -0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0188    0.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6401   -0.3106    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8832    0.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4591   -0.2120    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8609    0.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5141    1.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1188    1.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0203    2.6373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8394    1.4165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6800    0.6070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8060   -0.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2012   -1.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4806   -1.1200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4067   -1.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7021   -1.1106    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5427   -0.3011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1640    0.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3234   -0.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1041   -0.8344    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7254   -0.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5061   -0.5583    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3467    0.2511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 24 29  1  0  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 17 32  1  0  0  0  0
 21 32  1  0  0  0  0
 32 33  1  1  0  0  0
 18 34  1  0  0  0  0
 14 34  1  0  0  0  0
 34 35  1  1  0  0  0
 35 36  1  0  0  0  0
 34 37  1  0  0  0  0
 37 38  1  0  0  0  0
 12 38  1  0  0  0  0
 38 39  1  6  0  0  0
 39 40  1  0  0  0  0
  5 40  1  0  0  0  0
 10 40  1  0  0  0  0
 40 41  1  1  0  0  0
M  END

     RDKit          3D

 85 91  0  0  0  0  0  0  0  0999 V2000
   -5.5131   -0.7604    5.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8924   -0.8497    3.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8033   -1.6263    3.2441 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2824   -0.1040    2.6303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6357   -0.1838    1.2742 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2051    1.1104    0.7357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6344    0.7931   -0.6918 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.4840    1.8670   -1.2819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4188    0.6182   -1.3909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9013   -0.5965   -1.0186 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8776   -0.9096   -1.9059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7708   -0.1481   -1.5236 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7108   -0.1151   -2.5653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4108    0.3849   -2.0269 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6087    0.5417   -3.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9013    1.0972   -2.5001 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3739    0.0038   -1.5286 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3749   -0.0467   -0.4279 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9448   -0.8962    0.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0772   -0.0330    1.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1880   -0.0439    0.2479 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9559   -1.3358    0.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1209    1.0880    0.6200 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2763    0.6401    1.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5595    0.6724    1.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3909    0.1563    2.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6383    0.0066    2.1534 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5549   -0.1897    3.1540 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2188    0.0981    2.7899 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5687    1.5939   -0.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2392    1.5694   -1.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7786    0.1430   -1.1567 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5956   -0.6851   -1.9621 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0245   -0.4869   -0.8908 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0009   -1.9407   -1.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3508   -2.7402   -0.1945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9662   -0.2878    0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3582   -0.6486   -0.1906 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2920   -0.1634    0.7310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5105   -0.7123    0.4125 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4187   -2.0939    0.7057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4297   -0.4922    5.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7701   -1.6655    5.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0823    0.0853    5.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4557   -0.9309    1.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0345    1.4173    1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4089    1.8952    0.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1277   -0.2114   -0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3227    2.0461   -2.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3698    2.7814   -0.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5581    1.5713   -1.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7094   -1.3635   -1.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1657    0.9052   -1.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0407    0.6293   -3.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5986   -1.0715   -3.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5985    1.4022   -1.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7865   -0.3629   -3.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2427    1.3249   -3.8055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6224    1.9749   -1.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6304    1.2719   -3.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526   -0.9512   -2.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2585    0.9927   -0.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4579   -1.8111    0.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2615   -1.0864    1.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7199    0.9792    1.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3741   -0.5324    2.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8701   -1.9185   -0.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0322   -1.1980    0.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4853   -1.9953    1.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5608    1.9107    1.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9527    1.0188    0.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8609    0.8787    3.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6382   -0.8112    2.9303 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9691    2.6241   -0.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2755    0.8892   -1.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5899    2.3280   -1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4801    1.6869   -2.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0007   -1.2603   -2.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0430   -2.2194   -1.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6306   -2.1866   -2.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4310   -3.0844    0.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7304   -0.8848    1.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9261    0.7764    0.5318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4368   -1.7669   -0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3692   -2.6339   -0.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5 40  1  0
 40 41  1  1
 40 39  1  0
 39 38  1  0
 38 37  1  0
 37 34  1  0
 34 35  1  6
 35 36  1  0
 34 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 21 23  1  0
 23 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  6
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  7  1  0
 10 40  1  0
 12 38  1  0
 18 34  1  0
 32 21  1  0
 29 24  1  0
 32 17  1  0
  8 49  1  0
  8 50  1  0
  8 51  1  0
  7 48  1  1
  6 46  1  0
  6 47  1  0
  5 45  1  1
  1 42  1  0
  1 43  1  0
  1 44  1  0
 41 85  1  0
 38 84  1  6
 37 82  1  0
 37 83  1  0
 35 79  1  0
 35 80  1  0
 36 81  1  0
 14 56  1  1
 15 57  1  0
 15 58  1  0
 16 59  1  0
 16 60  1  0
 17 61  1  6
 18 62  1  1
 19 63  1  0
 19 64  1  0
 20 65  1  0
 20 66  1  0
 22 67  1  0
 22 68  1  0
 22 69  1  0
 23 70  1  1
 30 74  1  0
 30 75  1  0
 31 76  1  0
 31 77  1  0
 33 78  1  0
 25 71  1  0
 29 72  1  0
 29 73  1  0
 13 54  1  0
 13 55  1  0
 12 53  1  1
 10 52  1  1
M  END


  Mrv1652309052217172D          

 41 47  0  0  1  0            999 V2000
   -4.4299    2.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5893    1.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3700    1.0700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9680    0.7939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1274   -0.0155    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9081   -0.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0675   -1.0917    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8483   -1.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4462   -1.6345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6655   -1.3678    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0442   -1.9106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2635   -1.6439    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6422   -2.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8615   -1.9200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2402   -2.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5405   -2.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6999   -1.3867    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0786   -0.8439    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2380   -0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0188    0.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6401   -0.3106    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8832    0.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4591   -0.2120    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8609    0.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5141    1.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1188    1.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0203    2.6373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8394    1.4165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6800    0.6070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8060   -0.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2012   -1.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4806   -1.1200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4067   -1.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7021   -1.1106    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5427   -0.3011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1640    0.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3234   -0.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1041   -0.8344    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7254   -0.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5061   -0.5583    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3467    0.2511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 24 29  1  0  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 17 32  1  0  0  0  0
 21 32  1  0  0  0  0
 32 33  1  1  0  0  0
 18 34  1  0  0  0  0
 14 34  1  0  0  0  0
 34 35  1  1  0  0  0
 35 36  1  0  0  0  0
 34 37  1  0  0  0  0
 37 38  1  0  0  0  0
 12 38  1  0  0  0  0
 38 39  1  6  0  0  0
 39 40  1  0  0  0  0
  5 40  1  0  0  0  0
 10 40  1  0  0  0  0
 40 41  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0215609

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@H](OC(C)=O)[C@]2(O)O[C@@H]3C[C@@]4(CO)[C@@H](CC[C@@H]5[C@@H]4CC[C@]4(C)[C@H](CC[C@]54O)C4=CC(=O)OC4)C[C@H]3O[C@@H]2O1

> <INCHI_IDENTIFIER>
InChI=1S/C31H44O10/c1-16-10-25(39-17(2)33)31(36)27(38-16)40-23-12-19-4-5-22-21(29(19,15-32)13-24(23)41-31)6-8-28(3)20(7-9-30(22,28)35)18-11-26(34)37-14-18/h11,16,19-25,27,32,35-36H,4-10,12-15H2,1-3H3/t16-,19+,20-,21+,22-,23-,24-,25+,27+,28-,29-,30+,31+/m1/s1

> <INCHI_KEY>
GLXUNTFWMNVCKD-SVDYBJNLSA-N

> <FORMULA>
C31H44O10

> <MOLECULAR_WEIGHT>
576.683

> <EXACT_MASS>
576.293447617

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
62.02203669719957

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,5S,7R,9S,10S,12R,14R,15S,18R,19R,22S,23R)-10,22-dihydroxy-14-(hydroxymethyl)-7,18-dimethyl-19-(5-oxo-2,5-dihydrofuran-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0^{3,12}.0^{5,10}.0^{15,23}.0^{18,22}]pentacosan-9-yl acetate

> <JCHEM_LOGP>
2.0911937663333324

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.428621116211177

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.180164300135969

> <JCHEM_PKA_STRONGEST_BASIC>
0.2422119230729366

> <JCHEM_POLAR_SURFACE_AREA>
140.98000000000002

> <JCHEM_REFRACTIVITY>
143.658

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,5S,7R,9S,10S,12R,14R,15S,18R,19R,22S,23R)-10,22-dihydroxy-14-(hydroxymethyl)-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0^{3,12}.0^{5,10}.0^{15,23}.0^{18,22}]pentacosan-9-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -8.269   4.006   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.567   2.495   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0     -10.024   1.997   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -7.407   1.482   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -7.704  -0.029   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.162  -0.527   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.459  -2.038   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -10.917  -2.536   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -8.300  -3.051   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -6.842  -2.553   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.683  -3.566   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.225  -3.069   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.065  -4.082   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.608  -3.584   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.448  -4.597   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.009  -4.099   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.307  -2.588   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.147  -1.575   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.444  -0.064   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.902   0.433   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.061  -0.580   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.515   0.892   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.590  -0.396   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.340   0.949   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.693   2.347   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.822   3.394   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.638   4.923   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       7.167   2.644   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.869   1.133   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.238  -1.793   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.109  -2.841   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.764  -2.091   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.626  -3.625   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.311  -2.073   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.013  -0.562   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.173   0.451   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -2.470  -1.060   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -3.928  -1.558   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -5.087  -0.544   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -6.545  -1.042   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -6.247   0.469   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   40                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   40                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   38                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   34                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   32                                                  
CONECT   18   17   19   34                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   32                                             
CONECT   22   21                                                            
CONECT   23   21   24   30                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   24                                                       
CONECT   30   23   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   17   21   33                                             
CONECT   33   32                                                            
CONECT   34   18   14   35   37                                             
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   34   38                                                       
CONECT   38   37   12   39                                                  
CONECT   39   38   40                                                       
CONECT   40   39    5   10   41                                             
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   94    0
END

View in JSmol

Synonyms

Value	Source
(1S,3R,5S,7R,9S,10S,12R,14R,15S,18R,19R,22S,23R)-10,22-Dihydroxy-14-(hydroxymethyl)-7,18-dimethyl-19-(5-oxo-2,5-dihydrofuran-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0,.0,.0,.0,]pentacosan-9-yl acetic acid	Generator

Chemical Formula

C₃₁H₄₄O₁₀

Average Mass

576.6830 Da

Monoisotopic Mass

576.29345 Da

IUPAC Name

Traditional Name

(1S,3R,5S,7R,9S,10S,12R,14R,15S,18R,19R,22S,23R)-10,22-dihydroxy-14-(hydroxymethyl)-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0^{3,12}.0^{5,10}.0^{15,23}.0^{18,22}]pentacosan-9-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@H](OC(C)=O)[C@]2(O)O[C@@H]3C[C@@]4(CO)[C@@H](CC[C@@H]5[C@@H]4CC[C@]4(C)[C@H](CC[C@]54O)C4=CC(=O)OC4)C[C@H]3O[C@@H]2O1

InChI Identifier

InChI=1S/C31H44O10/c1-16-10-25(39-17(2)33)31(36)27(38-16)40-23-12-19-4-5-22-21(29(19,15-32)13-24(23)41-31)6-8-28(3)20(7-9-30(22,28)35)18-11-26(34)37-14-18/h11,16,19-25,27,32,35-36H,4-10,12-15H2,1-3H3/t16-,19+,20-,21+,22-,23-,24-,25+,27+,28-,29-,30+,31+/m1/s1

InChI Key

GLXUNTFWMNVCKD-SVDYBJNLSA-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
Asclepias curassavica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Cardenolide glycosides and derivatives

Alternative Parents

Substituents

Cardanolide-glycoside
19-hydroxysteroid
14-hydroxysteroid
Hydroxysteroid
Para-dioxane
2-furanone
Dicarboxylic acid or derivatives
Oxane
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Hemiacetal
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Acetal
Oxacycle
Carboxylic acid derivative
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxide
Primary alcohol
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	2.09	ChemAxon
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	0.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	140.98 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	143.66 m³·mol⁻¹	ChemAxon
Polarizability	62.02 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

8546366

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10370921

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3r,5s,7r,9s,10s,12r,14r,15s,18r,19r,22s,23r)-10,22-dihydroxy-14-(hydroxymethyl)-7,18-dimethyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-9-yl acetate (NP0215609)

MOL for NP0215609 ((1s,3r,5s,7r,9s,10s,12r,14r,15s,18r,19r,22s,23r)-10,22-dihydroxy-14-(hydroxymethyl)-7,18-dimethyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-9-yl acetate)

3D MOL for NP0215609 ((1s,3r,5s,7r,9s,10s,12r,14r,15s,18r,19r,22s,23r)-10,22-dihydroxy-14-(hydroxymethyl)-7,18-dimethyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-9-yl acetate)

3D SDF for NP0215609 ((1s,3r,5s,7r,9s,10s,12r,14r,15s,18r,19r,22s,23r)-10,22-dihydroxy-14-(hydroxymethyl)-7,18-dimethyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-9-yl acetate)

3D-SDF for NP0215609 ((1s,3r,5s,7r,9s,10s,12r,14r,15s,18r,19r,22s,23r)-10,22-dihydroxy-14-(hydroxymethyl)-7,18-dimethyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-9-yl acetate)

PDB for NP0215609 ((1s,3r,5s,7r,9s,10s,12r,14r,15s,18r,19r,22s,23r)-10,22-dihydroxy-14-(hydroxymethyl)-7,18-dimethyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-9-yl acetate)

3D PDB for NP0215609 ((1s,3r,5s,7r,9s,10s,12r,14r,15s,18r,19r,22s,23r)-10,22-dihydroxy-14-(hydroxymethyl)-7,18-dimethyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-9-yl acetate)

SMILES for NP0215609 ((1s,3r,5s,7r,9s,10s,12r,14r,15s,18r,19r,22s,23r)-10,22-dihydroxy-14-(hydroxymethyl)-7,18-dimethyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-9-yl acetate)

INCHI for NP0215609 ((1s,3r,5s,7r,9s,10s,12r,14r,15s,18r,19r,22s,23r)-10,22-dihydroxy-14-(hydroxymethyl)-7,18-dimethyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-9-yl acetate)

Structure for NP0215609 ((1s,3r,5s,7r,9s,10s,12r,14r,15s,18r,19r,22s,23r)-10,22-dihydroxy-14-(hydroxymethyl)-7,18-dimethyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-9-yl acetate)

3D Structure for NP0215609 ((1s,3r,5s,7r,9s,10s,12r,14r,15s,18r,19r,22s,23r)-10,22-dihydroxy-14-(hydroxymethyl)-7,18-dimethyl-19-(5-oxo-2h-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]pentacosan-9-yl acetate)