NP-MRD: Showing NP-Card for 3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid (NP0229903)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 10:10:10 UTC

Updated at

2022-09-06 10:10:10 UTC

NP-MRD ID

NP0229903

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid

Description

11-Hydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecane-2-carboxylic acid 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. 3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid is found in Antiaris toxicaria. 11-Hydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecane-2-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251507322D          

 39 44  0  0  0  0            999 V2000
    7.7663   -2.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0466   -1.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5148   -0.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7951    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2632    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685    1.4085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2889   -1.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6061   -2.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5793   -2.8729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0452   -1.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2351   -0.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9749   -1.1035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0784   -1.1393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6072    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8875    0.9934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1390   -0.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9511   -0.2681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8587   -1.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3905   -1.8199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 22  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 24  1  0  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
 10 30  1  0  0  0  0
  6 30  1  0  0  0  0
  9 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
  4 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
  2 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END

     RDKit          3D

 81 86  0  0  0  0  0  0  0  0999 V2000
   -7.1557   -1.9528    2.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2705   -1.0320    1.3013 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5567   -1.8452    0.4496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8073   -1.1001   -0.4869 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1032   -0.0696    0.1138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7282   -0.1678   -0.0736 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1514   -0.3292    1.3275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6501   -0.4035    1.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0460    0.8017    0.6272 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4029    2.0026    1.4416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9920    1.9753    2.5404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0430    3.2385    0.9233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6523    1.0034   -0.7289 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2783   -0.0143   -1.7528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1793   -0.4676   -1.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9354    0.5943   -0.8851 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4562    0.6864    0.5379 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0316   -0.3494    1.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3272   -0.9254    0.9716 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1741   -0.0125    0.1313 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7062    1.1468    0.9643 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3100   -0.8752   -0.4105 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5988   -0.6534    0.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7073   -0.1874   -0.3255 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7758   -0.1034    0.6594 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9514    0.2837    0.4888 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2708   -0.5367    1.8684 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9258   -0.9232    1.6740 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3518   -0.5484   -1.9006 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8851   -0.2712   -2.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4101    0.5444   -1.0171 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9339    1.8424   -1.2674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1582    1.0905   -0.6442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8460   -0.4372   -1.3892 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8861   -1.3217   -1.6797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4719    0.6607   -0.5164 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.3453    1.4503   -1.2202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1788   -0.0625    0.6119 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.6222    0.8505    1.5895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6325   -2.9285    2.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1151   -2.1507    1.5871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4285   -1.4427    3.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6084   -0.5134    2.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1801   -1.8215   -1.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5621   -1.0707   -0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5732    0.4776    1.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5509   -1.3206    1.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4083   -1.3426    0.7548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3406   -0.4410    2.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7589    3.8464    0.5405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3383    2.0333   -1.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8700   -0.9256   -1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4664    0.4674   -2.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5439   -0.5224   -2.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2568   -1.4079   -1.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6097    1.5678   -1.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8687    1.6776    0.9076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3706   -1.2189    1.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2257    0.1039    2.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9469   -1.2879    1.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1291   -1.8505    0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4833    1.0138    2.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2799    2.1274    0.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7990    1.2880    0.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0212   -1.9697   -0.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8637    0.1011   -1.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3214   -0.4267    2.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8954   -2.0164    1.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7059   -1.3941   -2.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9969    0.3180   -2.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8572    0.3685   -3.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3974   -1.2409   -2.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6490    2.0868   -2.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4711    1.9297    0.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5213    1.3256   -1.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3954    0.0116   -2.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2783   -1.1677   -2.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6341    1.2172   -0.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0223    2.4017   -1.1335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0936   -0.6042    0.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5572    1.1194    1.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 13  1  0
 13 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  1
 20 22  1  0
 22 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  6
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 13 33  1  0
  9 10  1  1
 10 12  1  0
 10 11  2  0
  4 34  1  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  1  0
 38  2  1  0
 33  6  1  0
 17  9  1  0
 31 20  1  0
 28 23  1  0
 31 16  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  2 43  1  1
  4 44  1  6
  6 45  1  6
  7 46  1  0
  7 47  1  0
  8 48  1  0
  8 49  1  0
 13 51  1  6
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  6
 17 57  1  1
 18 58  1  0
 18 59  1  0
 19 60  1  0
 19 61  1  0
 21 62  1  0
 21 63  1  0
 21 64  1  0
 22 65  1  6
 29 69  1  0
 29 70  1  0
 30 71  1  0
 30 72  1  0
 32 73  1  0
 24 66  1  0
 28 67  1  0
 28 68  1  0
 33 74  1  0
 33 75  1  0
 12 50  1  0
 34 76  1  6
 35 77  1  0
 36 78  1  1
 37 79  1  0
 38 80  1  6
 39 81  1  0
M  END


  Mrv1533004251507322D          

 39 44  0  0  0  0            999 V2000
    7.7663   -2.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0466   -1.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5148   -0.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7951    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2632    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685    1.4085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2889   -1.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6061   -2.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5793   -2.8729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0452   -1.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2351   -0.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9749   -1.1035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0784   -1.1393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6072    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8875    0.9934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1390   -0.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9511   -0.2681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8587   -1.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3905   -1.8199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 22  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 24  1  0  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
 10 30  1  0  0  0  0
  6 30  1  0  0  0  0
  9 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
  4 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
  2 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0229903

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OC2CCC3(C(CCC4C3CCC3(C)C(CCC43O)C3=CC(=O)OC3)C2)C(O)=O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C29H42O10/c1-14-22(31)23(32)24(33)25(38-14)39-17-5-9-28(26(34)35)16(12-17)3-4-20-19(28)6-8-27(2)18(7-10-29(20,27)36)15-11-21(30)37-13-15/h11,14,16-20,22-25,31-33,36H,3-10,12-13H2,1-2H3,(H,34,35)

> <INCHI_KEY>
OKJYWYPYIBXZKZ-UHFFFAOYSA-N

> <FORMULA>
C29H42O10

> <MOLECULAR_WEIGHT>
550.645

> <EXACT_MASS>
550.277797552

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
58.90011969374937

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
11-hydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-2-carboxylic acid

> <ALOGPS_LOGP>
1.35

> <JCHEM_LOGP>
1.535121507

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.183036165284012

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.150897881457595

> <JCHEM_PKA_STRONGEST_BASIC>
0.26893449667730474

> <JCHEM_POLAR_SURFACE_AREA>
162.98

> <JCHEM_REFRACTIVITY>
136.22739999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.91e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-hydroxy-15-methyl-14-(5-oxo-2H-furan-3-yl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      14.497  -3.939   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.020  -2.491   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      14.028  -1.314   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      14.551   0.135   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.355   2.629   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.406  -2.959   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.131  -3.824   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.081  -5.363   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -0.084  -2.878   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.439  -1.430   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.420  -2.060   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       9.480  -2.127   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      16.067   0.406   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      16.590   1.854   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      17.059  -0.771   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      18.575  -0.500   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      16.536  -2.220   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      17.529  -3.397   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   38                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   34                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   30                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14   31                                             
CONECT   10    9   11   30                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   22                                             
CONECT   18   17                                                            
CONECT   19   17   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   13   17   23                                             
CONECT   23   22                                                            
CONECT   24   19   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   24                                                       
CONECT   30   10    6                                                       
CONECT   31    9   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34    4   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36    2   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Value	Source
11-Hydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetracyclo[8.7.0.0,.0,]heptadecane-2-carboxylate	Generator
11-Hydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-2-carboxylate	Generator

Chemical Formula

C₂₉H₄₂O₁₀

Average Mass

550.6450 Da

Monoisotopic Mass

550.27780 Da

IUPAC Name

11-hydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-2-carboxylic acid

Traditional Name

11-hydroxy-15-methyl-14-(5-oxo-2H-furan-3-yl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1OC(OC2CCC3(C(CCC4C3CCC3(C)C(CCC43O)C3=CC(=O)OC3)C2)C(O)=O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C29H42O10/c1-14-22(31)23(32)24(33)25(38-14)39-17-5-9-28(26(34)35)16(12-17)3-4-20-19(28)6-8-27(2)18(7-10-29(20,27)36)15-11-21(30)37-13-15/h11,14,16-20,22-25,31-33,36H,3-10,12-13H2,1-2H3,(H,34,35)

InChI Key

OKJYWYPYIBXZKZ-UHFFFAOYSA-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
Antiaris toxicaria	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
Steroidal glycoside
19-hydroxysteroid
19-oxosteroid
Hydroxysteroid
14-hydroxysteroid
Oxosteroid
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Oxane
Dicarboxylic acid or derivatives
2-furanone
Monosaccharide
Cyclic alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Dihydrofuran
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Lactone
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Polyol
Alcohol
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
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
logP	1.35	ALOGPS
logP	1.54	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.15	ChemAxon
pKa (Strongest Basic)	0.27	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.98 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	136.23 m³·mol⁻¹	ChemAxon
Polarizability	58.9 Å³	ChemAxon
Number of Rings	6	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

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

56659783

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid (NP0229903)

MOL for NP0229903 (3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid)

3D MOL for NP0229903 (3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid)

3D SDF for NP0229903 (3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid)

3D-SDF for NP0229903 (3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid)

PDB for NP0229903 (3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid)

3D PDB for NP0229903 (3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid)

SMILES for NP0229903 (3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid)

INCHI for NP0229903 (3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid)

Structure for NP0229903 (3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid)

3D Structure for NP0229903 (3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid)