NP-MRD: Showing NP-Card for (1s,3r,5s,6s,7s,9r,10r,13r,14r,16s,18r,20r,22s,24s,26r)-7,13,26-trihydroxy-1-methoxy-5,9,24-trimethyl-10-(6-oxopyran-3-yl)-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-8-one (NP0169152)

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Record Information

Version

2.0

Created at

2022-09-03 05:03:49 UTC

Updated at

2022-09-03 05:03:50 UTC

NP-MRD ID

NP0169152

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3r,5s,6s,7s,9r,10r,13r,14r,16s,18r,20r,22s,24s,26r)-7,13,26-trihydroxy-1-methoxy-5,9,24-trimethyl-10-(6-oxopyran-3-yl)-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-8-one

Description

Tyledoside D belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. (1s,3r,5s,6s,7s,9r,10r,13r,14r,16s,18r,20r,22s,24s,26r)-7,13,26-trihydroxy-1-methoxy-5,9,24-trimethyl-10-(6-oxopyran-3-yl)-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-8-one is found in Tylecodon grandiflorus. (1s,3r,5s,6s,7s,9r,10r,13r,14r,16s,18r,20r,22s,24s,26r)-7,13,26-trihydroxy-1-methoxy-5,9,24-trimethyl-10-(6-oxopyran-3-yl)-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-8-one was first documented in 1998 (PMID: 9629586). Based on a literature review very few articles have been published on Tyledoside D (PMID: 12356172).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032207032D          

 42 49  0  0  1  0            999 V2000
    6.8334    5.1101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1335    4.6733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1618    3.8488    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9463    3.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3831    2.8936    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.1902    3.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2679    2.0766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6545    1.5249    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8299    1.4966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1801    2.0049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5667    1.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7822    1.7085    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1688    1.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3844    1.4122    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5999    1.6676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2133    2.2193    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8267    2.7710    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6556    3.5780    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2690    4.1297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711    3.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7000    4.6405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2577    3.2817    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0032    4.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4373    3.3684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0252    4.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7998    4.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2120    4.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7991    5.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2112    6.2272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0259    5.5120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380    4.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1013    2.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7141    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288    2.4746    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2568    1.6678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6111    2.5156    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4401    3.3227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2245    3.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0090    2.8119    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3967    3.5402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1177    2.6253    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3106    2.4542    0.0000 O   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  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 16 15  1  6  0  0  0
 14 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
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 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
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 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 25 31  2  0  0  0  0
 24 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 16 34  1  0  0  0  0
 22 34  1  0  0  0  0
 34 35  1  6  0  0  0
 17 36  1  0  0  0  0
 12 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
 39 38  1  1  0  0  0
 10 39  1  0  0  0  0
 39 40  1  0  0  0  0
  3 40  1  0  0  0  0
  8 41  1  0  0  0  0
  3 41  1  0  0  0  0
 41 42  1  1  0  0  0
M  END

     RDKit          3D

 82 89  0  0  0  0  0  0  0  0999 V2000
   -5.8598   -1.7658    2.4760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6929   -1.1599    2.1301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7614   -0.1167    1.2719 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4908    1.0386    1.9921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4907    2.1844    0.9706 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9142    2.6328    0.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7919    1.8968   -0.1717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2479    0.8275   -0.8972 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2800    0.3715   -1.7580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9996    0.4319   -1.3010 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1153   -0.3188   -2.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6897   -0.0232   -1.8648 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3254   -0.2269   -2.9057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6349   -0.7736   -2.4976 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4910   -2.0633   -1.9028 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0630    2.2802    1.0782 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2965    2.5720    1.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3424    1.6776    1.5508 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4622    1.9488    2.0943 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1407    0.5836    0.8794 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0059    0.2677    0.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8772    0.2634   -1.6349 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4326   -1.1855   -1.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3236   -1.2060   -0.6265 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2921   -2.5196   -0.1012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3755   -0.7010   -0.5308 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5642   -2.1771   -0.5559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3505   -0.1228    0.4698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7967   -0.2563    0.0239 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5323    0.4462    0.9678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5872   -0.3452    0.0352 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3679   -1.5229   -0.6079 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  3  2  1  1
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  9 10  1  0
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 38 78  1  0
 38 79  1  0
 39 80  1  6
 41 81  1  1
 42 82  1  0
M  END


  Mrv1652309032207032D          

 42 49  0  0  1  0            999 V2000
    6.8334    5.1101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1335    4.6733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1618    3.8488    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9463    3.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3831    2.8936    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.1902    3.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2679    2.0766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6545    1.5249    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8299    1.4966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1801    2.0049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5667    1.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7822    1.7085    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1688    1.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3844    1.4122    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5999    1.6676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2133    2.2193    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8267    2.7710    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6556    3.5780    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2690    4.1297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711    3.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7000    4.6405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2577    3.2817    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0032    4.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4373    3.3684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0252    4.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7998    4.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2120    4.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7991    5.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2112    6.2272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0259    5.5120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380    4.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1013    2.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7141    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288    2.4746    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2568    1.6678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6111    2.5156    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4401    3.3227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2245    3.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0090    2.8119    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3967    3.5402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1177    2.6253    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3106    2.4542    0.0000 O   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  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 16 15  1  6  0  0  0
 14 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
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 25 31  2  0  0  0  0
 24 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 16 34  1  0  0  0  0
 22 34  1  0  0  0  0
 34 35  1  6  0  0  0
 17 36  1  0  0  0  0
 12 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
 39 38  1  1  0  0  0
 10 39  1  0  0  0  0
 39 40  1  0  0  0  0
  3 40  1  0  0  0  0
  8 41  1  0  0  0  0
  3 41  1  0  0  0  0
 41 42  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0169152

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@]12C[C@H](C)O[C@@H](O[C@@H]3C[C@@H]4C[C@@H]5O[C@]55[C@H]([C@H](O)C(=O)[C@]6(C)[C@H](CC[C@]56O)C5=COC(=O)C=C5)[C@@]4(C)C[C@H]3O1)[C@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C31H40O11/c1-14-11-29(37-4)25(35)26(39-14)40-18-9-16-10-20-31(42-20)23(27(16,2)12-19(18)41-29)22(33)24(34)28(3)17(7-8-30(28,31)36)15-5-6-21(32)38-13-15/h5-6,13-14,16-20,22-23,25-26,33,35-36H,7-12H2,1-4H3/t14-,16+,17+,18+,19+,20-,22-,23+,25+,26-,27-,28-,29-,30+,31-/m0/s1

> <INCHI_KEY>
BKVAXXAKDQXAAJ-RFLILGNUSA-N

> <FORMULA>
C31H40O11

> <MOLECULAR_WEIGHT>
588.65

> <EXACT_MASS>
588.257062108

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
60.89163129875173

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,5S,6S,7S,9R,10R,13R,14R,16S,18R,20R,22S,24S,26R)-7,13,26-trihydroxy-1-methoxy-5,9,24-trimethyl-10-(2-oxo-2H-pyran-5-yl)-2,15,21,23-tetraoxaheptacyclo[20.3.1.0^{3,20}.0^{5,18}.0^{6,14}.0^{9,13}.0^{14,16}]hexacosan-8-one

> <ALOGPS_LOGP>
1.11

> <JCHEM_LOGP>
1.580331420333331

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.758217928768776

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.536762963263456

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6461834259969645

> <JCHEM_POLAR_SURFACE_AREA>
153.51

> <JCHEM_REFRACTIVITY>
143.22959999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.51e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,5S,6S,7S,9R,10R,13R,14R,16S,18R,20R,22S,24S,26R)-7,13,26-trihydroxy-1-methoxy-5,9,24-trimethyl-10-(6-oxopyran-3-yl)-2,15,21,23-tetraoxaheptacyclo[20.3.1.0^{3,20}.0^{5,18}.0^{6,14}.0^{9,13}.0^{14,16}]hexacosan-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      12.756   9.539   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.449   8.724   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.502   7.184   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.966   6.708   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.782   5.401   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.288   5.721   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.567   3.876   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      12.422   2.847   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.883   2.794   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.670   3.742   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.525   2.713   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.060   3.189   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.915   2.159   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.451   2.636   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.986   3.113   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.131   4.143   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.276   5.172   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.957   6.679   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.102   7.709   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.493   7.156   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.173   8.662   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.348   6.126   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.873   7.591   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.816   6.288   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.047   7.622   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.493   7.623   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.262   8.957   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.492  10.290   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.261  11.624   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.048  10.289   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.818   8.955   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.189   4.881   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.333   3.850   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667   4.619   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.346   3.113   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       6.741   4.696   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.421   6.202   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.886   5.726   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.350   5.249   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      10.074   6.608   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      11.420   4.901   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       9.913   4.581   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   40   41                                             
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   41                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   39                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   36                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   16                                                       
CONECT   16   15   14   17   34                                             
CONECT   17   16   18   36                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24   34                                             
CONECT   23   22                                                            
CONECT   24   22   25   32                                                  
CONECT   25   24   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   25                                                       
CONECT   32   24   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   16   22   35                                             
CONECT   35   34                                                            
CONECT   36   17   12   37   38                                             
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   10   40                                                  
CONECT   40   39    3                                                       
CONECT   41    8    3   42                                                  
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₀O₁₁

Average Mass

588.6500 Da

Monoisotopic Mass

588.25706 Da

IUPAC Name

(1S,3R,5S,6S,7S,9R,10R,13R,14R,16S,18R,20R,22S,24S,26R)-7,13,26-trihydroxy-1-methoxy-5,9,24-trimethyl-10-(2-oxo-2H-pyran-5-yl)-2,15,21,23-tetraoxaheptacyclo[20.3.1.0^{3,20}.0^{5,18}.0^{6,14}.0^{9,13}.0^{14,16}]hexacosan-8-one

Traditional Name

(1S,3R,5S,6S,7S,9R,10R,13R,14R,16S,18R,20R,22S,24S,26R)-7,13,26-trihydroxy-1-methoxy-5,9,24-trimethyl-10-(6-oxopyran-3-yl)-2,15,21,23-tetraoxaheptacyclo[20.3.1.0^{3,20}.0^{5,18}.0^{6,14}.0^{9,13}.0^{14,16}]hexacosan-8-one

CAS Registry Number

Not Available

SMILES

CO[C@@]12C[C@H](C)O[C@@H](O[C@@H]3C[C@@H]4C[C@@H]5O[C@]55[C@H]([C@H](O)C(=O)[C@]6(C)[C@H](CC[C@]56O)C5=COC(=O)C=C5)[C@@]4(C)C[C@H]3O1)[C@H]2O

InChI Identifier

InChI=1S/C31H40O11/c1-14-11-29(37-4)25(35)26(39-14)40-18-9-16-10-20-31(42-20)23(27(16,2)12-19(18)41-29)22(33)24(34)28(3)17(7-8-30(28,31)36)15-5-6-21(32)38-13-15/h5-6,13-14,16-20,22-23,25-26,33,35-36H,7-12H2,1-4H3/t14-,16+,17+,18+,19+,20-,22-,23+,25+,26-,27-,28-,29-,30+,31-/m0/s1

InChI Key

BKVAXXAKDQXAAJ-RFLILGNUSA-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
Tylecodon grandiflorus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Bufanolides and derivatives

Alternative Parents

Substituents

Bufanolide-skeleton
Ketal
Pyranone
Oxepane
Dioxepane
1,4-dioxepane
Pyran
Oxane
Heteroaromatic compound
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Lactone
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Oxirane
Dialkyl ether
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	1.11	ALOGPS
logP	1.58	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	11.54	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	153.51 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	143.23 m³·mol⁻¹	ChemAxon
Polarizability	60.89 Å³	ChemAxon
Number of Rings	8	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

132581133

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Botha CJ, Gehring R, Van Rooyen JM, Venter D: The effect of three bufadienolide cardiac glycosides on contraction of isolated rat jejunum. Onderstepoort J Vet Res. 2002 Sep;69(3):243-6. [PubMed:12356172 ]
Botha CJ, Kellerman TS, Schultz RA, Erasmus GL, Vleggaar R, Retief E: Krimpsiekte in a sheep following a single dose of Tylecodon ventricosus (Burm. f.) Toelken and the isolation of tyledoside D from this plant species. Onderstepoort J Vet Res. 1998 Mar;65(1):17-23. [PubMed:9629586 ]
LOTUS database [Link]

Showing NP-Card for (1s,3r,5s,6s,7s,9r,10r,13r,14r,16s,18r,20r,22s,24s,26r)-7,13,26-trihydroxy-1-methoxy-5,9,24-trimethyl-10-(6-oxopyran-3-yl)-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-8-one (NP0169152)

MOL for NP0169152 ((1s,3r,5s,6s,7s,9r,10r,13r,14r,16s,18r,20r,22s,24s,26r)-7,13,26-trihydroxy-1-methoxy-5,9,24-trimethyl-10-(6-oxopyran-3-yl)-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-8-one)

3D MOL for NP0169152 ((1s,3r,5s,6s,7s,9r,10r,13r,14r,16s,18r,20r,22s,24s,26r)-7,13,26-trihydroxy-1-methoxy-5,9,24-trimethyl-10-(6-oxopyran-3-yl)-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-8-one)

3D SDF for NP0169152 ((1s,3r,5s,6s,7s,9r,10r,13r,14r,16s,18r,20r,22s,24s,26r)-7,13,26-trihydroxy-1-methoxy-5,9,24-trimethyl-10-(6-oxopyran-3-yl)-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-8-one)

3D-SDF for NP0169152 ((1s,3r,5s,6s,7s,9r,10r,13r,14r,16s,18r,20r,22s,24s,26r)-7,13,26-trihydroxy-1-methoxy-5,9,24-trimethyl-10-(6-oxopyran-3-yl)-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-8-one)

PDB for NP0169152 ((1s,3r,5s,6s,7s,9r,10r,13r,14r,16s,18r,20r,22s,24s,26r)-7,13,26-trihydroxy-1-methoxy-5,9,24-trimethyl-10-(6-oxopyran-3-yl)-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-8-one)

3D PDB for NP0169152 ((1s,3r,5s,6s,7s,9r,10r,13r,14r,16s,18r,20r,22s,24s,26r)-7,13,26-trihydroxy-1-methoxy-5,9,24-trimethyl-10-(6-oxopyran-3-yl)-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-8-one)

SMILES for NP0169152 ((1s,3r,5s,6s,7s,9r,10r,13r,14r,16s,18r,20r,22s,24s,26r)-7,13,26-trihydroxy-1-methoxy-5,9,24-trimethyl-10-(6-oxopyran-3-yl)-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-8-one)

INCHI for NP0169152 ((1s,3r,5s,6s,7s,9r,10r,13r,14r,16s,18r,20r,22s,24s,26r)-7,13,26-trihydroxy-1-methoxy-5,9,24-trimethyl-10-(6-oxopyran-3-yl)-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-8-one)

Structure for NP0169152 ((1s,3r,5s,6s,7s,9r,10r,13r,14r,16s,18r,20r,22s,24s,26r)-7,13,26-trihydroxy-1-methoxy-5,9,24-trimethyl-10-(6-oxopyran-3-yl)-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-8-one)

3D Structure for NP0169152 ((1s,3r,5s,6s,7s,9r,10r,13r,14r,16s,18r,20r,22s,24s,26r)-7,13,26-trihydroxy-1-methoxy-5,9,24-trimethyl-10-(6-oxopyran-3-yl)-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-8-one)