NP-MRD: Showing NP-Card for 5-{13,25,26-trihydroxy-1-methoxy-5,9,24-trimethyl-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-10-yl}pyran-2-one (NP0255566)

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Record Information

Version

1.0

Created at

2022-09-07 20:06:44 UTC

Updated at

2022-09-07 20:06:44 UTC

NP-MRD ID

NP0255566

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-{13,25,26-trihydroxy-1-methoxy-5,9,24-trimethyl-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-10-yl}pyran-2-one

Description

Cotyledoside 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. 5-{13,25,26-trihydroxy-1-methoxy-5,9,24-trimethyl-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-10-yl}pyran-2-one is found in Tylecodon wallichii. Cotyledoside is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171522572D          

 41 48  0  0  0  0            999 V2000
    7.4097    3.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1366    3.4177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1622    2.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3960    2.2871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0059    1.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2223    1.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6070    1.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4386    2.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7754    0.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5590    0.2029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1742    0.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8223    0.2420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6469    0.2676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2622    0.8172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3802    1.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1879    1.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9458    2.3351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4563    2.9832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6953    1.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2497    2.1019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1601   -0.0887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3765    0.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5929    0.4273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081    0.9770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8234    1.5266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6550    2.3342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8714    2.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562    2.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0043    2.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4360    2.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0975    1.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7084    0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4245    1.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2498    0.4287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0263    2.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2013    2.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917    3.5675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2070    4.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7973    4.9964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0320    4.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4416    3.5610    0.0000 C   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
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 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
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 19  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  0  0  0  0
  9 21  1  0  0  0  0
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 23 24  1  0  0  0  0
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 24 25  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
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 32 33  1  0  0  0  0
 24 33  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 30 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  2  0  0  0  0
 35 41  1  0  0  0  0
M  END

     RDKit          3D

 83 90  0  0  0  0  0  0  0  0999 V2000
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    3.9758    2.6381    0.5430 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2498    1.4054    0.0738 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2242    0.8229   -0.6606 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3196    0.0271   -0.0009 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0965    0.0499   -0.9365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1728   -1.0668   -0.8795 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1139   -1.7330   -2.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2704   -0.6949   -0.6175 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5101    0.1350    0.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9212    0.7217    0.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9423   -0.3534    0.2582 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1405   -0.9412    1.6632 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1544   -2.4041    0.8886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7735   -3.1400   -0.2737 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2701   -3.4138   -0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5069   -2.1734    0.0764 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9691   -2.4707   -0.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6639   -1.2725    0.5252 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9586   -1.7253    0.6516 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8061   -0.8277    0.1679 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1091   -0.9255   -0.0545 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4946    0.3316   -0.5917 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7032    0.8599    0.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4606    1.3224   -0.8748 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0234    1.2296   -2.2207 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6452    0.3798    1.0862 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8371    0.2000    2.1479 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2469    2.6470    2.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4963    4.1810    1.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4235    0.2191   -2.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4269   -1.0034   -2.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1301   -1.8044   -2.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2078    1.3840    1.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.6285    1.2969    1.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1064    3.6414    2.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5112    2.2942   -1.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.6777    0.4135   -2.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7 30  1  0
 30 29  1  0
 29 28  1  0
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 41 83  1  0
M  END


  Mrv1533004171522572D          

 41 48  0  0  0  0            999 V2000
    7.4097    3.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1366    3.4177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3960    2.2871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2223    1.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6070    1.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4386    2.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7754    0.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5590    0.2029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1742    0.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8223    0.2420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6469    0.2676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2622    0.8172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3802    1.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1879    1.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9458    2.3351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.6953    1.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2497    2.1019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1601   -0.0887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3765    0.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5929    0.4273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081    0.9770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8234    1.5266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6550    2.3342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8714    2.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562    2.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0043    2.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4360    2.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0975    1.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7084    0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4245    1.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2498    0.4287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0263    2.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2013    2.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917    3.5675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2070    4.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7973    4.9964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0320    4.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4416    3.5610    0.0000 C   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
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 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
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 19  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 24 33  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 30 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  2  0  0  0  0
 35 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0255566

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC12OC3CC4(C)C(CC5OC55C4CCC4(C)C(CCC54O)C4=COC(=O)C=C4)CC3OC(OC(C)C1O)C2O

> <INCHI_IDENTIFIER>
InChI=1S/C31H42O10/c1-15-24(33)31(36-4)25(34)26(38-15)39-19-11-17-12-22-30(41-22)21(27(17,2)13-20(19)40-31)8-9-28(3)18(7-10-29(28,30)35)16-5-6-23(32)37-14-16/h5-6,14-15,17-22,24-26,33-35H,7-13H2,1-4H3

> <INCHI_KEY>
QHKQFMBHXNVPCG-UHFFFAOYSA-N

> <FORMULA>
C31H42O10

> <MOLECULAR_WEIGHT>
574.667

> <EXACT_MASS>
574.277797552

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
59.53627105201721

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-{13,25,26-trihydroxy-1-methoxy-5,9,24-trimethyl-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-10-yl}-2H-pyran-2-one

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
2.176485912333333

> <ALOGPS_LOGS>
-3.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.356249478898501

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.40321241267358

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5631307641725094

> <JCHEM_POLAR_SURFACE_AREA>
136.44000000000003

> <JCHEM_REFRACTIVITY>
142.65370000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-{13,25,26-trihydroxy-1-methoxy-5,9,24-trimethyl-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-10-yl}pyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      13.831   7.108   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      15.188   6.380   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      15.236   4.840   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      13.806   4.269   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      13.078   2.912   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.615   3.394   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.466   2.368   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.152   3.876   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.781   0.860   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.243   0.379   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.392   1.405   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      14.602   0.452   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      16.141   0.500   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      17.289   1.525   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      17.510   3.050   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.017   3.364   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.699   4.359   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      17.652   5.569   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      16.231   2.783   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      17.266   3.923   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.632  -0.166   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.169   0.316   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.707   0.798   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.855   1.824   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.004   2.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.689   4.357   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.227   4.839   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.078   3.813   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.608   5.279   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.547   3.980   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.915   2.576   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.056   1.541   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.392   2.305   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.066   0.800   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       3.782   5.317   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.243   5.323   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       1.478   6.659   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       2.253   7.990   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       1.488   9.327   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       3.793   7.984   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.558   6.647   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   17   19                                             
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   25                                             
CONECT    8    7                                                            
CONECT    9    7   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    3   18                                                  
CONECT   18   17                                                            
CONECT   19   13    3   20                                                  
CONECT   20   19                                                            
CONECT   21    9   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22   24                                                       
CONECT   24   23   22   25   33                                             
CONECT   25   24    7   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30   33                                             
CONECT   29   28                                                            
CONECT   30   28   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   24   28   34                                             
CONECT   34   33                                                            
CONECT   35   30   36   41                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   35                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₂O₁₀

Average Mass

574.6670 Da

Monoisotopic Mass

574.27780 Da

IUPAC Name

5-{13,25,26-trihydroxy-1-methoxy-5,9,24-trimethyl-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-10-yl}-2H-pyran-2-one

Traditional Name

5-{13,25,26-trihydroxy-1-methoxy-5,9,24-trimethyl-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-10-yl}pyran-2-one

CAS Registry Number

Not Available

SMILES

COC12OC3CC4(C)C(CC5OC55C4CCC4(C)C(CCC54O)C4=COC(=O)C=C4)CC3OC(OC(C)C1O)C2O

InChI Identifier

InChI=1S/C31H42O10/c1-15-24(33)31(36-4)25(34)26(38-15)39-19-11-17-12-22-30(41-22)21(27(17,2)13-20(19)40-31)8-9-28(3)18(7-10-29(28,30)35)16-5-6-23(32)37-14-16/h5-6,14-15,17-22,24-26,33-35H,7-13H2,1-4H3

InChI Key

QHKQFMBHXNVPCG-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
Tylecodon wallichii	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
1,4-dioxepane
Ketal
Dioxepane
Oxepane
Pyranone
Monosaccharide
Oxane
Pyran
Cyclic alcohol
Heteroaromatic compound
Tertiary alcohol
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Ether
Oxirane
Dialkyl ether
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
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	2.78	ALOGPS
logP	2.18	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	11.4	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	136.44 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	142.65 m³·mol⁻¹	ChemAxon
Polarizability	59.54 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

162820

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-{13,25,26-trihydroxy-1-methoxy-5,9,24-trimethyl-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-10-yl}pyran-2-one (NP0255566)

MOL for NP0255566 (5-{13,25,26-trihydroxy-1-methoxy-5,9,24-trimethyl-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-10-yl}pyran-2-one)

3D MOL for NP0255566 (5-{13,25,26-trihydroxy-1-methoxy-5,9,24-trimethyl-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-10-yl}pyran-2-one)

3D SDF for NP0255566 (5-{13,25,26-trihydroxy-1-methoxy-5,9,24-trimethyl-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-10-yl}pyran-2-one)

3D-SDF for NP0255566 (5-{13,25,26-trihydroxy-1-methoxy-5,9,24-trimethyl-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-10-yl}pyran-2-one)

PDB for NP0255566 (5-{13,25,26-trihydroxy-1-methoxy-5,9,24-trimethyl-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-10-yl}pyran-2-one)

3D PDB for NP0255566 (5-{13,25,26-trihydroxy-1-methoxy-5,9,24-trimethyl-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-10-yl}pyran-2-one)

SMILES for NP0255566 (5-{13,25,26-trihydroxy-1-methoxy-5,9,24-trimethyl-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-10-yl}pyran-2-one)

INCHI for NP0255566 (5-{13,25,26-trihydroxy-1-methoxy-5,9,24-trimethyl-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-10-yl}pyran-2-one)

Structure for NP0255566 (5-{13,25,26-trihydroxy-1-methoxy-5,9,24-trimethyl-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-10-yl}pyran-2-one)

3D Structure for NP0255566 (5-{13,25,26-trihydroxy-1-methoxy-5,9,24-trimethyl-2,15,21,23-tetraoxaheptacyclo[20.3.1.0³,²⁰.0⁵,¹⁸.0⁶,¹⁴.0⁹,¹³.0¹⁴,¹⁶]hexacosan-10-yl}pyran-2-one)