NP-MRD: Showing NP-Card for 4-(3a-hydroxy-7-{[4-hydroxy-5-({4-hydroxy-5-[(4-hydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl)-5h-furan-2-one (NP0176069)

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Record Information

Version

2.0

Created at

2022-09-03 13:40:16 UTC

Updated at

2022-09-03 13:40:16 UTC

NP-MRD ID

NP0176069

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(3a-hydroxy-7-{[4-hydroxy-5-({4-hydroxy-5-[(4-hydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl)-5h-furan-2-one

Description

4-(11-Hydroxy-5-{[4-hydroxy-5-({4-hydroxy-5-[(4-hydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-14-yl)-2,5-dihydrofuran-2-one 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. 4-(3a-hydroxy-7-{[4-hydroxy-5-({4-hydroxy-5-[(4-hydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl)-5h-furan-2-one is found in Digitalis purpurea. 4-(11-Hydroxy-5-{[4-hydroxy-5-({4-hydroxy-5-[(4-hydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-14-yl)-2,5-dihydrofuran-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231514222D          

 65 73  0  0  0  0            999 V2000
    9.4481    2.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6360    2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3557    1.6241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5435    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0117    2.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2920    2.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7602    3.5162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1041    3.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3844    3.8066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8526    4.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0405    4.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5087    4.9228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6966    4.7776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7890    5.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2572    6.3295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5375    7.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0056    7.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2859    8.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7541    9.1427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0981    8.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3784    9.4332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1905    9.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7223    8.9477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5344    9.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0662    8.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8784    8.6074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8147    9.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6268   10.0140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2829   10.4995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5632   11.2754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4708   10.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9390   10.9850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6299    8.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4420    8.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3496    7.2506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    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
    4.5466   -0.5086    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
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    1.0596   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    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
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    5.9193    1.1884    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
  6  8  1  0  0  0  0
  2  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
 12 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
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 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
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
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 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
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 31 32  1  0  0  0  0
 20 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 16 35  1  0  0  0  0
 14 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 10 38  1  0  0  0  0
  4 39  1  0  0  0  0
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 47 48  1  0  0  0  0
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 43 49  1  0  0  0  0
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 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
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 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 48 57  1  0  0  0  0
 52 57  1  0  0  0  0
 57 58  1  0  0  0  0
 54 59  1  0  0  0  0
 59 60  2  0  0  0  0
 60 61  1  0  0  0  0
 61 62  2  0  0  0  0
 61 63  1  0  0  0  0
 63 64  1  0  0  0  0
 59 64  1  0  0  0  0
 45 65  1  0  0  0  0
 40 65  1  0  0  0  0
M  END

     RDKit          3D

139147  0  0  0  0  0  0  0  0999 V2000
    0.1174   -2.2440   -0.8786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4278   -0.8902   -0.3615 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.6489    0.4163    0.0583 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0021    0.4605    0.4862 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5298    1.7893    0.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9984    1.8594   -0.2172 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7608    0.6520    0.2023 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7802    0.5920    1.6942 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1072   -0.5786   -0.4391 C   0  0  1  0  0  0  0  0  0  0  0  0
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    8.1438    0.6946   -0.4239 C   0  0  2  0  0  0  0  0  0  0  0  0
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   10.9166    0.1570   -2.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004231514222D          

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M  END
> <DATABASE_ID>
NP0176069

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(CC(O)C1OC1CC(O)C(OC2CC(O)C(OC3OC(CO)C(O)C(O)C3O)C(C)O2)C(C)O1)OC1CCC2(C)C(CCC3C2CCC2(C)C(CCC32O)C2=CC(=O)OC2)C1

> <INCHI_IDENTIFIER>
InChI=1S/C47H74O18/c1-21-41(63-36-17-31(50)42(22(2)59-36)64-37-18-32(51)43(23(3)60-37)65-44-40(55)39(54)38(53)33(19-48)62-44)30(49)16-35(58-21)61-26-8-11-45(4)25(15-26)6-7-29-28(45)9-12-46(5)27(10-13-47(29,46)56)24-14-34(52)57-20-24/h14,21-23,25-33,35-44,48-51,53-56H,6-13,15-20H2,1-5H3

> <INCHI_KEY>
BZJBLHNKKRCQEQ-UHFFFAOYSA-N

> <FORMULA>
C47H74O18

> <MOLECULAR_WEIGHT>
927.091

> <EXACT_MASS>
926.487515543

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
139

> <JCHEM_AVERAGE_POLARIZABILITY>
101.65983479214162

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(11-hydroxy-5-{[4-hydroxy-5-({4-hydroxy-5-[(4-hydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl)-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
0.24

> <JCHEM_LOGP>
1.8266560933333353

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.18881357944474

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.182631941451659

> <JCHEM_PKA_STRONGEST_BASIC>
0.24220689832874898

> <JCHEM_POLAR_SURFACE_AREA>
261.97999999999996

> <JCHEM_REFRACTIVITY>
224.1306000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.03e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(11-hydroxy-5-{[4-hydroxy-5-({4-hydroxy-5-[(4-hydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl)-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      17.636   4.751   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.120   4.480   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      15.597   3.032   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      14.081   2.761   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.089   3.938   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.612   5.386   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.619   6.564   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      15.128   5.657   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      15.651   7.106   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      14.658   8.283   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.142   8.012   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.150   9.189   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.634   8.918   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.673  10.638   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.680  11.815   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.203  13.263   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.211  14.441   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.734  15.889   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.741  17.066   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      13.250  16.160   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.773  17.609   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      15.289  17.880   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      16.282  16.702   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      17.798  16.973   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.790  15.796   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      20.306  16.067   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      18.321  18.422   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      19.837  18.693   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      17.328  19.599   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      17.851  21.047   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      15.812  19.328   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      14.819  20.505   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      14.242  14.983   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      15.758  15.254   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      13.719  13.534   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      14.189  10.909   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      14.712  12.357   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      15.181   9.731   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0       5.355   2.629   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       2.406  -2.959   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       1.131  -3.824   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0       1.081  -5.363   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      -0.084  -2.878   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0       0.439  -1.430   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   39                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   38                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   36                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   35                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   33                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   22   32                                                  
CONECT   32   31                                                            
CONECT   33   20   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   16                                                       
CONECT   36   14   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   10                                                       
CONECT   39    4   40                                                       
CONECT   40   39   41   65                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   45   49                                             
CONECT   44   43                                                            
CONECT   45   43   46   65                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49   57                                                  
CONECT   49   48   43   50                                                  
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53   54   57                                             
CONECT   53   52                                                            
CONECT   54   52   55   59                                                  
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   48   52   58                                             
CONECT   58   57                                                            
CONECT   59   54   60   64                                                  
CONECT   60   59   61                                                       
CONECT   61   60   62   63                                                  
CONECT   62   61                                                            
CONECT   63   61   64                                                       
CONECT   64   63   59                                                       
CONECT   65   45   40                                                       
MASTER        0    0    0    0    0    0    0    0   65    0  146    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₇H₇₄O₁₈

Average Mass

927.0910 Da

Monoisotopic Mass

926.48752 Da

IUPAC Name

4-(11-hydroxy-5-{[4-hydroxy-5-({4-hydroxy-5-[(4-hydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl)-2,5-dihydrofuran-2-one

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1OC(CC(O)C1OC1CC(O)C(OC2CC(O)C(OC3OC(CO)C(O)C(O)C3O)C(C)O2)C(C)O1)OC1CCC2(C)C(CCC3C2CCC2(C)C(CCC32O)C2=CC(=O)OC2)C1

InChI Identifier

InChI=1S/C47H74O18/c1-21-41(63-36-17-31(50)42(22(2)59-36)64-37-18-32(51)43(23(3)60-37)65-44-40(55)39(54)38(53)33(19-48)62-44)30(49)16-35(58-21)61-26-8-11-45(4)25(15-26)6-7-29-28(45)9-12-46(5)27(10-13-47(29,46)56)24-14-34(52)57-20-24/h14,21-23,25-33,35-44,48-51,53-56H,6-13,15-20H2,1-5H3

InChI Key

BZJBLHNKKRCQEQ-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
Digitalis purpurea	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
Oligosaccharide
14-hydroxysteroid
Hydroxysteroid
Glycosyl compound
O-glycosyl compound
2-furanone
Oxane
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Dihydrofuran
Carboxylic acid ester
Secondary alcohol
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Acetal
Polyol
Monocarboxylic acid or derivatives
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Primary alcohol
Carbonyl group
Organooxygen compound
Organic oxide
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	0.24	ALOGPS
logP	1.83	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	0.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	261.98 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	224.13 m³·mol⁻¹	ChemAxon
Polarizability	101.66 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

13178062

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-(3a-hydroxy-7-{[4-hydroxy-5-({4-hydroxy-5-[(4-hydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl)-5h-furan-2-one (NP0176069)

MOL for NP0176069 (4-(3a-hydroxy-7-{[4-hydroxy-5-({4-hydroxy-5-[(4-hydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl)-5h-furan-2-one)

3D MOL for NP0176069 (4-(3a-hydroxy-7-{[4-hydroxy-5-({4-hydroxy-5-[(4-hydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl)-5h-furan-2-one)

3D SDF for NP0176069 (4-(3a-hydroxy-7-{[4-hydroxy-5-({4-hydroxy-5-[(4-hydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl)-5h-furan-2-one)

3D-SDF for NP0176069 (4-(3a-hydroxy-7-{[4-hydroxy-5-({4-hydroxy-5-[(4-hydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl)-5h-furan-2-one)

PDB for NP0176069 (4-(3a-hydroxy-7-{[4-hydroxy-5-({4-hydroxy-5-[(4-hydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl)-5h-furan-2-one)

3D PDB for NP0176069 (4-(3a-hydroxy-7-{[4-hydroxy-5-({4-hydroxy-5-[(4-hydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl)-5h-furan-2-one)

SMILES for NP0176069 (4-(3a-hydroxy-7-{[4-hydroxy-5-({4-hydroxy-5-[(4-hydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl)-5h-furan-2-one)

INCHI for NP0176069 (4-(3a-hydroxy-7-{[4-hydroxy-5-({4-hydroxy-5-[(4-hydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl)-5h-furan-2-one)

Structure for NP0176069 (4-(3a-hydroxy-7-{[4-hydroxy-5-({4-hydroxy-5-[(4-hydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl)-5h-furan-2-one)

3D Structure for NP0176069 (4-(3a-hydroxy-7-{[4-hydroxy-5-({4-hydroxy-5-[(4-hydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-6-methyloxan-2-yl]oxy}-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl)-5h-furan-2-one)