NP-MRD: Showing NP-Card for 6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-4-hydroxy-2-methyloxan-3-yl acetate (NP0153891)

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Record Information

Version

2.0

Created at

2022-09-02 10:37:22 UTC

Updated at

2022-09-02 10:37:22 UTC

NP-MRD ID

NP0153891

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-4-hydroxy-2-methyloxan-3-yl acetate

Description

Beta-Acetyldigitoxin 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. 6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-4-hydroxy-2-methyloxan-3-yl acetate is found in Digitalis ferruginea. Beta-Acetyldigitoxin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004181502342D          

 57 64  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
    8.4708   10.3543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7223    8.9477    0.0000 C   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
    7.6011    5.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8814    6.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1329    5.2133    0.0000 O   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
    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
    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
  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  2  0  0  0  0
 22 24  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 16 27  1  0  0  0  0
 14 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 10 30  1  0  0  0  0
  4 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 35 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 40 49  1  0  0  0  0
 44 49  1  0  0  0  0
 49 50  1  0  0  0  0
 46 51  1  0  0  0  0
 51 52  2  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 53 55  1  0  0  0  0
 55 56  1  0  0  0  0
 51 56  1  0  0  0  0
 37 57  1  0  0  0  0
 32 57  1  0  0  0  0
M  END

     RDKit          3D

123130  0  0  0  0  0  0  0  0999 V2000
  -13.9427    2.6723    2.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6545    1.6235    1.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -12.1172    0.1910   -0.1471 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.2974    0.6288   -1.3141 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.4311   -0.4734   -2.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9386    0.7157   -1.0223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4140   -0.5217   -0.6514 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.0407   -0.2967   -0.3904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2410   -1.0371   -1.2702 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4007   -1.9750   -0.4478 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7456   -2.9191   -1.2265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3867   -1.1585    0.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5659   -0.3078   -0.6267 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2317   -0.6798   -0.4595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4290    0.3206    0.0560 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3651    0.7940   -0.9076 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4999   -0.2048   -1.2815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5826    1.8672   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0890    1.0936    1.0130 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8133    0.1192    0.4060 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1778    0.1860    0.5163 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6874   -1.1196    1.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0916   -1.4550    0.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8524    0.4109    1.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2197   -0.2350    0.2439 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0357   -0.1719    1.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.5416   -0.8020   -0.5335 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6463   -0.0628   -0.6092 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7929   -0.8387   -0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0092   -0.4640   -0.0815 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3285   -2.0782    0.2028 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9352   -2.1338   -0.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2608    1.1215   -1.4472 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7740    1.4914   -1.4061 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4458    1.0167    0.0065 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0327    1.9990    0.8453 O   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.6272   -0.4391   -3.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4399   -1.4822   -1.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.8983   -1.6211   -1.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4565   -3.4728   -1.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8943   -0.5171    1.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7462   -1.8972    0.8747 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004181502342D          

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M  END
> <DATABASE_ID>
NP0153891

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C43H66O14/c1-21-38(54-24(4)44)31(45)18-36(52-21)56-40-23(3)53-37(19-33(40)47)57-39-22(2)51-35(17-32(39)46)55-27-9-12-41(5)26(16-27)7-8-30-29(41)10-13-42(6)28(11-14-43(30,42)49)25-15-34(48)50-20-25/h15,21-23,26-33,35-40,45-47,49H,7-14,16-20H2,1-6H3

> <INCHI_KEY>
AFTNEYIAJGSGIX-UHFFFAOYSA-N

> <FORMULA>
C43H66O14

> <MOLECULAR_WEIGHT>
806.987

> <EXACT_MASS>
806.445256805

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
123

> <JCHEM_AVERAGE_POLARIZABILITY>
89.07081617888778

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-6-({4-hydroxy-6-[(4-hydroxy-6-{[11-hydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-2-methyloxan-3-yl)oxy]-2-methyloxan-3-yl}oxy)-2-methyloxan-3-yl acetate

> <ALOGPS_LOGP>
2.85

> <JCHEM_LOGP>
4.0386171493333345

> <ALOGPS_LOGS>
-4.82

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.463783784052389

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.182635995734942

> <JCHEM_PKA_STRONGEST_BASIC>
0.24222921447765167

> <JCHEM_POLAR_SURFACE_AREA>
188.89999999999998

> <JCHEM_REFRACTIVITY>
200.86880000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-6-({4-hydroxy-6-[(4-hydroxy-6-{[11-hydroxy-2,15-dimethyl-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-2-methyloxan-3-yl)oxy]-2-methyloxan-3-yl}oxy)-2-methyloxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-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      15.812  19.328   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      16.282  16.702   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.242  14.983   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.758  15.254   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      13.719  13.534   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      14.189  10.909   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.712  12.357   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      15.181   9.731   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       5.355   2.629   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       2.406  -2.959   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       1.131  -3.824   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       1.081  -5.363   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      -0.084  -2.878   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0       0.439  -1.430   0.000  0.00  0.00           C+0
HETATM   57  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   31                                                  
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   30                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   28                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   27                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   16                                                       
CONECT   28   14   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   10                                                       
CONECT   31    4   32                                                       
CONECT   32   31   33   57                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37   41                                             
CONECT   36   35                                                            
CONECT   37   35   38   57                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41   49                                                  
CONECT   41   40   35   42                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45   46   49                                             
CONECT   45   44                                                            
CONECT   46   44   47   51                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   40   44   50                                             
CONECT   50   49                                                            
CONECT   51   46   52   56                                                  
CONECT   52   51   53                                                       
CONECT   53   52   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   56                                                       
CONECT   56   55   51                                                       
CONECT   57   37   32                                                       
MASTER        0    0    0    0    0    0    0    0   57    0  128    0
END

View in JSmol

Synonyms

Value	Source
b-Acetyldigitoxin	Generator
Β-acetyldigitoxin	Generator

Chemical Formula

C₄₃H₆₆O₁₄

Average Mass

806.9870 Da

Monoisotopic Mass

806.44526 Da

IUPAC Name

4-hydroxy-6-({4-hydroxy-6-[(4-hydroxy-6-{[11-hydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-2-methyloxan-3-yl)oxy]-2-methyloxan-3-yl}oxy)-2-methyloxan-3-yl acetate

Traditional Name

4-hydroxy-6-({4-hydroxy-6-[(4-hydroxy-6-{[11-hydroxy-2,15-dimethyl-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-2-methyloxan-3-yl)oxy]-2-methyloxan-3-yl}oxy)-2-methyloxan-3-yl acetate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C43H66O14/c1-21-38(54-24(4)44)31(45)18-36(52-21)56-40-23(3)53-37(19-33(40)47)57-39-22(2)51-35(17-32(39)46)55-27-9-12-41(5)26(16-27)7-8-30-29(41)10-13-42(6)28(11-14-43(30,42)49)25-15-34(48)50-20-25/h15,21-23,26-33,35-40,45-47,49H,7-14,16-20H2,1-6H3

InChI Key

AFTNEYIAJGSGIX-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 ferruginea	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
Dicarboxylic acid or derivatives
Oxane
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	2.85	ALOGPS
logP	4.04	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	0.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	188.9 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	200.87 m³·mol⁻¹	ChemAxon
Polarizability	89.07 Å³	ChemAxon
Number of Rings	8	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

164799

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-4-hydroxy-2-methyloxan-3-yl acetate (NP0153891)

MOL for NP0153891 (6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-4-hydroxy-2-methyloxan-3-yl acetate)

3D MOL for NP0153891 (6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-4-hydroxy-2-methyloxan-3-yl acetate)

3D SDF for NP0153891 (6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-4-hydroxy-2-methyloxan-3-yl acetate)

3D-SDF for NP0153891 (6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-4-hydroxy-2-methyloxan-3-yl acetate)

PDB for NP0153891 (6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-4-hydroxy-2-methyloxan-3-yl acetate)

3D PDB for NP0153891 (6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-4-hydroxy-2-methyloxan-3-yl acetate)

SMILES for NP0153891 (6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-4-hydroxy-2-methyloxan-3-yl acetate)

INCHI for NP0153891 (6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-4-hydroxy-2-methyloxan-3-yl acetate)

Structure for NP0153891 (6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-4-hydroxy-2-methyloxan-3-yl acetate)

3D Structure for NP0153891 (6-({6-[(6-{[3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-4-hydroxy-2-methyloxan-3-yl)oxy]-4-hydroxy-2-methyloxan-3-yl}oxy)-4-hydroxy-2-methyloxan-3-yl acetate)