NP-MRD: Showing NP-Card for 3a-hydroxy-7-({4-hydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate (NP0197417)

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Record Information

Version

2.0

Created at

2022-09-04 15:40:36 UTC

Updated at

2022-09-04 15:40:36 UTC

NP-MRD ID

NP0197417

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

11-Hydroxy-5-({4-hydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-13-yl acetate belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety. 3a-hydroxy-7-({4-hydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate is found in Cryptostegia grandiflora. 11-Hydroxy-5-({4-hydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-13-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261505372D          

 61 68  0  0  0  0            999 V2000
    8.6935    6.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8814    6.6199    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
    8.1329    5.2133    0.0000 C   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
    8.3844    3.8066    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
    8.6360    2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4481    2.5452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3557    1.6241    0.0000 C   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
    7.2632    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
    0.5607    0.9312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4155    1.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3604    2.0237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0452   -1.5420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8377   -1.7713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2889   -1.5854    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
    7.0117    2.1096    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0405    4.2921    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2572    6.3295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3496    7.2506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.4420    8.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9738    7.5410    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
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    5.7541    9.1427    0.0000 O   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
    5.1935    7.5909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 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
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 21 30  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 28 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 27 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
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 18 42  1  0  0  0  0
 13 42  1  0  0  0  0
 11 43  1  0  0  0  0
 43 44  1  0  0  0  0
  7 44  1  0  0  0  0
 44 45  1  0  0  0  0
  5 46  1  0  0  0  0
 46 47  1  0  0  0  0
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  3 49  1  0  0  0  0
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 53 56  1  0  0  0  0
 56 57  1  0  0  0  0
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 58 59  1  0  0  0  0
 58 60  1  0  0  0  0
 51 60  1  0  0  0  0
 60 61  1  0  0  0  0
M  END

     RDKit          3D

129136  0  0  0  0  0  0  0  0999 V2000
    8.6514   -2.9700   -1.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1015   -2.5057    0.0312 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9648   -1.5557    0.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2894   -0.5311    1.0106 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0089   -0.2399    0.4750 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1390    0.5148    1.7430 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1850    0.0939    2.8405 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3965    1.0688    0.7280 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1140    2.0913   -0.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5709    1.8396   -0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.7164    0.9978   -0.9954 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -7.5982   -0.6677   -0.7441 C   0  0  2  0  0  0  0  0  0  0  0  0
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   11.6120   -1.3703   -0.4723 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004261505372D          

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M  END
> <DATABASE_ID>
NP0197417

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1CC(OC2C(O)CC(OC3CCC4(C)C(CCC5C4CCC4(C)C(C(CC54O)OC(C)=O)C4=CC(=O)OC4)C3)OC2C)OC(C)C1OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C44H68O17/c1-20-39(60-34-16-29(53-6)40(21(2)56-34)61-41-38(51)37(50)36(49)31(18-45)59-41)28(47)15-33(55-20)58-25-9-11-42(4)24(14-25)7-8-27-26(42)10-12-43(5)35(23-13-32(48)54-19-23)30(57-22(3)46)17-44(27,43)52/h13,20-21,24-31,33-41,45,47,49-52H,7-12,14-19H2,1-6H3

> <INCHI_KEY>
SGGQTRPBTCNENJ-UHFFFAOYSA-N

> <FORMULA>
C44H68O17

> <MOLECULAR_WEIGHT>
869.011

> <EXACT_MASS>
868.44565073

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
129

> <JCHEM_AVERAGE_POLARIZABILITY>
93.25394059317372

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
11-hydroxy-5-({4-hydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-13-yl acetate

> <ALOGPS_LOGP>
0.99

> <JCHEM_LOGP>
1.352636820333335

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.196677705101324

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.819475535744042

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083565219918

> <JCHEM_POLAR_SURFACE_AREA>
238.58999999999995

> <JCHEM_REFRACTIVITY>
210.22330000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-hydroxy-5-({4-hydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-2,15-dimethyl-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-13-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      16.228  12.628   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      14.712  12.357   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      14.189  10.909   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.181   9.731   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.658   8.283   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      15.651   7.106   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      15.128   5.657   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.120   4.480   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      17.636   4.751   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      15.597   3.032   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.081   2.761   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.355   2.629   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       1.047   1.738   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.776   3.254   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.673   3.777   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.953   4.247   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.439  -1.430   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.084  -2.878   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -1.564  -3.306   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       1.131  -3.824   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       2.406  -2.959   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      13.089   3.938   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      13.612   5.386   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      12.619   6.564   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      13.142   8.012   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      12.150   9.189   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      10.634   8.918   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      12.673  10.638   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      11.680  11.815   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      12.203  13.263   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      13.719  13.534   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      14.242  14.983   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      15.758  15.254   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      16.751  14.077   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      13.250  16.160   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      13.773  17.609   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      11.734  15.889   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      10.741  17.066   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      11.211  14.441   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0       9.695  14.170   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   49                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   46                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   44                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   43                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   42                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   22                                             
CONECT   17   16                                                            
CONECT   18   16   19   42                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   16   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27   30                                             
CONECT   26   25                                                            
CONECT   27   25   28   36                                                  
CONECT   28   27   29   32                                                  
CONECT   29   28   30                                                       
CONECT   30   29   21   25   31                                             
CONECT   31   30                                                            
CONECT   32   28   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   27   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   36                                                       
CONECT   42   18   13                                                       
CONECT   43   11   44                                                       
CONECT   44   43    7   45                                                  
CONECT   45   44                                                            
CONECT   46    5   47                                                       
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47    3   50                                                  
CONECT   50   49   51                                                       
CONECT   51   50   52   60                                                  
CONECT   52   51   53                                                       
CONECT   53   52   54   56                                                  
CONECT   54   53   55                                                       
CONECT   55   54                                                            
CONECT   56   53   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58   51   61                                                  
CONECT   61   60                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  136    0
END

View in JSmol

Synonyms

Value	Source
11-Hydroxy-5-({4-hydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0,.0,]heptadecan-13-yl acetic acid	Generator
11-Hydroxy-5-({4-hydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-13-yl acetic acid	Generator

Chemical Formula

C₄₄H₆₈O₁₇

Average Mass

869.0110 Da

Monoisotopic Mass

868.44565 Da

IUPAC Name

11-hydroxy-5-({4-hydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-13-yl acetate

Traditional Name

11-hydroxy-5-({4-hydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-2,15-dimethyl-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-13-yl acetate

CAS Registry Number

Not Available

SMILES

COC1CC(OC2C(O)CC(OC3CCC4(C)C(CCC5C4CCC4(C)C(C(CC54O)OC(C)=O)C4=CC(=O)OC4)C3)OC2C)OC(C)C1OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C44H68O17/c1-20-39(60-34-16-29(53-6)40(21(2)56-34)61-41-38(51)37(50)36(49)31(18-45)59-41)28(47)15-33(55-20)58-25-9-11-42(4)24(14-25)7-8-27-26(42)10-12-43(5)35(23-13-32(48)54-19-23)30(57-22(3)46)17-44(27,43)52/h13,20-21,24-31,33-41,45,47,49-52H,7-12,14-19H2,1-6H3

InChI Key

SGGQTRPBTCNENJ-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
Cryptostegia grandiflora	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
Steroid ester
14-hydroxysteroid
Hydroxysteroid
Glycosyl compound
O-glycosyl compound
2-furanone
Oxane
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Cyclic alcohol
Dihydrofuran
Secondary alcohol
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Ether
Acetal
Organic oxygen compound
Primary alcohol
Carbonyl group
Alcohol
Hydrocarbon derivative
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	0.99	ALOGPS
logP	1.35	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	6.82	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	238.59 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	210.22 m³·mol⁻¹	ChemAxon
Polarizability	93.25 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

78200696

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3a-hydroxy-7-({4-hydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate (NP0197417)

MOL for NP0197417 (3a-hydroxy-7-({4-hydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate)

3D MOL for NP0197417 (3a-hydroxy-7-({4-hydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate)

3D SDF for NP0197417 (3a-hydroxy-7-({4-hydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate)

3D-SDF for NP0197417 (3a-hydroxy-7-({4-hydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate)

PDB for NP0197417 (3a-hydroxy-7-({4-hydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate)

3D PDB for NP0197417 (3a-hydroxy-7-({4-hydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate)

SMILES for NP0197417 (3a-hydroxy-7-({4-hydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate)

INCHI for NP0197417 (3a-hydroxy-7-({4-hydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate)

Structure for NP0197417 (3a-hydroxy-7-({4-hydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate)

3D Structure for NP0197417 (3a-hydroxy-7-({4-hydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-methyloxan-2-yl}oxy)-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate)