NP-MRD: Showing NP-Card for 2,3a,5a-trihydroxy-7-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde (NP0196182)

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Record Information

Version

2.0

Created at

2022-09-04 14:12:53 UTC

Updated at

2022-09-04 14:12:53 UTC

NP-MRD ID

NP0196182

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,3a,5a-trihydroxy-7-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde

Description

7,11,13-Trihydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecane-2-carbaldehyde 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. 2,3a,5a-trihydroxy-7-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde is found in Strophanthus kombe. 7,11,13-Trihydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecane-2-carbaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251505142D          

 62 69  0  0  0  0            999 V2000
   -3.6264   -3.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0946   -4.1952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2825   -4.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0022   -3.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901   -3.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098   -2.3529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -2.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -1.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -1.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -1.9173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069   -1.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751   -0.5107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -1.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -1.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3228   -0.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -1.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -2.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7927   -2.5812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -2.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -2.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4850   -3.0585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7781   -3.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -2.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9660   -3.4691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0646   -0.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7474    0.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7742    1.2229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3987   -0.1080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9385   -4.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4067   -5.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7507   -4.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0310   -5.4566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8431   -5.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3749   -4.9711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1870   -5.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7188   -4.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4385   -3.7097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9704   -3.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7825   -3.2242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3143   -2.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1264   -2.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6582   -2.1080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0340   -1.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5658   -1.1869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2219   -1.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9416   -0.8965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6901   -2.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8779   -2.1579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4673   -5.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2794   -6.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9355   -6.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2158   -7.2989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5916   -7.0085    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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 10 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
 19 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
 22 24  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 10 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
  7 29  1  0  0  0  0
 18 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 30 35  1  0  0  0  0
  5 36  1  0  0  0  0
 36 37  1  0  0  0  0
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 37 39  1  0  0  0  0
  3 39  1  0  0  0  0
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 43 44  1  0  0  0  0
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 45 46  1  0  0  0  0
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 47 48  1  0  0  0  0
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 49 50  1  0  0  0  0
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 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
 53 54  1  0  0  0  0
 53 55  1  0  0  0  0
 46 55  1  0  0  0  0
 55 56  1  0  0  0  0
 43 57  1  0  0  0  0
 57 58  1  0  0  0  0
 57 59  1  0  0  0  0
 59 60  1  0  0  0  0
 59 61  1  0  0  0  0
 41 61  1  0  0  0  0
 61 62  1  0  0  0  0
M  END

     RDKit          3D

126133  0  0  0  0  0  0  0  0999 V2000
    2.0798    3.5279    0.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3663    2.7836   -0.5143 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5921    1.6282   -0.5713 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5661    1.9052   -1.6632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2264    0.5965   -1.8029 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.0188    0.1972   -0.4066 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3854   -1.1987    0.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8994   -1.3245   -0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5322   -0.3224    0.8281 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1662   -0.6374    2.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5773    0.0720    3.1651 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.5701   -1.7278    1.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0802   -1.5283    1.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6604   -1.1075    0.0600 C   0  0  1  0  0  0  0  0  0  0  0  0
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  -11.0173   -0.3646    0.7198 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.8914   -1.0869   -1.5908 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3378    0.7603    2.3884 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004251505142D          

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M  END
> <DATABASE_ID>
NP0196182

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1CC(OC2CCC3(C=O)C4CCC5(C)C(C(O)CC5(O)C4CCC3(O)C2)C2=CC(=O)OC2)OC(C)C1OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C42H64O20/c1-18-36(62-38-35(52)33(50)31(48)26(61-38)16-57-37-34(51)32(49)30(47)25(14-43)60-37)24(55-3)11-28(58-18)59-20-4-8-40(17-44)21-5-7-39(2)29(19-10-27(46)56-15-19)23(45)13-42(39,54)22(21)6-9-41(40,53)12-20/h10,17-18,20-26,28-38,43,45,47-54H,4-9,11-16H2,1-3H3

> <INCHI_KEY>
BJRXMZMULNHQIY-UHFFFAOYSA-N

> <FORMULA>
C42H64O20

> <MOLECULAR_WEIGHT>
888.954

> <EXACT_MASS>
888.399094461

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_ATOM_COUNT>
126

> <JCHEM_AVERAGE_POLARIZABILITY>
92.47184103770657

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7,11,13-trihydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-2-carbaldehyde

> <ALOGPS_LOGP>
-2.01

> <JCHEM_LOGP>
-3.2350540439999995

> <ALOGPS_LOGS>
-2.70

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.908408506505273

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.831021978888354

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2035897614064712

> <JCHEM_POLAR_SURFACE_AREA>
310.28

> <JCHEM_REFRACTIVITY>
206.4025

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.77e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,11,13-trihydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-15-methyl-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-2-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -6.769  -6.654   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.777  -7.831   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.261  -7.560   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.737  -6.112   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.221  -5.841   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.698  -4.392   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.182  -4.121   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.341  -2.673   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.857  -2.402   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.850  -3.579   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.373  -2.131   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.380  -0.953   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.366  -3.308   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.889  -1.859   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.405  -1.588   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.398  -2.766   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.069  -1.380   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.937  -2.816   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.365  -4.295   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.813  -4.818   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.090  -5.159   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.874  -4.214   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.505  -5.709   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.358  -4.485   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.835  -5.934   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.319  -6.205   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.326  -5.027   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.803  -6.476   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.810  -5.298   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.882  -1.600   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.454  -0.121   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.728   0.744   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      10.779   2.283   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      11.944  -0.202   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      11.421  -1.650   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -1.229  -7.018   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -1.752  -8.466   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.759  -9.644   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -3.268  -8.737   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -3.791 -10.186   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -5.307 -10.457   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -6.300  -9.279   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -7.816  -9.551   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -8.809  -8.373   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -8.285  -6.925   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -9.278  -5.747   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0     -10.794  -6.019   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0     -11.787  -4.841   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -13.303  -5.112   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0     -14.295  -3.935   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0     -11.263  -3.393   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0     -12.256  -2.216   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      -9.748  -3.122   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      -9.224  -1.673   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      -8.755  -4.299   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      -7.239  -4.028   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      -8.339 -10.999   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      -9.855 -11.270   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      -7.346 -12.176   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      -7.869 -13.625   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0      -5.830 -11.905   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      -4.838 -13.082   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   39                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   36                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   29                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   13   27                                             
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   22                                             
CONECT   17   16                                                            
CONECT   18   16   19   30                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   16   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   13   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   10   28   29                                             
CONECT   28   27                                                            
CONECT   29   27    7                                                       
CONECT   30   18   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   30                                                       
CONECT   36    5   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37    3   40                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   61                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   57                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47   55                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   51                                                  
CONECT   49   48   50                                                       
CONECT   50   49                                                            
CONECT   51   48   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   46   56                                                  
CONECT   56   55                                                            
CONECT   57   43   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57   60   61                                                  
CONECT   60   59                                                            
CONECT   61   59   41   62                                                  
CONECT   62   61                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  138    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₂H₆₄O₂₀

Average Mass

888.9540 Da

Monoisotopic Mass

888.39909 Da

IUPAC Name

7,11,13-trihydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-2-carbaldehyde

Traditional Name

7,11,13-trihydroxy-5-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-15-methyl-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-2-carbaldehyde

CAS Registry Number

Not Available

SMILES

COC1CC(OC2CCC3(C=O)C4CCC5(C)C(C(O)CC5(O)C4CCC3(O)C2)C2=CC(=O)OC2)OC(C)C1OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C42H64O20/c1-18-36(62-38-35(52)33(50)31(48)26(61-38)16-57-37-34(51)32(49)30(47)25(14-43)60-37)24(55-3)11-28(58-18)59-20-4-8-40(17-44)21-5-7-39(2)29(19-10-27(46)56-15-19)23(45)13-42(39,54)22(21)6-9-41(40,53)12-20/h10,17-18,20-26,28-38,43,45,47-54H,4-9,11-16H2,1-3H3

InChI Key

BJRXMZMULNHQIY-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
Strophanthus kombe	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
19-oxosteroid
14-hydroxysteroid
5-hydroxysteroid
Hydroxysteroid
16-hydroxysteroid
Oxosteroid
Disaccharide
Glycosyl compound
O-glycosyl compound
2-furanone
Oxane
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Primary alcohol
Aldehyde
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	ALOGPS
logP	-3.2	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	6.83	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	310.28 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	206.4 m³·mol⁻¹	ChemAxon
Polarizability	92.47 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,3a,5a-trihydroxy-7-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde (NP0196182)

MOL for NP0196182 (2,3a,5a-trihydroxy-7-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

3D MOL for NP0196182 (2,3a,5a-trihydroxy-7-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

3D SDF for NP0196182 (2,3a,5a-trihydroxy-7-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

3D-SDF for NP0196182 (2,3a,5a-trihydroxy-7-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

PDB for NP0196182 (2,3a,5a-trihydroxy-7-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

3D PDB for NP0196182 (2,3a,5a-trihydroxy-7-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

SMILES for NP0196182 (2,3a,5a-trihydroxy-7-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

INCHI for NP0196182 (2,3a,5a-trihydroxy-7-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

Structure for NP0196182 (2,3a,5a-trihydroxy-7-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)

3D Structure for NP0196182 (2,3a,5a-trihydroxy-7-[(4-methoxy-6-methyl-5-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthrene-9a-carbaldehyde)