NP-MRD: Showing NP-Card for (1r,3as,3br,5as,7s,9as,9bs,11ar)-9a-formyl-3a-hydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-5a-yl acetate (NP0236020)

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Record Information

Version

2.0

Created at

2022-09-06 18:48:56 UTC

Updated at

2022-09-06 18:48:56 UTC

NP-MRD ID

NP0236020

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3as,3br,5as,7s,9as,9bs,11ar)-9a-formyl-3a-hydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-5a-yl acetate

Description

Thesiuside belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. (1r,3as,3br,5as,7s,9as,9bs,11ar)-9a-formyl-3a-hydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-5a-yl acetate is found in Kalanchoe laciniata. (1r,3as,3br,5as,7s,9as,9bs,11ar)-9a-formyl-3a-hydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-5a-yl acetate was first documented in 1987 (PMID: 3444621). Based on a literature review very few articles have been published on Thesiuside (PMID: 9226414).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062220482D          

 44 49  0  0  1  0            999 V2000
   -0.9259   -3.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6456   -2.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1665   -2.7171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1774   -2.2316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8971   -1.4557    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3653   -2.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4468   -1.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7271   -1.1653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1953   -0.5346    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4756    0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2877    0.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8195   -0.2441    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.6441   -0.2709    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1505    0.3804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8396    1.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1632    1.6830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4741    0.9189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
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 33 42  1  0  0  0  0
 42 43  1  1  0  0  0
 31 44  1  0  0  0  0
  5 44  1  0  0  0  0
M  END

     RDKit          3D

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 27 70  1  0
M  END


  Mrv1652309062220482D          

 44 49  0  0  1  0            999 V2000
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   -0.6456   -2.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1665   -2.7171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1774   -2.2316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8971   -1.4557    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3653   -2.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4468   -1.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7271   -1.1653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1953   -0.5346    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4756    0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2877    0.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8195   -0.2441    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1794    0.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6441   -0.2709    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1505    0.3804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8396    1.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3459    1.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1632    1.6830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6695    2.3344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4741    0.9189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9677    0.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8734   -1.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1906   -1.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392   -1.0201    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3416   -1.8210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6168   -0.6798    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3365    0.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8683    0.7268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1486   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9608   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2411   -0.9702    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0532   -1.1154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5850   -0.4847    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3971   -0.6299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9289    0.0008    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7411   -0.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0214   -0.9204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6486    0.7767    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1805    1.4074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8365    0.9219    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5562    1.6978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3047    0.2912    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4926    0.4364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7092   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  2  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  8 24  1  0  0  0  0
 12 24  1  0  0  0  0
 24 25  1  1  0  0  0
  9 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  2  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  1  0  0  0
 33 32  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  6  0  0  0
 36 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
 40 41  1  6  0  0  0
 40 42  1  0  0  0  0
 33 42  1  0  0  0  0
 42 43  1  1  0  0  0
 31 44  1  0  0  0  0
  5 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0236020

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@]12CC[C@@H]3[C@H](CC[C@]4(C)[C@H](CC[C@]34O)C3=COC(=O)C=C3)[C@]1(CC[C@@H](C2)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H44O12/c1-17(35)44-31-11-7-22-21(6-9-29(2)20(8-12-32(22,29)40)18-3-4-24(36)41-15-18)30(31,16-34)10-5-19(13-31)42-28-27(39)26(38)25(37)23(14-33)43-28/h3-4,15-16,19-23,25-28,33,37-40H,5-14H2,1-2H3/t19-,20+,21-,22+,23+,25+,26-,27+,28+,29+,30-,31-,32-/m0/s1

> <INCHI_KEY>
QLPDNWKGCHCDMK-KXPUILCXSA-N

> <FORMULA>
C32H44O12

> <MOLECULAR_WEIGHT>
620.692

> <EXACT_MASS>
620.283276857

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
64.47316950596178

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5S,7S,10R,11S,14S,15R)-2-formyl-11-hydroxy-15-methyl-14-(2-oxo-2H-pyran-5-yl)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-7-yl acetate

> <JCHEM_LOGP>
-0.25196615600000155

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.200095053471589

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.210574231898722

> <JCHEM_PKA_STRONGEST_BASIC>
0.2958843149188227

> <JCHEM_POLAR_SURFACE_AREA>
189.27999999999997

> <JCHEM_REFRACTIVITY>
152.3298

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,7S,10R,11S,14S,15R)-2-formyl-11-hydroxy-15-methyl-14-(6-oxopyran-3-yl)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-7-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.728  -6.791   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.205  -5.343   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.311  -5.072   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.198  -4.166   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.675  -2.717   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.682  -3.895   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.834  -3.624   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.357  -2.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.365  -0.998   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.888   0.451   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.404   0.722   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.396  -0.456   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.068   0.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.936  -0.506   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.881   0.710   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.301   2.137   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.246   3.352   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.771   3.142   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.716   4.357   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.352   1.715   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.406   0.499   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.364  -1.985   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.089  -2.849   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.873  -1.904   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.504  -3.399   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.151  -1.269   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.628   0.179   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.621   1.357   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.144  -0.092   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.660  -0.363   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.183  -1.811   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -5.699  -2.082   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -6.692  -0.905   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -8.208  -1.176   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -9.201   0.001   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -10.717  -0.270   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0     -11.240  -1.718   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -8.677   1.450   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -9.670   2.627   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -7.162   1.721   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -6.638   3.169   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -6.169   0.544   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -4.653   0.815   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -3.191  -2.988   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   26   44                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   24                                                  
CONECT    9    8   10   26                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   24                                             
CONECT   13   12                                                            
CONECT   14   12   15   22                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   15                                                       
CONECT   22   14   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    8   12   25                                             
CONECT   25   24                                                            
CONECT   26    9    5   27   29                                             
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   44                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   42                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   38                                                  
CONECT   36   35   37                                                       
CONECT   37   36                                                            
CONECT   38   35   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   33   43                                                  
CONECT   43   42                                                            
CONECT   44   31    5                                                       
MASTER        0    0    0    0    0    0    0    0   44    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₄O₁₂

Average Mass

620.6920 Da

Monoisotopic Mass

620.28328 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@]12CC[C@@H]3[C@H](CC[C@]4(C)[C@H](CC[C@]34O)C3=COC(=O)C=C3)[C@]1(CC[C@@H](C2)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C=O

InChI Identifier

InChI=1S/C32H44O12/c1-17(35)44-31-11-7-22-21(6-9-29(2)20(8-12-32(22,29)40)18-3-4-24(36)41-15-18)30(31,16-34)10-5-19(13-31)42-28-27(39)26(38)25(37)23(14-33)43-28/h3-4,15-16,19-23,25-28,33,37-40H,5-14H2,1-2H3/t19-,20+,21-,22+,23+,25+,26-,27+,28+,29+,30-,31-,32-/m0/s1

InChI Key

QLPDNWKGCHCDMK-KXPUILCXSA-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
Kalanchoe laciniata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Bufanolides and derivatives

Alternative Parents

Substituents

Bufanolide-skeleton
Steroidal glycoside
Steroid ester
19-oxosteroid
14-hydroxysteroid
Hydroxysteroid
Oxosteroid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Pyranone
Monosaccharide
Oxane
Pyran
Cyclic alcohol
Heteroaromatic compound
Tertiary alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Polyol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Acetal
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxygen compound
Aldehyde
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source

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

14135794

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Van der Walt JJ, Van Rooyen JM, Kellerman TS, Carmeliet EE, Verdonck F: Neurospecificity of phyto-bufadienolides is not related to differences in Na+/K+ pump inhibition. Eur J Pharmacol. 1997 Jun 25;329(2-3):201-11. doi: 10.1016/s0014-2999(97)10091-7. [PubMed:9226414 ]
Anderson LA, Joubert JP, Schultz RA, Kellerman TS, Pienaar BJ: Experimental evidence that the active principle of the poisonous plant Thesium lineatum L.f. (Santalaceae) is a bufadienolide. Onderstepoort J Vet Res. 1987 Dec;54(4):645-50. [PubMed:3444621 ]
LOTUS database [Link]

Showing NP-Card for (1r,3as,3br,5as,7s,9as,9bs,11ar)-9a-formyl-3a-hydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-5a-yl acetate (NP0236020)

MOL for NP0236020 ((1r,3as,3br,5as,7s,9as,9bs,11ar)-9a-formyl-3a-hydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-5a-yl acetate)

3D MOL for NP0236020 ((1r,3as,3br,5as,7s,9as,9bs,11ar)-9a-formyl-3a-hydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-5a-yl acetate)

3D SDF for NP0236020 ((1r,3as,3br,5as,7s,9as,9bs,11ar)-9a-formyl-3a-hydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-5a-yl acetate)

3D-SDF for NP0236020 ((1r,3as,3br,5as,7s,9as,9bs,11ar)-9a-formyl-3a-hydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-5a-yl acetate)

PDB for NP0236020 ((1r,3as,3br,5as,7s,9as,9bs,11ar)-9a-formyl-3a-hydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-5a-yl acetate)

3D PDB for NP0236020 ((1r,3as,3br,5as,7s,9as,9bs,11ar)-9a-formyl-3a-hydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-5a-yl acetate)

SMILES for NP0236020 ((1r,3as,3br,5as,7s,9as,9bs,11ar)-9a-formyl-3a-hydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-5a-yl acetate)

INCHI for NP0236020 ((1r,3as,3br,5as,7s,9as,9bs,11ar)-9a-formyl-3a-hydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-5a-yl acetate)

Structure for NP0236020 ((1r,3as,3br,5as,7s,9as,9bs,11ar)-9a-formyl-3a-hydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-5a-yl acetate)

3D Structure for NP0236020 ((1r,3as,3br,5as,7s,9as,9bs,11ar)-9a-formyl-3a-hydroxy-11a-methyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydro-1h-cyclopenta[a]phenanthren-5a-yl acetate)