NP-MRD: Showing NP-Card for (1r,3as,3br,5as,7s,9ar,9bs,11ar)-3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid (NP0199748)

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Record Information

Version

2.0

Created at

2022-09-04 18:26:58 UTC

Updated at

2022-09-04 18:26:58 UTC

NP-MRD ID

NP0199748

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3as,3br,5as,7s,9ar,9bs,11ar)-3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid

Description

(1S,2R,5S,7S,10R,11S,14R,15R)-11-hydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecane-2-carboxylic acid 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. (1r,3as,3br,5as,7s,9ar,9bs,11ar)-3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid is found in Asclepias subulata. Based on a literature review very few articles have been published on (1S,2R,5S,7S,10R,11S,14R,15R)-11-hydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecane-2-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042220262D          

 40 45  0  0  1  0            999 V2000
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2974   -2.2757    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1095   -2.1305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6413   -2.7612    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4534   -2.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9852   -3.2467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
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 11 12  1  1  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
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 15 16  1  6  0  0  0
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 11 24  1  0  0  0  0
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  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
 27 29  1  0  0  0  0
  6 30  1  0  0  0  0
  2 30  1  0  0  0  0
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 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  2 34  1  0  0  0  0
 34 35  1  1  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 35 40  1  0  0  0  0
M  END

     RDKit          3D

 82 87  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309042220262D          

 40 45  0  0  1  0            999 V2000
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.1095   -2.1305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6413   -2.7612    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4534   -2.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9852   -3.2467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3610   -3.5371    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.8928   -4.1678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5489   -3.6824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2686   -4.4583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0171   -3.0516    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2049   -3.1969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4772   -3.4514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5807   -3.4873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3708   -0.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7912   -3.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1084   -4.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0816   -5.2209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4570   -3.8899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7373   -3.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  1  0  0  0
 11 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  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
 27 29  1  0  0  0  0
  6 30  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  2 34  1  0  0  0  0
 34 35  1  1  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 35 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0199748

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@H](CC[C@]34C(O)=O)O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@]1(O)CC[C@@H]2C1=CC(=O)OC1

> <INCHI_IDENTIFIER>
InChI=1S/C29H42O11/c1-27-7-5-18-19(29(27,37)9-6-17(27)14-10-21(31)38-13-14)3-2-15-11-16(4-8-28(15,18)26(35)36)39-25-24(34)23(33)22(32)20(12-30)40-25/h10,15-20,22-25,30,32-34,37H,2-9,11-13H2,1H3,(H,35,36)/t15-,16-,17+,18-,19+,20+,22+,23-,24+,25+,27+,28+,29-/m0/s1

> <INCHI_KEY>
SXVHBFOGLKOOJH-KBGAPDEESA-N

> <FORMULA>
C29H42O11

> <MOLECULAR_WEIGHT>
566.644

> <EXACT_MASS>
566.272712172

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
59.22448249579728

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,7S,10R,11S,14R,15R)-11-hydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-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}]heptadecane-2-carboxylic acid

> <JCHEM_LOGP>
0.4882115403333328

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.183036037885271

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.150897879932529

> <JCHEM_PKA_STRONGEST_BASIC>
0.2689242446179112

> <JCHEM_POLAR_SURFACE_AREA>
183.20999999999998

> <JCHEM_REFRACTIVITY>
137.77110000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,7S,10R,11S,14R,15R)-11-hydroxy-15-methyl-14-(5-oxo-2H-furan-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}]heptadecane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      17.355  -4.248   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      18.871  -3.977   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      19.864  -5.154   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.380  -4.883   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      22.372  -6.061   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      19.341  -6.603   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      20.333  -7.780   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      17.825  -6.874   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      17.301  -8.322   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      16.832  -5.696   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      15.316  -5.967   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.224  -6.443   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      12.284  -6.510   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.210  -7.342   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.936  -8.206   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       3.886  -9.746   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       2.720  -7.261   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       3.243  -5.813   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   30   34                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    7   30                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   26                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   24                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   13   23                                                  
CONECT   23   22                                                            
CONECT   24   11   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    9    5   27                                             
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30    6    2   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33    2   35                                                  
CONECT   35   34   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   35                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,5S,7S,10R,11S,14R,15R)-11-Hydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0,.0,]heptadecane-2-carboxylate	Generator

Chemical Formula

C₂₉H₄₂O₁₁

Average Mass

566.6440 Da

Monoisotopic Mass

566.27271 Da

IUPAC Name

Traditional Name

(1S,2R,5S,7S,10R,11S,14R,15R)-11-hydroxy-15-methyl-14-(5-oxo-2H-furan-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}]heptadecane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@H](CC[C@]34C(O)=O)O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@]1(O)CC[C@@H]2C1=CC(=O)OC1

InChI Identifier

InChI=1S/C29H42O11/c1-27-7-5-18-19(29(27,37)9-6-17(27)14-10-21(31)38-13-14)3-2-15-11-16(4-8-28(15,18)26(35)36)39-25-24(34)23(33)22(32)20(12-30)40-25/h10,15-20,22-25,30,32-34,37H,2-9,11-13H2,1H3,(H,35,36)/t15-,16-,17+,18-,19+,20+,22+,23-,24+,25+,27+,28+,29-/m0/s1

InChI Key

SXVHBFOGLKOOJH-KBGAPDEESA-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
Asclepias subulata	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-hydroxysteroid
19-oxosteroid
Oxosteroid
Hydroxysteroid
14-hydroxysteroid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Dicarboxylic acid or derivatives
2-furanone
Oxane
Monosaccharide
Fatty acyl
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Lactone
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Carboxylic acid
Acetal
Oxacycle
Organoheterocyclic compound
Carbonyl group
Organic oxide
Primary alcohol
Hydrocarbon derivative
Alcohol
Organic oxygen compound
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	0.49	ChemAxon
pKa (Strongest Acidic)	4.15	ChemAxon
pKa (Strongest Basic)	0.27	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	183.21 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	137.77 m³·mol⁻¹	ChemAxon
Polarizability	59.22 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

162875549

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3as,3br,5as,7s,9ar,9bs,11ar)-3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid (NP0199748)

MOL for NP0199748 ((1r,3as,3br,5as,7s,9ar,9bs,11ar)-3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid)

3D MOL for NP0199748 ((1r,3as,3br,5as,7s,9ar,9bs,11ar)-3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid)

3D SDF for NP0199748 ((1r,3as,3br,5as,7s,9ar,9bs,11ar)-3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid)

3D-SDF for NP0199748 ((1r,3as,3br,5as,7s,9ar,9bs,11ar)-3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid)

PDB for NP0199748 ((1r,3as,3br,5as,7s,9ar,9bs,11ar)-3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid)

3D PDB for NP0199748 ((1r,3as,3br,5as,7s,9ar,9bs,11ar)-3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid)

SMILES for NP0199748 ((1r,3as,3br,5as,7s,9ar,9bs,11ar)-3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid)

INCHI for NP0199748 ((1r,3as,3br,5as,7s,9ar,9bs,11ar)-3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid)

Structure for NP0199748 ((1r,3as,3br,5as,7s,9ar,9bs,11ar)-3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid)

3D Structure for NP0199748 ((1r,3as,3br,5as,7s,9ar,9bs,11ar)-3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-tetradecahydrocyclopenta[a]phenanthrene-9a-carboxylic acid)