NP-MRD: Showing NP-Card for oleandrigenin (NP0238221)

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Record Information

Version

1.0

Created at

2022-09-06 21:34:31 UTC

Updated at

2022-09-06 21:34:31 UTC

NP-MRD ID

NP0238221

Secondary Accession Numbers

None

Natural Product Identification

Common Name

oleandrigenin

Description

Oleandrigenin belongs to the class of organic compounds known as cardenolides and derivatives. These are steroid lactones containing a furan-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. oleandrigenin is found in Chrysolina americana, Cryptostegia madagascariensis, Mandevilla pentlandiana and Nerium oleander. It was first documented in 1995 (PMID: 7739045). Based on a literature review a significant number of articles have been published on oleandrigenin (PMID: 10952541) (PMID: 12054363) (PMID: 12416031) (PMID: 19274509).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062223342D          

 31 35  0  0  1  0            999 V2000
    1.1419   -0.3243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9178   -0.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5485   -0.0728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0630   -1.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  1  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
    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
    4.9853   -1.5952    0.0000 C   0  0  2  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  2  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
    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  1  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
    5.5171   -2.2259    0.0000 C   0  0  1  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
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  1  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
  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
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
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 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
M  END

     RDKit          3D

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   -5.0304   -3.2522   -1.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6847   -2.6352   -0.8138 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5181   -1.2792   -0.6511 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0013   -1.0134   -0.8216 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5708   -1.8529    0.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9904   -1.3960    0.5261 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7081   -1.6634   -0.6380 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9908    0.0460    0.8996 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6324    0.6882    0.9122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8265    0.4081   -0.3314 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3203    1.3311   -1.4207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3898    0.5750    0.0185 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0971    1.8578    0.7562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2577    1.6186    1.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2805    1.3419    0.3629 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2897    2.4723    0.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0433    0.0640    0.7771 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2400    0.3591    1.5738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5014    0.1176    1.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3491    0.6063    2.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6232    0.5113    2.5013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4913    1.1552    3.3602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1703    0.9984    2.9356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6337   -2.5156   -1.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5449   -3.3647   -0.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9395   -4.2325   -1.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5517   -1.5927   -0.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7332   -0.2213   -2.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8594    0.8643   -1.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1345    1.4161   -1.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3610   -0.4882   -2.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0669   -1.2344   -2.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514   -2.0595   -0.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8989   -2.4679   -1.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6825   -1.0977   -1.6916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9638   -1.7030    1.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5627   -2.9318   -0.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4141   -2.0478    1.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9781   -2.6181   -0.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3863    0.1201    1.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7131    0.6338    0.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7947    1.7906    0.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0536    0.4369    1.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2427    0.8865   -2.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    2.3458   -1.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4336    1.4412   -1.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0562   -0.2703    0.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5292    2.4638    2.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
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 31 26  1  0
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 20  9  1  0
 18 12  1  0
  1 32  1  0
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 31 66  1  0
 31 67  1  0
M  END


  Mrv1652309062223342D          

 31 35  0  0  1  0            999 V2000
    1.1419   -0.3243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9178   -0.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5485   -0.0728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    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
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  5  6  1  0  0  0  0
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 26 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0238221

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O6/c1-14(26)31-20-12-25(29)19-5-4-16-11-17(27)6-8-23(16,2)18(19)7-9-24(25,3)22(20)15-10-21(28)30-13-15/h10,16-20,22,27,29H,4-9,11-13H2,1-3H3/t16-,17+,18+,19-,20+,22+,23+,24-,25+/m1/s1

> <INCHI_KEY>
IWCNCUVTGOMGKG-YOVVEKLRSA-N

> <FORMULA>
C25H36O6

> <MOLECULAR_WEIGHT>
432.557

> <EXACT_MASS>
432.251188879

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
47.64163669613303

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5S,7R,10R,11S,13S,14R,15R)-5,11-dihydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl acetate

> <JCHEM_LOGP>
2.1269211943333346

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.07756081688596

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.819477336942312

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569537958757385

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
114.34099999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,7R,10R,11S,13S,14R,15R)-5,11-dihydroxy-2,15-dimethyl-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-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       2.132  -0.605   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.580  -1.129   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.757  -0.136   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.851  -2.645   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.210  -7.342   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.936  -8.206   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.886  -9.746   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.720  -7.261   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.243  -5.813   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   25                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   23                                             
CONECT    8    7                                                            
CONECT    9    7   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   12   19   20                                             
CONECT   19   18                                                            
CONECT   20   18    9   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    7   24   25                                             
CONECT   24   23                                                            
CONECT   25   23    5   26                                                  
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   26                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
16-Acetylgitoxigenin	ChEBI
16-O-Acetylgitoxigenin	ChEBI
16beta-Acetoxy-3beta,14-dihydroxy-5beta,14beta-card-20(22)-enolide	ChEBI
3beta,14,16beta-Trihydroxy-5-betacard-20(22)-enolide 16-acetate	ChEBI
Gitoxigenin 16-acetate	ChEBI
Oleandrisenin	ChEBI
16b-Acetoxy-3b,14-dihydroxy-5b,14b-card-20(22)-enolide	Generator
16Β-acetoxy-3β,14-dihydroxy-5β,14β-card-20(22)-enolide	Generator
3b,14,16b-Trihydroxy-5-betacard-20(22)-enolide 16-acetate	Generator
3b,14,16b-Trihydroxy-5-betacard-20(22)-enolide 16-acetic acid	Generator
3beta,14,16beta-Trihydroxy-5-betacard-20(22)-enolide 16-acetic acid	Generator
3Β,14,16β-trihydroxy-5-betacard-20(22)-enolide 16-acetate	Generator
3Β,14,16β-trihydroxy-5-betacard-20(22)-enolide 16-acetic acid	Generator
Gitoxigenin 16-acetic acid	Generator
3 alpha,14-Dihydroxy-16 beta-acetoxy-5 beta,14 beta- card-20(22)-enolide	MeSH

Chemical Formula

C₂₅H₃₆O₆

Average Mass

432.5570 Da

Monoisotopic Mass

432.25119 Da

IUPAC Name

(1S,2S,5S,7R,10R,11S,13S,14R,15R)-5,11-dihydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl acetate

Traditional Name

(1S,2S,5S,7R,10R,11S,13S,14R,15R)-5,11-dihydroxy-2,15-dimethyl-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl acetate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C25H36O6/c1-14(26)31-20-12-25(29)19-5-4-16-11-17(27)6-8-23(16,2)18(19)7-9-24(25,3)22(20)15-10-21(28)30-13-15/h10,16-20,22,27,29H,4-9,11-13H2,1-3H3/t16-,17+,18+,19-,20+,22+,23+,24-,25+/m1/s1

InChI Key

IWCNCUVTGOMGKG-YOVVEKLRSA-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
Chrysolina americana	LOTUS Database	35616633
Cryptostegia madagascariensis	LOTUS Database	35616633
Mandevilla pentlandiana	LOTUS Database	35616633
Nerium oleander	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cardenolides and derivatives. These are steroid lactones containing a furan-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

Cardenolides and derivatives

Alternative Parents

Substituents

Cardanolide-skeleton
Steroid ester
3-hydroxysteroid
3-beta-hydroxysteroid
14-hydroxysteroid
Hydroxysteroid
2-furanone
Dicarboxylic acid or derivatives
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Dihydrofuran
Carboxylic acid ester
Secondary alcohol
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Alcohol
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:63508 )
steroid ester (CHEBI:63508 )
14beta-hydroxy steroid (CHEBI:63508 )

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	2.13	ChemAxon
pKa (Strongest Acidic)	6.82	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	114.34 m³·mol⁻¹	ChemAxon
Polarizability	47.64 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00058635

Chemspider ID

7978627

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9802865

PDB ID

Not Available

ChEBI ID

63508

Good Scents ID

Not Available

References

General References

Jeffrey PD, Schildbach JF, Chang CY, Kussie PH, Margolies MN, Sheriff S: Structure and specificity of the anti-digoxin antibody 40-50. J Mol Biol. 1995 Apr 28;248(2):344-60. doi: 10.1016/s0022-2836(95)80055-7. [PubMed:7739045 ]
Wang X, Plomley JB, Newman RA, Cisneros A: LC/MS/MS analyses of an oleander extract for cancer treatment. Anal Chem. 2000 Aug 1;72(15):3547-52. doi: 10.1021/ac991425a. [PubMed:10952541 ]
Arao T, Fuke C, Takaesu H, Nakamoto M, Morinaga Y, Miyazaki T: Simultaneous determination of cardenolides by sonic spray ionization liquid chromatography-ion trap mass spectrometry--a fatal case of oleander poisoning. J Anal Toxicol. 2002 May-Jun;26(4):222-7. doi: 10.1093/jat/26.4.222. [PubMed:12054363 ]
Ni D, Madden TL, Johansen M, Felix E, Ho DH, Newman RA: Murine pharmacokinetics and metabolism of oleandrin, a cytotoxic component of Nerium oleander. J Exp Ther Oncol. 2002 Sep-Oct;2(5):278-85. doi: 10.1046/j.1359-4117.2002.01052.x. [PubMed:12416031 ]
Tiwary AK, Poppenga RH, Puschner B: In vitro study of the effectiveness of three commercial adsorbents for binding oleander toxins. Clin Toxicol (Phila). 2009 Mar;47(3):213-8. doi: 10.1080/15563650802590314. [PubMed:19274509 ]
LOTUS database [Link]

Showing NP-Card for oleandrigenin (NP0238221)

MOL for NP0238221 (oleandrigenin)

3D MOL for NP0238221 (oleandrigenin)

3D SDF for NP0238221 (oleandrigenin)

3D-SDF for NP0238221 (oleandrigenin)

PDB for NP0238221 (oleandrigenin)

3D PDB for NP0238221 (oleandrigenin)

SMILES for NP0238221 (oleandrigenin)

INCHI for NP0238221 (oleandrigenin)

Structure for NP0238221 (oleandrigenin)

3D Structure for NP0238221 (oleandrigenin)