NP-MRD: Showing NP-Card for 5,6-Dehydrouzarigenin (NP0072584)

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Record Information

Version

2.0

Created at

2022-04-28 17:54:55 UTC

Updated at

2022-04-28 17:54:55 UTC

NP-MRD ID

NP0072584

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,6-Dehydrouzarigenin

Description

Xysmalogenin belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. 5,6-Dehydrouzarigenin is found in Asclepias curassavica L. , Gomphocarpus sinaicus and Periploca sepium . 5,6-Dehydrouzarigenin was first documented in 2002 (PMID: 12918871). Based on a literature review a small amount of articles have been published on Xysmalogenin (PMID: 25193007) (PMID: 34451840) (PMID: 16902853).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219542D          

 27 31  0  0  1  0            999 V2000
    6.1708   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.5577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.7528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8269    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3587   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.1684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2889   -1.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6061   -2.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5793   -2.8729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0452   -1.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2351   -0.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685    1.4085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2632    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  9 11  1  1  0  0  0
  8 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 15 25  1  1  0  0  0
 14 26  1  1  0  0  0
  2 27  1  1  0  0  0
M  END

     RDKit          3D

 59 63  0  0  0  0  0  0  0  0999 V2000
   -2.2786    0.2180    2.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2419    0.3218    0.6958 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7688    1.6366    0.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5845    1.4716   -1.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8856    0.7425   -0.7849 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8251    1.5984   -0.2099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5849   -0.4404    0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1302   -0.7536    0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6633   -1.9232   -0.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2358   -2.2932   -0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3753   -1.2480    0.4213 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8628    0.1278    0.1130 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0761    1.1931    0.6342 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2544    0.6172    1.3596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9986   -0.4271    0.5682 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9645   -1.1353    1.4799 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5972    0.2033   -0.6368 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8445    0.9407   -0.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9461    2.2542   -0.7550 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2861    2.7326   -0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6943    3.9353   -0.6744 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0022    1.6527   -0.0414 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1684    0.5254   -0.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7194   -1.0114   -1.5610 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2849   -1.5444   -1.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0506   -1.5070    0.0380 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3772   -2.7749    0.5409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4037    0.6062    2.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4714   -0.8185    2.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1759    0.8075    2.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4028    2.1164    0.9355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9433    2.3414   -0.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0549    0.8871   -1.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7999    2.4828   -1.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3121    0.3811   -1.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6630    1.6525   -0.7211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8861   -0.1461    1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1237   -1.3520   -0.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3896   -2.6332   -0.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1489   -3.2289    0.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8855   -2.5848   -1.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4460   -1.3881    1.5239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9593    0.2274   -0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3594    1.8995   -0.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4602    1.8414    1.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9139    0.1454    2.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9451    1.4296    1.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3640   -1.9541    1.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7623   -1.6803    0.9605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2944   -0.5001    2.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8118    0.8290   -1.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1411    2.8840   -1.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6072   -0.2983   -0.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1740    0.2191    1.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9051   -0.6875   -2.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4157   -1.7529   -1.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6386   -0.7960   -1.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2015   -2.5571   -1.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1647   -3.4853   -0.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  1
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  5  1  0
  5  6  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  1
 11 26  1  0
 26 27  1  1
 26 25  1  0
 25 24  1  0
 24 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 26 15  1  0
 23 18  1  0
 17 15  1  0
  2 12  1  0
  2  8  1  0
 16 48  1  0
 16 49  1  0
 16 50  1  0
 14 46  1  0
 14 47  1  0
 13 44  1  0
 13 45  1  0
 12 43  1  6
 11 42  1  1
 10 40  1  0
 10 41  1  0
  9 39  1  0
  7 37  1  0
  7 38  1  0
  5 35  1  6
  6 36  1  0
  4 33  1  0
  4 34  1  0
  3 31  1  0
  3 32  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 27 59  1  0
 25 57  1  0
 25 58  1  0
 24 55  1  0
 24 56  1  0
 17 51  1  6
 19 52  1  0
 23 53  1  0
 23 54  1  0
M  END


  Mrv1652304282219542D          

 27 31  0  0  1  0            999 V2000
    6.1708   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.5577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.7528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8269    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3587   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.1684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2889   -1.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6061   -2.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5793   -2.8729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0452   -1.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2351   -0.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685    1.4085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2632    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  9 11  1  1  0  0  0
  8 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 15 25  1  1  0  0  0
 14 26  1  1  0  0  0
  2 27  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0072584

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@]34C)[C@@]1(O)CC[C@@H]2C1=CC(=O)OC1

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O4/c1-21-8-5-16(24)12-15(21)3-4-19-18(21)6-9-22(2)17(7-10-23(19,22)26)14-11-20(25)27-13-14/h3,11,16-19,24,26H,4-10,12-13H2,1-2H3/t16-,17+,18-,19+,21-,22+,23-/m0/s1

> <INCHI_KEY>
ZICGJBPBLVXOBM-MITUEXOSSA-N

> <FORMULA>
C23H32O4

> <MOLECULAR_WEIGHT>
372.505

> <EXACT_MASS>
372.23005951

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
41.8170148194507

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(1S,2R,5S,10R,11S,14R,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
2.85

> <JCHEM_LOGP>
2.6617751056666665

> <ALOGPS_LOGS>
-4.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.204289500980078

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.182633784422031

> <JCHEM_PKA_STRONGEST_BASIC>
0.28379565508329274

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
104.49059999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.45e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(1S,2R,5S,10R,11S,14R,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.406  -2.959   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.131  -3.824   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.081  -5.363   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.084  -2.878   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.439  -1.430   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.355   2.629   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8    4   10   11                                             
CONECT   10    9    1                                                       
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   18   26                                             
CONECT   15   14    7   16   25                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   19                                                       
CONECT   25   15                                                            
CONECT   26   14                                                            
CONECT   27    2                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₂O₄

Average Mass

372.5050 Da

Monoisotopic Mass

372.23006 Da

IUPAC Name

4-[(1S,2R,5S,10R,11S,14R,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2,5-dihydrofuran-2-one

Traditional Name

4-[(1S,2R,5S,10R,11S,14R,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@]34C)[C@@]1(O)CC[C@@H]2C1=CC(=O)OC1

InChI Identifier

InChI=1S/C23H32O4/c1-21-8-5-16(24)12-15(21)3-4-19-18(21)6-9-22(2)17(7-10-23(19,22)26)14-11-20(25)27-13-14/h3,11,16-19,24,26H,4-10,12-13H2,1-2H3/t16-,17+,18-,19+,21-,22+,23-/m0/s1

InChI Key

ZICGJBPBLVXOBM-MITUEXOSSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 curassavica	Plant	KNApSAcK
Gomphocarpus sinaicus	LOTUS Database	35616633
Periploca sepium	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Steroid lactones

Alternative Parents

Substituents

Steroid lactone
Androgen-skeleton
Androstane-skeleton
3-hydroxy-delta-5-steroid
3-hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
14-hydroxysteroid
Hydroxysteroid
Delta-5-steroid
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Cyclic alcohol
Dihydrofuran
Carboxylic acid ester
Secondary alcohol
Lactone
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	2.85	ALOGPS
logP	2.66	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	0.28	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	104.49 m³·mol⁻¹	ChemAxon
Polarizability	41.82 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

C00032536

Chemspider ID

19953393

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12302371

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Vermaak I, Enslin GM, Idowu TO, Viljoen AM: Xysmalobium undulatum (uzara) - review of an antidiarrhoeal traditional medicine. J Ethnopharmacol. 2014 Oct 28;156:135-46. doi: 10.1016/j.jep.2014.08.016. Epub 2014 Sep 1. [PubMed:25193007 ]
Thakur A, Moyo P, van der Westhuizen CJ, Yang HO, Maharaj V: A Novel Cardenolide Glycoside Isolated from Xysmalobium undulatum Reduces Levels of the Alzheimer's Disease-Associated beta-Amyloid Peptides Abeta42 In Vitro. Pharmaceuticals (Basel). 2021 Jul 29;14(8):743. doi: 10.3390/ph14080743. [PubMed:34451840 ]
Schaller F, Kreis W: Cardenolide genin pattern in Isoplexis plants and shoot cultures. Planta Med. 2006 Oct;72(12):1149-56. doi: 10.1055/s-2006-947194. Epub 2006 Aug 10. [PubMed:16902853 ]
Gavidia I, Seitz HU, Perez-Bermudez P, Vogler B: LC-NMR applied to the characterisation of cardiac glycosides from three micropropagated Isoplexis species. Phytochem Anal. 2002 Sep-Oct;13(5):266-71. doi: 10.1002/pca.655. [PubMed:12918871 ]

Showing NP-Card for 5,6-Dehydrouzarigenin (NP0072584)

MOL for NP0072584 (5,6-Dehydrouzarigenin)

3D MOL for NP0072584 (5,6-Dehydrouzarigenin)

3D SDF for NP0072584 (5,6-Dehydrouzarigenin)

3D-SDF for NP0072584 (5,6-Dehydrouzarigenin)

PDB for NP0072584 (5,6-Dehydrouzarigenin)

3D PDB for NP0072584 (5,6-Dehydrouzarigenin)

SMILES for NP0072584 (5,6-Dehydrouzarigenin)

INCHI for NP0072584 (5,6-Dehydrouzarigenin)

Structure for NP0072584 (5,6-Dehydrouzarigenin)

3D Structure for NP0072584 (5,6-Dehydrouzarigenin)