NP-MRD: Showing NP-Card for Uzarigenin (NP0072542)

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Record Information

Version

2.0

Created at

2022-04-28 17:53:06 UTC

Updated at

2022-04-28 17:53:06 UTC

NP-MRD ID

NP0072542

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Uzarigenin

Description

Uzarigenin, also known as digitoxigenin, 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. Thus, uzarigenin is considered to be a sterol. Uzarigenin is found in Asclepias albicans, Asclepias curassavica L. , Gomphocarpus fruticosus, Asclepias tuberosa, Calotropis gigantea , Calotropis procera, Coronilla valentina, Erysimum inconspicuum, Gomphocarpus sinaicus and Nerium odorum. Uzarigenin was first documented in 2013 (PMID: 23621895). Based on a literature review a small amount of articles have been published on Uzarigenin (PMID: 26595507) (PMID: 34961397) (PMID: 31734772) (PMID: 25193007).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219532D          

 27 31  0  0  1  0            999 V2000
    7.2632    0.7029    0.0000 O   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
    6.1708   -0.2182    0.0000 C   0  0  0  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
    4.8269    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  2  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
    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  2  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
    4.5466   -0.5086    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 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
 10 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
  5 27  1  1  0  0  0
M  END

     RDKit          3D

 61 65  0  0  0  0  0  0  0  0999 V2000
   -2.4826   -0.9479   -1.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3098   -0.4223    0.1800 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9023   -1.3925    1.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3765   -1.5550    0.9838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1251   -0.2550    1.0327 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4108   -0.4451    0.5303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4742    0.8248    0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0011    0.9024    0.4061 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4254    1.9259   -0.5336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9940    2.1948   -0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2437    0.9127   -0.2030 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8299   -0.2324    0.5457 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0422   -1.4810    0.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1348   -1.3177   -0.6047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9639   -0.0929   -0.3698 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5789    0.3379   -1.7002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0712   -0.2949    0.6071 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4105   -0.5053    0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4610    0.2722    0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6071   -0.2419   -0.5079 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7727    0.2788   -0.5253 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1800   -1.3825   -1.1624 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8192   -1.6219   -0.8601 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0238    0.8923    1.5667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4951    1.1002    1.6033 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1954    1.0742    0.1510 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7213    2.2640   -0.3939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5567   -0.8842   -1.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3018   -0.4650   -1.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7514   -2.0360   -1.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4294   -2.3811    1.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7398   -0.9955    2.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7643   -2.1940    1.8115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6071   -2.1136    0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2393    0.0905    2.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4233   -1.0619   -0.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7069    0.7096   -0.8741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9200    1.7906    0.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7473    1.2279    1.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3451    1.4220   -1.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0116    2.8369   -0.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5073    2.9659   -0.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0404    2.4716    1.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2824    0.6441   -1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8336    0.0167    1.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7301   -2.2193   -0.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2606   -1.9215    1.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990   -2.1992   -0.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8108   -1.3408   -1.6697 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6338    0.5785   -1.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0181    1.2467   -2.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3622   -0.4221   -2.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8185   -1.1979    1.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5287    1.1810    0.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8133   -2.5390   -0.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2053   -1.7322   -1.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4221    0.6574    2.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4270    1.8121    1.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2552    2.0539    2.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1129    0.2463    2.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6529    2.9596    0.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  6
 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  1  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  6
 11 26  1  0
 26 27  1  6
 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 50  1  0
 16 51  1  0
 16 52  1  0
 14 48  1  0
 14 49  1  0
 13 46  1  0
 13 47  1  0
 12 45  1  1
 11 44  1  6
 10 42  1  0
 10 43  1  0
  9 40  1  0
  9 41  1  0
  8 39  1  1
  7 37  1  0
  7 38  1  0
  5 35  1  1
  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 61  1  0
 25 59  1  0
 25 60  1  0
 24 57  1  0
 24 58  1  0
 17 53  1  1
 19 54  1  0
 23 55  1  0
 23 56  1  0
M  END


  Mrv1652304282219532D          

 27 31  0  0  1  0            999 V2000
    7.2632    0.7029    0.0000 O   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
    6.1708   -0.2182    0.0000 C   0  0  0  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
    4.8269    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  2  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
    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  2  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
    4.5466   -0.5086    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 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
 10 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
  5 27  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0072542

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H34O4/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/h11,15-19,24,26H,3-10,12-13H2,1-2H3/t15-,16-,17+,18-,19+,21-,22+,23-/m0/s1

> <INCHI_KEY>
XZTUSOXSLKTKJQ-CIXPXFMPSA-N

> <FORMULA>
C23H34O4

> <MOLECULAR_WEIGHT>
374.521

> <EXACT_MASS>
374.245709575

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
42.474455443581206

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.72

> <JCHEM_LOGP>
3.0673545870000005

> <ALOGPS_LOGS>
-4.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.29639631666254

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.1826362243603645

> <JCHEM_PKA_STRONGEST_BASIC>
0.25300168391701294

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
103.64059999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.44e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(1S,2S,5S,7S,10R,11S,14R,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-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  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.494   0.228   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  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11   27                                             
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10    5   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   18   26                                             
CONECT   15   14   10   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    5                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Value	Source
Digitoxigenin	MeSH

Chemical Formula

C₂₃H₃₄O₄

Average Mass

374.5210 Da

Monoisotopic Mass

374.24571 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C23H34O4/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/h11,15-19,24,26H,3-10,12-13H2,1-2H3/t15-,16-,17+,18-,19+,21-,22+,23-/m0/s1

InChI Key

XZTUSOXSLKTKJQ-CIXPXFMPSA-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 albicans	Plant	KNApSAcK
Asclepias curassavica	Plant	KNApSAcK
Asclepias fruticosa	LOTUS Database	35616633
Asclepias tuberosa	LOTUS Database	35616633
Calotropis gigantea	Plant	KNApSAcK
Calotropis procera	LOTUS Database	35616633
Coronilla valentina	LOTUS Database	35616633
Erysimum inconspicuum	LOTUS Database	35616633
Gomphocarpus sinaicus	LOTUS Database	35616633
Nerium oleander	Plant	KNApSAcK

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
3-hydroxysteroid
3-beta-hydroxysteroid
14-hydroxysteroid
Hydroxysteroid
2-furanone
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
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	2.72	ALOGPS
logP	3.07	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	0.25	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	103.64 m³·mol⁻¹	ChemAxon
Polarizability	42.47 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

C00032469

Chemspider ID

83738

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92760

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Marzouk AM, Osman SM, Gohar AA: A new pregnane glycoside from Gomphocarpus fruticosus growing in Egypt. Nat Prod Res. 2016;30(9):1060-7. doi: 10.1080/14786419.2015.1107059. Epub 2015 Nov 23. [PubMed:26595507 ]
Kar B, Kundu CN, Pati S, Bhattacharya D: Discovery of phyto-compounds as novel inhibitors against NDM-1 and VIM-1 protein through virtual screening and molecular modelling. J Biomol Struct Dyn. 2021 Dec 28:1-14. doi: 10.1080/07391102.2021.2019125. [PubMed:34961397 ]
Wen C, Huang W, He MM, Deng WL, Yu HH: Cloning and characterization of a glycosyltransferase from Catharanthus roseus for glycosylation of cardiotonic steroids and phenolic compounds. Biotechnol Lett. 2020 Jan;42(1):135-142. doi: 10.1007/s10529-019-02756-5. Epub 2019 Nov 16. [PubMed:31734772 ]
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 ]
Moreno Y Banuls L, Katz A, Miklos W, Cimmino A, Tal DM, Ainbinder E, Zehl M, Urban E, Evidente A, Kopp B, Berger W, Feron O, Karlish S, Kiss R: Hellebrin and its aglycone form hellebrigenin display similar in vitro growth inhibitory effects in cancer cells and binding profiles to the alpha subunits of the Na+/K+-ATPase. Mol Cancer. 2013 Apr 26;12:33. doi: 10.1186/1476-4598-12-33. [PubMed:23621895 ]

Showing NP-Card for Uzarigenin (NP0072542)

MOL for NP0072542 (Uzarigenin)

3D MOL for NP0072542 (Uzarigenin)

3D SDF for NP0072542 (Uzarigenin)

3D-SDF for NP0072542 (Uzarigenin)

PDB for NP0072542 (Uzarigenin)

3D PDB for NP0072542 (Uzarigenin)

SMILES for NP0072542 (Uzarigenin)

INCHI for NP0072542 (Uzarigenin)

Structure for NP0072542 (Uzarigenin)

3D Structure for NP0072542 (Uzarigenin)