NP-MRD: Showing NP-Card for gitoxigenin (NP0164136)

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Record Information

Version

2.0

Created at

2022-09-02 22:57:39 UTC

Updated at

2022-09-02 22:57:39 UTC

NP-MRD ID

NP0164136

Secondary Accession Numbers

None

Natural Product Identification

Common Name

gitoxigenin

Description

Gitoxigenin 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, gitoxigenin is considered to be a sterol lipid molecule. gitoxigenin is found in Digitalis grandiflora, Digitalis obscura, Digitalis purpurea and Strophanthus divaricatus. Gitoxigenin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306031607282D          

 34 38  0  0  1  0            999 V2000
    4.5466    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307    1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2351    1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2889    2.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596    1.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072   -0.2182    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4511    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0148    0.7029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4830    0.0722    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3367    0.1741    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0452    2.3670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660    0.9666    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8269    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3905    0.9934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6708    0.2174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2632    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5607   -0.1062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8377    2.5963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685   -0.5835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6061    2.8734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6390    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7314   -0.5086    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027    0.8481    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2951   -0.0730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7346    0.7382    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0723    0.3152    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 13  9  2  0  0  0  0
 13 12  1  0  0  0  0
 14  3  1  0  0  0  0
 14 10  1  0  0  0  0
 15  5  1  0  0  0  0
 15 10  1  0  0  0  0
 16  6  1  0  0  0  0
 17  4  1  0  0  0  0
 17 16  1  0  0  0  0
 18 11  1  0  0  0  0
 19  9  1  0  0  0  0
 20 13  1  1  0  0  0
 20 18  1  0  0  0  0
 21  1  1  6  0  0  0
 21  7  1  0  0  0  0
 21 14  1  0  0  0  0
 21 16  1  0  0  0  0
 22  2  1  6  0  0  0
 22  8  1  0  0  0  0
 22 20  1  0  0  0  0
 23 11  1  0  0  0  0
 23 17  1  0  0  0  0
 23 22  1  0  0  0  0
 15 24  1  6  0  0  0
 18 25  1  6  0  0  0
 26 19  2  0  0  0  0
 23 27  1  6  0  0  0
 28 12  1  0  0  0  0
 28 19  1  0  0  0  0
 14 29  1  6  0  0  0
 15 30  1  1  0  0  0
 16 31  1  1  0  0  0
 17 32  1  6  0  0  0
 18 33  1  1  0  0  0
 20 34  1  1  0  0  0
M  END

     RDKit          3D

 62 66  0  0  0  0  0  0  0  0999 V2000
    2.8955   -1.1405    1.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3941   -0.4344    0.4277 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2487   -0.9677   -0.6924 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2308   -0.0171   -1.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9105    0.8765   -0.2785 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0553    0.2158    0.2199 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0794    1.2677    0.8937 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6099    1.0360    0.6932 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1009    1.9503   -0.3587 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9943    1.2875   -1.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2185    0.4613   -0.1987 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9421   -0.7887    0.2337 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2568   -1.3231    1.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1867   -1.1939    1.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9292   -0.2531    0.6470 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2300    1.0520    1.3290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1604   -0.8960    0.0456 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3909   -0.1311    0.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4430   -0.4713    0.8543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5000    0.5100    0.7143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6478    0.4619    1.2930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0447    1.4868   -0.1434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7387    1.1155   -0.5789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7868   -1.3418   -1.3569 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1823   -0.4700   -2.3358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2501   -1.3152   -1.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1297    0.0663   -0.6193 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7517    0.9878   -1.4061 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7364   -0.5128    2.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5540   -2.1678    1.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0198   -1.1980    1.5951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7737   -1.9261   -0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5583   -1.2895   -1.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7944    0.5453   -2.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0485   -0.6339   -1.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2958    1.7663   -0.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3339   -0.5069   -0.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4022    0.8042    1.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2126    2.3749    1.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1234    1.2356    1.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8620    2.4280   -0.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5801    2.8044    0.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3822    0.7361   -2.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3010    2.0907   -1.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1263    1.0871    0.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8955   -1.4955   -0.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5520   -2.4125    1.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7482   -0.8532    2.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4824   -0.9027    2.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6823   -2.1964    1.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5306    1.1300    2.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0143    1.9470    0.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2860    1.1449    1.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3384   -1.9027    0.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5492   -1.3587    1.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8527    0.9235   -1.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0987    1.9749   -0.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1288   -2.3705   -1.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7717   -0.7308   -3.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0427   -2.1274   -0.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7611   -1.4120   -2.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3262    0.9729   -2.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  6
 27 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  1
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
 15 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
 17 24  1  0
 23 18  1  0
 15 27  1  0
 12 11  1  0
  2  8  1  0
 24 58  1  6
 25 59  1  0
 26 60  1  0
 26 61  1  0
 28 62  1  0
 11 45  1  1
 10 43  1  0
 10 44  1  0
  9 41  1  0
  9 42  1  0
  8 40  1  1
  7 38  1  0
  7 39  1  0
  5 36  1  6
  6 37  1  0
  4 34  1  0
  4 35  1  0
  3 32  1  0
  3 33  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 12 46  1  6
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 16 51  1  0
 16 52  1  0
 16 53  1  0
 17 54  1  1
 19 55  1  0
 23 56  1  0
 23 57  1  0
M  END


  Mrv1652306031607282D          

 34 38  0  0  1  0            999 V2000
    4.5466    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307    1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2351    1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2889    2.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596    1.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072   -0.2182    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4511    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0148    0.7029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4830    0.0722    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3367    0.1741    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0452    2.3670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660    0.9666    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8269    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3905    0.9934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6708    0.2174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2632    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5607   -0.1062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8377    2.5963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685   -0.5835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6061    2.8734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6390    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7314   -0.5086    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027    0.8481    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2951   -0.0730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7346    0.7382    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0723    0.3152    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 13  9  2  0  0  0  0
 13 12  1  0  0  0  0
 14  3  1  0  0  0  0
 14 10  1  0  0  0  0
 15  5  1  0  0  0  0
 15 10  1  0  0  0  0
 16  6  1  0  0  0  0
 17  4  1  0  0  0  0
 17 16  1  0  0  0  0
 18 11  1  0  0  0  0
 19  9  1  0  0  0  0
 20 13  1  1  0  0  0
 20 18  1  0  0  0  0
 21  1  1  6  0  0  0
 21  7  1  0  0  0  0
 21 14  1  0  0  0  0
 21 16  1  0  0  0  0
 22  2  1  6  0  0  0
 22  8  1  0  0  0  0
 22 20  1  0  0  0  0
 23 11  1  0  0  0  0
 23 17  1  0  0  0  0
 23 22  1  0  0  0  0
 15 24  1  6  0  0  0
 18 25  1  6  0  0  0
 26 19  2  0  0  0  0
 23 27  1  6  0  0  0
 28 12  1  0  0  0  0
 28 19  1  0  0  0  0
 14 29  1  6  0  0  0
 15 30  1  1  0  0  0
 16 31  1  1  0  0  0
 17 32  1  6  0  0  0
 18 33  1  1  0  0  0
 20 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0164136

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H34O5/c1-21-7-5-15(24)10-14(21)3-4-17-16(21)6-8-22(2)20(13-9-19(26)28-12-13)18(25)11-23(17,22)27/h9,14-18,20,24-25,27H,3-8,10-12H2,1-2H3/t14-,15+,16+,17-,18+,20+,21+,22-,23+/m1/s1

> <INCHI_KEY>
PVAMXWLZJKTXFW-VQMOFDJESA-N

> <FORMULA>
C23H34O5

> <MOLECULAR_WEIGHT>
390.52

> <EXACT_MASS>
390.240624195

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
42.95643109395478

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(1S,2S,5S,7R,10R,11S,13S,14R,15R)-5,11,13-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
1.47

> <JCHEM_LOGP>
1.685795784

> <ALOGPS_LOGS>
-3.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.006886908931843

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.831025624007749

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569547743403967

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
105.18950000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(1S,2S,5S,7R,10R,11S,13S,14R,15R)-5,11,13-trihydroxy-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                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0       8.487   2.489   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.791   3.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.541  -1.585   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.025  -1.314   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.519   1.947   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.971   2.761   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.003   2.218   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.455   3.032   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.439   2.970   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.049  -0.678   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.770  -0.539   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.406   4.499   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.978   3.020   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.533  -0.407   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.042   0.499   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.494   1.312   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.502   0.135   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.495   0.325   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.084   4.418   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.923   1.804   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.010   1.041   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.462   1.854   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.986   0.406   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.558   0.228   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.047  -0.198   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -1.564   4.846   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.355  -1.089   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       1.131   5.364   0.000  0.00  0.00           O+0
HETATM   29  H   UNK     0      10.526   0.770   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      12.565  -0.949   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.978   1.583   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       8.017  -0.136   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.371   1.378   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.868   0.588   0.000  0.00  0.00           H+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3    4   14                                                       
CONECT    4    3   17                                                       
CONECT    5    7   15                                                       
CONECT    6    8   16                                                       
CONECT    7    5   21                                                       
CONECT    8    6   22                                                       
CONECT    9   13   19                                                       
CONECT   10   14   15                                                       
CONECT   11   18   23                                                       
CONECT   12   13   28                                                       
CONECT   13    9   12   20                                                  
CONECT   14    3   10   21   29                                             
CONECT   15    5   10   24   30                                             
CONECT   16    6   17   21   31                                             
CONECT   17    4   16   23   32                                             
CONECT   18   11   20   25   33                                             
CONECT   19    9   26   28                                                  
CONECT   20   13   18   22   34                                             
CONECT   21    1    7   14   16                                             
CONECT   22    2    8   20   23                                             
CONECT   23   11   17   22   27                                             
CONECT   24   15                                                            
CONECT   25   18                                                            
CONECT   26   19                                                            
CONECT   27   23                                                            
CONECT   28   12   19                                                       
CONECT   29   14                                                            
CONECT   30   15                                                            
CONECT   31   16                                                            
CONECT   32   17                                                            
CONECT   33   18                                                            
CONECT   34   20                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
16beta-Hydroxydigitoxigenin	ChEBI
16b-Hydroxydigitoxigenin	Generator
16Β-hydroxydigitoxigenin	Generator

Chemical Formula

C₂₃H₃₄O₅

Average Mass

390.5200 Da

Monoisotopic Mass

390.24062 Da

IUPAC Name

4-[(1S,2S,5S,7R,10R,11S,13S,14R,15R)-5,11,13-trihydroxy-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,7R,10R,11S,13S,14R,15R)-5,11,13-trihydroxy-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

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

InChI Identifier

InChI=1S/C23H34O5/c1-21-7-5-15(24)10-14(21)3-4-17-16(21)6-8-22(2)20(13-9-19(26)28-12-13)18(25)11-23(17,22)27/h9,14-18,20,24-25,27H,3-8,10-12H2,1-2H3/t14-,15+,16+,17-,18+,20+,21+,22-,23+/m1/s1

InChI Key

PVAMXWLZJKTXFW-VQMOFDJESA-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
Digitalis grandiflora	LOTUS Database	35616633
Digitalis obscura	LOTUS Database	35616633
Digitalis purpurea	LOTUS Database	35616633
Strophanthus divaricatus	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
3-hydroxysteroid
14-hydroxysteroid
Hydroxysteroid
16-beta-hydroxysteroid
16-hydroxysteroid
3-beta-hydroxysteroid
2-furanone
Cyclic alcohol
Dihydrofuran
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Organooxygen compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:38105 )
16beta-hydroxy steroid (CHEBI:38105 )
14beta-hydroxy steroid (CHEBI:38105 )
Cardanolides and derivatives (LMST01120003 )

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	1.47	ALOGPS
logP	1.69	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	6.83	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	105.19 m³·mol⁻¹	ChemAxon
Polarizability	42.96 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

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

348482

PDB ID

Not Available

ChEBI ID

38105

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for gitoxigenin (NP0164136)

MOL for NP0164136 (gitoxigenin)

3D MOL for NP0164136 (gitoxigenin)

3D SDF for NP0164136 (gitoxigenin)

3D-SDF for NP0164136 (gitoxigenin)

PDB for NP0164136 (gitoxigenin)

3D PDB for NP0164136 (gitoxigenin)

SMILES for NP0164136 (gitoxigenin)

INCHI for NP0164136 (gitoxigenin)

Structure for NP0164136 (gitoxigenin)

3D Structure for NP0164136 (gitoxigenin)