NP-MRD: Showing NP-Card for 3beta,5beta,14beta-Trihydroxy-19-oxo-bufa-20,22-dienolide 3-O-beta-D-glucopyranoside (NP0073518)

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Record Information

Version

2.0

Created at

2022-04-28 18:45:24 UTC

Updated at

2022-04-28 18:45:24 UTC

NP-MRD ID

NP0073518

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3beta,5beta,14beta-Trihydroxy-19-oxo-bufa-20,22-dienolide 3-O-beta-D-glucopyranoside

Description

Hellebrigenin, also known as bufotalidin, belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. Thus, hellebrigenin is considered to be a sterol. 3beta,5beta,14beta-Trihydroxy-19-oxo-bufa-20,22-dienolide 3-O-beta-D-glucopyranoside is found in Bufo bufo, Bufo gargarizans, Bufotes viridis, Helleborus caucasicus, Kalanchoe gracilis, Kalanchoe laciniata, Rhinella marina and Sclerophrys mauritanica. 3beta,5beta,14beta-Trihydroxy-19-oxo-bufa-20,22-dienolide 3-O-beta-D-glucopyranoside was first documented in 2019 (PMID: 31265888). Based on a literature review a small amount of articles have been published on Hellebrigenin (PMID: 33460706) (PMID: 34513690) (PMID: 32445663) (PMID: 32426183).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220452D          

 30 34  0  0  1  0            999 V2000
    4.2475    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278    1.3777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9960    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    0.8922    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9035    1.6682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4354    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    1.8134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5596    1.1827    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8399    0.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.3279    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4672    2.1038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9990    2.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111    2.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    2.0770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5867    1.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    0.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637    2.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6810    2.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1873    3.2668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8764    4.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3828    4.6823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0592    4.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5528    3.4925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1073    2.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451    0.5269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6232    2.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1551    3.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4641    0.1163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399    1.2325    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  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  6  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 15 18  1  6  0  0  0
 18 19  2  0  0  0  0
 19 20  1  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  2  0  0  0  0
 18 24  1  0  0  0  0
 12 25  1  6  0  0  0
 11 26  1  6  0  0  0
  5 27  1  6  0  0  0
 27 28  2  0  0  0  0
  4 29  1  6  0  0  0
  2 30  1  6  0  0  0
M  END

     RDKit          3D

 62 66  0  0  0  0  0  0  0  0999 V2000
    2.7972   -0.6279   -1.2842 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8505   -0.2210   -0.1397 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1412   -1.5079    0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1439   -1.5813   -0.6228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0296   -0.5608    0.0094 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4775    0.8007   -0.2726 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0111    1.6795    0.8698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2978    1.1131    1.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1797    0.4995    0.3756 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5784    1.5152   -0.4796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3703   -0.0882    1.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2716   -0.8877    0.2398 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1899   -0.0709   -0.4165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5493   -1.8230   -0.6874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1164   -1.9467   -0.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4596   -0.6194   -0.3716 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5485   -0.3320   -1.8507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1842   -1.2099   -2.6027 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9676    0.9064   -0.5135 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1543    1.1102   -1.9079 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5674    2.1550    0.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4674    1.6807    1.2374 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7591    0.2352    0.9971 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1857    0.0810    0.7198 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8421    0.8896   -0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1949    0.7219   -0.4088 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8450   -0.2778    0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0818   -0.4212    0.0656 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1971   -1.0386    1.1387 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9091   -0.8895    1.3698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9685    0.2038   -1.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2590   -1.4010   -1.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6872   -1.1431   -0.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8365   -1.4485    1.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7639   -2.3888    0.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1359   -1.2265   -1.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5602   -2.6054   -0.6186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9623   -0.7256    1.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0653    1.1851   -1.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2118    2.7005    0.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2697    1.6250    1.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1311    0.4487    2.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8722    1.9863    1.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3748    1.2883   -1.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9473    0.7285    1.5841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9861   -0.7271    1.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8928   -1.5420    0.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4836   -0.4301   -1.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4695   -1.4269   -1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9843   -2.8461   -0.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1084   -2.2551    0.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6118   -2.6852   -0.7947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9092    0.5873   -2.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1941    2.0555   -2.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2115    2.7292   -0.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8103    2.8676    0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4183    2.2922    1.2718 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0461    1.7896    2.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4359   -0.3968    1.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3575    1.6789   -0.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7066    1.3709   -1.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4565   -1.5734    2.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  6
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
 17 18  2  0
  6 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 30  2  0
 30 29  1  0
 29 27  1  0
 27 28  2  0
 27 26  1  0
 26 25  2  0
 19  2  1  0
 25 24  1  0
 23  2  1  0
 16  5  1  0
 16  9  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  1
  6 39  1  6
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  1
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 17 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 23 59  1  1
 30 62  1  0
 26 61  1  0
 25 60  1  0
M  END


  Mrv1652304282220452D          

 30 34  0  0  1  0            999 V2000
    4.2475    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278    1.3777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9960    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    0.8922    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9035    1.6682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4354    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    1.8134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5596    1.1827    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8399    0.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.3279    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4672    2.1038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9990    2.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111    2.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    2.0770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5867    1.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    0.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637    2.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6810    2.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1873    3.2668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8764    4.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3828    4.6823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0592    4.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5528    3.4925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1073    2.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451    0.5269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6232    2.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1551    3.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4641    0.1163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399    1.2325    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  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  6  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 15 18  1  6  0  0  0
 18 19  2  0  0  0  0
 19 20  1  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  2  0  0  0  0
 18 24  1  0  0  0  0
 12 25  1  6  0  0  0
 11 26  1  6  0  0  0
  5 27  1  6  0  0  0
 27 28  2  0  0  0  0
  4 29  1  6  0  0  0
  2 30  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0073518

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O6/c1-21-8-5-18-19(6-10-23(28)12-16(26)4-9-22(18,23)14-25)24(21,29)11-7-17(21)15-2-3-20(27)30-13-15/h2-3,13-14,16-19,26,28-29H,4-12H2,1H3/t16-,17+,18-,19+,21+,22-,23-,24-/m0/s1

> <INCHI_KEY>
TVKPTWJPKVSGJB-XHCIOXAKSA-N

> <FORMULA>
C24H32O6

> <MOLECULAR_WEIGHT>
416.514

> <EXACT_MASS>
416.21988875

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
44.04339399757278

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5S,7S,10R,11S,14S,15R)-5,7,11-trihydroxy-15-methyl-14-(2-oxo-2H-pyran-5-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-2-carbaldehyde

> <ALOGPS_LOGP>
1.39

> <JCHEM_LOGP>
1.0777440793333322

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.302563573407674

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.064862183805445

> <JCHEM_PKA_STRONGEST_BASIC>
0.2958659271409827

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
110.76499999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,7S,10R,11S,14S,15R)-5,7,11-trihydroxy-15-methyl-14-(6-oxopyran-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-2-carbaldehyde

> <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       7.929   4.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.452   2.572   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.459   1.394   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.943   1.666   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.420   3.114   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.413   4.291   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.904   3.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.911   2.208   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.434   0.759   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.950   0.488   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.395   2.479   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.872   3.927   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.865   5.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.381   4.833   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.667   3.877   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.095   2.398   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.179   1.534   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.612   5.093   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.138   4.882   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.083   6.098   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.503   7.525   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.448   8.740   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.977   7.735   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.032   6.519   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.200   5.313   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.764   0.984   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.897   4.562   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.889   5.740   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       6.466   0.217   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       9.968   2.301   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10   29                                             
CONECT    5    4    6    7   27                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   17   26                                             
CONECT   12   11   13   15   25                                             
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   12   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   11                                                       
CONECT   18   15   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   18                                                       
CONECT   25   12                                                            
CONECT   26   11                                                            
CONECT   27    5   28                                                       
CONECT   28   27                                                            
CONECT   29    4                                                            
CONECT   30    2                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Value	Source
Bufotalidin	Kegg
(3beta,5beta)-3,5,14-Trihydroxy-19-oxobufa-20,22-dienolide	Kegg
(3b,5b)-3,5,14-Trihydroxy-19-oxobufa-20,22-dienolide	Generator
(3Β,5β)-3,5,14-trihydroxy-19-oxobufa-20,22-dienolide	Generator

Chemical Formula

C₂₄H₃₂O₆

Average Mass

416.5140 Da

Monoisotopic Mass

416.21989 Da

IUPAC Name

(1S,2S,5S,7S,10R,11S,14S,15R)-5,7,11-trihydroxy-15-methyl-14-(2-oxo-2H-pyran-5-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-2-carbaldehyde

Traditional Name

(1S,2S,5S,7S,10R,11S,14S,15R)-5,7,11-trihydroxy-15-methyl-14-(6-oxopyran-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-2-carbaldehyde

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C24H32O6/c1-21-8-5-18-19(6-10-23(28)12-16(26)4-9-22(18,23)14-25)24(21,29)11-7-17(21)15-2-3-20(27)30-13-15/h2-3,13-14,16-19,26,28-29H,4-12H2,1H3/t16-,17+,18-,19+,21+,22-,23-,24-/m0/s1

InChI Key

TVKPTWJPKVSGJB-XHCIOXAKSA-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
Bufo bufo	LOTUS Database	35616633
Bufo gargarizans	LOTUS Database	35616633
Bufotes viridis	LOTUS Database	35616633
Helleborus caucasicus	Plant	KNApSAcK
Kalanchoe gracilis	Plant	KNApSAcK
Kalanchoe laciniata	LOTUS Database	35616633
Rhinella marina	LOTUS Database	35616633
Sclerophrys mauritanica	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Bufanolides and derivatives

Alternative Parents

Substituents

Bufanolide-skeleton
19-oxosteroid
3-hydroxysteroid
14-hydroxysteroid
5-hydroxysteroid
Hydroxysteroid
Oxosteroid
3-beta-hydroxysteroid
Pyranone
Pyran
Cyclic alcohol
Heteroaromatic compound
Tertiary alcohol
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Aldehyde
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Bufanolides and derivatives (C16969 )

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	1.39	ALOGPS
logP	1.08	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	14.06	ChemAxon
pKa (Strongest Basic)	0.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	110.76 m³·mol⁻¹	ChemAxon
Polarizability	44.04 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

C00033905

Chemspider ID

227825

KEGG Compound ID

C16969

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

259577

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Oliveira RS, Borges BT, Leal AP, de Brum Vieira P, Silva DB, Hyslop S, Vinade L, Dos Santos TG, Carlini CR, Orchard I, Lange AB, Dal Belo CA: Chemical and functional analyses of Rhinella icterica (Spix, 1824) toad secretion screened on contractions of the heart and oviduct in Locusta migratoria. J Insect Physiol. 2021 Feb-Mar;129:104192. doi: 10.1016/j.jinsphys.2021.104192. Epub 2021 Jan 16. [PubMed:33460706 ]
Zhang Y, Yuan B, Bian B, Zhao H, Kiyomi A, Hayashi H, Iwatani Y, Sugiura M, Takagi N: Cytotoxic Effects of Hellebrigenin and Arenobufagin Against Human Breast Cancer Cells. Front Oncol. 2021 Aug 26;11:711220. doi: 10.3389/fonc.2021.711220. eCollection 2021. [PubMed:34513690 ]
Brillatz T, Jacmin M, Vougogiannopoulou K, Petrakis EA, Kalpoutzakis E, Houriet J, Pellissier L, Rutz A, Marcourt L, Queiroz EF, Crawford AD, Skaltsounis AL, Wolfender JL: Antiseizure potential of the ancient Greek medicinal plant Helleborus odorus subsp. cyclophyllus and identification of its main active principles. J Ethnopharmacol. 2020 Sep 15;259:112954. doi: 10.1016/j.jep.2020.112954. Epub 2020 May 21. [PubMed:32445663 ]
Wei X, He J, Gao B, Han L, Mao Y, Zhao H, Si N, Wang H, Yang J, Bian B: Hellebrigenin anti-pancreatic cancer effects based on apoptosis and autophage. PeerJ. 2020 May 8;8:e9011. doi: 10.7717/peerj.9011. eCollection 2020. [PubMed:32426183 ]
Abdelfatah S, Lu X, Schmeda-Hirschmann G, Efferth T: Cytotoxicity and antimitotic activity of Rhinella schneideri and Rhinella marina venoms. J Ethnopharmacol. 2019 Oct 5;242:112049. doi: 10.1016/j.jep.2019.112049. Epub 2019 Jun 29. [PubMed:31265888 ]

Showing NP-Card for 3beta,5beta,14beta-Trihydroxy-19-oxo-bufa-20,22-dienolide 3-O-beta-D-glucopyranoside (NP0073518)

MOL for NP0073518 (3beta,5beta,14beta-Trihydroxy-19-oxo-bufa-20,22-dienolide 3-O-beta-D-glucopyranoside)

3D MOL for NP0073518 (3beta,5beta,14beta-Trihydroxy-19-oxo-bufa-20,22-dienolide 3-O-beta-D-glucopyranoside)

3D SDF for NP0073518 (3beta,5beta,14beta-Trihydroxy-19-oxo-bufa-20,22-dienolide 3-O-beta-D-glucopyranoside)

3D-SDF for NP0073518 (3beta,5beta,14beta-Trihydroxy-19-oxo-bufa-20,22-dienolide 3-O-beta-D-glucopyranoside)

PDB for NP0073518 (3beta,5beta,14beta-Trihydroxy-19-oxo-bufa-20,22-dienolide 3-O-beta-D-glucopyranoside)

3D PDB for NP0073518 (3beta,5beta,14beta-Trihydroxy-19-oxo-bufa-20,22-dienolide 3-O-beta-D-glucopyranoside)

SMILES for NP0073518 (3beta,5beta,14beta-Trihydroxy-19-oxo-bufa-20,22-dienolide 3-O-beta-D-glucopyranoside)

INCHI for NP0073518 (3beta,5beta,14beta-Trihydroxy-19-oxo-bufa-20,22-dienolide 3-O-beta-D-glucopyranoside)

Structure for NP0073518 (3beta,5beta,14beta-Trihydroxy-19-oxo-bufa-20,22-dienolide 3-O-beta-D-glucopyranoside)

3D Structure for NP0073518 (3beta,5beta,14beta-Trihydroxy-19-oxo-bufa-20,22-dienolide 3-O-beta-D-glucopyranoside)