NP-MRD: Showing NP-Card for telocinobufagin (NP0040764)

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Record Information

Version

2.0

Created at

2021-06-20 22:50:19 UTC

Updated at

2021-06-30 00:14:51 UTC

NP-MRD ID

NP0040764

Secondary Accession Numbers

None

Natural Product Identification

Common Name

telocinobufagin

Provided By

JEOL Database JEOL Logo

Description

Telocinobufagin 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, telocinobufagin is considered to be a sterol. telocinobufagin is found in Bufo bankorensis, Bufo bufo, Bufo gargarizans, Chan'Su and Rhinella marina. telocinobufagin was first documented in 2020 (PMID: 33299459). Based on a literature review a small amount of articles have been published on Telocinobufagin (PMID: 33664806) (PMID: 33460706) (PMID: 32678501) (PMID: 32549266).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100503D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306212100503D          

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   -2.8111    5.4836   -4.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9290    1.5970   -1.2514 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.1654    1.2446   -2.5264 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0228    1.1337    2.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3662    1.4841    0.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0416   -2.0798    4.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7468   -1.6210    4.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0271   -1.5675    1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2582   -2.7866    2.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5590   -2.1384    1.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1377   -0.6564   -0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3240   -2.1771    0.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1409   -1.1827   -0.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2296   -0.7275   -1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6123    1.4609   -0.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2572    0.6438    1.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1069    2.8814    2.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1302    3.3247    1.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1494    4.1894    0.8843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8217    2.5924    1.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1254    3.7829   -1.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1961    4.9398   -1.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2018    3.8338   -2.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9150    3.6872   -0.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7387    5.5840   -2.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9842    6.5401   -4.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2242    1.7224   -4.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6435    1.6183   -0.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4934    1.2327   -2.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8465   -0.2595   -1.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8957    0.3301    0.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6868    1.6760   -2.7106 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  2  1  1  6  0  0  0
 16 28  1  0  0  0  0
  4  3  1  0  0  0  0
  5  7  1  0  0  0  0
  2 13  1  0  0  0  0
 28 27  1  0  0  0  0
 27 26  1  0  0  0  0
 18 16  1  0  0  0  0
 18 26  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 16 17  1  6  0  0  0
 13 12  1  0  0  0  0
 28 29  1  6  0  0  0
  7  8  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  2  3  1  0  0  0  0
  2  8  1  0  0  0  0
 13 14  1  0  0  0  0
 12 28  1  0  0  0  0
 19 25  2  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 16 15  1  0  0  0  0
 22 23  2  0  0  0  0
 15 14  1  0  0  0  0
  8  9  1  1  0  0  0
  5  6  1  0  0  0  0
 12 46  1  6  0  0  0
  6 38  1  0  0  0  0
  4 35  1  0  0  0  0
  4 36  1  0  0  0  0
  5 37  1  1  0  0  0
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  3 33  1  0  0  0  0
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 10 42  1  0  0  0  0
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 13 47  1  1  0  0  0
 15 50  1  0  0  0  0
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  1 30  1  0  0  0  0
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  1 32  1  0  0  0  0
 27 61  1  0  0  0  0
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 18 55  1  1  0  0  0
 26 59  1  0  0  0  0
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 29 63  1  0  0  0  0
 20 56  1  0  0  0  0
 21 57  1  0  0  0  0
 25 58  1  0  0  0  0
  9 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040764

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C([H])([H])C([H])([H])[C@]2(C([H])([H])[H])[C@@]3([H])C([H])([H])C([H])([H])[C@]4(C([H])([H])[H])[C@@]([H])(C5=C([H])OC(=O)C([H])=C5[H])C([H])([H])C([H])([H])[C@]4(O[H])[C@]3([H])C([H])([H])C([H])([H])[C@]2(O[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O5/c1-21-9-5-16(25)13-23(21,27)11-7-19-18(21)6-10-22(2)17(8-12-24(19,22)28)15-3-4-20(26)29-14-15/h3-4,14,16-19,25,27-28H,5-13H2,1-2H3/t16-,17+,18-,19+,21+,22+,23-,24-/m0/s1

> <INCHI_KEY>
PBSOJKPTQWWJJD-ZBDZJSKLSA-N

> <FORMULA>
C24H34O5

> <MOLECULAR_WEIGHT>
402.531

> <EXACT_MASS>
402.240624195

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
44.02510040068109

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.11

> <JCHEM_LOGP>
2.0446677326666665

> <ALOGPS_LOGS>
-3.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.320705708695314

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.223752248209504

> <JCHEM_PKA_STRONGEST_BASIC>
0.2689892736317283

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
109.97319999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.07e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 63 67  0  0  0  0  0  0  0  0999 V2000
    3.1371    1.5081    1.6667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8686    0.6850    2.0299 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6810    0.8642    3.5684 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5966   -0.0267    4.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8159   -1.5004    3.8468 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9559   -1.9867    4.5530 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9907   -1.7327    2.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0962   -0.8410    1.7246 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3370   -1.2543    2.3280 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2118   -1.1009    0.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0237   -0.5757   -0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7374    0.9134   -0.3091 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6139    1.2009    1.2143 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2884    2.6901    1.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9629    3.1265    0.6827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8745    2.8929   -0.8516 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1154    3.9148   -1.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3211    3.0058   -1.4543 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4420    3.5310   -2.8808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6762    4.9497   -3.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8111    5.4836   -4.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7302    4.6466   -5.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8482    5.1530   -6.5900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5221    3.3080   -5.2959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3883    2.7910   -3.9973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9290    1.5970   -1.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7832    0.6419   -0.8990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4782    1.4189   -1.1390 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1654    1.2446   -2.5264 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0228    1.1337    2.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3662    1.4841    0.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0306    2.5582    1.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6283    0.6427    4.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4675    1.9085    3.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3885    0.2906    3.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6011    0.1134    5.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416   -2.0798    4.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7468   -1.6210    4.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0271   -1.5675    1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2582   -2.7866    2.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5590   -2.1384    1.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1377   -0.6564   -0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3240   -2.1771    0.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1409   -1.1827   -0.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2296   -0.7275   -1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6123    1.4609   -0.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2572    0.6438    1.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1069    2.8814    2.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1302    3.3247    1.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1494    4.1894    0.8843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8217    2.5924    1.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1254    3.7829   -1.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1961    4.9398   -1.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2018    3.8338   -2.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9150    3.6872   -0.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7387    5.5840   -2.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9842    6.5401   -4.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2242    1.7224   -4.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6435    1.6183   -0.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4934    1.2327   -2.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8465   -0.2595   -1.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8957    0.3301    0.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6868    1.6760   -2.7106 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  2  1  1  6
 16 28  1  0
  4  3  1  0
  5  7  1  0
  2 13  1  0
 28 27  1  0
 27 26  1  0
 18 16  1  0
 18 26  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 16 17  1  6
 13 12  1  0
 28 29  1  6
  7  8  1  0
 18 19  1  0
 19 20  1  0
  2  3  1  0
  2  8  1  0
 13 14  1  0
 12 28  1  0
 19 25  2  0
 20 21  2  0
 21 22  1  0
 22 24  1  0
 24 25  1  0
 16 15  1  0
 22 23  2  0
 15 14  1  0
  8  9  1  1
  5  6  1  0
 12 46  1  6
  6 38  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  1
  7 39  1  0
  7 40  1  0
  3 33  1  0
  3 34  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 13 47  1  1
 15 50  1  0
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 14 48  1  0
 14 49  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 27 61  1  0
 27 62  1  0
 18 55  1  1
 26 59  1  0
 26 60  1  0
 17 52  1  0
 17 53  1  0
 17 54  1  0
 29 63  1  0
 20 56  1  0
 21 57  1  0
 25 58  1  0
  9 41  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       3.137   1.508   1.667  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.869   0.685   2.030  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.681   0.864   3.568  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.597  -0.027   4.172  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.816  -1.500   3.847  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.956  -1.987   4.553  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.991  -1.733   2.345  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.096  -0.841   1.725  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.337  -1.254   2.328  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.212  -1.101   0.213  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.024  -0.576  -0.583  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.737   0.913  -0.309  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.614   1.201   1.214  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.288   2.690   1.443  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.963   3.127   0.683  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.875   2.893  -0.852  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.115   3.915  -1.447  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.321   3.006  -1.454  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.442   3.531  -2.881  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.676   4.950  -3.051  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.811   5.484  -4.269  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.730   4.647  -5.479  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.848   5.153  -6.590  0.00  0.00           O+0
HETATM   24  O   UNK     0      -2.522   3.308  -5.296  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.388   2.791  -3.997  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.929   1.597  -1.251  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.783   0.642  -0.899  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.478   1.419  -1.139  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.165   1.245  -2.526  0.00  0.00           O+0
HETATM   30  H   UNK     0       4.023   1.134   2.192  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.366   1.484   0.599  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.031   2.558   1.958  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.628   0.643   4.079  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.468   1.909   3.820  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.389   0.291   3.813  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.601   0.113   5.260  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.042  -2.080   4.206  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.747  -1.621   4.104  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.027  -1.567   1.853  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.258  -2.787   2.192  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.559  -2.138   1.981  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.138  -0.656  -0.174  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.324  -2.177   0.026  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.141  -1.183  -0.355  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.230  -0.728  -1.649  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.612   1.461  -0.684  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.257   0.644   1.577  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.107   2.881   2.505  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.130   3.325   1.151  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.149   4.189   0.884  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.822   2.592   1.109  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.125   3.783  -1.047  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.196   4.940  -1.216  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.202   3.834  -2.535  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.915   3.687  -0.827  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.739   5.584  -2.172  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.984   6.540  -4.426  0.00  0.00           H+0
HETATM   58  H   UNK     0      -2.224   1.722  -4.047  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.644   1.618  -0.419  0.00  0.00           H+0
HETATM   60  H   UNK     0      -3.493   1.233  -2.116  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.847  -0.260  -1.519  0.00  0.00           H+0
HETATM   62  H   UNK     0      -1.896   0.330   0.144  0.00  0.00           H+0
HETATM   63  H   UNK     0       0.687   1.676  -2.711  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    1   13    3    8                                             
CONECT    3    4    2   33   34                                             
CONECT    4    5    3   35   36                                             
CONECT    5    4    7    6   37                                             
CONECT    6    5   38                                                       
CONECT    7    5    8   39   40                                             
CONECT    8   10    7    2    9                                             
CONECT    9    8   41                                                       
CONECT   10    8   11   42   43                                             
CONECT   11   10   12   44   45                                             
CONECT   12   11   13   28   46                                             
CONECT   13    2   12   14   47                                             
CONECT   14   13   15   48   49                                             
CONECT   15   16   14   50   51                                             
CONECT   16   28   18   17   15                                             
CONECT   17   16   52   53   54                                             
CONECT   18   16   26   19   55                                             
CONECT   19   18   20   25                                                  
CONECT   20   19   21   56                                                  
CONECT   21   20   22   57                                                  
CONECT   22   21   24   23                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   19   24   58                                                  
CONECT   26   27   18   59   60                                             
CONECT   27   28   26   61   62                                             
CONECT   28   16   27   29   12                                             
CONECT   29   28   63                                                       
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    3                                                            
CONECT   34    3                                                            
CONECT   35    4                                                            
CONECT   36    4                                                            
CONECT   37    5                                                            
CONECT   38    6                                                            
CONECT   39    7                                                            
CONECT   40    7                                                            
CONECT   41    9                                                            
CONECT   42   10                                                            
CONECT   43   10                                                            
CONECT   44   11                                                            
CONECT   45   11                                                            
CONECT   46   12                                                            
CONECT   47   13                                                            
CONECT   48   14                                                            
CONECT   49   14                                                            
CONECT   50   15                                                            
CONECT   51   15                                                            
CONECT   52   17                                                            
CONECT   53   17                                                            
CONECT   54   17                                                            
CONECT   55   18                                                            
CONECT   56   20                                                            
CONECT   57   21                                                            
CONECT   58   25                                                            
CONECT   59   26                                                            
CONECT   60   26                                                            
CONECT   61   27                                                            
CONECT   62   27                                                            
CONECT   63   29                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  134    0
END

RDKit          3D

63 67  0  0  0  0  0  0  0  0999 V2000
    3.1371    1.5081    1.6667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8686    0.6850    2.0299 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6810    0.8642    3.5684 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5966   -0.0267    4.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8159   -1.5004    3.8468 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9559   -1.9867    4.5530 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9907   -1.7327    2.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0962   -0.8410    1.7246 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3370   -1.2543    2.3280 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2118   -1.1009    0.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0237   -0.5757   -0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7374    0.9134   -0.3091 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6139    1.2009    1.2143 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2884    2.6901    1.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9629    3.1265    0.6827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8745    2.8929   -0.8516 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1154    3.9148   -1.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3211    3.0058   -1.4543 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4420    3.5310   -2.8808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6762    4.9497   -3.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8111    5.4836   -4.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7302    4.6466   -5.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8482    5.1530   -6.5900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5221    3.3080   -5.2959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3883    2.7910   -3.9973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9290    1.5970   -1.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7832    0.6419   -0.8990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4782    1.4189   -1.1390 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1654    1.2446   -2.5264 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0228    1.1337    2.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3662    1.4841    0.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0306    2.5582    1.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6283    0.6427    4.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4675    1.9085    3.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3885    0.2906    3.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6011    0.1134    5.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416   -2.0798    4.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7468   -1.6210    4.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0271   -1.5675    1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2582   -2.7866    2.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5590   -2.1384    1.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1377   -0.6564   -0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3240   -2.1771    0.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1409   -1.1827   -0.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2296   -0.7275   -1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6123    1.4609   -0.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2572    0.6438    1.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1069    2.8814    2.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1302    3.3247    1.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1494    4.1894    0.8843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8217    2.5924    1.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1254    3.7829   -1.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1961    4.9398   -1.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2018    3.8338   -2.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9150    3.6872   -0.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7387    5.5840   -2.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9842    6.5401   -4.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2242    1.7224   -4.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6435    1.6183   -0.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4934    1.2327   -2.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8465   -0.2595   -1.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8957    0.3301    0.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6868    1.6760   -2.7106 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  2  1  1  6
 16 28  1  0
  4  3  1  0
  5  7  1  0
  2 13  1  0
 28 27  1  0
 27 26  1  0
 18 16  1  0
 18 26  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 16 17  1  6
 13 12  1  0
 28 29  1  6
  7  8  1  0
 18 19  1  0
 19 20  1  0
  2  3  1  0
  2  8  1  0
 13 14  1  0
 12 28  1  0
 19 25  2  0
 20 21  2  0
 21 22  1  0
 22 24  1  0
 24 25  1  0
 16 15  1  0
 22 23  2  0
 15 14  1  0
  8  9  1  1
  5  6  1  0
 12 46  1  6
  6 38  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  1
  7 39  1  0
  7 40  1  0
  3 33  1  0
  3 34  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 13 47  1  1
 15 50  1  0
 15 51  1  0
 14 48  1  0
 14 49  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 27 61  1  0
 27 62  1  0
 18 55  1  1
 26 59  1  0
 26 60  1  0
 17 52  1  0
 17 53  1  0
 17 54  1  0
 29 63  1  0
 20 56  1  0
 21 57  1  0
 25 58  1  0
  9 41  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₄O₅

Average Mass

402.5310 Da

Monoisotopic Mass

402.24062 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C([H])([H])C([H])([H])[C@]2(C([H])([H])[H])[C@@]3([H])C([H])([H])C([H])([H])[C@]4(C([H])([H])[H])[C@@]([H])(C5=C([H])OC(=O)C([H])=C5[H])C([H])([H])C([H])([H])[C@]4(O[H])[C@]3([H])C([H])([H])C([H])([H])[C@]2(O[H])C1([H])[H]

InChI Identifier

InChI=1S/C24H34O5/c1-21-9-5-16(25)13-23(21,27)11-7-19-18(21)6-10-22(2)17(8-12-24(19,22)28)15-3-4-20(26)29-14-15/h3-4,14,16-19,25,27-28H,5-13H2,1-2H3/t16-,17+,18-,19+,21+,22+,23-,24-/m0/s1

InChI Key

PBSOJKPTQWWJJD-ZBDZJSKLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Bufo bankorensis	LOTUS Database	35616633
Bufo bufo	LOTUS Database	35616633
Bufo gargarizans	LOTUS Database	35616633
Chan'Su	JEOL database	Zhang, X., et al, Phytochem. 72, 1779 (2011)
Rhinella marina	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
3-hydroxysteroid
14-hydroxysteroid
5-hydroxysteroid
Hydroxysteroid
3-beta-hydroxysteroid
Pyranone
Pyran
Tertiary alcohol
Heteroaromatic compound
Cyclic alcohol
Secondary alcohol
Lactone
Polyol
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

steroid lactone (CHEBI:80908 )
Bufanolide and derivatives [Fig] (C17072 )

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	2.11	ALOGPS
logP	2.04	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	14.22	ChemAxon
pKa (Strongest Basic)	0.27	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	109.97 m³·mol⁻¹	ChemAxon
Polarizability	44.03 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

228185

KEGG Compound ID

C17072

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gao Y, Shi L, Cao Z, Zhu X, Li F, Wang R, Xu J, Zhong J, Zhang B, Lu S: Erratum: Telocinobufagin inhibits the epithelial-to-mesenchymal transition of breast cancer cells through the PI3K/Akt/Snail signaling pathway. Oncol Lett. 2021 Apr;21(4):242. doi: 10.3892/ol.2021.12503. Epub 2021 Jan 31. [PubMed:33664806 ]
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 ]
Liu P, Yang P, Zhang L: Mode of Action of Shan-Zhu-Yu (Cornus officinalis Sieb. et Zucc.) in the Treatment of Depression Based on Network Pharmacology. Evid Based Complement Alternat Med. 2020 Nov 22;2020:8838888. doi: 10.1155/2020/8838888. eCollection 2020. [PubMed:33299459 ]
Yu P, Ma J, Du Y, Wang Q, Chen C, Bai X, He L, Zou D: An efficient strategy based on liquid-liquid extraction and pH-zone-refining counter-current chromatography for selective enrichment, separation, and purification of alkaloids and organic Acids from natural products. J Sep Sci. 2020 Sep;43(18):3607-3614. doi: 10.1002/jssc.202000528. Epub 2020 Aug 4. [PubMed:32678501 ]
Oliveira RS, Borges BT, Leal AP, Lailowski MM, Bordon KCF, Souza VQ, Vinade L, Santos TGD, Hyslop S, Moura S, Arantes EC, Corrado AP, Dal Belo CA: Chemical and Pharmacological Screening of Rhinella icterica (Spix 1824) Toad Parotoid Secretion in Avian Preparations. Toxins (Basel). 2020 Jun 15;12(6). pii: toxins12060396. doi: 10.3390/toxins12060396. [PubMed:32549266 ]
Zhang, X., et al. (2011). Zhang, X., et al, Phytochem. 72, 1779 (2011). Phytochem..

Showing NP-Card for telocinobufagin (NP0040764)

MOL for NP0040764 (telocinobufagin)

3D MOL for NP0040764 (telocinobufagin)

3D SDF for NP0040764 (telocinobufagin)

3D-SDF for NP0040764 (telocinobufagin)

PDB for NP0040764 (telocinobufagin)

3D PDB for NP0040764 (telocinobufagin)

SMILES for NP0040764 (telocinobufagin)

INCHI for NP0040764 (telocinobufagin)

Structure for NP0040764 (telocinobufagin)

3D Structure for NP0040764 (telocinobufagin)