NP-MRD: Showing NP-Card for (2s)-2-[(8-{[(1r,2s,3as,3br,5ar,7s,9as,9bs,11ar)-2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid (NP0253346)

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Record Information

Version

2.0

Created at

2022-09-07 17:11:33 UTC

Updated at

2022-09-07 17:11:33 UTC

NP-MRD ID

NP0253346

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-[(8-{[(1r,2s,3as,3br,5ar,7s,9as,9bs,11ar)-2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid

Description

Bufotoxin 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. (2s)-2-[(8-{[(1r,2s,3as,3br,5ar,7s,9as,9bs,11ar)-2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid is found in Bufo bufo, Bufo gargarizans and Phrynoidis asper. (2s)-2-[(8-{[(1r,2s,3as,3br,5ar,7s,9as,9bs,11ar)-2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid was first documented in 2018 (PMID: 30574112). Based on a literature review a small amount of articles have been published on Bufotoxin (PMID: 35202644) (PMID: 32015920) (PMID: 30816222).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072219112D          

 54 58  0  0  1  0            999 V2000
   -7.4918    4.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1154    3.6362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8950    3.9062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9595    2.8261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1799    2.5560    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5033    3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8453    2.5302    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6582    3.3337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0352    2.6861    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7651    3.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9550    3.6216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4149    2.9980    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6048    3.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0647    2.5302    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2546    2.6861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9845    1.2829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957    2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6358    1.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4459    1.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7159    2.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5261    2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0662    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961    1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3362    0.6593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9860    1.1270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7159    0.3475    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9058    0.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6358   -0.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1744   -0.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4444   -1.5234    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2546   -1.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246   -2.4589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7946   -1.0557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560   -0.2762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0662   -0.1202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9860   -1.0557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3347    1.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1449    1.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6850    2.2184    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9550    1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4951    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7651    1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5753    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1154    1.7507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4654    1.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9402    1.7666    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.4379    1.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1170    0.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6147   -0.3093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4334   -0.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9311   -0.8652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7543    0.5528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2566    1.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  4  0  0  0
 24 26  2  0  0  0  0
 27 26  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 27 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 14 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 12 40  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
  9 42  1  0  0  0  0
 42 43  1  1  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
  7 45  1  0  0  0  0
 45 46  1  1  0  0  0
 45 47  1  0  0  0  0
  5 47  1  0  0  0  0
 47 48  1  1  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 50 51  1  0  0  0  0
 51 52  2  0  0  0  0
 51 53  1  0  0  0  0
 53 54  1  0  0  0  0
 48 54  2  0  0  0  0
M  END

     RDKit          3D

114118  0  0  0  0  0  0  0  0999 V2000
   13.6349    0.4545   -0.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.2409   -0.3735   -0.1438 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8284   -1.4144    0.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7161   -2.4827    0.7194 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4913   -1.4966    0.9031 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4471   -1.3365   -0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0971   -1.4347    0.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9746   -1.3530   -0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7046   -0.1566   -1.2886 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4592   -0.5332   -2.0324 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3031   -0.3378   -1.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2305   -0.7395   -2.4036 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9967    0.2794   -0.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0588   -0.6844    0.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6895   -0.1548    1.7827 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9830    1.1848    1.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6412    1.6799    3.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7396    0.7808    3.8890 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4287    0.5557    3.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6543   -0.2678    3.8730 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9364    1.1466    2.1351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3618    0.8325    1.6693 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1397    2.1365    1.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5302    1.9327    1.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5897    1.2723   -0.1791 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1604    2.3790   -1.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0074    0.9677   -0.4624 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5641    1.6987   -1.6940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0469    1.6490   -1.5471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6572    0.3020   -1.3484 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.1576   -0.1748   -2.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7575    0.4410   -0.3092 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.0389    0.9099   -0.8150 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0539    0.1025   -1.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2214    0.6877   -1.7093 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4256    2.0524   -1.7051 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5045    2.5854   -2.1068 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4467    2.7832   -1.2638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3371    2.2789   -0.8483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7428   -0.7378    0.5754 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.4001   -1.8832    0.1702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3023   -2.4899    1.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0288   -3.7158    0.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5260   -2.0058    2.1749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2277   -1.0308    0.6276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7732   -0.7524   -0.7925 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9354   -1.9670   -1.4863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3090   -0.4719   -0.7412 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5886   -1.2999    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1246   -1.1957    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6423    0.1494   -0.3702 C   0  0  2  0  0  0  0  0  0  0  0  0
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    9.6992    0.1371   -2.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.3637   -3.4629    0.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
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   11.6329   -2.1295   -0.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6495   -0.3235   -0.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3508   -0.8814   -3.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8329    0.4986    0.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4481    1.2415   -0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5943   -1.6469    0.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2191   -0.8825   -0.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0525   -0.9270    2.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6204   -0.1022    2.3815 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7174    1.9105    1.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1298    1.1321    1.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5822    1.9098    3.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1189    2.6541    2.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5608    1.2968    4.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2494   -0.1766    4.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3692   -0.7457   -3.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1199   -0.6781   -2.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.9632   -0.9493   -1.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  0
 55114  1  0
M  END


  Mrv1652309072219112D          

 54 58  0  0  1  0            999 V2000
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  1  2  1  0  0  0  0
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  5  6  1  0  0  0  0
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  9 42  1  0  0  0  0
 42 43  1  1  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
  7 45  1  0  0  0  0
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  5 47  1  0  0  0  0
 47 48  1  1  0  0  0
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 49 50  2  0  0  0  0
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 51 53  1  0  0  0  0
 53 54  1  0  0  0  0
 48 54  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0253346

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C[C@]2(O)[C@@H]3CC[C@@H]4C[C@H](CC[C@]4(C)[C@H]3CC[C@]2(C)[C@H]1C1=COC(=O)C=C1)OC(=O)CCCCCCC(O)=N[C@@H](CCCNC(N)=N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C40H60N4O10/c1-24(45)53-31-22-40(51)29-14-13-26-21-27(16-18-38(26,2)28(29)17-19-39(40,3)35(31)25-12-15-33(47)52-23-25)54-34(48)11-7-5-4-6-10-32(46)44-30(36(49)50)9-8-20-43-37(41)42/h12,15,23,26-31,35,51H,4-11,13-14,16-22H2,1-3H3,(H,44,46)(H,49,50)(H4,41,42,43)/t26-,27+,28+,29-,30+,31+,35+,38+,39-,40+/m1/s1

> <INCHI_KEY>
HDTHCLKLBSPBIS-JBXNKDOXSA-N

> <FORMULA>
C40H60N4O10

> <MOLECULAR_WEIGHT>
756.938

> <EXACT_MASS>
756.430944148

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
114

> <JCHEM_AVERAGE_POLARIZABILITY>
83.57912308815739

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(8-{[(1S,2S,5S,7R,10R,11S,13S,14S,15R)-13-(acetyloxy)-11-hydroxy-2,15-dimethyl-14-(2-oxo-2H-pyran-5-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid

> <JCHEM_LOGP>
2.0299579511829093

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
5.824746433369547

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7551223568289536

> <JCHEM_PKA_STRONGEST_BASIC>
12.1474933780868

> <JCHEM_POLAR_SURFACE_AREA>
230.92

> <JCHEM_REFRACTIVITY>
208.8828000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(8-{[(1S,2S,5S,7R,10R,11S,13S,14S,15R)-13-(acetyloxy)-11-hydroxy-2,15-dimethyl-14-(6-oxopyran-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0     -13.985   7.796   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -15.149   6.788   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0     -16.604   7.292   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0     -14.858   5.275   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0     -13.403   4.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -12.139   5.652   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.911   4.723   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0     -10.562   6.223   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -9.399   5.014   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.895   6.469   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.383   6.760   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.375   5.596   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.862   5.887   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.854   4.723   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.342   5.014   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.838   2.395   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.179   4.141   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.187   2.977   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.699   3.268   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.203   4.723   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.715   5.014   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.723   3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.219   2.395   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.228   1.231   0.000  0.00  0.00           O+0
HETATM   26  N   UNK     0       3.707   2.104   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       3.203   0.649   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.691   0.358   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.187  -1.098   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.326  -1.389   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0      -0.830  -2.844   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0      -2.342  -3.135   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0      -2.846  -4.590   0.000  0.00  0.00           N+0
HETATM   34  N   UNK     0      -3.350  -1.971   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       4.211  -0.515   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.723  -0.224   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       3.707  -1.971   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -4.358   3.268   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -5.870   2.977   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -6.879   4.141   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -7.383   2.686   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -8.391   3.850   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -8.895   2.395   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -10.407   2.104   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -11.415   3.268   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -12.069   1.873   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -12.955   3.298   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -13.884   2.070   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -13.285   0.651   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     -14.214  -0.577   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0     -15.742  -0.387   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0     -16.671  -1.615   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0     -16.341   1.032   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0     -15.412   2.260   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   47                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   45                                             
CONECT    8    7                                                            
CONECT    9    7   10   42                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   40                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   38                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   35                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   27   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   14   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   12   41   42                                             
CONECT   41   40                                                            
CONECT   42   40    9   43                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44    7   46   47                                             
CONECT   46   45                                                            
CONECT   47   45    5   48                                                  
CONECT   48   47   49   54                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   54                                                       
CONECT   54   53   48                                                       
MASTER        0    0    0    0    0    0    0    0   54    0  116    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₀H₆₀N₄O₁₀

Average Mass

756.9380 Da

Monoisotopic Mass

756.43094 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C[C@]2(O)[C@@H]3CC[C@@H]4C[C@H](CC[C@]4(C)[C@H]3CC[C@]2(C)[C@H]1C1=COC(=O)C=C1)OC(=O)CCCCCCC(O)=N[C@@H](CCCNC(N)=N)C(O)=O

InChI Identifier

InChI=1S/C40H60N4O10/c1-24(45)53-31-22-40(51)29-14-13-26-21-27(16-18-38(26,2)28(29)17-19-39(40,3)35(31)25-12-15-33(47)52-23-25)54-34(48)11-7-5-4-6-10-32(46)44-30(36(49)50)9-8-20-43-37(41)42/h12,15,23,26-31,35,51H,4-11,13-14,16-22H2,1-3H3,(H,44,46)(H,49,50)(H4,41,42,43)/t26-,27+,28+,29-,30+,31+,35+,38+,39-,40+/m1/s1

InChI Key

HDTHCLKLBSPBIS-JBXNKDOXSA-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
Bufo bufo	LOTUS Database	35616633
Bufo gargarizans	LOTUS Database	35616633
Phrynoidis asper	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
Steroid ester
Hydroxysteroid
14-hydroxysteroid
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
Alpha-amino acid or derivatives
Tricarboxylic acid or derivatives
Pyranone
Fatty amide
Fatty acyl
Pyran
N-acyl-amine
Tertiary alcohol
Heteroaromatic compound
Cyclic alcohol
Guanidine
Carboxylic acid ester
Carboxamide group
Lactone
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Organopnictogen compound
Alcohol
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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

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

16735711

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bufotoxin

METLIN ID

Not Available

PubChem Compound

20054854

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Barsuglia J, Davis AK, Palmer R, Lancelotta R, Windham-Herman AM, Peterson K, Polanco M, Grant R, Griffiths RR: Intensity of Mystical Experiences Occasioned by 5-MeO-DMT and Comparison With a Prior Psilocybin Study. Front Psychol. 2018 Dec 6;9:2459. doi: 10.3389/fpsyg.2018.02459. eCollection 2018. [PubMed:30574112 ]
Oliveira AR, Magalhaes MTQ, Oliveira Dos Santos D, Souza LDR, Andrade PR, Carvalho TP, Santos BPOD, Magalhaes AR, Coelho CM, Tinoco HP, Melo MM, Paixao TAD, Santos RL: Natural cururu toad (Rhinella sp.) poisoning in a free-ranging lesser grison (Galictis cuja): Outcomes in a new susceptible predator with a novel peptide description. Toxicon. 2022 Apr 30;210:44-48. doi: 10.1016/j.toxicon.2022.02.015. Epub 2022 Feb 21. [PubMed:35202644 ]
Pejic R, Simic Prskalo M, Simic J: Ocular Hypotonia and Transient Decrease of Vision as a Consequence of Exposure to a Common Toad Poison. Case Rep Ophthalmol Med. 2020 Jan 16;2020:2983947. doi: 10.1155/2020/2983947. eCollection 2020. [PubMed:32015920 ]
Bokony V, Uveges B, Verebelyi V, Ujhegyi N, Moricz AM: Toads phenotypically adjust their chemical defences to anthropogenic habitat change. Sci Rep. 2019 Feb 28;9(1):3163. doi: 10.1038/s41598-019-39587-3. [PubMed:30816222 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2-[(8-{[(1r,2s,3as,3br,5ar,7s,9as,9bs,11ar)-2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid (NP0253346)

MOL for NP0253346 ((2s)-2-[(8-{[(1r,2s,3as,3br,5ar,7s,9as,9bs,11ar)-2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid)

3D MOL for NP0253346 ((2s)-2-[(8-{[(1r,2s,3as,3br,5ar,7s,9as,9bs,11ar)-2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid)

3D SDF for NP0253346 ((2s)-2-[(8-{[(1r,2s,3as,3br,5ar,7s,9as,9bs,11ar)-2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid)

3D-SDF for NP0253346 ((2s)-2-[(8-{[(1r,2s,3as,3br,5ar,7s,9as,9bs,11ar)-2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid)

PDB for NP0253346 ((2s)-2-[(8-{[(1r,2s,3as,3br,5ar,7s,9as,9bs,11ar)-2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid)

3D PDB for NP0253346 ((2s)-2-[(8-{[(1r,2s,3as,3br,5ar,7s,9as,9bs,11ar)-2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid)

SMILES for NP0253346 ((2s)-2-[(8-{[(1r,2s,3as,3br,5ar,7s,9as,9bs,11ar)-2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid)

INCHI for NP0253346 ((2s)-2-[(8-{[(1r,2s,3as,3br,5ar,7s,9as,9bs,11ar)-2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid)

Structure for NP0253346 ((2s)-2-[(8-{[(1r,2s,3as,3br,5ar,7s,9as,9bs,11ar)-2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid)

3D Structure for NP0253346 ((2s)-2-[(8-{[(1r,2s,3as,3br,5ar,7s,9as,9bs,11ar)-2-(acetyloxy)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-tetradecahydrocyclopenta[a]phenanthren-7-yl]oxy}-1-hydroxy-8-oxooctylidene)amino]-5-carbamimidamidopentanoic acid)