NP-MRD: Showing NP-Card for Wilfornine A (NP0080944)

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Record Information

Version

2.0

Created at

2022-04-29 01:54:55 UTC

Updated at

2022-04-29 01:54:55 UTC

NP-MRD ID

NP0080944

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Wilfornine A

Description

(1S,3S,15R,18R,19R,20R,21R,22S,23S,24R,25S,26S)-19,20,22,23,25-pentakis(acetyloxy)-21-[(acetyloxy)methyl]-26-hydroxy-3,15,26-trimethyl-6,16-dioxo-2,5,17-trioxa-11-azapentacyclo[16.7.1.0¹,²¹.0³,²⁴.0⁷,¹²]Hexacosa-7(12),8,10-trien-15-yl benzoate belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Wilfornine A is found in Tripterygium wilfordii . Based on a literature review very few articles have been published on (1S,3S,15R,18R,19R,20R,21R,22S,23S,24R,25S,26S)-19,20,22,23,25-pentakis(acetyloxy)-21-[(acetyloxy)methyl]-26-hydroxy-3,15,26-trimethyl-6,16-dioxo-2,5,17-trioxa-11-azapentacyclo[16.7.1.0¹,²¹.0³,²⁴.0⁷,¹²]Hexacosa-7(12),8,10-trien-15-yl benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292203542D          

 66 71  0  0  1  0            999 V2000
    2.4079    2.5894    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2632    3.4017    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7645    3.3806    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5032    3.7479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1907    3.2919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1394    2.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4007    2.1011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    2.0124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5656    2.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2531    1.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2019    1.1003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4632    0.7329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7757    1.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0370    0.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9858   -0.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2470   -0.3691    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4738    0.0968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5146    0.9953    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3700    1.8075    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0010    2.3389    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.7132    2.5572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8564    3.1511    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.9739    5.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8292    5.8383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0807    3.4319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4143    2.5353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0653    3.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9519    3.8593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4058    2.0883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8922    0.7447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8126    1.8378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1164    0.4639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0282   -0.3483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8040   -0.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6028   -0.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6008   -1.1144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6622   -3.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3084   -2.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5927    4.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1897    2.3262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    1.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1345    1.2541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9326    0.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 20 19  1  6  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
  1 24  1  0  0  0  0
 24 25  1  1  0  0  0
  3 25  1  0  0  0  0
 24 26  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 29 35  1  6  0  0  0
 35 36  1  0  0  0  0
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 36 38  1  0  0  0  0
 23 39  1  6  0  0  0
 39 40  1  0  0  0  0
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 22 44  1  6  0  0  0
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 21 48  1  6  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 49 51  1  0  0  0  0
 16 52  1  1  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 53 55  1  0  0  0  0
 55 56  2  0  0  0  0
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 58 59  1  0  0  0  0
 59 60  2  0  0  0  0
 55 60  1  0  0  0  0
 16 61  1  6  0  0  0
  3 62  1  6  0  0  0
  1 63  1  6  0  0  0
 63 64  1  0  0  0  0
 64 65  2  0  0  0  0
 64 66  1  0  0  0  0
M  END

     RDKit          3D

117122  0  0  0  0  0  0  0  0999 V2000
   -6.2988    2.6286   -1.7093 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2108   -2.3925   -4.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8802   -2.2238    0.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1397   -1.7898    0.5684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6801    0.1161   -0.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3427   -0.4071   -0.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5542    0.5645    3.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5801    3.0606    0.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6501    4.3078   -0.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7506    3.0482   -0.7797 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7562    0.6502   -0.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7132   -0.6095   -0.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0250    0.1891    0.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6142    2.6298   -4.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8455    3.0733   -4.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7797    0.5640   -1.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8564    4.0734   -3.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4602    4.6803   -1.8341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2436    4.7704   -3.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1917    0.9340    2.8346 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  2  0
  2  4  1  0
  4  5  1  0
  6  5  1  1
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
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 19 20  1  0
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 23 24  1  6
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 29 30  2  0
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 31 32  2  0
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 33 34  2  0
 34 35  1  0
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 37 38  1  0
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  1 68  1  0
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 37 93  1  0
 37 94  1  0
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 49104  1  0
 53105  1  1
 54106  1  6
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 57109  1  0
 59110  1  6
 62111  1  0
 62112  1  0
 62113  1  0
 65114  1  0
 65115  1  0
 65116  1  0
 66117  1  0
M  END


  Mrv1652304292203542D          

 66 71  0  0  1  0            999 V2000
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    2.2632    3.4017    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.1394    2.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4007    2.1011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    2.0124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5656    2.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2531    1.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2019    1.1003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4058    2.0883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8126    1.8378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1164    0.4639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0282   -0.3483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8040   -0.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6028   -0.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6008   -1.1144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4232   -1.1806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8917   -0.5016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6622   -3.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3084   -2.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8342   -1.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5927    4.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1345    1.2541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9326    0.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 20 19  1  6  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
  1 24  1  0  0  0  0
 24 25  1  1  0  0  0
  3 25  1  0  0  0  0
 24 26  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 29 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 23 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 22 44  1  6  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
 21 48  1  6  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 49 51  1  0  0  0  0
 16 52  1  1  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 53 55  1  0  0  0  0
 55 56  2  0  0  0  0
 56 57  1  0  0  0  0
 57 58  2  0  0  0  0
 58 59  1  0  0  0  0
 59 60  2  0  0  0  0
 55 60  1  0  0  0  0
 16 61  1  6  0  0  0
  3 62  1  6  0  0  0
  1 63  1  6  0  0  0
 63 64  1  0  0  0  0
 64 65  2  0  0  0  0
 64 66  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0080944

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@]12[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]3[C@H](OC(C)=O)[C@@]11O[C@]3(C)COC(=O)C3=CC=CN=C3CC[C@@](C)(OC(=O)C3=CC=CC=C3)C(=O)O[C@H]([C@H](OC(C)=O)[C@@H]2OC(C)=O)[C@]1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C45H51NO20/c1-22(47)57-21-44-36(62-26(5)51)32(59-23(2)48)31-34(61-25(4)50)45(44)43(9,56)35(33(60-24(3)49)37(44)63-27(6)52)64-40(55)41(7,65-38(53)28-14-11-10-12-15-28)18-17-30-29(16-13-19-46-30)39(54)58-20-42(31,8)66-45/h10-16,19,31-37,56H,17-18,20-21H2,1-9H3/t31-,32+,33+,34+,35-,36-,37+,41-,42-,43+,44-,45+/m1/s1

> <INCHI_KEY>
YJDNHPICMWQYIV-AZTWRUOYSA-N

> <FORMULA>
C45H51NO20

> <MOLECULAR_WEIGHT>
925.89

> <EXACT_MASS>
925.300443046

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
117

> <JCHEM_AVERAGE_POLARIZABILITY>
90.36504711484311

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3S,15R,18R,19R,20R,21R,22S,23S,24R,25S,26S)-19,20,22,23,25-pentakis(acetyloxy)-21-[(acetyloxy)methyl]-26-hydroxy-3,15,26-trimethyl-6,16-dioxo-2,5,17-trioxa-11-azapentacyclo[16.7.1.0^{1,21}.0^{3,24}.0^{7,12}]hexacosa-7,9,11-trien-15-yl benzoate

> <ALOGPS_LOGP>
2.45

> <JCHEM_LOGP>
1.1726170173333292

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.735136636327432

> <JCHEM_PKA_STRONGEST_BASIC>
2.714854836265149

> <JCHEM_POLAR_SURFACE_AREA>
279.0499999999999

> <JCHEM_REFRACTIVITY>
214.27609999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,15R,18R,19R,20R,21R,22S,23S,24R,25S,26S)-19,20,22,23,25-pentakis(acetyloxy)-21-[(acetyloxy)methyl]-26-hydroxy-3,15,26-trimethyl-6,16-dioxo-2,5,17-trioxa-11-azapentacyclo[16.7.1.0^{1,21}.0^{3,24}.0^{7,12}]hexacosa-7,9,11-trien-15-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       4.495   4.834   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.225   6.350   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.160   6.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.539   6.996   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.823   6.145   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.727   4.608   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.348   3.922   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.010   3.756   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.389   4.442   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.672   3.591   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.577   2.054   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      10.198   1.368   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       8.915   2.219   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.536   1.534   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.440  -0.003   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.061  -0.689   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.618   0.181   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.920   1.691   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.094  -0.045   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.409   1.334   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.961   1.858   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.691   3.374   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.869   4.366   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.686   4.088   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.065   4.773   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.508   2.412   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.048   2.407   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.469   1.208   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.599   5.882   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.777   6.874   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.507   8.390   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.685   9.382   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.133   8.858   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.415  10.898   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.151   6.406   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -0.119   7.922   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -1.568   8.447   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       1.059   8.914   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.653   5.312   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -0.773   4.733   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -1.989   5.679   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -1.777   7.204   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -3.415   5.099   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -0.757   3.898   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -1.935   2.906   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -1.665   1.390   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -3.383   3.430   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -0.217   0.866   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       0.053  -0.650   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       1.501  -1.174   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      -1.125  -1.642   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       6.722  -2.080   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       8.257  -2.204   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       9.131  -0.936   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0       8.917  -3.595   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      10.452  -3.719   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      11.112  -5.110   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      10.238  -6.377   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       8.703  -6.254   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       8.042  -4.863   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       5.291  -2.022   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       4.840   7.817   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0       5.954   4.342   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0       6.258   2.833   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0       7.718   2.341   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0       5.474   1.507   0.000  0.00  0.00           C+0
CONECT    1    2   24   63                                                  
CONECT    2    1    3   30                                                  
CONECT    3    2    4   25   62                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   52   61                                             
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22   48                                                  
CONECT   22   21   23   44                                                  
CONECT   23   22   24   29   39                                             
CONECT   24   23    1   25   26                                             
CONECT   25   24    3                                                       
CONECT   26   24   20   27   28                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   23   30   35                                                  
CONECT   30   29    2   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   29   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   23   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   22   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45                                                            
CONECT   48   21   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49                                                            
CONECT   52   16   53                                                       
CONECT   53   52   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   56   60                                                  
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   55                                                       
CONECT   61   16                                                            
CONECT   62    3                                                            
CONECT   63    1   64                                                       
CONECT   64   63   65   66                                                  
CONECT   65   64                                                            
CONECT   66   64                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  142    0
END

View in JSmol

Synonyms

Value	Source
(1S,3S,15R,18R,19R,20R,21R,22S,23S,24R,25S,26S)-19,20,22,23,25-Pentakis(acetyloxy)-21-[(acetyloxy)methyl]-26-hydroxy-3,15,26-trimethyl-6,16-dioxo-2,5,17-trioxa-11-azapentacyclo[16.7.1.0,.0,.0,]hexacosa-7(12),8,10-trien-15-yl benzoic acid	Generator

Chemical Formula

C₄₅H₅₁NO₂₀

Average Mass

925.8900 Da

Monoisotopic Mass

925.30044 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@]12[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]3[C@H](OC(C)=O)[C@@]11O[C@]3(C)COC(=O)C3=CC=CN=C3CC[C@@](C)(OC(=O)C3=CC=CC=C3)C(=O)O[C@H]([C@H](OC(C)=O)[C@@H]2OC(C)=O)[C@]1(C)O

InChI Identifier

InChI=1S/C45H51NO20/c1-22(47)57-21-44-36(62-26(5)51)32(59-23(2)48)31-34(61-25(4)50)45(44)43(9,56)35(33(60-24(3)49)37(44)63-27(6)52)64-40(55)41(7,65-38(53)28-14-11-10-12-15-28)18-17-30-29(16-13-19-46-30)39(54)58-20-42(31,8)66-45/h10-16,19,31-37,56H,17-18,20-21H2,1-9H3/t31-,32+,33+,34+,35-,36-,37+,41-,42-,43+,44-,45+/m1/s1

InChI Key

YJDNHPICMWQYIV-AZTWRUOYSA-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
Tripterygium wilfordii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Agarofuran
Benzoate ester
Pyridine carboxylic acid
Benzoic acid or derivatives
Benzoyl
Oxepane
Benzenoid
Pyridine
Monosaccharide
Monocyclic benzene moiety
Heteroaromatic compound
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Lactone
Carboxylic acid ester
Oxacycle
Azacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
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
logP	2.45	ALOGPS
logP	1.17	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	12.74	ChemAxon
pKa (Strongest Basic)	2.71	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	279.05 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	214.28 m³·mol⁻¹	ChemAxon
Polarizability	90.37 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163082308

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Wilfornine A (NP0080944)

MOL for NP0080944 (Wilfornine A)

3D MOL for NP0080944 (Wilfornine A)

3D SDF for NP0080944 (Wilfornine A)

3D-SDF for NP0080944 (Wilfornine A)

PDB for NP0080944 (Wilfornine A)

3D PDB for NP0080944 (Wilfornine A)

SMILES for NP0080944 (Wilfornine A)

INCHI for NP0080944 (Wilfornine A)

Structure for NP0080944 (Wilfornine A)

3D Structure for NP0080944 (Wilfornine A)