NP-MRD: Showing NP-Card for (1r,3s,4r,5s)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid (NP0157620)

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Record Information

Version

2.0

Created at

2022-09-02 15:02:34 UTC

Updated at

2022-09-02 15:02:34 UTC

NP-MRD ID

NP0157620

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3s,4r,5s)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid

Description

(1r,3s,4r,5s)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid is found in Cussonia arborea and Tanacetum balsamita.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022217022D          

 37 39  0  0  1  0            999 V2000
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9033   -1.7933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4336   -0.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9639   -0.2428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6211   -0.7315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
  2 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  6  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
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 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 28 35  1  0  0  0  0
 22 36  1  0  0  0  0
 14 36  1  0  0  0  0
 36 37  1  1  0  0  0
M  END

     RDKit          3D

 61 63  0  0  0  0  0  0  0  0999 V2000
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   -2.8363    1.8359    0.9308 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.4177    1.5810   -0.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9813    0.3509   -0.9291 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3240    0.2474   -1.3172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1788   -0.7605   -0.7943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6937   -2.0239   -1.0443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8531   -0.5998   -0.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0890    0.7001    1.0479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7063    0.6873    1.4378 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6418    0.0422    2.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0768   -1.3513    2.7745 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1801   -1.6585    4.1316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9604   -2.3639    2.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3447   -2.3108    1.0453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4040   -3.4133    3.0117 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2825   -1.2722    2.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0905   -0.9378    0.6873 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4042   -0.6813    0.1627 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0331   -1.5040   -0.7475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4233   -2.5171   -1.1273 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3634   -1.2184   -1.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0043   -0.1592   -0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3315    0.2192   -1.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0497   -0.5284   -2.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3156   -0.1427   -2.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8911    0.9995   -2.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1451    1.4407   -2.5024 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1865    1.7810   -1.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7171    2.9343   -0.6961 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9286    1.3697   -0.8296 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1603    0.1679    0.3763 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9116    1.2077   -0.2286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8066    2.7463    0.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3057   -0.1926    0.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7488    2.7070   -0.1032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0801    2.4453   -0.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8645    1.0868   -1.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6579   -2.1028   -1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2208   -1.4839   -0.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4557    1.7796    1.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0007    0.6279    3.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6385   -0.0120    3.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6245   -2.5217    4.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7134   -4.2923    2.6627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8394   -2.2188    2.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8308   -0.4539    2.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7806   -1.9012    0.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8106   -1.8918   -1.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4911    0.4814   -0.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6506   -1.4438   -2.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8988   -0.7222   -3.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3387    1.9540   -0.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5028   -0.1797   -0.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7863    1.2320    0.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
 37 36  1  0
 36 22  1  0
 22 21  1  0
 21 16  1  0
 16 17  1  1
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 15 14  1  0
 14 13  1  0
 13  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 16 18  1  0
 18 20  1  0
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 22 23  1  0
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 24 25  2  0
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 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 33 35  2  0
 14 36  1  0
 12  5  1  0
 35 28  1  0
 37 61  1  0
 36 60  1  6
 22 52  1  6
 21 50  1  0
 21 51  1  0
 17 48  1  0
 15 46  1  0
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 14 45  1  1
  3 38  1  0
  4 39  1  0
  6 40  1  0
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 12 44  1  0
 20 49  1  0
 26 53  1  0
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 29 55  1  0
 30 56  1  0
 32 57  1  0
 34 58  1  0
 35 59  1  0
M  END


  Mrv1652309022217022D          

 37 39  0  0  1  0            999 V2000
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9033   -1.7933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4336   -0.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9639   -0.2428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6211   -0.7315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
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  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
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  5 12  1  0  0  0  0
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 16 18  1  6  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
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 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
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 29 30  1  0  0  0  0
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 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 28 35  1  0  0  0  0
 22 36  1  0  0  0  0
 14 36  1  0  0  0  0
 36 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0157620

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1[C@H](C[C@@](O)(C[C@@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(O)=O)OC(=O)\C=C\C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23-,25+/m0/s1

> <INCHI_KEY>
KRZBCHWVBQOTNZ-ZSGFIFMUSA-N

> <FORMULA>
C25H24O12

> <MOLECULAR_WEIGHT>
516.455

> <EXACT_MASS>
516.126776213

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
49.81725505564839

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3S,4R,5S)-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
2.158230316666666

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.907552884792997

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2760207075026906

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6040694695270155

> <JCHEM_POLAR_SURFACE_AREA>
211.27999999999997

> <JCHEM_REFRACTIVITY>
126.76419999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,4R,5S)-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.003 -16.170   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.336 -14.630   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.153  -3.347   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.143  -1.633   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.133  -0.453   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.626  -1.365   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      14.670  -2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.337   0.000   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.338   3.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      18.672   4.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      20.005   3.850   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      21.339   4.620   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      20.005   2.310   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      21.339   1.540   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      18.672   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      14.670  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5                                                       
CONECT   13    2   14                                                       
CONECT   14   13   15   36                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18   21                                             
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16   22                                                       
CONECT   22   21   23   36                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   35                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   28                                                       
CONECT   36   22   14   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₄O₁₂

Average Mass

516.4550 Da

Monoisotopic Mass

516.12678 Da

IUPAC Name

(1R,3S,4R,5S)-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid

Traditional Name

(1R,3S,4R,5S)-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

O[C@H]1[C@H](C[C@@](O)(C[C@@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(O)=O)OC(=O)\C=C\C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23-,25+/m0/s1

InChI Key

KRZBCHWVBQOTNZ-ZSGFIFMUSA-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
Cussonia arborea	LOTUS Database	35616633
Tanacetum balsamita	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	2.05	ALOGPS
logP	2.16	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.28	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	211.28 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	126.76 m³·mol⁻¹	ChemAxon
Polarizability	49.82 Å³	ChemAxon
Number of Rings	3	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

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3s,4r,5s)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid (NP0157620)

MOL for NP0157620 ((1r,3s,4r,5s)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid)

3D MOL for NP0157620 ((1r,3s,4r,5s)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid)

3D SDF for NP0157620 ((1r,3s,4r,5s)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid)

3D-SDF for NP0157620 ((1r,3s,4r,5s)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid)

PDB for NP0157620 ((1r,3s,4r,5s)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid)

3D PDB for NP0157620 ((1r,3s,4r,5s)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid)

SMILES for NP0157620 ((1r,3s,4r,5s)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid)

INCHI for NP0157620 ((1r,3s,4r,5s)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid)

Structure for NP0157620 ((1r,3s,4r,5s)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid)

3D Structure for NP0157620 ((1r,3s,4r,5s)-3,5-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid)