NP-MRD: Showing NP-Card for Vaticaside C (NP0072549)

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Record Information

Version

2.0

Created at

2022-04-28 17:53:24 UTC

Updated at

2022-04-28 17:53:24 UTC

NP-MRD ID

NP0072549

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Vaticaside C

Description

(1R,2R,3R,9S,10S,17S)-3-[(2R,3S)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]Nonadeca-4(18),5,7(19),11(16),12,14-hexaene-5,13,15-triol belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Vaticaside C is found in Cotylelobium lanceolatum. Based on a literature review very few articles have been published on (1R,2R,3R,9S,10S,17S)-3-[(2R,3S)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]Nonadeca-4(18),5,7(19),11(16),12,14-hexaene-5,13,15-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219532D          

 79 91  0  0  1  0            999 V2000
    2.9894    0.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1730    0.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6586    1.6187    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8336    1.6187    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3192    0.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5028    0.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2461   -0.1886    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0639   -1.0419    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2448   -1.1404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8981   -0.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1097   -0.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0739    0.6557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5309    1.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5185    2.0417    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2993    2.3084    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5362    3.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9703    3.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2072    4.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0100    4.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5759    4.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3390    3.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2469    5.4694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1561    2.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9046    2.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5793    2.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5053    3.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6828    4.6348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3574    5.1097    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1060    4.7629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7806    5.2378    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7066    6.0595    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9581    6.4063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2834    5.9314    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.8841    7.2280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3813    6.5344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5292    4.8910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2038    5.3659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2639    3.7906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8067    3.1693    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3836    2.4611    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7078    1.7025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2130    1.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5372    0.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3563    0.1853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8512    0.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6703    0.7469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5269    1.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0424   -0.3763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6284    3.2433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1033    2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.2718    3.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9752    3.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0934    3.4651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4260   -1.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9823   -2.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7329   -2.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9272   -3.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3709   -2.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2893   -3.4787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0166    2.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5518    3.0436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9098    3.7869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7325    3.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1972    3.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8393    2.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0904    4.5919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9613    1.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5661    0.6557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3825   -0.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5942   -0.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9873   -0.7098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1449    2.0211    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  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  2  0  0  0  0
  7  6  1  6  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 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
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 19 22  1  0  0  0  0
 14 23  1  1  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 27 29  1  0  0  0  0
 30 29  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 30 35  1  0  0  0  0
 35 36  1  1  0  0  0
 34 37  1  6  0  0  0
 33 38  1  1  0  0  0
 32 39  1  6  0  0  0
 39 40  1  0  0  0  0
 26 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 25 43  1  0  0  0  0
 43 44  1  6  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  2  0  0  0  0
 44 50  1  0  0  0  0
 46 51  1  0  0  0  0
 42 52  1  6  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 54 55  2  0  0  0  0
 55 56  1  0  0  0  0
 56 57  2  0  0  0  0
 52 57  1  0  0  0  0
 55 58  1  0  0  0  0
 12 59  1  0  0  0  0
  8 60  1  1  0  0  0
 60 61  2  0  0  0  0
 61 62  1  0  0  0  0
 62 63  2  0  0  0  0
 63 64  1  0  0  0  0
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  3 67  1  1  0  0  0
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 70 73  1  0  0  0  0
  2 74  1  0  0  0  0
 74 75  2  0  0  0  0
 75 76  1  0  0  0  0
 76 77  2  0  0  0  0
  1 77  1  0  0  0  0
 76 78  1  0  0  0  0
 74 79  1  0  0  0  0
M  END

     RDKit          3D

131143  0  0  0  0  0  0  0  0999 V2000
   -4.9244    5.6956    3.4793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5495    5.5798    3.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3686    4.8887    1.8396 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9518    3.6240    1.9564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9386    2.9691    0.6998 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1113    1.6248    0.9544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2869    0.6134    0.5909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1193    0.8336   -0.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2483   -0.1931   -0.4900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0382    0.1443   -1.2245 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9005   -0.9502   -1.4193 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8500   -2.0281   -2.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2155   -2.1481   -3.1713 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8413   -2.9914   -2.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8820   -2.8514   -1.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9041   -1.7739   -0.5304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9416   -0.8209   -0.5389 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711    0.4451    0.2344 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2105    1.1351    0.3117 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0766    2.5717    0.5581 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6829    4.8796    0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7380    5.3465    1.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0214   -0.6340    3.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0792   -2.0209    0.3444 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9737   -2.6805   -0.6145 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1969   -3.3123   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2818   -4.5713    0.3696 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4956   -5.1090    0.7369 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6786   -4.4218    0.5592 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9077   -4.9571    0.9267 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6151   -3.1703   -0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4014   -2.6428   -0.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0287   -3.6714   -1.1447 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8252    1.2169   -0.5115 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2518    2.1249   -1.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0465    1.7149   -2.5921 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9979    3.9034   -3.5712 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1962    4.3144   -2.5331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375    3.4325   -1.5554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6313   -1.4795   -0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7840   -1.7255    0.5481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6090   -0.7177    0.9143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7412   -1.1878    1.6106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8254   -2.5953    1.3607 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8428   -2.8391    0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6860   -3.9202    0.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6661   -4.1314   -0.4732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8565   -3.3073   -1.5583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8396   -3.5071   -2.5190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0004   -2.2273   -1.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0164   -1.9999   -0.7301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4204   -2.9898    1.0394 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282219532D          

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 48 50  2  0  0  0  0
 44 50  1  0  0  0  0
 46 51  1  0  0  0  0
 42 52  1  6  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 54 55  2  0  0  0  0
 55 56  1  0  0  0  0
 56 57  2  0  0  0  0
 52 57  1  0  0  0  0
 55 58  1  0  0  0  0
 12 59  1  0  0  0  0
  8 60  1  1  0  0  0
 60 61  2  0  0  0  0
 61 62  1  0  0  0  0
 62 63  2  0  0  0  0
 63 64  1  0  0  0  0
 64 65  2  0  0  0  0
 60 65  1  0  0  0  0
 63 66  1  0  0  0  0
  3 67  1  1  0  0  0
 67 68  2  0  0  0  0
 68 69  1  0  0  0  0
 69 70  2  0  0  0  0
 70 71  1  0  0  0  0
 71 72  2  0  0  0  0
 67 72  1  0  0  0  0
 70 73  1  0  0  0  0
  2 74  1  0  0  0  0
 74 75  2  0  0  0  0
 75 76  1  0  0  0  0
 76 77  2  0  0  0  0
  1 77  1  0  0  0  0
 76 78  1  0  0  0  0
 74 79  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0072549

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC(=CC3=C2O[C@H]([C@H]3C2=CC(O)=CC(O)=C2)C2=CC=C(O)C=C2)[C@H]2[C@@H]([C@@H]3[C@@H](C4=CC=C(O)C=C4)C4=C(C=C(O)C=C4O)[C@@H]4[C@H](OC5=CC(O)=C2C3=C45)C2=CC=C(O)C=C2)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C62H52O17/c63-25-45-56(73)57(74)58(75)62(78-45)77-44-20-31(19-40-46(30-17-36(68)21-37(69)18-30)59(79-61(40)44)28-5-13-34(66)14-6-28)49-47(26-1-9-32(64)10-2-26)54-48(27-3-11-33(65)12-4-27)50-39(22-38(70)23-41(50)71)51-53-43(24-42(72)52(49)55(53)54)76-60(51)29-7-15-35(67)16-8-29/h1-24,45-49,51,54,56-60,62-75H,25H2/t45-,46+,47+,48+,49+,51+,54-,56-,57+,58-,59+,60-,62-/m1/s1

> <INCHI_KEY>
WFUXCNKDJDHZQF-QBJZPYBASA-N

> <FORMULA>
C62H52O17

> <MOLECULAR_WEIGHT>
1069.081

> <EXACT_MASS>
1068.320450214

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
131

> <JCHEM_AVERAGE_POLARIZABILITY>
109.18816148556522

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3R,9S,10S,17S)-3-[(2R,3S)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0^{4,18}.0^{7,19}.0^{11,16}]nonadeca-4,6,11(16),12,14,18-hexaene-5,13,15-triol

> <ALOGPS_LOGP>
5.62

> <JCHEM_LOGP>
8.162293626

> <ALOGPS_LOGS>
-4.98

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
13

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.104103741251347

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.703958584668934

> <JCHEM_PKA_STRONGEST_BASIC>
-5.453814623081773

> <JCHEM_POLAR_SURFACE_AREA>
299.90999999999997

> <JCHEM_REFRACTIVITY>
285.2544

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3R,9S,10S,17S)-3-[(2R,3S)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-5-yl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0^{4,18}.0^{7,19}.0^{11,16}]nonadeca-4,6,11(16),12,14,18-hexaene-5,13,15-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.580   0.316   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.923   1.817   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.963   3.021   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.423   3.021   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.463   1.817   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.805   0.316   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.193  -0.352   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.853  -1.945   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.324  -2.129   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.676  -0.731   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.205  -0.277   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.138   1.224   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.991   2.271   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.968   3.811   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.425   4.309   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.868   5.784   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.811   6.905   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.253   8.380   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.752   8.734   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.808   7.614   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.366   6.139   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.194  10.210   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.291   4.698   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.689   4.050   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.948   4.937   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.810   6.471   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.413   7.118   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.153   6.231   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.275   8.652   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.534   9.538   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -3.931   8.891   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -5.190   9.777   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.052  11.311   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.655  11.958   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.396  11.072   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -0.998  11.719   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -3.517  13.492   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -6.312  12.198   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -6.588   9.130   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -7.847  10.016   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -4.226   7.076   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -5.239   5.916   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -4.449   4.594   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -5.055   3.178   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -4.131   1.946   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -4.736   0.530   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -6.265   0.346   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -7.189   1.578   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -8.718   1.394   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -6.584   2.994   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      -3.812  -0.702   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      -6.773   6.054   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -7.659   4.795   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -9.193   4.933   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -9.841   6.330   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      -8.954   7.590   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      -7.420   7.451   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0     -11.374   6.468   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      -1.609   1.678   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0       4.891  -3.082   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       6.395  -2.751   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       7.434  -3.888   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0       6.968  -5.356   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0       5.464  -5.687   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0       4.426  -4.550   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0       8.007  -6.494   0.000  0.00  0.00           O+0
HETATM   67  C   UNK     0       5.631   4.409   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0       4.763   5.681   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0       5.432   7.069   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0       6.967   7.184   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0       7.835   5.912   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0       7.167   4.524   0.000  0.00  0.00           C+0
HETATM   73  O   UNK     0       7.635   8.571   0.000  0.00  0.00           O+0
HETATM   74  C   UNK     0       7.395   2.271   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0       8.523   1.224   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0       8.181  -0.277   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0       6.709  -0.731   0.000  0.00  0.00           C+0
HETATM   78  O   UNK     0       9.310  -1.325   0.000  0.00  0.00           O+0
HETATM   79  O   UNK     0       7.737   3.773   0.000  0.00  0.00           O+0
CONECT    1    2    7   77                                                  
CONECT    2    1    3   74                                                  
CONECT    3    2    4   67                                                  
CONECT    4    3    5   15                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7    9   60                                                  
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   59                                                  
CONECT   13   12    5   14                                                  
CONECT   14   13   15   23                                                  
CONECT   15   14    4   16                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   19                                                            
CONECT   23   14   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   43                                                  
CONECT   26   25   27   41                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27   23                                                       
CONECT   29   27   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   39                                                  
CONECT   33   32   34   38                                                  
CONECT   34   33   35   37                                                  
CONECT   35   34   30   36                                                  
CONECT   36   35                                                            
CONECT   37   34                                                            
CONECT   38   33                                                            
CONECT   39   32   40                                                       
CONECT   40   39                                                            
CONECT   41   26   42                                                       
CONECT   42   41   43   52                                                  
CONECT   43   42   25   44                                                  
CONECT   44   43   45   50                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   51                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   44                                                       
CONECT   51   46                                                            
CONECT   52   42   53   57                                                  
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56   58                                                  
CONECT   56   55   57                                                       
CONECT   57   56   52                                                       
CONECT   58   55                                                            
CONECT   59   12                                                            
CONECT   60    8   61   65                                                  
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   64   66                                                  
CONECT   64   63   65                                                       
CONECT   65   64   60                                                       
CONECT   66   63                                                            
CONECT   67    3   68   72                                                  
CONECT   68   67   69                                                       
CONECT   69   68   70                                                       
CONECT   70   69   71   73                                                  
CONECT   71   70   72                                                       
CONECT   72   71   67                                                       
CONECT   73   70                                                            
CONECT   74    2   75   79                                                  
CONECT   75   74   76                                                       
CONECT   76   75   77   78                                                  
CONECT   77   76    1                                                       
CONECT   78   76                                                            
CONECT   79   74                                                            
MASTER        0    0    0    0    0    0    0    0   79    0  182    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₆₂H₅₂O₁₇

Average Mass

1069.0810 Da

Monoisotopic Mass

1068.32045 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC(=CC3=C2O[C@H]([C@H]3C2=CC(O)=CC(O)=C2)C2=CC=C(O)C=C2)[C@H]2[C@@H]([C@@H]3[C@@H](C4=CC=C(O)C=C4)C4=C(C=C(O)C=C4O)[C@@H]4[C@H](OC5=CC(O)=C2C3=C45)C2=CC=C(O)C=C2)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C62H52O17/c63-25-45-56(73)57(74)58(75)62(78-45)77-44-20-31(19-40-46(30-17-36(68)21-37(69)18-30)59(79-61(40)44)28-5-13-34(66)14-6-28)49-47(26-1-9-32(64)10-2-26)54-48(27-3-11-33(65)12-4-27)50-39(22-38(70)23-41(50)71)51-53-43(24-42(72)52(49)55(53)54)76-60(51)29-7-15-35(67)16-8-29/h1-24,45-49,51,54,56-60,62-75H,25H2/t45-,46+,47+,48+,49+,51+,54-,56-,57+,58-,59+,60-,62-/m1/s1

InChI Key

WFUXCNKDJDHZQF-QBJZPYBASA-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
Cotylelobium lanceolatum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Stilbene glycoside
Lignan glycoside
Linear 1,7-diphenylheptane skeleton
Neolignan skeleton
1-phenylcoumaran
Phenolic glycoside
Dibenzocycloheptene
Stilbene
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Coumaran
Indane
Benzofuran
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Acetal
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
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	5.62	ALOGPS
logP	8.16	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	8.7	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	299.91 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	285.25 m³·mol⁻¹	ChemAxon
Polarizability	109.19 Å³	ChemAxon
Number of Rings	13	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

154497656

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Vaticaside C (NP0072549)

MOL for NP0072549 (Vaticaside C)

3D MOL for NP0072549 (Vaticaside C)

3D SDF for NP0072549 (Vaticaside C)

3D-SDF for NP0072549 (Vaticaside C)

PDB for NP0072549 (Vaticaside C)

3D PDB for NP0072549 (Vaticaside C)

SMILES for NP0072549 (Vaticaside C)

INCHI for NP0072549 (Vaticaside C)

Structure for NP0072549 (Vaticaside C)

3D Structure for NP0072549 (Vaticaside C)