NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6s)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate (NP0237291)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Show more...Show more...

Record Information

Version

2.0

Created at

2022-09-06 20:23:35 UTC

Updated at

2022-09-06 20:23:36 UTC

NP-MRD ID

NP0237291

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6s)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate

Description

Helichrysoside belongs to the class of organic compounds known as flavonoid 3-o-p-coumaroyl glycosides. These are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring. [(2r,3s,4s,5r,6s)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate is found in Castanea sativa, Helichrysum stoechas, Marrubium cylleneum, Melastoma candidum, Pinus banksiana, Rosa canina and Sarcopyramis bodinieri. [(2r,3s,4s,5r,6s)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate was first documented in 2010 (PMID: 20506820). Helichrysoside is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 31847420) (PMID: 23377133) (PMID: 21762034).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309272006312D          

 44 48  0  0  0  0            999 V2000
 9998.584710000.1144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1557 9999.2857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7309 9999.2857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.304110001.7706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.299110003.8332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.728310003.0082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.0115 9997.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7262 9997.4473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.4399 9997.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1556 9997.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8671 9997.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.7258 9998.6838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.4399 9996.2088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1557 9998.6838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1557 9997.0317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5826 9996.2067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.013610002.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.299210003.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.584610002.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.584610001.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.299110001.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.013710001.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.731010001.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.016410001.3546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.016410000.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.730910000.1172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.157110001.7671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.442610001.3546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.442610000.5295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.157110000.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.871610000.5295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.871610001.3546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5840 9998.6832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.8695 9998.2707    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.8695 9997.4456    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.5840 9997.0332    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2985 9997.4456    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.2985 9998.2707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.0117 9998.2721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.2972 9998.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.5827 9998.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.5826 9997.4470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.2971 9997.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.0117 9997.4470    0.0000 C   0  0  0  0  0  0  0  0  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
  9 13  2  0  0  0  0
 10 11  2  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 17  1  0  0  0  0
 18  5  1  0  0  0  0
 17  6  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26  3  1  0  0  0  0
 24  4  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 28  1  0  0  0  0
 27 32  1  0  0  0  0
  1 31  1  0  0  0  0
 32 20  1  0  0  0  0
 30  2  2  0  0  0  0
 28 23  2  0  0  0  0
 26 29  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 39  1  0  0  0  0
 11 42  1  0  0  0  0
 39 12  1  0  0  0  0
 33 38  1  0  0  0  0
 37 38  1  0  0  0  0
 33  1  1  6  0  0  0
 37  7  1  6  0  0  0
 36 16  1  1  0  0  0
 35 15  1  6  0  0  0
 34 14  1  1  0  0  0
M  END

     RDKit          3D

 70 74  0  0  0  0  0  0  0  0999 V2000
    2.5749   -0.6279    1.6650 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1827   -0.8622    0.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6458   -0.9954    0.6394 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3337   -0.8828    1.7412 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7807   -1.0053    1.8475 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4096   -0.8691    3.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7717   -0.9849    3.1680 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5877   -1.2384    2.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9575   -1.3447    2.2563 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9557   -1.3746    0.8689 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5870   -1.2596    0.7589 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4645   -0.9827   -0.5666 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0292   -0.8550   -0.6240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5615   -1.0454   -2.0216 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7970   -0.9282   -2.1743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2625    0.2982   -1.8172 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4991    0.4675   -0.4165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6413    0.9888    0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7308    0.2534    0.4510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7882   -1.1843    0.3223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7253   -2.0346    0.2116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8761   -3.4272    0.1485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1155   -4.0069    0.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2759   -5.4028    0.1345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2078   -3.1738    0.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4776   -3.7549    0.3619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0393   -1.8096    0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8273    0.8317    0.9413 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9326    2.0996    1.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1036    2.6652    1.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2068    4.0281    1.8220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3765    4.5586    2.3362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1403    4.8369    1.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9785    4.2903    0.9794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8982    5.0667    0.6402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8701    2.9166    0.7900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7098    2.3849    0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7691    3.1572   -0.0043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4939    1.4090   -2.4384 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3305    2.4266   -2.9268 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3886    0.8921   -3.5544 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0836    1.9107   -4.1907 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3135   -0.1984   -3.0380 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8510   -0.9754   -4.0521 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1630   -1.1954   -0.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7781   -0.6821    2.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7755   -0.6664    3.9405 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2431   -0.8712    4.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3131   -2.2910    2.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5886   -1.5750    0.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1725   -1.3785   -0.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6055   -1.6681    0.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7969    0.1452   -0.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8000   -2.1221   -2.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3238    0.4198   -2.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7349   -1.6348    0.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0057   -4.0492    0.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1671   -5.8425    0.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2814   -3.1304    0.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9326   -1.1908    0.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8896    1.9803    1.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1521    3.9608    2.5756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1765    5.9052    1.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9651    6.0667    0.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1690    1.9030   -1.7102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8982    2.0209   -3.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2765    0.4176   -4.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7834    2.7845   -3.8514 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1419    0.3008   -2.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0678   -1.8652   -3.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
 44 43  1  0
 43 14  1  0
 14 13  1  0
 13 12  1  0
 12  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  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 33 34  1  0
 34 35  1  0
 34 36  2  0
 36 37  1  0
 37 38  2  0
 19 20  1  0
 20 27  2  0
 27 25  1  0
 25 26  1  0
 25 23  2  0
 23 24  1  0
 23 22  1  0
 22 21  2  0
 16 39  1  0
 39 40  1  0
 39 41  1  0
 41 42  1  0
 41 43  1  0
 11  5  1  0
 37 18  1  0
 21 20  1  0
 36 29  1  0
 44 70  1  0
 43 69  1  1
 14 54  1  6
 13 52  1  0
 13 53  1  0
  3 45  1  0
  4 46  1  0
  6 47  1  0
  7 48  1  0
  9 49  1  0
 10 50  1  0
 11 51  1  0
 16 55  1  6
 30 61  1  0
 32 62  1  0
 33 63  1  0
 35 64  1  0
 27 60  1  0
 26 59  1  0
 24 58  1  0
 22 57  1  0
 21 56  1  0
 39 65  1  1
 40 66  1  0
 41 67  1  6
 42 68  1  0
M  END

  Mrv1652309272006312D          

 44 48  0  0  0  0            999 V2000
 9998.584710000.1144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1557 9999.2857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7309 9999.2857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.304110001.7706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.299110003.8332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.728310003.0082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.0115 9997.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7262 9997.4473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.4399 9997.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1556 9997.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8671 9997.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.7258 9998.6838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.4399 9996.2088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1557 9998.6838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1557 9997.0317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5826 9996.2067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.013610002.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.299210003.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.584610002.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.584610001.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.299110001.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.013710001.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.731010001.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.016410001.3546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.016410000.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.730910000.1172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.157110001.7671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.442610001.3546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.442610000.5295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.157110000.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.871610000.5295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.871610001.3546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5840 9998.6832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.8695 9998.2707    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.8695 9997.4456    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.5840 9997.0332    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2985 9997.4456    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.2985 9998.2707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.0117 9998.2721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.2972 9998.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.5827 9998.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.5826 9997.4470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.2971 9997.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.0117 9997.4470    0.0000 C   0  0  0  0  0  0  0  0  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
  9 13  2  0  0  0  0
 10 11  2  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 17  1  0  0  0  0
 18  5  1  0  0  0  0
 17  6  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26  3  1  0  0  0  0
 24  4  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 28  1  0  0  0  0
 27 32  1  0  0  0  0
  1 31  1  0  0  0  0
 32 20  1  0  0  0  0
 30  2  2  0  0  0  0
 28 23  2  0  0  0  0
 26 29  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 39  1  0  0  0  0
 11 42  1  0  0  0  0
 39 12  1  0  0  0  0
 33 38  1  0  0  0  0
 37 38  1  0  0  0  0
 33  1  1  6  0  0  0
 37  7  1  6  0  0  0
 36 16  1  1  0  0  0
 35 15  1  6  0  0  0
 34 14  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0237291

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C=C2)O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC(O)=C(O)C=C2)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H26O14/c31-15-5-1-13(2-6-15)3-8-22(36)41-12-21-24(37)26(39)27(40)30(43-21)44-29-25(38)23-19(35)10-16(32)11-20(23)42-28(29)14-4-7-17(33)18(34)9-14/h1-11,21,24,26-27,30-35,37,39-40H,12H2/b8-3+/t21-,24-,26+,27-,30+/m1/s1

> <INCHI_KEY>
NBAZENYUDPJQIH-DVQXAVRRSA-N

> <FORMULA>
C30H26O14

> <MOLECULAR_WEIGHT>
610.524

> <EXACT_MASS>
610.132255517

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
59.6262661955469

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
2.585490100333333

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.860186521386145

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.371996893267462

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649110339111198

> <JCHEM_POLAR_SURFACE_AREA>
232.89999999999995

> <JCHEM_REFRACTIVITY>
150.82409999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8664.0258666.880   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8661.3578665.333   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8658.6988665.333   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8656.0348669.972   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8665.3588673.822   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8668.0268672.282   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8666.6888661.130   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8668.0228661.902   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8669.3548661.130   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8670.6908661.902   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8672.0198661.130   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8677.3558664.210   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8669.3548659.590   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8661.3578664.210   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8661.3578661.126   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8664.0218659.586   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0    8666.6928671.512   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8665.3598672.282   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8664.0258671.512   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8664.0258669.972   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8665.3588669.202   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8666.6928669.972   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8658.6988669.965   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8657.3648669.195   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8657.3648667.655   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8658.6988666.885   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0    8661.3608669.965   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0    8660.0268669.195   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8660.0268667.655   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8661.3608666.885   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8662.6948667.655   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8662.6948669.195   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8664.0238664.209   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0    8662.6908663.439   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0    8662.6908661.898   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0    8664.0238661.129   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0    8665.3578661.898   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0    8665.3578663.439   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0    8676.0228663.441   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0    8674.6888664.211   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0    8673.3548663.441   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0    8673.3548661.901   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0    8674.6888661.131   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0    8676.0228661.901   0.000  0.00  0.00           C+0
CONECT    1   31   33                                                       
CONECT    2   30                                                            
CONECT    3   26                                                            
CONECT    4   24                                                            
CONECT    5   18                                                            
CONECT    6   17                                                            
CONECT    7    8   37                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   42                                                       
CONECT   12   39                                                            
CONECT   13    9                                                            
CONECT   14   34                                                            
CONECT   15   35                                                            
CONECT   16   36                                                            
CONECT   17   18   22    6                                                  
CONECT   18   17   19    5                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   32                                                  
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   24   28                                                       
CONECT   24   23   25    4                                                  
CONECT   25   24   26                                                       
CONECT   26   25    3   29                                                  
CONECT   27   28   32                                                       
CONECT   28   29   27   23                                                  
CONECT   29   28   30   26                                                  
CONECT   30   29   31    2                                                  
CONECT   31   30   32    1                                                  
CONECT   32   31   27   20                                                  
CONECT   33   34   38    1                                                  
CONECT   34   33   35   14                                                  
CONECT   35   34   36   15                                                  
CONECT   36   35   37   16                                                  
CONECT   37   36   38    7                                                  
CONECT   38   33   37                                                       
CONECT   39   40   44   12                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   11                                                  
CONECT   43   42   44                                                       
CONECT   44   43   39                                                       
MASTER        0    0    0    0    0    0    0    0   44    0   96    0
END

View in JSmol

Synonyms

Value	Source
Quercetin 3-beta-D-(6"-O-p-coumaroyl) glucoside	PhytoBank
Quercetin 3-β-D-(6"-O-p-coumaroyl) glucoside	PhytoBank
Quercetin 3-β-D-(6″-O-p-coumaroyl) glucoside	PhytoBank
Quercetin 3-O-beta-D-(6"-O-p-coumaroyl) glucoside	PhytoBank
Quercetin 3-O-β-D-(6"-O-p-coumaroyl) glucoside	PhytoBank
Quercetin 3-O-β-D-(6″-O-p-coumaroyl) glucoside	PhytoBank
Quercetin 3-O-beta-D-(6''-O-(E)-p-coumaryl)glucopyranoside	PhytoBank
Quercetin 3-O-β-D-(6''-O-(E)-p-coumaryl)glucopyranoside	PhytoBank
Quercetin 3-O-β-D-(6’’-O-(E)-p-coumaryl)glucopyranoside	PhytoBank

Chemical Formula

C₃₀H₂₆O₁₄

Average Mass

610.5240 Da

Monoisotopic Mass

610.13226 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

[(2R,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C=C2)O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC(O)=C(O)C=C2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C30H26O14/c31-15-5-1-13(2-6-15)3-8-22(36)41-12-21-24(37)26(39)27(40)30(43-21)44-29-25(38)23-19(35)10-16(32)11-20(23)42-28(29)14-4-7-17(33)18(34)9-14/h1-11,21,24,26-27,30-35,37,39-40H,12H2/b8-3+/t21-,24-,26+,27-,30+/m1/s1

InChI Key

NBAZENYUDPJQIH-DVQXAVRRSA-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
Castanea sativa	LOTUS Database	35616633
Helichrysum stoechas	LOTUS Database	35616633
Marrubium cylleneum	LOTUS Database	35616633
Melastoma candidum	LOTUS Database	35616633
Pinus banksiana	LOTUS Database	35616633
Rosa canina	LOTUS Database	35616633
Sarcopyramis bodinieri	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid 3-o-p-coumaroyl glycosides. These are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid 3-O-p-coumaroyl glycosides

Alternative Parents

Substituents

Flavonoid 3-o-6-p-coumaroyl-glycoside
Flavonoid-3-o-glycoside
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Flavone
Coumaric acid ester
Hydroxycinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid or derivatives
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Chromone
Benzopyran
1-benzopyran
Catechol
Styrene
Pyranone
Phenol
Fatty acid ester
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Pyran
Oxane
Monosaccharide
Fatty acyl
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Monocarboxylic acid or derivatives
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.82	ALOGPS
logP	2.59	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	232.9 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	150.82 m³·mol⁻¹	ChemAxon
Polarizability	59.63 Å³	ChemAxon
Number of Rings	5	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

23291786

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5317991

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu B, Zhang T, Zhang X, Ye W, Li Y: [Chemical constituents of Laggera pterodonta]. Zhongguo Zhong Yao Za Zhi. 2010 Mar;35(5):602-6. doi: 10.4268/cjcmm20100513. [PubMed:20506820 ]
Morikawa T, Nagatomo A, Oka T, Miki Y, Taira N, Shibano-Kitahara M, Hori Y, Muraoka O, Ninomiya K: Glucose Tolerance-Improving Activity of Helichrysoside in Mice and Its Structural Requirements for Promoting Glucose and Lipid Metabolism. Int J Mol Sci. 2019 Dec 14;20(24):6322. doi: 10.3390/ijms20246322. [PubMed:31847420 ]
Ndhlala AR, Aderogba MA, Ncube B, Van Staden J: Anti-oxidative and cholinesterase inhibitory effects of leaf extracts and their isolated compounds from two closely related Croton species. Molecules. 2013 Feb 1;18(2):1916-32. doi: 10.3390/molecules18021916. [PubMed:23377133 ]
Aderogba MA, McGaw LJ, Bezabih M, Abegaz BM: Isolation and characterisation of novel antioxidant constituents of Croton zambesicus leaf extract. Nat Prod Res. 2011 Aug;25(13):1224-33. doi: 10.1080/14786419.2010.532499. Epub 2011 Jul 18. [PubMed:21762034 ]
LOTUS database [Link]

Showing NP-Card for [(2r,3s,4s,5r,6s)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate (NP0237291)

MOL for NP0237291 ([(2r,3s,4s,5r,6s)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D MOL for NP0237291 ([(2r,3s,4s,5r,6s)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D SDF for NP0237291 ([(2r,3s,4s,5r,6s)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D-SDF for NP0237291 ([(2r,3s,4s,5r,6s)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

PDB for NP0237291 ([(2r,3s,4s,5r,6s)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D PDB for NP0237291 ([(2r,3s,4s,5r,6s)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

SMILES for NP0237291 ([(2r,3s,4s,5r,6s)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

INCHI for NP0237291 ([(2r,3s,4s,5r,6s)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

Structure for NP0237291 ([(2r,3s,4s,5r,6s)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D Structure for NP0237291 ([(2r,3s,4s,5r,6s)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)