NP-MRD: Showing NP-Card for 3-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one (NP0142724)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-01 21:19:48 UTC

Updated at

2022-09-01 21:19:48 UTC

NP-MRD ID

NP0142724

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

Description

Kaempferol 3-apiosyl-(1->2)-glucoside belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Thus, kaempferol 3-apiosyl-(1->2)-glucoside is considered to be a flavonoid. 3-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one is found in Securidaca diversifolia. Based on a literature review very few articles have been published on Kaempferol 3-apiosyl-(1->2)-glucoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309012223192D          

 41 45  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2296   -3.7080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0366   -3.8795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4491   -3.1650    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1166   -3.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0012   -2.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7462   -1.7673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8971   -2.5519    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0686   -1.7450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   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
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  1  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  6  0  0  0
 21 22  1  0  0  0  0
 19 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  1  0  0  0
  3 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 26 32  1  0  0  0  0
 25 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
  2 41  1  0  0  0  0
 34 41  1  0  0  0  0
M  END

     RDKit          3D

 69 73  0  0  0  0  0  0  0  0999 V2000
    1.7685    2.0676   -2.5913 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4279    1.7648   -1.5795 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8222    1.1949   -0.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4721    0.9952   -0.5577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0466   -0.2147   -1.1336 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1808   -0.0010   -2.5403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1255   -1.0903   -3.2964 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9861   -0.6154   -4.4637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3320   -1.6813   -5.2736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7935   -2.2035   -2.5403 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1422   -3.0409   -1.9362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659   -1.7335   -1.6136 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0990   -1.6212   -2.2255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4696   -0.4261   -0.8774 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7661   -0.5850    0.4569 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8434    0.1995    0.8645 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5747    1.0311    1.9047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4254    0.8156    2.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6450    0.1557    2.3449 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4739    1.0446    1.7091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3839   -0.6720    3.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5255   -1.5607    3.9889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9624   -0.7359    1.2989 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8281   -1.0449    0.2659 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6224    0.9064    0.6033 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1299    0.3147    1.8504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8253    0.2824    2.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4371   -0.3598    3.3893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3414   -0.9653    4.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8964   -1.5884    5.3883 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708   -0.9270    3.8584 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0408   -0.3005    2.7011 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9397    1.1624    0.5243 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5429    1.6804   -0.4912 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9094    1.9211   -0.5124 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5164    2.4732   -1.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8984    2.7146   -1.6242 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7775    2.8047   -2.7252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4287    2.5571   -2.6803 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6770    2.8841   -3.7906 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7866    2.0086   -1.6074 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5976   -1.0426   -0.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8047   -1.4980   -3.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8679   -0.0484   -4.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3697    0.1093   -5.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4918   -2.1904   -5.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3040   -2.8432   -3.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4850   -3.7067   -2.5841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9614   -2.4967   -0.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4964   -0.7252   -2.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1344    0.3416   -1.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2562    0.8078    0.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7184    1.7530    3.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9624    0.0960    3.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9552    0.6713    0.9330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8989    0.0167    4.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1567   -1.2522    2.8227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9640   -1.9910    4.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5278   -1.6279    1.7977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7101   -1.3257    0.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0901    0.7659    1.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6172   -0.3896    3.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5786   -2.0321    5.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3626   -1.4105    4.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0756   -0.2701    2.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5087    1.6725    0.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4372    2.4675   -0.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2777    3.2465   -3.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0670    3.2913   -4.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3 25  2  0
 25 33  1  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  1  0
 36 38  2  0
 38 39  1  0
 39 40  1  0
 39 41  2  0
 41  2  1  0
  2  1  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  2  0
  5 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 19 23  1  0
 23 24  1  0
 14 12  1  0
 12 13  1  0
 12 10  1  0
 10 11  1  0
 10  7  1  0
  2  3  1  0
 32 26  1  0
 23 16  1  0
 41 34  1  0
  9 46  1  0
  8 44  1  0
  8 45  1  0
  7 43  1  6
  5 42  1  1
 35 66  1  0
 37 67  1  0
 38 68  1  0
 40 69  1  0
 27 61  1  0
 28 62  1  0
 30 63  1  0
 31 64  1  0
 32 65  1  0
 14 51  1  6
 16 52  1  6
 18 53  1  0
 18 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 22 58  1  0
 23 59  1  1
 24 60  1  0
 12 49  1  1
 13 50  1  0
 10 47  1  6
 11 48  1  0
M  END

  Mrv1652309012223192D          

 41 45  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2296   -3.7080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0366   -3.8795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4491   -3.1650    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1166   -3.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0012   -2.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7462   -1.7673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8971   -2.5519    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0686   -1.7450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   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
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  1  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  6  0  0  0
 21 22  1  0  0  0  0
 19 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  1  0  0  0
  3 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 26 32  1  0  0  0  0
 25 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
  2 41  1  0  0  0  0
 34 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0142724

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@H](O[C@@H]2OC[C@](O)(CO)[C@H]2O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O15/c27-7-15-17(32)19(34)22(41-25-23(35)26(36,8-28)9-37-25)24(39-15)40-21-18(33)16-13(31)5-12(30)6-14(16)38-20(21)10-1-3-11(29)4-2-10/h1-6,15,17,19,22-25,27-32,34-36H,7-9H2/t15-,17-,19+,22-,23+,24+,25+,26-/m1/s1

> <INCHI_KEY>
MNBRHJWOHPGQIW-CFSZRLFJSA-N

> <FORMULA>
C26H28O15

> <MOLECULAR_WEIGHT>
580.495

> <EXACT_MASS>
580.142820202

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
54.961143749308306

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
-0.19

> <JCHEM_LOGP>
-1.117769034333333

> <ALOGPS_LOGS>
-2.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.869674543461571

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.372346381580845

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1423791405643646

> <JCHEM_POLAR_SURFACE_AREA>
245.28999999999996

> <JCHEM_REFRACTIVITY>
133.96480000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 01-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-SEP-22         0                                  
HETATM    1  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.162  -6.922   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -5.668  -7.242   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.438  -5.908   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -7.684  -6.813   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -7.469  -4.764   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -6.993  -3.299   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -5.408  -4.764   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.728  -3.257   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   41                                                  
CONECT    3    2    4   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    5   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   23                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23   19   16   24                                                  
CONECT   24   23                                                            
CONECT   25    3   26   33                                                  
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   26                                                       
CONECT   33   25   34                                                       
CONECT   34   33   35   41                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39    2   34                                                  
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₈O₁₅

Average Mass

580.4950 Da

Monoisotopic Mass

580.14282 Da

IUPAC Name

3-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Traditional Name

3-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@H](O[C@@H]2OC[C@](O)(CO)[C@H]2O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C26H28O15/c27-7-15-17(32)19(34)22(41-25-23(35)26(36,8-28)9-37-25)24(39-15)40-21-18(33)16-13(31)5-12(30)6-14(16)38-20(21)10-1-3-11(29)4-2-10/h1-6,15,17,19,22-25,27-32,34-36H,7-9H2/t15-,17-,19+,22-,23+,24+,25+,26-/m1/s1

InChI Key

MNBRHJWOHPGQIW-CFSZRLFJSA-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
Securidaca diversifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Disaccharide
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Pyran
Monocyclic benzene moiety
Benzenoid
Oxane
Tertiary alcohol
Heteroaromatic compound
Vinylogous acid
Oxolane
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Acetal
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Primary 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	-0.19	ALOGPS
logP	-1.1	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	245.29 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	133.96 m³·mol⁻¹	ChemAxon
Polarizability	54.96 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

C00005161

Chemspider ID

10306212

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21722034

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one (NP0142724)

MOL for NP0142724 (3-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

3D MOL for NP0142724 (3-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

3D SDF for NP0142724 (3-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

3D-SDF for NP0142724 (3-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

PDB for NP0142724 (3-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

3D PDB for NP0142724 (3-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

SMILES for NP0142724 (3-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

INCHI for NP0142724 (3-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

Structure for NP0142724 (3-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)

3D Structure for NP0142724 (3-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one)