NP-MRD: Showing NP-Card for (2s,3r,4s,5r,6r)-3,5-dihydroxy-2-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)phenoxy]-6-(hydroxymethyl)oxan-4-yl (2e)-3-phenylprop-2-enoate (NP0197499)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 15:46:39 UTC

Updated at

2022-09-04 15:46:39 UTC

NP-MRD ID

NP0197499

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5r,6r)-3,5-dihydroxy-2-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)phenoxy]-6-(hydroxymethyl)oxan-4-yl (2e)-3-phenylprop-2-enoate

Description

Skullcapflavone I 2'-(3'-O-trans-cinnamoyl)glucoside belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. (2s,3r,4s,5r,6r)-3,5-dihydroxy-2-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)phenoxy]-6-(hydroxymethyl)oxan-4-yl (2e)-3-phenylprop-2-enoate is found in Aphis serpylli. Based on a literature review very few articles have been published on Skullcapflavone I 2'-(3'-O-trans-cinnamoyl)glucoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042217462D          

 44 48  0  0  1  0            999 V2000
   -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
    0.7145   -1.2375    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 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
    2.8579    0.8250    0.0000 O   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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    1.4289   -1.6500    0.0000 C   0  0  0  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
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 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
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  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  2  0  0  0  0
 32 37  1  0  0  0  0
 26 38  1  0  0  0  0
 19 38  1  0  0  0  0
 38 39  1  1  0  0  0
 11 40  1  0  0  0  0
 40 41  1  0  0  0  0
  7 41  1  0  0  0  0
 41 42  2  0  0  0  0
  3 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
M  END

     RDKit          3D

 74 78  0  0  0  0  0  0  0  0999 V2000
    7.0277   -0.5746   -3.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8338   -0.6275   -2.6610 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7320   -0.2315   -1.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8443    0.2289   -0.7042 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7709    0.6405    0.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9204    1.0945    1.2349 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5504    0.5543    1.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4474    0.9444    2.6001 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4176    1.3913    3.2917 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1940    0.8419    3.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0695    0.3619    2.5240 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8453    0.3337    3.3165 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8816    0.4910    4.6838 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7188    0.5588    5.4565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5040    0.4644    4.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6003    0.3079    3.4987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5984    0.2368    2.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4456    0.0885    1.4237 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2907   -0.0622    0.1340 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3910    1.2183   -0.4809 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0717    1.1538   -1.8209 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4493    2.4653   -2.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1191    2.3992   -3.8301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4622    1.0788   -1.8435 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9873    1.3364   -3.0862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7978   -0.2977   -1.3390 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1882   -0.3880   -1.0276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1032   -1.1294   -1.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7596   -1.8013   -2.7096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5346   -1.1588   -1.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9676   -0.4861   -0.2998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3738   -0.4896    0.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3494   -1.1745   -0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6598   -1.1756   -0.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0095   -0.4433    0.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0415    0.2593    1.6410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7345    0.2537    1.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0058   -0.7614   -0.2027 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6957   -2.1294   -0.4221 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2203    0.0078    1.2939 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3841    0.0821    0.6662 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5123   -0.3051   -0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4514   -0.7963   -1.4045 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3051   -2.2276   -1.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9208   -1.2608   -4.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9311   -0.8984   -2.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2348    0.4369   -3.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8185    0.3061   -1.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0948    1.4131    2.1162 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1235    1.1667    4.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8174    0.5453    5.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7763    0.6816    6.5044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4414    0.5137    5.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5478    0.2274    2.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1273   -0.6927   -0.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5151    0.2892   -2.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5427    2.6073   -2.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1503    3.2644   -1.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9708    2.3293   -4.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7909    1.8904   -1.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8484    0.5854   -3.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6770   -0.9734   -2.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2268   -1.7489   -1.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2258    0.0980    0.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1108   -1.7578   -1.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4112   -1.7456   -0.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0395   -0.4330    1.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3978    0.8187    2.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9869    0.8031    1.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6747   -0.8032    0.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1694   -2.3861   -0.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2206   -2.5125   -1.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6470   -2.6177   -0.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9009   -2.6800   -2.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 40  1  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
 43 44  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 26 38  1  0
 38 39  1  0
 42  3  1  0
 17 12  1  0
 38 19  1  0
 41  7  1  0
 37 32  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
  4 48  1  0
  6 49  1  0
 10 50  1  0
 44 72  1  0
 44 73  1  0
 44 74  1  0
 13 51  1  0
 14 52  1  0
 15 53  1  0
 16 54  1  0
 19 55  1  6
 21 56  1  6
 22 57  1  0
 22 58  1  0
 23 59  1  0
 24 60  1  1
 25 61  1  0
 26 62  1  6
 30 63  1  0
 31 64  1  0
 33 65  1  0
 34 66  1  0
 35 67  1  0
 36 68  1  0
 37 69  1  0
 38 70  1  1
 39 71  1  0
M  END


  Mrv1652309042217462D          

 44 48  0  0  1  0            999 V2000
   -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
    0.7145   -1.2375    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 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
    2.8579    0.8250    0.0000 O   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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    1.4289   -1.6500    0.0000 C   0  0  0  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
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 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
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  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  2  0  0  0  0
 32 37  1  0  0  0  0
 26 38  1  0  0  0  0
 19 38  1  0  0  0  0
 38 39  1  1  0  0  0
 11 40  1  0  0  0  0
 40 41  1  0  0  0  0
  7 41  1  0  0  0  0
 41 42  2  0  0  0  0
  3 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0197499

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)C=C(OC2=C1OC)C1=CC=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](OC(=O)\C=C\C2=CC=CC=C2)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C32H30O12/c1-39-23-15-20(35)26-19(34)14-22(41-30(26)29(23)40-2)18-10-6-7-11-21(18)42-32-28(38)31(27(37)24(16-33)43-32)44-25(36)13-12-17-8-4-3-5-9-17/h3-15,24,27-28,31-33,35,37-38H,16H2,1-2H3/b13-12+/t24-,27-,28-,31+,32-/m1/s1

> <INCHI_KEY>
KVSAMGNYVGLEFR-GMWGBGIWSA-N

> <FORMULA>
C32H30O12

> <MOLECULAR_WEIGHT>
606.58

> <EXACT_MASS>
606.173726406

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
59.72121732258563

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6R)-3,5-dihydroxy-2-[2-(5-hydroxy-7,8-dimethoxy-4-oxo-4H-chromen-2-yl)phenoxy]-6-(hydroxymethyl)oxan-4-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_LOGP>
3.4607345486666645

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.24291993980793

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.879652488781214

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9811118265495473

> <JCHEM_POLAR_SURFACE_AREA>
170.44

> <JCHEM_REFRACTIVITY>
155.5715

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6R)-3,5-dihydroxy-2-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)phenoxy]-6-(hydroxymethyl)oxan-4-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000 -16.940   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       5.335  -3.080   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
HETATM   42  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   42                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   41                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   40                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   38                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   38                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   32                                                       
CONECT   38   26   19   39                                                  
CONECT   39   38                                                            
CONECT   40   11   41                                                       
CONECT   41   40    7   42                                                  
CONECT   42   41    3   43                                                  
CONECT   43   42   44                                                       
CONECT   44   43                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₃₀O₁₂

Average Mass

606.5800 Da

Monoisotopic Mass

606.17373 Da

IUPAC Name

(2S,3R,4S,5R,6R)-3,5-dihydroxy-2-[2-(5-hydroxy-7,8-dimethoxy-4-oxo-4H-chromen-2-yl)phenoxy]-6-(hydroxymethyl)oxan-4-yl (2E)-3-phenylprop-2-enoate

Traditional Name

(2S,3R,4S,5R,6R)-3,5-dihydroxy-2-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)phenoxy]-6-(hydroxymethyl)oxan-4-yl (2E)-3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)C=C(OC2=C1OC)C1=CC=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](OC(=O)\C=C\C2=CC=CC=C2)[C@H]1O

InChI Identifier

InChI=1S/C32H30O12/c1-39-23-15-20(35)26-19(34)14-22(41-30(26)29(23)40-2)18-10-6-7-11-21(18)42-32-28(38)31(27(37)24(16-33)43-32)44-25(36)13-12-17-8-4-3-5-9-17/h3-15,24,27-28,31-33,35,37-38H,16H2,1-2H3/b13-12+/t24-,27-,28-,31+,32-/m1/s1

InChI Key

KVSAMGNYVGLEFR-GMWGBGIWSA-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
Aphis serpylli	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

8-O-methylated flavonoids

Alternative Parents

Substituents

7-methoxyflavonoid-skeleton
8-methoxyflavonoid-skeleton
Flavone
5-hydroxyflavonoid
Hydroxyflavonoid
Phenolic glycoside
Hexose monosaccharide
Cinnamic acid or derivatives
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Chromone
Benzopyran
1-benzopyran
Phenoxy compound
Styrene
Anisole
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Fatty acid ester
Benzenoid
Monocyclic benzene moiety
Fatty acyl
Monosaccharide
Oxane
Pyran
Heteroaromatic compound
Enoate ester
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Acetal
Monocarboxylic acid or derivatives
Ether
Organooxygen compound
Organic oxide
Carbonyl group
Primary alcohol
Organic oxygen compound
Alcohol
Hydrocarbon derivative
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	3.46	ChemAxon
pKa (Strongest Acidic)	7.88	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	170.44 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	155.57 m³·mol⁻¹	ChemAxon
Polarizability	59.72 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

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

100984954

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5r,6r)-3,5-dihydroxy-2-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)phenoxy]-6-(hydroxymethyl)oxan-4-yl (2e)-3-phenylprop-2-enoate (NP0197499)

MOL for NP0197499 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-2-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)phenoxy]-6-(hydroxymethyl)oxan-4-yl (2e)-3-phenylprop-2-enoate)

3D MOL for NP0197499 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-2-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)phenoxy]-6-(hydroxymethyl)oxan-4-yl (2e)-3-phenylprop-2-enoate)

3D SDF for NP0197499 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-2-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)phenoxy]-6-(hydroxymethyl)oxan-4-yl (2e)-3-phenylprop-2-enoate)

3D-SDF for NP0197499 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-2-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)phenoxy]-6-(hydroxymethyl)oxan-4-yl (2e)-3-phenylprop-2-enoate)

PDB for NP0197499 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-2-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)phenoxy]-6-(hydroxymethyl)oxan-4-yl (2e)-3-phenylprop-2-enoate)

3D PDB for NP0197499 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-2-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)phenoxy]-6-(hydroxymethyl)oxan-4-yl (2e)-3-phenylprop-2-enoate)

SMILES for NP0197499 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-2-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)phenoxy]-6-(hydroxymethyl)oxan-4-yl (2e)-3-phenylprop-2-enoate)

INCHI for NP0197499 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-2-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)phenoxy]-6-(hydroxymethyl)oxan-4-yl (2e)-3-phenylprop-2-enoate)

Structure for NP0197499 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-2-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)phenoxy]-6-(hydroxymethyl)oxan-4-yl (2e)-3-phenylprop-2-enoate)

3D Structure for NP0197499 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-2-[2-(5-hydroxy-7,8-dimethoxy-4-oxochromen-2-yl)phenoxy]-6-(hydroxymethyl)oxan-4-yl (2e)-3-phenylprop-2-enoate)