NP-MRD: Showing NP-Card for 3'-(4-Coumaroyloxy-3-methylbutyl-2(E)-enyl)-4,2',4'-trihydroxychalcone (NP0060652)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 05:40:06 UTC

Updated at

2022-04-28 05:40:06 UTC

NP-MRD ID

NP0060652

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3'-(4-Coumaroyloxy-3-methylbutyl-2(E)-enyl)-4,2',4'-trihydroxychalcone

Description

Isogemichalcone b belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position. Thus, isogemichalcone b is considered to be a flavonoid. 3'-(4-Coumaroyloxy-3-methylbutyl-2(E)-enyl)-4,2',4'-trihydroxychalcone is found in Artocarpus dadah and Hypericum geminiflorum. 3'-(4-Coumaroyloxy-3-methylbutyl-2(E)-enyl)-4,2',4'-trihydroxychalcone was first documented in 2002 (PMID: 11858749). Based on a literature review very few articles have been published on Isogemichalcone b.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282207402D          

 36 38  0  0  0  0            999 V2000
    2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -16.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -16.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -16.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -14.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -16.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -16.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -17.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -17.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -18.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -18.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -19.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -20.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -19.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -18.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -21.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -14.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 30 33  1  0  0  0  0
 17 34  1  0  0  0  0
 13 35  1  0  0  0  0
  1 36  1  0  0  0  0
M  END

     RDKit          3D

 62 64  0  0  0  0  0  0  0  0999 V2000
   -1.4442   -2.2819    0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7152   -1.3098   -0.9703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7992   -0.3953   -1.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000   -0.2819   -0.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5848   -0.5737   -1.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2811   -1.1091   -2.8186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0234   -1.4073   -3.2131 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3072   -1.3682   -3.6959 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5990   -1.1109   -3.3938 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9460   -0.5608   -2.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3323   -0.3122   -1.8723 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1750   -0.6078   -2.8018 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8167    0.2382   -0.6294 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1331    0.4431   -0.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6980    0.9889    0.7729 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0824    1.1631    0.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7152    1.6720    1.9557 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9914    2.0387    3.0748 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6387    2.5526    4.1980 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6282    1.8766    3.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9946    1.3584    1.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9058   -0.3093   -1.2924 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1577    0.2418   -0.0282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0072   -1.3355   -1.7348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1465   -1.1394   -1.0328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7923   -1.8246   -0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3606   -2.9182    0.3385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0424   -1.3328    0.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5445   -0.1826    0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7718    0.3923    0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5062   -0.2179    1.6240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6816    0.3830    2.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1361    1.5964    1.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3063    2.1239    2.1197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3946    2.1909    0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2393    1.6146    0.1468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9428   -1.9691    1.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3683   -2.4087    0.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8641   -3.2766   -0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0526    0.3125   -2.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6795   -0.8753    0.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6161    0.8342   -0.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1676   -1.7999   -4.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0793   -1.7993   -4.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3810   -1.3320   -4.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2168    0.5182    0.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7661    0.1749   -1.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6702    0.8762   -0.0442 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7867    1.7993    1.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7757    3.5532    4.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0362    2.1585    3.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9163    1.2424    1.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4007    0.4255    0.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8907   -0.6790   -2.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0168   -2.3893   -2.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5424   -1.9054    1.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9762    0.3415   -0.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2058   -1.1705    2.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2530   -0.1040    2.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2253    1.9529    1.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7375    3.1378    0.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6574    2.0869   -0.6239 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 33 35  1  0
 35 36  2  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 10 22  2  0
 22 23  1  0
 36 30  1  0
 22  5  1  0
 21 15  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
 24 54  1  0
 24 55  1  0
 28 56  1  0
 29 57  1  0
 31 58  1  0
 32 59  1  0
 34 60  1  0
 35 61  1  0
 36 62  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  7 43  1  0
  8 44  1  0
  9 45  1  0
 13 46  1  0
 14 47  1  0
 16 48  1  0
 17 49  1  0
 19 50  1  0
 20 51  1  0
 21 52  1  0
 23 53  1  0
M  END


  Mrv1652304282207402D          

 36 38  0  0  0  0            999 V2000
    2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -16.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -16.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -16.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -14.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -16.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -16.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -17.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -17.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -18.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -18.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -19.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -20.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -19.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -18.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -21.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -14.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 30 33  1  0  0  0  0
 17 34  1  0  0  0  0
 13 35  1  0  0  0  0
  1 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0060652

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(COC(=O)\C=C\C1=CC=C(O)C=C1)=C/CC1=C(O)C=CC(C(=O)\C=C\C2=CC=C(O)C=C2)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C29H26O7/c1-19(18-36-28(34)17-8-21-5-11-23(31)12-6-21)2-13-24-27(33)16-14-25(29(24)35)26(32)15-7-20-3-9-22(30)10-4-20/h2-12,14-17,30-31,33,35H,13,18H2,1H3/b15-7+,17-8+,19-2+

> <INCHI_KEY>
YKTQNXNBVRMYNF-YVMHTMGASA-N

> <FORMULA>
C29H26O7

> <MOLECULAR_WEIGHT>
486.52

> <EXACT_MASS>
486.167853177

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
52.68235071469236

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-4-{2,6-dihydroxy-3-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]phenyl}-2-methylbut-2-en-1-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
5.12

> <JCHEM_LOGP>
6.807750583000001

> <ALOGPS_LOGS>
-5.44

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.396984022174362

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.9249530641730725

> <JCHEM_PKA_STRONGEST_BASIC>
-5.954731948278064

> <JCHEM_POLAR_SURFACE_AREA>
124.29

> <JCHEM_REFRACTIVITY>
140.38580000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.78e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isogemichalcone B

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       4.001 -16.170   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335 -16.940   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335 -18.480   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001 -19.250   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667 -18.480   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667 -16.940   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001 -20.790   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667 -21.560   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667 -23.100   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334 -23.870   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.001 -23.870   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335 -23.100   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668 -23.870   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668 -25.410   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002 -26.180   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002 -27.720   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336 -28.490   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336 -30.030   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002 -30.800   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668 -30.030   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668 -28.490   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.335 -27.720   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.335 -30.800   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.001 -30.030   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.335 -32.340   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668 -33.110   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668 -34.650   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002 -35.420   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.002 -36.960   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668 -37.730   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335 -36.960   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.335 -35.420   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.668 -39.270   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      10.669 -27.720   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       8.002 -23.100   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.001 -14.630   0.000  0.00  0.00           O+0
CONECT    1    2    6   36                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   35                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18   34                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   16   22                                                  
CONECT   22   21                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
CONECT   33   30                                                            
CONECT   34   17                                                            
CONECT   35   13                                                            
CONECT   36    1                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₂₆O₇

Average Mass

486.5200 Da

Monoisotopic Mass

486.16785 Da

IUPAC Name

(2E)-4-{2,6-dihydroxy-3-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]phenyl}-2-methylbut-2-en-1-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

isogemichalcone B

CAS Registry Number

Not Available

SMILES

C\C(COC(=O)\C=C\C1=CC=C(O)C=C1)=C/CC1=C(O)C=CC(C(=O)\C=C\C2=CC=C(O)C=C2)=C1O

InChI Identifier

InChI=1S/C29H26O7/c1-19(18-36-28(34)17-8-21-5-11-23(31)12-6-21)2-13-24-27(33)16-14-25(29(24)35)26(32)15-7-20-3-9-22(30)10-4-20/h2-12,14-17,30-31,33,35H,13,18H2,1H3/b15-7+,17-8+,19-2+

InChI Key

YKTQNXNBVRMYNF-YVMHTMGASA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Artocarpus dadah	Plant	KNApSAcK
Hypericum geminiflorum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

3-prenylated chalcones

Alternative Parents

Substituents

3-prenylated chalcone
2'-hydroxychalcone
Cinnamylphenol
Coumaric acid ester
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Benzoyl
Resorcinol
Styrene
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated ketone
Enoate ester
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enone
Acryloyl-group
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120063 )

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	5.12	ALOGPS
logP	6.81	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	6.92	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	140.39 m³·mol⁻¹	ChemAxon
Polarizability	52.68 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	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

C00014451

Chemspider ID

24716808

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42607532

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Su BN, Cuendet M, Hawthorne ME, Kardono LB, Riswan S, Fong HH, Mehta RG, Pezzuto JM, Kinghorn AD: Constituents of the bark and twigs of Artocarpus dadah with cyclooxygenase inhibitory activity. J Nat Prod. 2002 Feb;65(2):163-9. doi: 10.1021/np010451c. [PubMed:11858749 ]

Showing NP-Card for 3'-(4-Coumaroyloxy-3-methylbutyl-2(E)-enyl)-4,2',4'-trihydroxychalcone (NP0060652)

MOL for NP0060652 (3'-(4-Coumaroyloxy-3-methylbutyl-2(E)-enyl)-4,2',4'-trihydroxychalcone)

3D MOL for NP0060652 (3'-(4-Coumaroyloxy-3-methylbutyl-2(E)-enyl)-4,2',4'-trihydroxychalcone)

3D SDF for NP0060652 (3'-(4-Coumaroyloxy-3-methylbutyl-2(E)-enyl)-4,2',4'-trihydroxychalcone)

3D-SDF for NP0060652 (3'-(4-Coumaroyloxy-3-methylbutyl-2(E)-enyl)-4,2',4'-trihydroxychalcone)

PDB for NP0060652 (3'-(4-Coumaroyloxy-3-methylbutyl-2(E)-enyl)-4,2',4'-trihydroxychalcone)

3D PDB for NP0060652 (3'-(4-Coumaroyloxy-3-methylbutyl-2(E)-enyl)-4,2',4'-trihydroxychalcone)

SMILES for NP0060652 (3'-(4-Coumaroyloxy-3-methylbutyl-2(E)-enyl)-4,2',4'-trihydroxychalcone)

INCHI for NP0060652 (3'-(4-Coumaroyloxy-3-methylbutyl-2(E)-enyl)-4,2',4'-trihydroxychalcone)

Structure for NP0060652 (3'-(4-Coumaroyloxy-3-methylbutyl-2(E)-enyl)-4,2',4'-trihydroxychalcone)

3D Structure for NP0060652 (3'-(4-Coumaroyloxy-3-methylbutyl-2(E)-enyl)-4,2',4'-trihydroxychalcone)