NP-MRD: Showing NP-Card for (3S)-3-hydroxy-1,7-bis(4-hydroxyphenyl)-6E-hepten-5-one (NP0043292)

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Record Information

Version

2.0

Created at

2021-06-21 00:44:32 UTC

Updated at

2021-06-30 00:18:53 UTC

NP-MRD ID

NP0043292

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3S)-3-hydroxy-1,7-bis(4-hydroxyphenyl)-6E-hepten-5-one

Provided By

JEOL Database JEOL Logo

Description

CHEMBL2332113 belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group. (3S)-3-hydroxy-1,7-bis(4-hydroxyphenyl)-6E-hepten-5-one is found in Viscum album. (3S)-3-hydroxy-1,7-bis(4-hydroxyphenyl)-6E-hepten-5-one was first documented in 2013 (Nhiem, N. X., et al.). Based on a literature review very few articles have been published on CHEMBL2332113.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102443D          

 43 44  0  0  0  0            999 V2000
    1.4530   -1.0184   -2.1879 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4503   -0.5058   -1.6844 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6446    0.6855   -0.8128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3434    1.4144   -0.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1052    2.5653    0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744    2.7770    1.6893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7978    3.8660    2.5477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2450    4.7548    2.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4557    5.8305    3.1259 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1069    4.5735    1.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9294    3.4837    0.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9462   -1.0279   -1.9712 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9558   -2.4757   -2.4741 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2935   -2.5335   -3.7432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3360   -3.5433   -1.5570 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1225   -3.8500   -0.2771 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0493   -2.8082    0.8120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1844   -2.3723    1.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2402   -1.4074    2.3270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9414   -0.8887    2.8438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9335    0.0635    3.8196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1735   -1.3261    2.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2284   -2.2872    1.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894    0.9187   -0.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3891    1.1710   -0.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7917    2.0844    1.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4795    3.9982    3.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2347    5.8453    3.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9118    5.2817    1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6032    3.3722   -0.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5745   -0.9458   -1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3658   -0.3756   -2.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9973   -2.7551   -2.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6311   -2.2441   -3.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2839   -4.4759   -2.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7096   -3.3061   -1.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7431   -4.7878    0.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1688   -4.0459   -0.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1156   -2.7805    0.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2078   -1.0791    2.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0101    0.3061    4.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0894   -0.9233    2.7989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2009   -2.6245    1.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  2  0  0  0  0
  2  3  1  0  0  0  0
 18 19  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 17 16  1  0  0  0  0
 13 14  1  0  0  0  0
 22 23  2  0  0  0  0
  2  1  2  0  0  0  0
 16 15  1  0  0  0  0
 11  5  1  0  0  0  0
 15 13  1  0  0  0  0
  5  6  2  0  0  0  0
 23 17  1  0  0  0  0
  6  7  1  0  0  0  0
 13 12  1  0  0  0  0
  7  8  2  0  0  0  0
 20 22  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12  2  1  0  0  0  0
  8  9  1  0  0  0  0
 19 40  1  0  0  0  0
 22 42  1  0  0  0  0
 23 43  1  0  0  0  0
 18 39  1  0  0  0  0
 16 37  1  0  0  0  0
 16 38  1  0  0  0  0
 15 35  1  0  0  0  0
 15 36  1  0  0  0  0
 13 33  1  6  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
  3 24  1  0  0  0  0
  4 25  1  0  0  0  0
 21 41  1  0  0  0  0
 14 34  1  0  0  0  0
 11 30  1  0  0  0  0
  6 26  1  0  0  0  0
  7 27  1  0  0  0  0
 10 29  1  0  0  0  0
  9 28  1  0  0  0  0
M  END

     RDKit          3D

 43 44  0  0  0  0  0  0  0  0999 V2000
    1.4530   -1.0184   -2.1879 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4503   -0.5058   -1.6844 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6446    0.6855   -0.8128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3434    1.4144   -0.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1052    2.5653    0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744    2.7770    1.6893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7978    3.8660    2.5477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2450    4.7548    2.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4557    5.8305    3.1259 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1069    4.5735    1.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9294    3.4837    0.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9462   -1.0279   -1.9712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9558   -2.4757   -2.4741 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2935   -2.5335   -3.7432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3360   -3.5433   -1.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1225   -3.8500   -0.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0493   -2.8082    0.8120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1844   -2.3723    1.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2402   -1.4074    2.3270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9414   -0.8887    2.8438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9335    0.0635    3.8196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1735   -1.3261    2.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2284   -2.2872    1.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894    0.9187   -0.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3891    1.1710   -0.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7917    2.0844    1.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4795    3.9982    3.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2347    5.8453    3.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9118    5.2817    1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6032    3.3722   -0.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5745   -0.9458   -1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3658   -0.3756   -2.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9973   -2.7551   -2.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6311   -2.2441   -3.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2839   -4.4759   -2.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7096   -3.3061   -1.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7431   -4.7878    0.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1688   -4.0459   -0.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1156   -2.7805    0.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2078   -1.0791    2.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0101    0.3061    4.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0894   -0.9233    2.7989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2009   -2.6245    1.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  2  0
  2  3  1  0
 18 19  1  0
  3  4  2  0
  4  5  1  0
 19 20  2  0
 20 21  1  0
 17 16  1  0
 13 14  1  0
 22 23  2  0
  2  1  2  0
 16 15  1  0
 11  5  1  0
 15 13  1  0
  5  6  2  0
 23 17  1  0
  6  7  1  0
 13 12  1  0
  7  8  2  0
 20 22  1  0
  8 10  1  0
 10 11  2  0
 12  2  1  0
  8  9  1  0
 19 40  1  0
 22 42  1  0
 23 43  1  0
 18 39  1  0
 16 37  1  0
 16 38  1  0
 15 35  1  0
 15 36  1  0
 13 33  1  6
 12 31  1  0
 12 32  1  0
  3 24  1  0
  4 25  1  0
 21 41  1  0
 14 34  1  0
 11 30  1  0
  6 26  1  0
  7 27  1  0
 10 29  1  0
  9 28  1  0
M  END


  Mrv1652306212102443D          

 43 44  0  0  0  0            999 V2000
    1.4530   -1.0184   -2.1879 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4503   -0.5058   -1.6844 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6446    0.6855   -0.8128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3434    1.4144   -0.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1052    2.5653    0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744    2.7770    1.6893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7978    3.8660    2.5477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2450    4.7548    2.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4557    5.8305    3.1259 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1069    4.5735    1.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9294    3.4837    0.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9462   -1.0279   -1.9712 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9558   -2.4757   -2.4741 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2935   -2.5335   -3.7432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3360   -3.5433   -1.5570 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1225   -3.8500   -0.2771 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0493   -2.8082    0.8120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1844   -2.3723    1.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2402   -1.4074    2.3270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9414   -0.8887    2.8438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9335    0.0635    3.8196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1735   -1.3261    2.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2284   -2.2872    1.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894    0.9187   -0.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3891    1.1710   -0.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7917    2.0844    1.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4795    3.9982    3.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2347    5.8453    3.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9118    5.2817    1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6032    3.3722   -0.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5745   -0.9458   -1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3658   -0.3756   -2.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9973   -2.7551   -2.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6311   -2.2441   -3.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2839   -4.4759   -2.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7096   -3.3061   -1.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7431   -4.7878    0.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1688   -4.0459   -0.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1156   -2.7805    0.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2078   -1.0791    2.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0101    0.3061    4.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0894   -0.9233    2.7989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2009   -2.6245    1.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  2  0  0  0  0
  2  3  1  0  0  0  0
 18 19  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 17 16  1  0  0  0  0
 13 14  1  0  0  0  0
 22 23  2  0  0  0  0
  2  1  2  0  0  0  0
 16 15  1  0  0  0  0
 11  5  1  0  0  0  0
 15 13  1  0  0  0  0
  5  6  2  0  0  0  0
 23 17  1  0  0  0  0
  6  7  1  0  0  0  0
 13 12  1  0  0  0  0
  7  8  2  0  0  0  0
 20 22  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12  2  1  0  0  0  0
  8  9  1  0  0  0  0
 19 40  1  0  0  0  0
 22 42  1  0  0  0  0
 23 43  1  0  0  0  0
 18 39  1  0  0  0  0
 16 37  1  0  0  0  0
 16 38  1  0  0  0  0
 15 35  1  0  0  0  0
 15 36  1  0  0  0  0
 13 33  1  6  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
  3 24  1  0  0  0  0
  4 25  1  0  0  0  0
 21 41  1  0  0  0  0
 14 34  1  0  0  0  0
 11 30  1  0  0  0  0
  6 26  1  0  0  0  0
  7 27  1  0  0  0  0
 10 29  1  0  0  0  0
  9 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043292

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)C([H])([H])[C@@]([H])(O[H])C([H])([H])C([H])([H])C2=C([H])C([H])=C(O[H])C([H])=C2[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-5,7-11,19-21,23H,6,12-13H2/b11-5+/t19-/m0/s1

> <INCHI_KEY>
CWFOAVBXINFPCW-RXERPNITSA-N

> <FORMULA>
C19H20O4

> <MOLECULAR_WEIGHT>
312.365

> <EXACT_MASS>
312.136159124

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
32.89822276509396

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1E,5S)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hept-1-en-3-one

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
3.795815887

> <ALOGPS_LOGS>
-4.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.319556030838054

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.018962081389152

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7717536212315057

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
90.6132

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.84e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1E,5S)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hept-1-en-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 43 44  0  0  0  0  0  0  0  0999 V2000
    1.4530   -1.0184   -2.1879 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4503   -0.5058   -1.6844 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6446    0.6855   -0.8128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3434    1.4144   -0.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1052    2.5653    0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744    2.7770    1.6893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7978    3.8660    2.5477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2450    4.7548    2.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4557    5.8305    3.1259 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1069    4.5735    1.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9294    3.4837    0.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9462   -1.0279   -1.9712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9558   -2.4757   -2.4741 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2935   -2.5335   -3.7432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3360   -3.5433   -1.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1225   -3.8500   -0.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0493   -2.8082    0.8120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1844   -2.3723    1.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2402   -1.4074    2.3270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9414   -0.8887    2.8438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9335    0.0635    3.8196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1735   -1.3261    2.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2284   -2.2872    1.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894    0.9187   -0.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3891    1.1710   -0.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7917    2.0844    1.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4795    3.9982    3.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2347    5.8453    3.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9118    5.2817    1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6032    3.3722   -0.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5745   -0.9458   -1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3658   -0.3756   -2.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9973   -2.7551   -2.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6311   -2.2441   -3.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2839   -4.4759   -2.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7096   -3.3061   -1.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7431   -4.7878    0.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1688   -4.0459   -0.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1156   -2.7805    0.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2078   -1.0791    2.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0101    0.3061    4.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0894   -0.9233    2.7989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2009   -2.6245    1.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  2  0
  2  3  1  0
 18 19  1  0
  3  4  2  0
  4  5  1  0
 19 20  2  0
 20 21  1  0
 17 16  1  0
 13 14  1  0
 22 23  2  0
  2  1  2  0
 16 15  1  0
 11  5  1  0
 15 13  1  0
  5  6  2  0
 23 17  1  0
  6  7  1  0
 13 12  1  0
  7  8  2  0
 20 22  1  0
  8 10  1  0
 10 11  2  0
 12  2  1  0
  8  9  1  0
 19 40  1  0
 22 42  1  0
 23 43  1  0
 18 39  1  0
 16 37  1  0
 16 38  1  0
 15 35  1  0
 15 36  1  0
 13 33  1  6
 12 31  1  0
 12 32  1  0
  3 24  1  0
  4 25  1  0
 21 41  1  0
 14 34  1  0
 11 30  1  0
  6 26  1  0
  7 27  1  0
 10 29  1  0
  9 28  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  O   UNK     0       1.453  -1.018  -2.188  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.450  -0.506  -1.684  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.645   0.686  -0.813  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.343   1.414  -0.274  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.105   2.565   0.609  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.974   2.777   1.689  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.798   3.866   2.548  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.245   4.755   2.316  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.456   5.830   3.126  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.107   4.574   1.242  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.929   3.484   0.386  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.946  -1.028  -1.971  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.956  -2.476  -2.474  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.294  -2.534  -3.743  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.336  -3.543  -1.557  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.123  -3.850  -0.277  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.049  -2.808   0.812  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.184  -2.372   1.318  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.240  -1.407   2.327  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.941  -0.889   2.844  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.934   0.064   3.820  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.174  -1.326   2.376  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.228  -2.287   1.366  0.00  0.00           C+0
HETATM   24  H   UNK     0       1.689   0.919  -0.630  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.389   1.171  -0.437  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.792   2.084   1.883  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.480   3.998   3.382  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.235   5.845   3.809  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.912   5.282   1.066  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.603   3.372  -0.460  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.575  -0.946  -1.084  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.366  -0.376  -2.747  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.997  -2.755  -2.672  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.631  -2.244  -3.589  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.284  -4.476  -2.137  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.710  -3.306  -1.333  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.743  -4.788   0.150  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.169  -4.046  -0.544  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.116  -2.781   0.930  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.208  -1.079   2.694  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.010   0.306   4.003  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.089  -0.923   2.799  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.201  -2.624   1.014  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    3    1   12                                                  
CONECT    3    2    4   24                                                  
CONECT    4    3    5   25                                                  
CONECT    5    4   11    6                                                  
CONECT    6    5    7   26                                                  
CONECT    7    6    8   27                                                  
CONECT    8    7   10    9                                                  
CONECT    9    8   28                                                       
CONECT   10    8   11   29                                                  
CONECT   11    5   10   30                                                  
CONECT   12   13    2   31   32                                             
CONECT   13   14   15   12   33                                             
CONECT   14   13   34                                                       
CONECT   15   16   13   35   36                                             
CONECT   16   17   15   37   38                                             
CONECT   17   18   16   23                                                  
CONECT   18   17   19   39                                                  
CONECT   19   18   20   40                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   41                                                       
CONECT   22   23   20   42                                                  
CONECT   23   22   17   43                                                  
CONECT   24    3                                                            
CONECT   25    4                                                            
CONECT   26    6                                                            
CONECT   27    7                                                            
CONECT   28    9                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31   12                                                            
CONECT   32   12                                                            
CONECT   33   13                                                            
CONECT   34   14                                                            
CONECT   35   15                                                            
CONECT   36   15                                                            
CONECT   37   16                                                            
CONECT   38   16                                                            
CONECT   39   18                                                            
CONECT   40   19                                                            
CONECT   41   21                                                            
CONECT   42   22                                                            
CONECT   43   23                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   88    0
END

RDKit          3D

43 44  0  0  0  0  0  0  0  0999 V2000
    1.4530   -1.0184   -2.1879 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4503   -0.5058   -1.6844 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6446    0.6855   -0.8128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3434    1.4144   -0.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1052    2.5653    0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744    2.7770    1.6893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7978    3.8660    2.5477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2450    4.7548    2.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4557    5.8305    3.1259 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1069    4.5735    1.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9294    3.4837    0.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9462   -1.0279   -1.9712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9558   -2.4757   -2.4741 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2935   -2.5335   -3.7432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3360   -3.5433   -1.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1225   -3.8500   -0.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0493   -2.8082    0.8120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1844   -2.3723    1.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2402   -1.4074    2.3270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9414   -0.8887    2.8438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9335    0.0635    3.8196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1735   -1.3261    2.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2284   -2.2872    1.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894    0.9187   -0.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3891    1.1710   -0.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7917    2.0844    1.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4795    3.9982    3.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2347    5.8453    3.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9118    5.2817    1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6032    3.3722   -0.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5745   -0.9458   -1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3658   -0.3756   -2.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9973   -2.7551   -2.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6311   -2.2441   -3.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2839   -4.4759   -2.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7096   -3.3061   -1.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7431   -4.7878    0.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1688   -4.0459   -0.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1156   -2.7805    0.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2078   -1.0791    2.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0101    0.3061    4.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0894   -0.9233    2.7989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2009   -2.6245    1.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  2  0
  2  3  1  0
 18 19  1  0
  3  4  2  0
  4  5  1  0
 19 20  2  0
 20 21  1  0
 17 16  1  0
 13 14  1  0
 22 23  2  0
  2  1  2  0
 16 15  1  0
 11  5  1  0
 15 13  1  0
  5  6  2  0
 23 17  1  0
  6  7  1  0
 13 12  1  0
  7  8  2  0
 20 22  1  0
  8 10  1  0
 10 11  2  0
 12  2  1  0
  8  9  1  0
 19 40  1  0
 22 42  1  0
 23 43  1  0
 18 39  1  0
 16 37  1  0
 16 38  1  0
 15 35  1  0
 15 36  1  0
 13 33  1  6
 12 31  1  0
 12 32  1  0
  3 24  1  0
  4 25  1  0
 21 41  1  0
 14 34  1  0
 11 30  1  0
  6 26  1  0
  7 27  1  0
 10 29  1  0
  9 28  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₀O₄

Average Mass

312.3650 Da

Monoisotopic Mass

312.13616 Da

IUPAC Name

(1E,5S)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hept-1-en-3-one

Traditional Name

(1E,5S)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hept-1-en-3-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)C([H])([H])[C@@]([H])(O[H])C([H])([H])C([H])([H])C2=C([H])C([H])=C(O[H])C([H])=C2[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C19H20O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-5,7-11,19-21,23H,6,12-13H2/b11-5+/t19-/m0/s1

InChI Key

CWFOAVBXINFPCW-RXERPNITSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Viscum album	JEOL database	Nhiem, N. X., et al, J. Nat. Prod. 76, 495 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Linear diarylheptanoids

Direct Parent

Curcuminoids

Alternative Parents

Substituents

Bis-desmethoxycurcumin
Cinnamic acid or derivatives
Hydroxycinnamic acid or derivatives
Fatty alcohol
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
B'-hydroxy-alpha,beta-unsaturated-ketone
Fatty acyl
Beta-hydroxy ketone
Monocyclic benzene moiety
Benzenoid
Enone
Acryloyl-group
Alpha,beta-unsaturated ketone
Secondary alcohol
Ketone
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	3.01	ALOGPS
logP	3.8	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	9.02	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	90.61 m³·mol⁻¹	ChemAxon
Polarizability	32.9 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

29417901

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71664797

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nhiem, N. X., et al. (2013). Nhiem, N. X., et al, J. Nat. Prod. 76, 495 (2013). J. Nat. Prod..

Showing NP-Card for (3S)-3-hydroxy-1,7-bis(4-hydroxyphenyl)-6E-hepten-5-one (NP0043292)

MOL for NP0043292 ((3S)-3-hydroxy-1,7-bis(4-hydroxyphenyl)-6E-hepten-5-one)

3D MOL for NP0043292 ((3S)-3-hydroxy-1,7-bis(4-hydroxyphenyl)-6E-hepten-5-one)

3D SDF for NP0043292 ((3S)-3-hydroxy-1,7-bis(4-hydroxyphenyl)-6E-hepten-5-one)

3D-SDF for NP0043292 ((3S)-3-hydroxy-1,7-bis(4-hydroxyphenyl)-6E-hepten-5-one)

PDB for NP0043292 ((3S)-3-hydroxy-1,7-bis(4-hydroxyphenyl)-6E-hepten-5-one)

3D PDB for NP0043292 ((3S)-3-hydroxy-1,7-bis(4-hydroxyphenyl)-6E-hepten-5-one)

SMILES for NP0043292 ((3S)-3-hydroxy-1,7-bis(4-hydroxyphenyl)-6E-hepten-5-one)

INCHI for NP0043292 ((3S)-3-hydroxy-1,7-bis(4-hydroxyphenyl)-6E-hepten-5-one)

Structure for NP0043292 ((3S)-3-hydroxy-1,7-bis(4-hydroxyphenyl)-6E-hepten-5-one)

3D Structure for NP0043292 ((3S)-3-hydroxy-1,7-bis(4-hydroxyphenyl)-6E-hepten-5-one)