NP-MRD: Showing NP-Card for 2-[(3,4-dihydroxyphenyl)methylidene]-4,6-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1-benzofuran-3-one (NP0319433)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 20:27:19 UTC

Updated at

2022-09-11 20:27:19 UTC

NP-MRD ID

NP0319433

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(3,4-dihydroxyphenyl)methylidene]-4,6-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1-benzofuran-3-one

Description

2-[(3,4-Dihydroxyphenyl)methylidene]-4,6-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-2,3-dihydro-1-benzofuran-3-one belongs to the class of organic compounds known as aurone o-glycosides. These are aurone flavonoids containing a carbohydrate moiety O-glycosidically bound to the aurone skeleton. 2-[(3,4-dihydroxyphenyl)methylidene]-4,6-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1-benzofuran-3-one is found in Zinnia elegans. 2-[(3,4-Dihydroxyphenyl)methylidene]-4,6-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-2,3-dihydro-1-benzofuran-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251511152D          

 43 47  0  0  0  0            999 V2000
    5.4957    5.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -0.5396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.7771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.7771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    3.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    4.3808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    3.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    4.3808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    5.6479    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 22  2  0  0  0  0
 22 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  4  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
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 27 34  1  0  0  0  0
 25 35  1  0  0  0  0
 35 36  1  0  0  0  0
 22 36  1  0  0  0  0
 36 37  2  0  0  0  0
  7 37  1  0  0  0  0
  5 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
  3 42  1  0  0  0  0
 42 43  1  0  0  0  0
M  END

     RDKit          3D

 73 77  0  0  0  0  0  0  0  0999 V2000
   -4.1174    0.1612    0.1277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2420    1.0406    0.0416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5259    2.4700    0.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7226    3.0800    0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8393    4.5128    0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8962    5.1025   -0.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9883    6.4789   -0.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0716    7.3055   -0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1834    8.6839   -0.0802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0202    6.7091    0.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0475    7.4760    1.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9266    5.3376    0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2878    3.0883   -0.0869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2721    2.1304   -0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0902    2.2249   -0.2170 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9214    1.0930   -0.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2636    1.2363   -0.3298 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2435    0.2596   -0.3707 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9317    0.3985   -1.5691 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2090   -0.0785   -1.5858 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2550    1.0200   -1.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1049    1.7979   -2.7943 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5116   -1.0850   -0.5145 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8575   -1.4398   -0.5865 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2393   -0.5808    0.8804 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9687   -1.6615    1.7139 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1504    0.4391    0.8316 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3237    0.2272    1.9605 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3479   -0.1742   -0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0145   -0.2719   -0.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6443   -1.4729    0.0158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1422   -2.7712    0.0202 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4044   -3.3567    1.2335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9406   -4.6364    1.3942 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2673   -5.2179    2.7512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7581   -6.5125    2.8178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3467   -5.5678    0.2730 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6946   -5.9169    0.3840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0478   -4.9413   -1.0701 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3524   -4.8050   -1.1385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6330   -3.5703   -1.1612 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0174   -3.5718   -1.2643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8000    0.8624   -0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5950    2.4465    0.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6194    4.4723   -1.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8219    6.9058   -1.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5034    9.2524    0.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2918    7.0171    1.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0924    4.8704    1.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5805    3.1787   -0.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8800   -0.7806   -0.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3313   -0.6382   -2.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2807    0.5893   -1.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1732    1.7102   -0.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5220    1.3524   -3.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8823   -1.9863   -0.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3543   -0.8603    0.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1451   -0.0803    1.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1110   -1.5130    2.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5112    1.4638    0.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3992    0.5544    1.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9648   -1.0611   -0.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0417   -2.7451   -0.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1704   -4.5777    1.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3391   -5.1679    2.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7350   -4.5837    3.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2189   -6.4424    3.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7766   -6.5189    0.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1901   -5.7790   -0.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4335   -5.5584   -1.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6681   -4.9174   -2.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2548   -3.0958   -2.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4174   -3.0101   -0.5318 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 34 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 39 41  1  0
 41 42  1  0
 30 43  2  0
 43  2  1  0
  2  1  2  0
  2  3  1  0
  3 13  1  0
 13 14  1  0
 14 15  2  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 18 27  1  0
 27 28  1  0
 27 25  1  0
 25 26  1  0
 25 23  1  0
 23 24  1  0
 23 20  1  0
 15 16  1  0
 12  5  1  0
 41 32  1  0
 14 43  1  0
 22 55  1  0
 21 53  1  0
 21 54  1  0
 20 52  1  6
 18 51  1  6
 29 62  1  0
 32 63  1  6
 34 64  1  1
 35 65  1  0
 35 66  1  0
 36 67  1  0
 37 68  1  1
 38 69  1  0
 39 70  1  6
 40 71  1  0
 41 72  1  6
 42 73  1  0
 15 50  1  0
  4 44  1  0
  6 45  1  0
  7 46  1  0
  9 47  1  0
 11 48  1  0
 12 49  1  0
 27 60  1  1
 28 61  1  0
 25 58  1  1
 26 59  1  0
 23 56  1  6
 24 57  1  0
M  END


  Mrv1533004251511152D          

 43 47  0  0  0  0            999 V2000
    5.4957    5.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -0.5396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.7771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.7771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    3.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    4.3808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    3.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    4.3808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    5.6479    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 22  2  0  0  0  0
 22 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  4  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
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 27 34  1  0  0  0  0
 25 35  1  0  0  0  0
 35 36  1  0  0  0  0
 22 36  1  0  0  0  0
 36 37  2  0  0  0  0
  7 37  1  0  0  0  0
  5 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
  3 42  1  0  0  0  0
 42 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0319433

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2=CC(OC3OC(CO)C(O)C(O)C3O)=C3C(=O)C(OC3=C2)=CC2=CC=C(O)C(O)=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O16/c28-7-16-20(33)22(35)24(37)26(42-16)39-10-5-13-18(19(32)15(40-13)4-9-1-2-11(30)12(31)3-9)14(6-10)41-27-25(38)23(36)21(34)17(8-29)43-27/h1-6,16-17,20-31,33-38H,7-8H2

> <INCHI_KEY>
VKSREXJNZIANJD-UHFFFAOYSA-N

> <FORMULA>
C27H30O16

> <MOLECULAR_WEIGHT>
610.521

> <EXACT_MASS>
610.153384886

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
58.96556856760785

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(3,4-dihydroxyphenyl)methylidene]-4,6-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-2,3-dihydro-1-benzofuran-3-one

> <ALOGPS_LOGP>
-0.70

> <JCHEM_LOGP>
-2.548123157000001

> <ALOGPS_LOGS>
-2.30

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.77531906825301

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.82849762280238

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6483953457596012

> <JCHEM_POLAR_SURFACE_AREA>
265.52

> <JCHEM_REFRACTIVITY>
139.2587

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.04e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(3,4-dihydroxyphenyl)methylidene]-4,6-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1-benzofuran-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  O   UNK     0      10.259  10.543   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.259   9.003   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.925   8.233   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.925   6.693   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.591   4.383   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.258  -1.007   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.591  -0.237   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.925  -1.007   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.259  -0.237   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.592  -1.007   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.925  -2.547   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.259  -3.317   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.591  -3.317   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.591  -4.857   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.258  -2.547   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.924  -3.317   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.650   0.132   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.090   4.177   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.630   4.177   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.400   5.510   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.630   6.844   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -3.400   8.178   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.090   6.844   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.320   8.178   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -0.320   5.510   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       6.258   8.233   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       4.924   9.003   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       7.591   9.003   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       7.591  10.543   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   42                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   38                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   37                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   22                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   11   21                                                  
CONECT   21   20                                                            
CONECT   22    9   23   36                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   35                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   27                                                       
CONECT   35   25   36                                                       
CONECT   36   35   22   37                                                  
CONECT   37   36    7                                                       
CONECT   38    5   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40    3   43                                                  
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₀O₁₆

Average Mass

610.5210 Da

Monoisotopic Mass

610.15338 Da

IUPAC Name

2-[(3,4-dihydroxyphenyl)methylidene]-4,6-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-2,3-dihydro-1-benzofuran-3-one

Traditional Name

2-[(3,4-dihydroxyphenyl)methylidene]-4,6-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1-benzofuran-3-one

CAS Registry Number

Not Available

SMILES

OCC1OC(OC2=CC(OC3OC(CO)C(O)C(O)C3O)=C3C(=O)C(OC3=C2)=CC2=CC=C(O)C(O)=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C27H30O16/c28-7-16-20(33)22(35)24(37)26(42-16)39-10-5-13-18(19(32)15(40-13)4-9-1-2-11(30)12(31)3-9)14(6-10)41-27-25(38)23(36)21(34)17(8-29)43-27/h1-6,16-17,20-31,33-38H,7-8H2

InChI Key

VKSREXJNZIANJD-UHFFFAOYSA-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
Zinnia elegans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aurone o-glycosides. These are aurone flavonoids containing a carbohydrate moiety O-glycosidically bound to the aurone skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Aurone O-glycosides

Alternative Parents

Substituents

Aurone-6-o-glycoside
Aurone-4-o-glycoside
Aurone
Phenolic glycoside
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Hexose monosaccharide
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Coumaran
Benzofuran
Catechol
Aryl ketone
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Monosaccharide
Oxane
Secondary alcohol
Ketone
Organoheterocyclic compound
Acetal
Oxacycle
Polyol
Primary alcohol
Aldehyde
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-0.7	ALOGPS
logP	-2.5	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	8.83	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	265.52 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	139.26 m³·mol⁻¹	ChemAxon
Polarizability	58.97 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

74819316

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(3,4-dihydroxyphenyl)methylidene]-4,6-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1-benzofuran-3-one (NP0319433)

MOL for NP0319433 (2-[(3,4-dihydroxyphenyl)methylidene]-4,6-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1-benzofuran-3-one)

3D MOL for NP0319433 (2-[(3,4-dihydroxyphenyl)methylidene]-4,6-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1-benzofuran-3-one)

3D SDF for NP0319433 (2-[(3,4-dihydroxyphenyl)methylidene]-4,6-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1-benzofuran-3-one)

3D-SDF for NP0319433 (2-[(3,4-dihydroxyphenyl)methylidene]-4,6-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1-benzofuran-3-one)

PDB for NP0319433 (2-[(3,4-dihydroxyphenyl)methylidene]-4,6-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1-benzofuran-3-one)

3D PDB for NP0319433 (2-[(3,4-dihydroxyphenyl)methylidene]-4,6-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1-benzofuran-3-one)

SMILES for NP0319433 (2-[(3,4-dihydroxyphenyl)methylidene]-4,6-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1-benzofuran-3-one)

INCHI for NP0319433 (2-[(3,4-dihydroxyphenyl)methylidene]-4,6-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1-benzofuran-3-one)

Structure for NP0319433 (2-[(3,4-dihydroxyphenyl)methylidene]-4,6-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1-benzofuran-3-one)

3D Structure for NP0319433 (2-[(3,4-dihydroxyphenyl)methylidene]-4,6-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1-benzofuran-3-one)