NP-MRD: Showing NP-Card for manniflavanone (NP0145265)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 00:25:33 UTC

Updated at

2022-09-02 00:25:33 UTC

NP-MRD ID

NP0145265

Secondary Accession Numbers

None

Natural Product Identification

Common Name

manniflavanone

Description

Manniflavanone belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. manniflavanone was first documented in 2013 (PMID: 24295222). Based on a literature review a small amount of articles have been published on manniflavanone (PMID: 28430433) (PMID: 26226176) (PMID: 26195084) (PMID: 26081368).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022202252D          

 43 48  0  0  1  0            999 V2000
   -1.1560   -0.0149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8205    0.7388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3054    1.4062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1259    1.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4614    0.5663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6108    1.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2752    2.7411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7602    3.4085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4548    2.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9698    2.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1494    2.2461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3356    1.5787    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1560    1.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6410    0.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4614    1.0837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7970    1.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6175    1.9236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3121    2.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6476    3.2585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4916    2.4186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5214   -0.2410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  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
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  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  2  0  0  0  0
 13 20  1  0  0  0  0
 12 21  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  2  0  0  0  0
 23 24  1  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
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 32 39  1  0  0  0  0
 31 40  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
 28 42  1  0  0  0  0
 42 43  2  0  0  0  0
M  END

     RDKit          3D

 65 70  0  0  0  0  0  0  0  0999 V2000
   -1.3071   -3.4369   -0.3803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5216   -2.3951    0.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2282   -2.5283    1.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3843   -3.7905    2.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8203   -4.8533    1.4526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0626   -3.9044    3.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5909   -2.7883    3.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2795   -2.8852    5.1301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4478   -1.5232    3.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7699   -1.4008    2.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6064   -0.1712    1.5373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4202   -0.2025    0.1089 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1724    1.1825   -0.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7773    1.7200   -1.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4975    3.0152   -1.8854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5781    3.7623   -1.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3106    5.0575   -1.6487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9562    3.2308   -0.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0103    3.9842    0.6550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2585    1.9521    0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1218   -1.0187   -0.0943 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6774   -0.9353   -1.4935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5573   -1.0330   -2.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9284   -1.2420   -2.3488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0441   -0.9340   -3.8200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2968   -0.7507   -4.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8462   -0.6465   -5.3050 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1924   -0.6600   -2.9680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7032   -0.7549   -1.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5993   -0.6635   -0.6610 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9849   -0.3996   -0.7297 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3488    0.4687    0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0137   -0.0515    1.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475    0.6456    2.8434 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8215    1.8789    2.7732 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0478    2.5666    3.9676 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1465    2.3823    1.5403 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7293    3.6365    1.4454 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9199    1.6949    0.3563 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5319   -0.0436   -2.0436 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7333   -0.7462   -2.3134 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6075   -0.4639   -3.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0872   -0.6411   -4.3078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9169   -5.7710    1.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1847   -4.8548    3.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2724   -3.0221    5.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8759   -0.6735    3.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2686   -0.6574   -0.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5301    1.2144   -2.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0103    3.4000   -2.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6849    5.7033   -1.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1824    4.9086    0.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7761    1.5462    1.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3834   -0.6351    0.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5777   -1.3165   -3.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6983   -1.0042   -4.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2999   -0.6904   -6.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4599   -1.4059   -0.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5594   -1.0410    1.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9796    0.2128    3.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8110    2.1949    4.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9063    4.1836    2.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1841    2.1012   -0.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7874    1.0107   -2.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4804   -1.7177   -2.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
 41 40  1  0
 40 31  1  0
 31 30  1  0
 30 29  1  0
 29 28  2  0
 28 26  1  0
 26 27  1  0
 26 25  2  0
 25 23  1  0
 23 24  1  0
 23 22  2  0
 22 21  1  0
 21 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  2  0
  9  7  1  0
  7  8  1  0
  7  6  2  0
  6  4  1  0
  4  5  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
 28 42  1  0
 42 43  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37 39  2  0
 42 40  1  0
 39 32  1  0
 22 29  1  0
  2 21  1  0
 20 13  1  0
  3 10  1  0
 41 65  1  0
 40 64  1  1
 31 58  1  1
 27 57  1  0
 25 56  1  0
 24 55  1  0
 21 54  1  1
 12 48  1  6
  9 47  1  0
  8 46  1  0
  6 45  1  0
  5 44  1  0
 14 49  1  0
 15 50  1  0
 17 51  1  0
 19 52  1  0
 20 53  1  0
 33 59  1  0
 34 60  1  0
 36 61  1  0
 38 62  1  0
 39 63  1  0
M  END


  Mrv1652309022202252D          

 43 48  0  0  1  0            999 V2000
   -1.1560   -0.0149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8205    0.7388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3054    1.4062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1259    1.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4614    0.5663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6108    1.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2752    2.7411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7602    3.4085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4548    2.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9698    2.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1494    2.2461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3356    1.5787    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1560    1.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6410    0.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4614    1.0837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7970    1.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6175    1.9236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3121    2.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6476    3.2585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4916    2.4186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5214   -0.2410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  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
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  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  2  0  0  0  0
 13 20  1  0  0  0  0
 12 21  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  2  0  0  0  0
 23 24  1  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
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 32 39  1  0  0  0  0
 31 40  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
 28 42  1  0  0  0  0
 42 43  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0145265

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@H](OC2=C(C(O)=CC(O)=C2[C@H]2[C@@H](OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C(O)=C2)C1=O)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H22O13/c31-12-7-17(36)21-20(8-12)42-28(10-1-3-13(32)15(34)5-10)24(25(21)39)22-18(37)9-19(38)23-26(40)27(41)29(43-30(22)23)11-2-4-14(33)16(35)6-11/h1-9,24,27-29,31-38,41H/t24-,27+,28+,29-/m1/s1

> <INCHI_KEY>
UKRJEVDCOVVSAB-ZLPBPMGLSA-N

> <FORMULA>
C30H22O13

> <MOLECULAR_WEIGHT>
590.493

> <EXACT_MASS>
590.106040768

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
56.315530727505944

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
3.34

> <JCHEM_LOGP>
4.051471431666666

> <ALOGPS_LOGS>
-3.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.073964870155226

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.170984180352237

> <JCHEM_PKA_STRONGEST_BASIC>
-5.0656890096451415

> <JCHEM_POLAR_SURFACE_AREA>
234.66999999999996

> <JCHEM_REFRACTIVITY>
146.4911

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-3,5,7-trihydroxy-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  O   UNK     0      -2.158  -0.028   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.532   1.379   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.437   2.625   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.968   2.464   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.595   1.057   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.874   3.710   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.247   5.117   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.152   6.363   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.716   5.278   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.810   4.032   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.279   4.193   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.626   2.947   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.158   3.108   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.063   1.862   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.595   2.023   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.221   3.430   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.753   3.591   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.316   4.676   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.942   6.083   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.784   4.515   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.840  -0.450   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   13                                                       
CONECT   21   12    2   22                                                  
CONECT   22   21   23   29                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   42                                                  
CONECT   29   28   22   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   40                                                  
CONECT   32   31   33   39                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   32                                                       
CONECT   40   31   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   28   43                                                  
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

View in JSmol

Synonyms

Value	Source
(2R,3S,2''R,3''r)-manniflavanone	MeSH

Chemical Formula

C₃₀H₂₂O₁₃

Average Mass

590.4930 Da

Monoisotopic Mass

590.10604 Da

IUPAC Name

(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl]-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-3,5,7-trihydroxy-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@H](OC2=C(C(O)=CC(O)=C2[C@H]2[C@@H](OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C(O)=C2)C1=O)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C30H22O13/c31-12-7-17(36)21-20(8-12)42-28(10-1-3-13(32)15(34)5-10)24(25(21)39)22-18(37)9-19(38)23-26(40)27(41)29(43-30(22)23)11-2-4-14(33)16(35)6-11/h1-9,24,27-29,31-38,41H/t24-,27+,28+,29-/m1/s1

InChI Key

UKRJEVDCOVVSAB-ZLPBPMGLSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

Bi- and polyflavonoid skeleton
Pyranoisoflavonoid
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Hydroxyisoflavonoid
7-hydroxyflavonoid
Flavanone
Flavanonol
Hydroxyflavonoid
Isoflavanone
Neolignan skeleton
Flavan
Isoflavan
Isoflavonoid skeleton
Isoflavonoid
Stilbene
Chromone
1-benzopyran
Chromane
Benzopyran
Catechol
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Secondary alcohol
Ketone
Organoheterocyclic compound
Ether
Oxacycle
Polyol
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

biflavonoid (CHEBI:27409 )
dihydroflavonols (CHEBI:27409 )

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	3.34	ALOGPS
logP	4.05	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.17	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	234.67 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	146.49 m³·mol⁻¹	ChemAxon
Polarizability	56.32 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00000978

Chemspider ID

28638981

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12831990

PDB ID

Not Available

ChEBI ID

27409

Good Scents ID

Not Available

References

General References

Acharya S, Stark TD, Oh ST, Jeon S, Pak SC, Kim M, Hur J, Matsutomo T, Hofmann T, Hill RA, Balemba OB: (2R,3S,2''R,3''R)-Manniflavanone Protects Proliferating Skeletal Muscle Cells against Oxidative Stress and Stimulates Myotube Formation. J Agric Food Chem. 2017 May 10;65(18):3636-3646. doi: 10.1021/acs.jafc.6b05161. Epub 2017 May 2. [PubMed:28430433 ]
Stark TD, Losch S, Wakamatsu J, Balemba OB, Frank O, Hofmann T: UPLC-ESI-TOF MS-Based Metabolite Profiling of the Antioxidative Food Supplement Garcinia buchananii. J Agric Food Chem. 2015 Aug 19;63(32):7169-79. doi: 10.1021/acs.jafc.5b02544. Epub 2015 Aug 6. [PubMed:26226176 ]
Stark TD, Losch S, Salger M, Balemba OB, Wakamatsu J, Frank O, Hofmann T: A new NMR approach for structure determination of thermally unstable biflavanones and application to phytochemicals from Garcinia buchananii. Magn Reson Chem. 2015 Oct;53(10):813-20. doi: 10.1002/mrc.4269. Epub 2015 Jul 20. [PubMed:26195084 ]
Balemba OB, Stark TD, Losch S, Patterson S, McMillan JS, Mawe GM, Hofmann T: (2R,3S,2'' R,3''R)-manniflavanone, a new gastrointestinal smooth muscle L-type calcium channel inhibitor, which underlies the spasmolytic properties of Garcinia buchananii stem bark extract. J Smooth Muscle Res. 2014;50:48-65. doi: 10.1540/jsmr.50.48. [PubMed:26081368 ]
Stark TD, Germann D, Balemba OB, Wakamatsu J, Hofmann T: New highly in vitro antioxidative 3,8''-linked Biflav(an)ones and Flavanone-C-glycosides from Garcinia buchananii stem bark. J Agric Food Chem. 2013 Dec 26;61(51):12572-81. doi: 10.1021/jf404783y. Epub 2013 Dec 12. [PubMed:24295222 ]
LOTUS database [Link]

Showing NP-Card for manniflavanone (NP0145265)

MOL for NP0145265 (manniflavanone)

3D MOL for NP0145265 (manniflavanone)

3D SDF for NP0145265 (manniflavanone)

3D-SDF for NP0145265 (manniflavanone)

PDB for NP0145265 (manniflavanone)

3D PDB for NP0145265 (manniflavanone)

SMILES for NP0145265 (manniflavanone)

INCHI for NP0145265 (manniflavanone)

Structure for NP0145265 (manniflavanone)

3D Structure for NP0145265 (manniflavanone)