NP-MRD: Showing NP-Card for Vitexin 2''-O-rhamnoside (NP0044061)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2021-11-12 23:47:55 UTC

Updated at

2021-11-26 17:45:00 UTC

NP-MRD ID

NP0044061

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Vitexin 2''-O-rhamnoside

Description

Vitexin 2''-O-alpha-L-rhamnoside, also known as 2''-O-rhamnosylvitexin or apigenin-8-C-glucoside-2'-rhamnoside, belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Thus, vitexin 2''-O-alpha-L-rhamnoside is considered to be a flavonoid. Vitexin 2''-O-alpha-L-rhamnoside is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Vitexin 2''-O-rhamnoside is found in Arrhenatherum spp., Avena spp., Camellia sinensis, Fortunella japonica , Cotoneaster orbicularis, Crataegus monogyna, Dacrycarpus dacrydioides, Machilus japonica, Podocarpus totara , Prosopis strombulifera , Ruscus aculeatus , Sophora microphylla and Tripterospermum japonicum. It was first documented in 2005 (PMID: 16223090). Based on a literature review a significant number of articles have been published on vitexin 2''-O-alpha-L-rhamnoside (PMID: 34756847) (PMID: 34758548) (PMID: 34758547) (PMID: 34758546).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100472D          

 41 45  0  0  1  0            999 V2000
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  2  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
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  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
   -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
    0.7145   -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  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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
    4.2868   -0.0000    0.0000 C   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
    5.0013    1.2375    0.0000 O   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
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   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
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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
  2  7  1  0  0  0  0
  6  8  1  1  0  0  0
  9  8  1  6  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
  9 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  2  0  0  0  0
 22 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
 29 32  1  0  0  0  0
 18 33  1  0  0  0  0
 16 34  1  0  0  0  0
 12 35  1  1  0  0  0
 35 36  1  0  0  0  0
 11 37  1  6  0  0  0
 10 38  1  1  0  0  0
  5 39  1  6  0  0  0
  4 40  1  6  0  0  0
  3 41  1  1  0  0  0
M  END

     RDKit          3D

 71 75  0  0  0  0  0  0  0  0999 V2000
    3.8787    0.1232    0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0446    1.2136    0.7249 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6884    0.9587    0.7684 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2931    0.6172   -0.5548 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0187    0.0391   -0.4919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0106   -1.2834   -0.6191 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3135   -2.0905    0.6054 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4597   -1.4891    1.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0347   -2.1941    3.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7013   -3.3837    2.9858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1592   -1.6513    4.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8231   -0.4441    4.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9724    0.0284    5.7288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3082    0.2364    3.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9882    1.4202    3.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1839    1.9493    4.5792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4740    2.0532    2.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2821    1.5060    1.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8000    2.1610   -0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3882    3.3950   -0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9308    4.0159   -1.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8726    3.3590   -2.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4094    3.9592   -3.5747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2975    2.1261   -2.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7680    1.5420   -1.3748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6257    0.3821    1.0381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1338   -0.2804    2.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3698   -3.2619    0.4914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0483   -4.0186   -0.6121 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0095   -5.1376   -0.6974 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7439   -5.9827   -1.7553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0328   -3.2982   -1.9220 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7355   -4.0616   -2.8526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7475   -1.9442   -1.7496 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8274   -1.2233   -2.9073 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4188    1.7792   -1.4363 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9318    1.4240   -2.7048 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1734    2.9419   -0.8601 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7194    3.6733   -1.9124 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2929    2.5539    0.0747 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4077    3.4935    1.1079 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8911    0.1217    0.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0997    0.2889   -0.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4840   -0.8986    0.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3532    1.2581    1.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967   -0.1891   -0.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1337   -1.6021   -0.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4422   -2.4371    0.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9659   -3.9496    2.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2015   -2.1584    5.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3888    0.8206    6.0442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0001    2.9678    2.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4359    3.9326    0.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3861    5.0078   -1.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3689    3.4952   -4.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2702    1.6336   -3.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3396    0.5755   -1.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0045   -4.5165   -0.4533 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0132   -5.7122    0.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9976   -4.6571   -0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -6.0648   -2.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9847   -3.0936   -2.2815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1993   -4.0822   -3.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7681   -2.2132   -1.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1108   -1.3686   -3.5684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3905    2.1667   -1.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1107    2.2662   -3.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4866    3.6382   -0.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6609    3.9390   -1.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2707    2.5192   -0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0126    3.1056    1.7973 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 40  1  0
 40 38  1  0
 38 36  1  0
 36  4  1  0
  4  3  1  0
  4  5  1  0
  5  6  1  0
  6 34  1  0
 34 32  1  0
 32 29  1  0
 29 28  1  0
 28  7  1  0
  7  8  1  0
  8  9  2  0
  9 11  1  0
 11 12  2  0
 12 14  1  0
 14 27  2  0
 27 26  1  0
 26 18  1  0
 18 17  2  0
 17 15  1  0
 15 16  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 24  1  0
 24 25  2  0
 22 23  1  0
 12 13  1  0
  9 10  1  0
 29 30  1  0
 30 31  1  0
 32 33  1  0
 34 35  1  0
 36 37  1  0
 38 39  1  0
 40 41  1  0
  3  2  1  0
  7  6  1  0
 27  8  1  0
 15 14  1  0
 25 19  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  2 45  1  1
 40 70  1  6
 38 68  1  1
 36 66  1  6
  4 46  1  6
  6 47  1  6
 34 64  1  1
 32 62  1  6
 29 58  1  1
  7 48  1  6
 11 50  1  0
 17 52  1  0
 20 53  1  0
 21 54  1  0
 24 56  1  0
 25 57  1  0
 23 55  1  0
 13 51  1  0
 10 49  1  0
 30 59  1  0
 30 60  1  0
 31 61  1  0
 33 63  1  0
 35 65  1  0
 37 67  1  0
 39 69  1  0
 41 71  1  0
M  END


  Mrv1652311132100472D          

 41 45  0  0  1  0            999 V2000
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  2  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
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  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
   -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
    0.7145   -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  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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
    4.2868   -0.0000    0.0000 C   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
    5.0013    1.2375    0.0000 O   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
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   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
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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
  2  7  1  0  0  0  0
  6  8  1  1  0  0  0
  9  8  1  6  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
  9 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  2  0  0  0  0
 22 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
 29 32  1  0  0  0  0
 18 33  1  0  0  0  0
 16 34  1  0  0  0  0
 12 35  1  1  0  0  0
 35 36  1  0  0  0  0
 11 37  1  6  0  0  0
 10 38  1  1  0  0  0
  5 39  1  6  0  0  0
  4 40  1  6  0  0  0
  3 41  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0044061

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2C2=C(O)C=C(O)C3=C2OC(=CC3=O)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O14/c1-9-19(33)21(35)23(37)27(38-9)41-26-22(36)20(34)16(8-28)40-25(26)18-13(31)6-12(30)17-14(32)7-15(39-24(17)18)10-2-4-11(29)5-3-10/h2-7,9,16,19-23,25-31,33-37H,8H2,1H3/t9-,16+,19-,20+,21+,22-,23+,25-,26+,27-/m0/s1

> <INCHI_KEY>
LYGPBZVKGHHTIE-HUBYJIGHSA-N

> <FORMULA>
C27H30O14

> <MOLECULAR_WEIGHT>
578.523

> <EXACT_MASS>
578.163555646

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
55.89121210261143

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
-0.10

> <JCHEM_LOGP>
-0.7745574503333336

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.001031483104741

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.172652770556342

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6121826114733837

> <JCHEM_POLAR_SURFACE_AREA>
236.05999999999995

> <JCHEM_REFRACTIVITY>
136.9018

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.82e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vitexin 2''-rhamnoside

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -8.002   4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   41                                                  
CONECT    4    3    5   40                                                  
CONECT    5    4    6   39                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   38                                                  
CONECT   11   10   12   37                                                  
CONECT   12   11   13   35                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   34                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   33                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   15   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   19   25                                                  
CONECT   25   24                                                            
CONECT   26   22   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30   26                                                       
CONECT   32   29                                                            
CONECT   33   18                                                            
CONECT   34   16                                                            
CONECT   35   12   36                                                       
CONECT   36   35                                                            
CONECT   37   11                                                            
CONECT   38   10                                                            
CONECT   39    5                                                            
CONECT   40    4                                                            
CONECT   41    3                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Value	Source
(1S)-1,5-Anhydro-2-O-(6-deoxy-alpha-L-mannopyranosyl)-1-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-D-glucitol	ChEBI
2''-O-Rhamnosylvitexin	ChEBI
2-O-Rhamnosylvitexin	ChEBI
Apigenin-8-C-glucoside-2'-rhamnoside	ChEBI
Vitexin 2''-rhamnoside	ChEBI
Vitexin-2''-rhamnoside	ChEBI
(1S)-1,5-Anhydro-2-O-(6-deoxy-a-L-mannopyranosyl)-1-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-D-glucitol	Generator
(1S)-1,5-Anhydro-2-O-(6-deoxy-α-L-mannopyranosyl)-1-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-D-glucitol	Generator
Vitexin 2''-O-a-L-rhamnoside	Generator
Vitexin 2''-O-α-L-rhamnoside	Generator
Vitexin-2-O-rhamnoside	MeSH

Chemical Formula

C₂₇H₃₀O₁₄

Average Mass

578.5230 Da

Monoisotopic Mass

578.16356 Da

IUPAC Name

8-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Traditional Name

vitexin 2''-rhamnoside

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2C2=C(O)C=C(O)C3=C2OC(=CC3=O)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C27H30O14/c1-9-19(33)21(35)23(37)27(38-9)41-26-22(36)20(34)16(8-28)40-25(26)18-13(31)6-12(30)17-14(32)7-15(39-24(17)18)10-2-4-11(29)5-3-10/h2-7,9,16,19-23,25-31,33-37H,8H2,1H3/t9-,16+,19-,20+,21+,22-,23+,25-,26+,27-/m0/s1

InChI Key

LYGPBZVKGHHTIE-HUBYJIGHSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol-d4, 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
Arrhenatherum spp.	Plant	KNApSAcK
Avena spp.	Plant	KNApSAcK
Camellia sinensis	LOTUS Database	35616633
Citrus japonica	Plant	KNApSAcK
Cotoneaster orbicularis	LOTUS Database	35616633
Crataegus monogyna	LOTUS Database	35616633
Dacrycarpus dacrydioides	LOTUS Database	35616633
Machilus japonica	LOTUS Database	35616633
Podocarpus totara	Plant	KNApSAcK
Prosopis strombulifera	Plant	KNApSAcK
Ruscus aculeatus	Plant	KNApSAcK
Sophora microphylla	Plant	KNApSAcK
Tripterospermum japonicum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid 8-C-glycosides

Alternative Parents

Substituents

Flavonoid-8-c-glycoside
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Phenolic glycoside
O-glycosyl compound
Glycosyl compound
C-glycosyl compound
Disaccharide
Chromone
1-benzopyran
Benzopyran
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Primary alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

disaccharide derivative (CHEBI:32298 )
C-glycosyl compound (CHEBI:32298 )
trihydroxyflavone (CHEBI:32298 )
flavones (C12628 )
Flavones and Flavonols (C12628 )

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	-0.1	ALOGPS
logP	-0.77	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	6.17	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	236.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	136.9 m³·mol⁻¹	ChemAxon
Polarizability	55.89 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00006217

Chemspider ID

4445348

KEGG Compound ID

C12628

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5282151

PDB ID

Not Available

ChEBI ID

32298

Good Scents ID

rw1698471

References

General References

Rayyan S, Fossen T, Solheim Nateland H, Andersen OM: Isolation and identification of flavonoids, including flavone rotamers, from the herbal drug 'Crataegi folium cum flore' (hawthorn). Phytochem Anal. 2005 Sep-Oct;16(5):334-41. doi: 10.1002/pca.853. [PubMed:16223090 ]
McDonagh MS, Wagner J, Ahmed AY, Morasco B, Kansagara D, Chou R: Living Systematic Review on Cannabis and Other Plant-Based Treatments for Chronic Pain - Quarterly Progress Report/Addendum: September 2021. 2020 Dec. [PubMed:34756847 ]
Zhang WB, Yang QB, Wu SF, Lu SH, Cheng M, Sheng Y, Zhang QC, Yang LF, Yu L, Yan SX: [Application of diffusion-weighted magnetic resonance imaging in evaluating the efficacy of radiotherapy and chemotherapy for esophageal cancer]. Zhonghua Yi Xue Za Zhi. 2021 Nov 9;101(41):3427-3430. doi: 10.3760/cma.j.cn112137-20210709-01544. [PubMed:34758548 ]
Sun Y, Wang DM, Yu H, Liu C, Ji TY, Wang S, Wu Y, Liu XY, Jiang YW, Cai LX, Liu QZ: [The screening of potential biological markers of seizure onset zone in focal cortical dysplasia based on bioinformatics analysis]. Zhonghua Yi Xue Za Zhi. 2021 Nov 9;101(41):3422-3426. doi: 10.3760/cma.j.cn112137-20210331-00779. [PubMed:34758547 ]
Dong HH, Cai YS, Liang XN, Miao JB, Chen QS, Gao YD, Li H: [Analysis of incidence and risk factors for postoperative venous thromboembolism in patients with stage a non-small-cell lung cancer]. Zhonghua Yi Xue Za Zhi. 2021 Nov 9;101(41):3417-3421. doi: 10.3760/cma.j.cn112137-20210418-00929. [PubMed:34758546 ]

Showing NP-Card for Vitexin 2''-O-rhamnoside (NP0044061)

MOL for NP0044061 (Vitexin 2''-O-rhamnoside)

3D MOL for NP0044061 (Vitexin 2''-O-rhamnoside)

3D SDF for NP0044061 (Vitexin 2''-O-rhamnoside)

3D-SDF for NP0044061 (Vitexin 2''-O-rhamnoside)

PDB for NP0044061 (Vitexin 2''-O-rhamnoside)

3D PDB for NP0044061 (Vitexin 2''-O-rhamnoside)

SMILES for NP0044061 (Vitexin 2''-O-rhamnoside)

INCHI for NP0044061 (Vitexin 2''-O-rhamnoside)

Structure for NP0044061 (Vitexin 2''-O-rhamnoside)

3D Structure for NP0044061 (Vitexin 2''-O-rhamnoside)