NP-MRD: Showing NP-Card for Grayanoside A (NP0044066)

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Record Information

Version

1.0

Created at

2021-11-12 23:48:12 UTC

Updated at

2021-11-26 17:45:03 UTC

NP-MRD ID

NP0044066

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Grayanoside A

Description

Grayanoside A belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Grayanoside A is found in Catalpa ovata, Fragaria ananassa , Prunus grayana and Rhododendron simsii. It was first documented in 2007 (PMID: 17637461). Based on a literature review a small amount of articles have been published on Grayanoside A (PMID: 19425115) (PMID: 27871058).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100482D          

 34 36  0  0  1  0            999 V2000
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  6 14  1  0  0  0  0
  3 15  2  0  0  0  0
 16  1  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 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
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 22 28  1  0  0  0  0
 18 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 16 33  1  0  0  0  0
 33 34  1  6  0  0  0
M  END

     RDKit          3D

 62 64  0  0  0  0  0  0  0  0999 V2000
    7.0436    1.6861    3.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8257    1.5515    2.2440 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2128    1.2997    1.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8199    1.1775    0.9597 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1914    0.9279   -0.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7473    0.7881   -0.3865 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8869    0.8848    0.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4367    0.7346    0.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6443    0.8341    1.3488 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9423    0.4838   -0.8705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4213    0.3208   -1.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0745   -0.8376   -0.4665 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3977   -0.8791   -0.8758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0792   -1.9882   -0.3837 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3945   -1.8194   -0.6258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3037   -1.8026    0.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2413   -0.7738    1.4170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3586    0.6233    0.9436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6536    1.1352    0.8005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8672    2.4296    0.3755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8125    3.2720    0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9870    4.5806   -0.3562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5505    2.7452    0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3167    1.4392    0.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4499   -3.1664   -1.1008 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1769   -4.3158   -1.0253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0703   -3.3380   -0.4962 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4067   -4.4375   -1.0241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2997   -2.0754   -0.8082 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9037   -2.0206   -0.0851 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0165    0.8062   -1.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3826    0.9222   -1.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9972    1.1742   -0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3772    1.2854   -0.0930 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7138    1.8678    4.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5118    0.7137    3.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3109    2.5250    3.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2191    1.2798    1.8608 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3272    0.5881   -1.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2461    1.0808    1.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4534    0.1101   -2.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9932    1.2610   -1.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0226   -0.6146    0.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8054   -2.0836    0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3148   -1.6547   -0.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4253   -2.8480    0.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0711   -0.9158    2.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3131   -0.8080    2.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5028    0.4975    1.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8665    2.8451    0.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0726    4.8193   -1.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6911    3.3644    0.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3157    1.0592    0.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2845   -2.8843   -2.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2044   -4.8188   -1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1390   -3.3902    0.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5204   -4.4023   -0.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0369   -2.1023   -1.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7326   -2.0389    0.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5425    0.6112   -2.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0000    0.8214   -2.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8221    1.4694    0.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  8  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  3 33  2  0
 33 34  1  0
 33 32  1  0
 32 31  2  0
  8  9  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 14 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 31  5  1  0
 29 12  1  0
 24 18  1  0
 11 41  1  0
 11 42  1  0
  7 40  1  0
  6 39  1  0
  4 38  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
 34 62  1  0
 32 61  1  0
 31 60  1  0
 12 43  1  1
 14 44  1  1
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 19 49  1  0
 20 50  1  0
 22 51  1  0
 23 52  1  0
 24 53  1  0
 25 54  1  6
 26 55  1  0
 27 56  1  1
 28 57  1  0
 29 58  1  6
 30 59  1  0
M  END


  Mrv1652311132100482D          

 34 36  0  0  1  0            999 V2000
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  6 14  1  0  0  0  0
  3 15  2  0  0  0  0
 16  1  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 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
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 22 28  1  0  0  0  0
 18 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 16 33  1  0  0  0  0
 33 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0044066

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(\C=C\C(=O)OC[C@H]2O[C@@H](OCCC3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H28O10/c1-31-18-12-15(4-8-17(18)26)5-9-20(27)33-13-19-21(28)22(29)23(30)24(34-19)32-11-10-14-2-6-16(25)7-3-14/h2-9,12,19,21-26,28-30H,10-11,13H2,1H3/b9-5+/t19-,21-,22+,23-,24-/m1/s1

> <INCHI_KEY>
UPASGSSMBIZMDX-WNENLGFLSA-N

> <FORMULA>
C24H28O10

> <MOLECULAR_WEIGHT>
476.478

> <EXACT_MASS>
476.168247102

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
48.516554332025954

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl]methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
1.43

> <JCHEM_LOGP>
1.992810417000001

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.362662373663548

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.701220319816807

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6490922422252465

> <JCHEM_POLAR_SURFACE_AREA>
155.14

> <JCHEM_REFRACTIVITY>
120.03490000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl]methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <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      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      14.670 -14.630   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      14.670 -16.170   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.003 -16.170   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      14.670  -0.770   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.338   3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.672   4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.005   3.850   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      21.339   4.620   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      20.005   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      18.672   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      17.338  -2.310   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      17.338  -5.390   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      14.670  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2   16                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    6                                                       
CONECT   15    3                                                            
CONECT   16    1   17   33                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   29                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   22                                                       
CONECT   29   18   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   16   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₈O₁₀

Average Mass

476.4780 Da

Monoisotopic Mass

476.16825 Da

IUPAC Name

[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl]methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Traditional Name

[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl]methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(\C=C\C(=O)OC[C@H]2O[C@@H](OCCC3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)=C1

InChI Identifier

InChI=1S/C24H28O10/c1-31-18-12-15(4-8-17(18)26)5-9-20(27)33-13-19-21(28)22(29)23(30)24(34-19)32-11-10-14-2-6-16(25)7-3-14/h2-9,12,19,21-26,28-30H,10-11,13H2,1H3/b9-5+/t19-,21-,22+,23-,24-/m1/s1

InChI Key

UPASGSSMBIZMDX-WNENLGFLSA-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
Catalpa ovata	LOTUS Database	35616633
Fragaria x ananassa	Plant	KNApSAcK
Prunus grayana	LOTUS Database	35616633
Rhododendron simsii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Methoxyphenol
Tyrosol derivative
Anisole
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Monocyclic benzene moiety
Fatty acyl
Oxane
Monosaccharide
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Secondary alcohol
Polyol
Carboxylic acid derivative
Acetal
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	1.43	ALOGPS
logP	1.99	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.7	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.14 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	120.03 m³·mol⁻¹	ChemAxon
Polarizability	48.52 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00056453

Chemspider ID

9908193

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11733480

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hanhineva K, Soininen P, Anttonen MJ, Kokko H, Rogachev I, Aharoni A, Laatikainen R, Karenlampi S: NMR and UPLC-qTOF-MS/MS characterisation of novel phenylethanol derivatives of phenylpropanoid glucosides from the leaves of strawberry (Fragaria x ananassa cv. Jonsok). Phytochem Anal. 2009 Sep-Oct;20(5):353-64. doi: 10.1002/pca.1133. [PubMed:19425115 ]
Khong DT, Judeh ZM: Short synthesis of phenylpropanoid glycoside grayanoside-A and analogues. Carbohydr Res. 2016 Dec 21;436:50-53. doi: 10.1016/j.carres.2016.11.010. Epub 2016 Nov 14. [PubMed:27871058 ]
Das SK, Reddy KA, Mukkanti K: Total synthesis of phenylpropanoid glycosides, grayanoside A and syringalide B, through a common intermediate. Carbohydr Res. 2007 Nov 5;342(15):2309-15. doi: 10.1016/j.carres.2007.06.022. Epub 2007 Jun 28. [PubMed:17637461 ]

Showing NP-Card for Grayanoside A (NP0044066)

MOL for NP0044066 (Grayanoside A)

3D MOL for NP0044066 (Grayanoside A)

3D SDF for NP0044066 (Grayanoside A)

3D-SDF for NP0044066 (Grayanoside A)

PDB for NP0044066 (Grayanoside A)

3D PDB for NP0044066 (Grayanoside A)

SMILES for NP0044066 (Grayanoside A)

INCHI for NP0044066 (Grayanoside A)

Structure for NP0044066 (Grayanoside A)

3D Structure for NP0044066 (Grayanoside A)