NP-MRD: Showing NP-Card for (2r,3r,4r,5r)-4,5,6-trihydroxy-1-oxo-2-[2-oxo-2-(3,4,5-trihydroxyphenyl)ethyl]hexan-3-yl 3,4,5-trihydroxybenzoate (NP0228647)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 08:22:56 UTC

Updated at

2022-09-06 08:22:56 UTC

NP-MRD ID

NP0228647

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4r,5r)-4,5,6-trihydroxy-1-oxo-2-[2-oxo-2-(3,4,5-trihydroxyphenyl)ethyl]hexan-3-yl 3,4,5-trihydroxybenzoate

Description

(2R,3R,4R,5R)-4,5,6-trihydroxy-1-oxo-2-[2-oxo-2-(3,4,5-trihydroxyphenyl)ethyl]hexan-3-yl 3,4,5-trihydroxybenzoate belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. (2r,3r,4r,5r)-4,5,6-trihydroxy-1-oxo-2-[2-oxo-2-(3,4,5-trihydroxyphenyl)ethyl]hexan-3-yl 3,4,5-trihydroxybenzoate is found in Ephedra alata. Based on a literature review very few articles have been published on (2R,3R,4R,5R)-4,5,6-trihydroxy-1-oxo-2-[2-oxo-2-(3,4,5-trihydroxyphenyl)ethyl]hexan-3-yl 3,4,5-trihydroxybenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062210222D          

 34 35  0  0  1  0            999 V2000
    0.3657   -3.8230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9058   -3.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6358   -2.4198    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1744   -2.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4444   -3.6671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246   -2.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0647   -3.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8748   -3.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4149   -3.8230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1449   -2.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9550   -2.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6048   -1.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8748   -1.0166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7946   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1758   -1.7961    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9058   -1.0166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957   -0.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4444   -1.4843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1744   -0.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9845    0.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2546    0.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0647    1.0103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9845    2.2575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957    1.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6358    1.9457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3657    0.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9860   -1.9520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5261   -1.3284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560   -2.7316    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7159   -3.3552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0662   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6062   -2.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  7 15  1  0  0  0  0
  3 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 20 28  1  0  0  0  0
 16 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
 33 34  1  0  0  0  0
M  END

     RDKit          3D

 56 57  0  0  0  0  0  0  0  0999 V2000
   -0.3742    3.0704    0.3107 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0949    1.9685    0.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1870    0.8284   -0.4496 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6013    0.9429   -0.7758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5944    0.6331    0.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2445    0.4358    1.4488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0193    0.5356   -0.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4423    0.7732   -1.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7845    0.6900   -1.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2022    0.9319   -2.9099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6878    0.3674   -0.6108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0294    0.2821   -0.9133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2725    0.1264    0.6893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2232   -0.1932    1.6438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9337    0.2137    0.9807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5270   -0.3890   -0.0976 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8859    0.1725    0.2009 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9813   -0.1295   -0.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8693   -0.9136   -1.4919 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2572    0.4628   -0.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3655    0.1462   -0.9143 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6163    0.6719   -0.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7173    0.3431   -1.3976 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7843    1.5349    0.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0565    2.0481    0.6856 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6832    1.8678    1.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8034    2.7277    2.2636 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4303    1.3264    0.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1976   -1.2800    1.0146 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4002   -2.1229    1.0857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8076   -2.3741    0.7768 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7713   -3.2865    1.8691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4892   -3.2380   -0.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7630   -3.8304   -0.2932 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6817    1.8344    1.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3626    1.2620   -1.3651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8824    0.4840   -1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7834    2.0451   -1.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7569    1.0372   -2.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5175    1.1631   -3.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3283    0.4581   -1.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1929   -0.2459    1.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5870    0.0288    1.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7882   -1.0105   -0.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2990   -0.5329   -1.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5936   -0.2909   -2.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2647    2.6776    1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6486    3.1542    2.5466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5914    1.6097    1.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0808   -0.8721    2.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4903   -2.4163    2.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8365   -2.0415    0.7431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9658   -2.7265    2.6657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6632   -2.7459   -1.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2158   -4.0901   -0.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1600   -4.1251   -1.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
 34 33  1  0
 33 31  1  0
 31 32  1  0
 31 29  1  0
 29 30  1  0
 29 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  2  0
 16  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
  3  2  1  0
  2  1  2  0
 28 20  1  0
 15  7  1  0
 34 56  1  0
 33 54  1  0
 33 55  1  0
 31 52  1  6
 32 53  1  0
 29 50  1  1
 30 51  1  0
 16 44  1  6
 21 45  1  0
 23 46  1  0
 25 47  1  0
 27 48  1  0
 28 49  1  0
  3 36  1  6
  4 37  1  0
  4 38  1  0
  8 39  1  0
 10 40  1  0
 12 41  1  0
 14 42  1  0
 15 43  1  0
  2 35  1  0
M  END


  Mrv1652309062210222D          

 34 35  0  0  1  0            999 V2000
    0.3657   -3.8230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9058   -3.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6358   -2.4198    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1744   -2.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4444   -3.6671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246   -2.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0647   -3.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8748   -3.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4149   -3.8230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1449   -2.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9550   -2.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6048   -1.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8748   -1.0166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7946   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1758   -1.7961    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9058   -1.0166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957   -0.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4444   -1.4843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1744   -0.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9845    0.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2546    0.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0647    1.0103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9845    2.2575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957    1.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6358    1.9457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3657    0.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9860   -1.9520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5261   -1.3284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560   -2.7316    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7159   -3.3552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0662   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6062   -2.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  7 15  1  0  0  0  0
  3 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 20 28  1  0  0  0  0
 16 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
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0228647

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@H](O)[C@@H](O)[C@H](OC(=O)C1=CC(O)=C(O)C(O)=C1)[C@@H](CC(=O)C1=CC(O)=C(O)C(O)=C1)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O13/c22-6-10(5-11(24)8-1-12(25)17(30)13(26)2-8)20(19(32)16(29)7-23)34-21(33)9-3-14(27)18(31)15(28)4-9/h1-4,6,10,16,19-20,23,25-32H,5,7H2/t10-,16+,19+,20+/m0/s1

> <INCHI_KEY>
DVPUPKPPHGCXOA-LCGBAKTPSA-N

> <FORMULA>
C21H22O13

> <MOLECULAR_WEIGHT>
482.394

> <EXACT_MASS>
482.106040768

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
45.190918123969006

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4R,5R)-4,5,6-trihydroxy-1-oxo-2-[2-oxo-2-(3,4,5-trihydroxyphenyl)ethyl]hexan-3-yl 3,4,5-trihydroxybenzoate

> <JCHEM_LOGP>
-0.7577419563333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.183759844821289

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.328172924722597

> <JCHEM_PKA_STRONGEST_BASIC>
-5.548931626799903

> <JCHEM_POLAR_SURFACE_AREA>
242.50999999999996

> <JCHEM_REFRACTIVITY>
112.37280000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4R,5R)-4,5,6-trihydroxy-1-oxo-2-[2-oxo-2-(3,4,5-trihydroxyphenyl)ethyl]hexan-3-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0       0.683  -7.136   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.691  -5.972   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.187  -4.517   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.326  -4.226   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.830  -6.845   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.846  -5.099   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.854  -6.263   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.366  -5.972   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -6.375  -7.136   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -5.870  -4.517   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -7.383  -4.226   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.862  -3.353   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.366  -1.898   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.350  -3.644   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.195  -3.353   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.691  -1.898   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.179  -1.607   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.830  -2.771   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.326  -0.151   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.838   0.140   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.342   1.595   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.854   1.886   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.334   2.759   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.838   4.214   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.179   2.468   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.187   3.632   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.683   1.013   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.707  -3.644   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.715  -2.480   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.211  -5.099   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.203  -6.263   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.723  -5.390   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.732  -4.226   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    7                                                       
CONECT   16    3   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   20                                                       
CONECT   29   16   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

View in JSmol

Synonyms

Value	Source
(2R,3R,4R,5R)-4,5,6-Trihydroxy-1-oxo-2-[2-oxo-2-(3,4,5-trihydroxyphenyl)ethyl]hexan-3-yl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₂₁H₂₂O₁₃

Average Mass

482.3940 Da

Monoisotopic Mass

482.10604 Da

IUPAC Name

(2R,3R,4R,5R)-4,5,6-trihydroxy-1-oxo-2-[2-oxo-2-(3,4,5-trihydroxyphenyl)ethyl]hexan-3-yl 3,4,5-trihydroxybenzoate

Traditional Name

(2R,3R,4R,5R)-4,5,6-trihydroxy-1-oxo-2-[2-oxo-2-(3,4,5-trihydroxyphenyl)ethyl]hexan-3-yl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

OC[C@@H](O)[C@@H](O)[C@H](OC(=O)C1=CC(O)=C(O)C(O)=C1)[C@@H](CC(=O)C1=CC(O)=C(O)C(O)=C1)C=O

InChI Identifier

InChI=1S/C21H22O13/c22-6-10(5-11(24)8-1-12(25)17(30)13(26)2-8)20(19(32)16(29)7-23)34-21(33)9-3-14(27)18(31)15(28)4-9/h1-4,6,10,16,19-20,23,25-32H,5,7H2/t10-,16+,19+,20+/m0/s1

InChI Key

DVPUPKPPHGCXOA-LCGBAKTPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ephedra alata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Butyrophenone
Benzoate ester
Pyrogallol derivative
Fatty alcohol
Benzoic acid or derivatives
Benzenetriol
Aryl alkyl ketone
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acyl
Benzenoid
Monosaccharide
Monocyclic benzene moiety
Secondary alcohol
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Primary alcohol
Aldehyde
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-0.76	ChemAxon
pKa (Strongest Acidic)	7.33	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	242.51 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	112.37 m³·mol⁻¹	ChemAxon
Polarizability	45.19 Å³	ChemAxon
Number of Rings	2	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162861538

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r,4r,5r)-4,5,6-trihydroxy-1-oxo-2-[2-oxo-2-(3,4,5-trihydroxyphenyl)ethyl]hexan-3-yl 3,4,5-trihydroxybenzoate (NP0228647)

MOL for NP0228647 ((2r,3r,4r,5r)-4,5,6-trihydroxy-1-oxo-2-[2-oxo-2-(3,4,5-trihydroxyphenyl)ethyl]hexan-3-yl 3,4,5-trihydroxybenzoate)

3D MOL for NP0228647 ((2r,3r,4r,5r)-4,5,6-trihydroxy-1-oxo-2-[2-oxo-2-(3,4,5-trihydroxyphenyl)ethyl]hexan-3-yl 3,4,5-trihydroxybenzoate)

3D SDF for NP0228647 ((2r,3r,4r,5r)-4,5,6-trihydroxy-1-oxo-2-[2-oxo-2-(3,4,5-trihydroxyphenyl)ethyl]hexan-3-yl 3,4,5-trihydroxybenzoate)

3D-SDF for NP0228647 ((2r,3r,4r,5r)-4,5,6-trihydroxy-1-oxo-2-[2-oxo-2-(3,4,5-trihydroxyphenyl)ethyl]hexan-3-yl 3,4,5-trihydroxybenzoate)

PDB for NP0228647 ((2r,3r,4r,5r)-4,5,6-trihydroxy-1-oxo-2-[2-oxo-2-(3,4,5-trihydroxyphenyl)ethyl]hexan-3-yl 3,4,5-trihydroxybenzoate)

3D PDB for NP0228647 ((2r,3r,4r,5r)-4,5,6-trihydroxy-1-oxo-2-[2-oxo-2-(3,4,5-trihydroxyphenyl)ethyl]hexan-3-yl 3,4,5-trihydroxybenzoate)

SMILES for NP0228647 ((2r,3r,4r,5r)-4,5,6-trihydroxy-1-oxo-2-[2-oxo-2-(3,4,5-trihydroxyphenyl)ethyl]hexan-3-yl 3,4,5-trihydroxybenzoate)

INCHI for NP0228647 ((2r,3r,4r,5r)-4,5,6-trihydroxy-1-oxo-2-[2-oxo-2-(3,4,5-trihydroxyphenyl)ethyl]hexan-3-yl 3,4,5-trihydroxybenzoate)

Structure for NP0228647 ((2r,3r,4r,5r)-4,5,6-trihydroxy-1-oxo-2-[2-oxo-2-(3,4,5-trihydroxyphenyl)ethyl]hexan-3-yl 3,4,5-trihydroxybenzoate)

3D Structure for NP0228647 ((2r,3r,4r,5r)-4,5,6-trihydroxy-1-oxo-2-[2-oxo-2-(3,4,5-trihydroxyphenyl)ethyl]hexan-3-yl 3,4,5-trihydroxybenzoate)