NP-MRD: Showing NP-Card for (2r,3s,4s,5s)-2,3,4,5,6-pentahydroxy-7-oxo-6-(3,4,5-trihydroxybenzoyl)-7-(3,4,5-trihydroxyphenyl)heptanal (NP0185275)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 00:37:53 UTC

Updated at

2022-09-04 00:37:53 UTC

NP-MRD ID

NP0185275

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4s,5s)-2,3,4,5,6-pentahydroxy-7-oxo-6-(3,4,5-trihydroxybenzoyl)-7-(3,4,5-trihydroxyphenyl)heptanal

Description

Digalloylglucose belongs to the class of organic compounds known as retro-dihydrochalcones. These are a form of normal dihydrochalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions. (2r,3s,4s,5s)-2,3,4,5,6-pentahydroxy-7-oxo-6-(3,4,5-trihydroxybenzoyl)-7-(3,4,5-trihydroxyphenyl)heptanal is found in Arctostaphylos uva-ursi and Fragaria ananassa. (2r,3s,4s,5s)-2,3,4,5,6-pentahydroxy-7-oxo-6-(3,4,5-trihydroxybenzoyl)-7-(3,4,5-trihydroxyphenyl)heptanal was first documented in 2021 (PMID: 34361622). Based on a literature review a small amount of articles have been published on Digalloylglucose (PMID: 35684087) (PMID: 35281888) (PMID: 33831729).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042202372D          

 34 35  0  0  1  0            999 V2000
    0.8546    2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0296    2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    2.2539    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0296    1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2079    2.2539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6204    2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    1.5395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2079    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4454    1.5395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579    2.2539    0.0000 O   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
   -3.2704    0.1105    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
   -1.3229    0.3263    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
   -1.4289   -0.8250    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
   -0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 O   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
   -3.5724    2.0625    0.0000 O   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
   -5.0013   -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
   -5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   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  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  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
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 15 23  1  0  0  0  0
 11 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 26 34  1  0  0  0  0
M  END

     RDKit          3D

 54 55  0  0  0  0  0  0  0  0999 V2000
    4.8783   -0.1847   -2.0332 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5241   -0.8064   -1.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2859   -0.0695    0.2158 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9016   -0.9839    1.1542 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3453    1.0953    0.0083 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0373    1.8812   -0.9779 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0146    0.7253   -0.5880 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4046    1.9838   -0.8822 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0551    0.0256    0.2942 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4463   -1.2547    0.6767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382   -0.1773   -0.4832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1365   -0.9984   -1.6028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2489   -0.9608    0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0304   -0.2829    0.9844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4918   -2.3794    0.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7248   -3.3060   -0.4624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0368   -4.6641   -0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2462   -5.5731   -1.1388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1424   -5.1298    0.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4906   -6.4737    0.2094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9342   -4.2340    0.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0727   -4.6539    1.5486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6049   -2.8835    0.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7499    1.0716   -1.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7891    1.0991   -2.3224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2197    2.2712   -0.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7395    3.3136   -1.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1927    4.4941   -0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6828    5.4522   -1.4771 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1510    4.6983    0.7305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5974    5.8732    1.3079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6554    3.7194    1.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6183    3.9373    2.9148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2017    2.5285    0.9758 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971   -1.8717   -1.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2696    0.3831    0.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6843   -1.5103    1.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2736    1.7671    0.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5649    2.7426   -1.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1758    0.2546   -1.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6523    2.6211   -0.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8959    0.5777    1.2157 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0633   -1.5614    1.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3910   -0.4240   -2.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1718   -3.0232   -0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5972   -5.2892   -1.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8935   -7.1225   -0.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3049   -5.6336    1.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2548   -2.2069    1.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7743    3.1537   -2.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0424    6.3502   -1.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9602    6.5986    0.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2514    3.2090    3.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8256    1.8315    1.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 11 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 34  2  0
 23 15  1  0
 34 26  1  0
  4 37  1  0
  3 36  1  1
  2 35  1  0
  5 38  1  1
  6 39  1  0
  7 40  1  6
  8 41  1  0
  9 42  1  1
 10 43  1  0
 12 44  1  0
 16 45  1  0
 18 46  1  0
 20 47  1  0
 22 48  1  0
 23 49  1  0
 27 50  1  0
 29 51  1  0
 31 52  1  0
 33 53  1  0
 34 54  1  0
M  END


  Mrv1652309042202372D          

 34 35  0  0  1  0            999 V2000
    0.8546    2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0296    2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    2.2539    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0296    1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2079    2.2539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6204    2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    1.5395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2079    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4454    1.5395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579    2.2539    0.0000 O   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
   -3.2704    0.1105    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
   -1.3229    0.3263    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
   -1.4289   -0.8250    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
   -0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 O   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
   -3.5724    2.0625    0.0000 O   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
   -5.0013   -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
   -5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   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  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  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
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 15 23  1  0  0  0  0
 11 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 26 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0185275

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O14/c21-5-12(26)15(29)16(30)19(33)20(34,17(31)6-1-8(22)13(27)9(23)2-6)18(32)7-3-10(24)14(28)11(25)4-7/h1-5,12,15-16,19,22-30,33-34H/t12-,15+,16-,19-/m0/s1

> <INCHI_KEY>
WPKPPVAFWNRBID-BVNXPQQUSA-N

> <FORMULA>
C20H20O14

> <MOLECULAR_WEIGHT>
484.366

> <EXACT_MASS>
484.085305324

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
43.54495408503233

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5S)-2,3,4,5,6-pentahydroxy-7-oxo-6-(3,4,5-trihydroxybenzoyl)-7-(3,4,5-trihydroxyphenyl)heptanal

> <JCHEM_LOGP>
-2.333015123999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.579119062114233

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.977522767656034

> <JCHEM_PKA_STRONGEST_BASIC>
-3.889177525433751

> <JCHEM_POLAR_SURFACE_AREA>
273.73999999999995

> <JCHEM_REFRACTIVITY>
108.89459999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S,5S)-2,3,4,5,6-pentahydroxy-7-oxo-6-(3,4,5-trihydroxybenzoyl)-7-(3,4,5-trihydroxyphenyl)heptanal

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0       1.595   5.541   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.055   5.541   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.715   4.207   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.055   2.874   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.255   4.207   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.025   5.541   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.025   2.874   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.255   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.565   2.874   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -5.335   4.207   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -6.105   0.206   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.469   0.609   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.334  -3.850   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -6.668  -3.850   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -6.668   3.850   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0     -10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0     -12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0     -12.003   2.310   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   24                                             
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   15                                                       
CONECT   24   11   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   34                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   26                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₀O₁₄

Average Mass

484.3660 Da

Monoisotopic Mass

484.08531 Da

IUPAC Name

(2R,3S,4S,5S)-2,3,4,5,6-pentahydroxy-7-oxo-6-(3,4,5-trihydroxybenzoyl)-7-(3,4,5-trihydroxyphenyl)heptanal

Traditional Name

(2R,3S,4S,5S)-2,3,4,5,6-pentahydroxy-7-oxo-6-(3,4,5-trihydroxybenzoyl)-7-(3,4,5-trihydroxyphenyl)heptanal

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H20O14/c21-5-12(26)15(29)16(30)19(33)20(34,17(31)6-1-8(22)13(27)9(23)2-6)18(32)7-3-10(24)14(28)11(25)4-7/h1-5,12,15-16,19,22-30,33-34H/t12-,15+,16-,19-/m0/s1

InChI Key

WPKPPVAFWNRBID-BVNXPQQUSA-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
Arctostaphylos uva-ursi	LOTUS Database	35616633
Fragaria x ananassa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as retro-dihydrochalcones. These are a form of normal dihydrochalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

Retro-dihydrochalcones

Alternative Parents

Substituents

Retro-dihydrochalcone
Cinnamylphenol
Heptose monosaccharide
Alkyl-phenylketone
Butyrophenone
Phenylketone
Pyrogallol derivative
Fatty alcohol
Benzenetriol
Aryl alkyl ketone
Aryl ketone
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acyl
Benzenoid
Monosaccharide
Beta-hydroxy ketone
Beta-hydroxy aldehyde
Monocyclic benzene moiety
Acyloin
Alpha-hydroxyaldehyde
Tertiary alcohol
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	-2.3	ChemAxon
pKa (Strongest Acidic)	6.98	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	273.74 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	108.89 m³·mol⁻¹	ChemAxon
Polarizability	43.54 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

C00054537

Chemspider ID

66424445

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

129628549

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Oledzka A, Cichocka K, Wolinski K, Melzig MF, Czerwinska ME: Potentially Bio-Accessible Metabolites from an Extract of Cornus mas Fruit after Gastrointestinal Digestion In Vitro and Gut Microbiota Ex Vivo Treatment. Nutrients. 2022 May 30;14(11):2287. doi: 10.3390/nu14112287. [PubMed:35684087 ]
Pekacar S, Deliorman Orhan D: Investigation of Antidiabetic Effect of Pistacia atlantica Leaves by Activity-Guided Fractionation and Phytochemical Content Analysis by LC-QTOF-MS. Front Pharmacol. 2022 Feb 25;13:826261. doi: 10.3389/fphar.2022.826261. eCollection 2022. [PubMed:35281888 ]
Augusti PR, Quatrin A, Mello R, Bochi VC, Rodrigues E, Prazeres ID, Macedo AC, Oliveira-Alves SC, Emanuelli T, Bronze MR, Serra AT: Antiproliferative Effect of Colonic Fermented Phenolic Compounds from Jaboticaba (Myrciaria trunciflora) Fruit Peel in a 3D Cell Model of Colorectal Cancer. Molecules. 2021 Jul 24;26(15):4469. doi: 10.3390/molecules26154469. [PubMed:34361622 ]
Tang C, Guo T, Zhang Z, Yang P, Song H: Rapid visualized characterization of phenolic taste compounds in tea extract by high-performance thin-layer chromatography coupled to desorption electrospray ionization mass spectrometry. Food Chem. 2021 Sep 1;355:129555. doi: 10.1016/j.foodchem.2021.129555. Epub 2021 Mar 13. [PubMed:33831729 ]
LOTUS database [Link]

Showing NP-Card for (2r,3s,4s,5s)-2,3,4,5,6-pentahydroxy-7-oxo-6-(3,4,5-trihydroxybenzoyl)-7-(3,4,5-trihydroxyphenyl)heptanal (NP0185275)

MOL for NP0185275 ((2r,3s,4s,5s)-2,3,4,5,6-pentahydroxy-7-oxo-6-(3,4,5-trihydroxybenzoyl)-7-(3,4,5-trihydroxyphenyl)heptanal)

3D MOL for NP0185275 ((2r,3s,4s,5s)-2,3,4,5,6-pentahydroxy-7-oxo-6-(3,4,5-trihydroxybenzoyl)-7-(3,4,5-trihydroxyphenyl)heptanal)

3D SDF for NP0185275 ((2r,3s,4s,5s)-2,3,4,5,6-pentahydroxy-7-oxo-6-(3,4,5-trihydroxybenzoyl)-7-(3,4,5-trihydroxyphenyl)heptanal)

3D-SDF for NP0185275 ((2r,3s,4s,5s)-2,3,4,5,6-pentahydroxy-7-oxo-6-(3,4,5-trihydroxybenzoyl)-7-(3,4,5-trihydroxyphenyl)heptanal)

PDB for NP0185275 ((2r,3s,4s,5s)-2,3,4,5,6-pentahydroxy-7-oxo-6-(3,4,5-trihydroxybenzoyl)-7-(3,4,5-trihydroxyphenyl)heptanal)

3D PDB for NP0185275 ((2r,3s,4s,5s)-2,3,4,5,6-pentahydroxy-7-oxo-6-(3,4,5-trihydroxybenzoyl)-7-(3,4,5-trihydroxyphenyl)heptanal)

SMILES for NP0185275 ((2r,3s,4s,5s)-2,3,4,5,6-pentahydroxy-7-oxo-6-(3,4,5-trihydroxybenzoyl)-7-(3,4,5-trihydroxyphenyl)heptanal)

INCHI for NP0185275 ((2r,3s,4s,5s)-2,3,4,5,6-pentahydroxy-7-oxo-6-(3,4,5-trihydroxybenzoyl)-7-(3,4,5-trihydroxyphenyl)heptanal)

Structure for NP0185275 ((2r,3s,4s,5s)-2,3,4,5,6-pentahydroxy-7-oxo-6-(3,4,5-trihydroxybenzoyl)-7-(3,4,5-trihydroxyphenyl)heptanal)

3D Structure for NP0185275 ((2r,3s,4s,5s)-2,3,4,5,6-pentahydroxy-7-oxo-6-(3,4,5-trihydroxybenzoyl)-7-(3,4,5-trihydroxyphenyl)heptanal)