NP-MRD: Showing NP-Card for 6-{[(2s,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-7,13,14-trihydroxy-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione (NP0318505)

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Record Information

Version

2.0

Created at

2022-09-11 19:02:51 UTC

Updated at

2022-09-11 19:02:52 UTC

NP-MRD ID

NP0318505

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-{[(2s,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-7,13,14-trihydroxy-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione

Description

4'-O-Arabinofuranosylellagic acid belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. 6-{[(2s,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-7,13,14-trihydroxy-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione is found in Rosa laevigata. Based on a literature review very few articles have been published on 4'-O-Arabinofuranosylellagic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112221022D          

 31 35  0  0  1  0            999 V2000
    3.4914   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6336   -1.5395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2980   -2.2931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9111   -2.8452    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8249   -3.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4923   -4.1506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6256   -2.4327    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3792   -2.7682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4540   -1.6257    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0061   -1.0126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    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  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  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  1  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  1  0  0  0
  7 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 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
 28 29  1  0  0  0  0
  2 29  1  0  0  0  0
 29 30  2  0  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
  4 31  1  0  0  0  0
 19 31  2  0  0  0  0
M  END

     RDKit          3D

 45 49  0  0  0  0  0  0  0  0999 V2000
    2.8910   -1.3737    4.3964 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6697   -1.1165    3.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4725   -0.8405    2.7270 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2227   -0.5669    1.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0668   -0.2819    1.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0344   -0.3089    2.0207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3473    0.0064   -0.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5377    0.2803   -0.7564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8376    0.4840   -0.7301 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5602   -0.3799   -1.5819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7076    0.2840   -1.9263 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7435    0.2513   -0.8400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8987    0.9208   -1.1913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2081    1.6478   -2.2625 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5802    1.5624   -3.5196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1432    1.8953   -1.2406 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5475    2.7303   -0.2064 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7099    0.0074   -1.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9767   -0.2747   -0.8051 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0603   -0.2917   -1.6616 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8339   -0.0316   -2.8839 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2665   -0.5656   -1.2228 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5107   -0.8355    0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7972   -1.1200    0.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8200   -1.1110   -0.4816 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0241   -1.3994    1.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3207   -1.6809    2.1920 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0245   -1.4129    2.7406 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7444   -1.1289    2.3112 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5033   -0.8451    0.9722 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2311   -0.5592    0.5256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0035   -0.1417    1.9571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3951    0.3935    0.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1605   -0.1382   -2.8515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0065   -0.8320   -0.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4118    0.6289    0.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4431    0.3111   -1.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9986    2.4244   -2.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6234    2.4396   -3.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2651    2.3438   -1.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5171    2.8376   -0.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4763    0.2321   -2.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6794   -0.9127   -1.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5837   -1.8959    3.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2190   -1.6359    3.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7 18  2  0
 18 19  1  0
 19 31  2  0
 31  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 29  1  0
 29 30  2  0
 30 23  1  0
 23 22  1  0
 22 20  1  0
 20 21  2  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  2  0
  4  5  2  0
  5  6  1  0
  9 16  1  0
 16 17  1  0
 16 14  1  0
 14 15  1  0
 14 11  1  0
  5  7  1  0
 20 19  1  0
 30 31  1  0
 28 29  1  0
 13 37  1  0
 12 35  1  0
 12 36  1  0
 11 34  1  6
  9 33  1  1
 18 42  1  0
 25 43  1  0
 27 44  1  0
 28 45  1  0
  6 32  1  0
 16 40  1  6
 17 41  1  0
 14 38  1  6
 15 39  1  0
M  END


  Mrv1652309112221022D          

 31 35  0  0  1  0            999 V2000
    3.4914   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6336   -1.5395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2980   -2.2931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9111   -2.8452    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8249   -3.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4923   -4.1506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6256   -2.4327    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3792   -2.7682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4540   -1.6257    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0061   -1.0126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    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  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  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  1  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  1  0  0  0
  7 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 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
 28 29  1  0  0  0  0
  2 29  1  0  0  0  0
 29 30  2  0  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
  4 31  1  0  0  0  0
 19 31  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0318505

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@H]1O[C@@H](OC2=CC3=C4C(OC(=O)C5=C4C(OC3=O)=C(O)C(O)=C5)=C2O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C19H14O12/c20-3-8-12(23)14(25)19(29-8)28-7-2-5-10-9-4(17(26)31-16(10)13(7)24)1-6(21)11(22)15(9)30-18(5)27/h1-2,8,12,14,19-25H,3H2/t8-,12-,14+,19+/m0/s1

> <INCHI_KEY>
UZDCOTMGNTTWIV-KPJJWNKPSA-N

> <FORMULA>
C19H14O12

> <MOLECULAR_WEIGHT>
434.309

> <EXACT_MASS>
434.048525891

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
39.047113238010574

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-{[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-7,13,14-trihydroxy-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(14),4(16),5,7,11(15),12-hexaene-3,10-dione

> <JCHEM_LOGP>
0.6781892666666669

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.580857073332998

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.829438511682519

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9811524001887983

> <JCHEM_POLAR_SURFACE_AREA>
192.44

> <JCHEM_REFRACTIVITY>
96.78949999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
6-{[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-7,13,14-trihydroxy-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(14),4(16),5,7,11(15),12-hexaene-3,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  O   UNK     0       6.517  -5.541   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.747  -4.207   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.207  -4.207   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.437  -2.874   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.897  -2.874   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.127  -4.207   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.127  -1.540   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.413  -1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.183  -2.874   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.556  -4.281   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.701  -5.311   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.540  -6.843   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.786  -7.748   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.034  -4.541   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.441  -5.167   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.714  -3.035   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.745  -1.890   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.897  -0.206   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.437  -0.206   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.207   1.127   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.437   2.461   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.747   1.127   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.517  -0.206   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.057  -0.206   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.827   1.127   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.827  -1.540   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.367  -1.540   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.057  -2.874   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.517  -2.874   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.747  -1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.207  -1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   31                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    9   17                                                  
CONECT   17   16                                                            
CONECT   18    7   19                                                       
CONECT   19   18   20   31                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   30                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28    2   30                                                  
CONECT   30   29   23   31                                                  
CONECT   31   30    4   19                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
4'-O-Arabinofuranosylellagate	Generator

Chemical Formula

C₁₉H₁₄O₁₂

Average Mass

434.3090 Da

Monoisotopic Mass

434.04853 Da

IUPAC Name

6-{[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-7,13,14-trihydroxy-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(14),4(16),5,7,11(15),12-hexaene-3,10-dione

Traditional Name

6-{[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-7,13,14-trihydroxy-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(14),4(16),5,7,11(15),12-hexaene-3,10-dione

CAS Registry Number

Not Available

SMILES

OC[C@@H]1O[C@@H](OC2=CC3=C4C(OC(=O)C5=C4C(OC3=O)=C(O)C(O)=C5)=C2O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C19H14O12/c20-3-8-12(23)14(25)19(29-8)28-7-2-5-10-9-4(17(26)31-16(10)13(7)24)1-6(21)11(22)15(9)30-18(5)27/h1-2,8,12,14,19-25H,3H2/t8-,12-,14+,19+/m0/s1

InChI Key

UZDCOTMGNTTWIV-KPJJWNKPSA-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
Rosa laevigata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Ellagic_acid
Phenolic glycoside
7,8-dihydroxycoumarin
O-glycosyl compound
Isocoumarin
Coumarin
Glycosyl compound
Pentose monosaccharide
Benzopyran
1-benzopyran
2-benzopyran
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Pyran
Monosaccharide
Benzenoid
Heteroaromatic compound
Oxolane
Secondary alcohol
Lactone
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Primary alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	0.68	ChemAxon
pKa (Strongest Acidic)	5.83	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	96.79 m³·mol⁻¹	ChemAxon
Polarizability	39.05 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

101129362

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-{[(2s,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-7,13,14-trihydroxy-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione (NP0318505)

MOL for NP0318505 (6-{[(2s,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-7,13,14-trihydroxy-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione)

3D MOL for NP0318505 (6-{[(2s,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-7,13,14-trihydroxy-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione)

3D SDF for NP0318505 (6-{[(2s,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-7,13,14-trihydroxy-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione)

3D-SDF for NP0318505 (6-{[(2s,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-7,13,14-trihydroxy-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione)

PDB for NP0318505 (6-{[(2s,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-7,13,14-trihydroxy-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione)

3D PDB for NP0318505 (6-{[(2s,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-7,13,14-trihydroxy-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione)

SMILES for NP0318505 (6-{[(2s,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-7,13,14-trihydroxy-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione)

INCHI for NP0318505 (6-{[(2s,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-7,13,14-trihydroxy-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione)

Structure for NP0318505 (6-{[(2s,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-7,13,14-trihydroxy-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione)

3D Structure for NP0318505 (6-{[(2s,3r,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-7,13,14-trihydroxy-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione)