NP-MRD: Showing NP-Card for 6,13-dihydroxy-7-methoxy-14-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione (NP0256435)

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Record Information

Version

2.0

Created at

2022-09-07 21:15:45 UTC

Updated at

2022-09-07 21:15:45 UTC

NP-MRD ID

NP0256435

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,13-dihydroxy-7-methoxy-14-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione

Description

3-Methylellagic acid 8-rhamnoside 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. 3-Methylellagic acid 8-rhamnoside is a constituent of Eucalyptus globulus (Tasmanian blue gum). 6,13-dihydroxy-7-methoxy-14-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-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 Eucalyptus globulus. 3-Methylellagic acid 8-rhamnoside is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061309332D          

 33 37  0  0  0  0            999 V2000
   -3.3000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1250   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000   -3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  2  0  0  0  0
  8  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12  5  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  8  2  0  0  0  0
 16  9  2  0  0  0  0
 17 10  2  0  0  0  0
 17 15  1  0  0  0  0
 18 11  2  0  0  0  0
 18 16  1  0  0  0  0
 19  7  1  0  0  0  0
 20  6  1  0  0  0  0
 21 14  1  0  0  0  0
 22  8  1  0  0  0  0
 23  9  1  0  0  0  0
 24 12  1  0  0  0  0
 25 13  1  0  0  0  0
 26 14  1  0  0  0  0
 27 19  2  0  0  0  0
 28 20  2  0  0  0  0
 29  2  1  0  0  0  0
 29 15  1  0  0  0  0
 30  5  1  0  0  0  0
 30 21  1  0  0  0  0
 31 17  1  0  0  0  0
 31 19  1  0  0  0  0
 32 18  1  0  0  0  0
 32 20  1  0  0  0  0
 33 16  1  0  0  0  0
 33 21  1  0  0  0  0
M  END

     RDKit          3D

 51 55  0  0  0  0  0  0  0  0999 V2000
    7.3520   -0.9066   -0.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3771   -0.7560    0.7403 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2033   -0.0378    0.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1429    1.3057    0.8753 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2914    1.9585    1.3592 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9606    2.0099    0.7035 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8513    1.3375    0.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6484    1.9712    0.0318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5737    3.1910    0.2995 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5887    1.3074   -0.4292 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6065    0.0341   -0.7259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5260   -0.6169   -1.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6695    0.1124   -1.3595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6593    0.2923   -0.3768 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8452   -0.2786   -0.8362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6437   -0.5472    0.2747 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1107   -0.5812   -0.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4043    0.4341    1.4034 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5739    0.4897    2.1631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1510    1.8001    0.8146 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3072    2.1869    0.1369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9464    1.7499   -0.1027 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2889    2.3899   -1.2858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3916   -1.9652   -1.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5168   -2.6168   -1.9627 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7728   -2.6813   -1.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8739   -2.0134   -0.8481 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0661   -2.6679   -0.6616 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1548   -3.9121   -0.9311 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1010   -1.9899   -0.2044 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0704   -0.7114    0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9049   -0.0034   -0.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7972   -0.6541   -0.5479 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6677    0.0855   -0.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1824   -1.5054    0.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9818   -1.4620   -1.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1442    1.4310    1.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9536    3.0465    0.9472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3530   -0.2480    0.5182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2870   -1.5470    0.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7082   -0.3134    0.8309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3572    0.0447   -0.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3770   -1.6443   -0.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6016    0.1032    2.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7289   -0.3450    2.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0030    2.5464    1.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2520    3.1053   -0.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0594    2.2547    0.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7385    2.1555   -2.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5351   -3.6063   -2.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7685   -3.7319   -1.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 33  2  0
 33 27  1  0
 27 26  2  0
 26 24  1  0
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 15 16  1  0
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 27 28  1  0
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 30 31  1  0
 31 32  2  0
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 32  7  1  0
 12 11  1  0
 22 14  1  0
 32 33  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  0
  6 38  1  0
 26 51  1  0
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 14 39  1  1
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 17 42  1  0
 17 43  1  0
 18 44  1  1
 19 45  1  0
 20 46  1  1
 21 47  1  0
 22 48  1  1
 23 49  1  0
M  END


  Mrv0541 05061309332D          

 33 37  0  0  0  0            999 V2000
   -3.3000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1250   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000   -3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  2  0  0  0  0
  8  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12  5  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  8  2  0  0  0  0
 16  9  2  0  0  0  0
 17 10  2  0  0  0  0
 17 15  1  0  0  0  0
 18 11  2  0  0  0  0
 18 16  1  0  0  0  0
 19  7  1  0  0  0  0
 20  6  1  0  0  0  0
 21 14  1  0  0  0  0
 22  8  1  0  0  0  0
 23  9  1  0  0  0  0
 24 12  1  0  0  0  0
 25 13  1  0  0  0  0
 26 14  1  0  0  0  0
 27 19  2  0  0  0  0
 28 20  2  0  0  0  0
 29  2  1  0  0  0  0
 29 15  1  0  0  0  0
 30  5  1  0  0  0  0
 30 21  1  0  0  0  0
 31 17  1  0  0  0  0
 31 19  1  0  0  0  0
 32 18  1  0  0  0  0
 32 20  1  0  0  0  0
 33 16  1  0  0  0  0
 33 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256435

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2C(=O)OC3=C4C(=CC(O)=C3OC3OC(C)C(O)C(O)C3O)C(=O)OC1=C24

> <INCHI_IDENTIFIER>
InChI=1S/C21H18O12/c1-5-12(24)13(25)14(26)21(30-5)33-16-9(23)4-7-11-10-6(20(28)32-18(11)16)3-8(22)15(29-2)17(10)31-19(7)27/h3-5,12-14,21-26H,1-2H3

> <INCHI_KEY>
UNIJYMVRSKZTJI-UHFFFAOYSA-N

> <FORMULA>
C21H18O12

> <MOLECULAR_WEIGHT>
462.3604

> <EXACT_MASS>
462.07982604

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
42.708010141102406

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,13-dihydroxy-7-methoxy-14-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione

> <ALOGPS_LOGP>
1.05

> <JCHEM_LOGP>
-0.05934165266666658

> <ALOGPS_LOGS>
-2.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.498352301346626

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.802195766510307

> <JCHEM_PKA_STRONGEST_BASIC>
-3.612200399223993

> <JCHEM_POLAR_SURFACE_AREA>
181.43999999999994

> <JCHEM_REFRACTIVITY>
105.69059999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.41e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,13-dihydroxy-7-methoxy-14-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -6.160  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.700   1.127   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.390  -2.874   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770  -0.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.390  -2.874   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.850  -2.874   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.770  -0.206   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.160  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.540  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.080  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.540  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.160  -4.207   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.390  -5.541   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.850  -5.541   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.390  -0.206   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.770  -2.874   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.850  -0.206   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.770  -2.874   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.540   1.127   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.080  -4.207   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.080  -4.207   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.700  -1.540   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -3.080  -1.540   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -7.700  -4.207   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -6.160  -6.875   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -3.080  -6.875   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.770   2.461   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       3.850  -5.541   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       6.160   1.127   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -3.850  -2.874   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       3.080   1.127   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       1.540  -4.207   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -1.540  -4.207   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   29                                                            
CONECT    3    6    8                                                       
CONECT    4    7    9                                                       
CONECT    5    1   12   30                                                  
CONECT    6    3   10   20                                                  
CONECT    7    4   11   19                                                  
CONECT    8    3   15   22                                                  
CONECT    9    4   16   23                                                  
CONECT   10    6   11   17                                                  
CONECT   11    7   10   18                                                  
CONECT   12    5   13   24                                                  
CONECT   13   12   14   25                                                  
CONECT   14   13   21   26                                                  
CONECT   15    8   17   29                                                  
CONECT   16    9   18   33                                                  
CONECT   17   10   15   31                                                  
CONECT   18   11   16   32                                                  
CONECT   19    7   27   31                                                  
CONECT   20    6   28   32                                                  
CONECT   21   14   30   33                                                  
CONECT   22    8                                                            
CONECT   23    9                                                            
CONECT   24   12                                                            
CONECT   25   13                                                            
CONECT   26   14                                                            
CONECT   27   19                                                            
CONECT   28   20                                                            
CONECT   29    2   15                                                       
CONECT   30    5   21                                                       
CONECT   31   17   19                                                       
CONECT   32   18   20                                                       
CONECT   33   16   21                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
3-Methylellagate 8-rhamnoside	Generator

Chemical Formula

C₂₁H₁₈O₁₂

Average Mass

462.3604 Da

Monoisotopic Mass

462.07983 Da

IUPAC Name

6,13-dihydroxy-7-methoxy-14-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione

Traditional Name

6,13-dihydroxy-7-methoxy-14-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2C(=O)OC3=C4C(=CC(O)=C3OC3OC(C)C(O)C(O)C3O)C(=O)OC1=C24

InChI Identifier

InChI=1S/C21H18O12/c1-5-12(24)13(25)14(26)21(30-5)33-16-9(23)4-7-11-10-6(20(28)32-18(11)16)3-8(22)15(29-2)17(10)31-19(7)27/h3-5,12-14,21-26H,1-2H3

InChI Key

UNIJYMVRSKZTJI-UHFFFAOYSA-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
Eucalyptus globulus	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

Not Available

Substituents

Not Available

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	1.05	ALOGPS
logP	-0.059	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	5.8	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	181.44 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	105.69 m³·mol⁻¹	ChemAxon
Polarizability	42.71 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0037079

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016067

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

73157208

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6,13-dihydroxy-7-methoxy-14-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione (NP0256435)

MOL for NP0256435 (6,13-dihydroxy-7-methoxy-14-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-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 NP0256435 (6,13-dihydroxy-7-methoxy-14-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-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 NP0256435 (6,13-dihydroxy-7-methoxy-14-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-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 NP0256435 (6,13-dihydroxy-7-methoxy-14-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-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 NP0256435 (6,13-dihydroxy-7-methoxy-14-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-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 NP0256435 (6,13-dihydroxy-7-methoxy-14-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-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 NP0256435 (6,13-dihydroxy-7-methoxy-14-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-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 NP0256435 (6,13-dihydroxy-7-methoxy-14-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-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 NP0256435 (6,13-dihydroxy-7-methoxy-14-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-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 NP0256435 (6,13-dihydroxy-7-methoxy-14-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione)