NP-MRD: Showing NP-Card for (8r,10s,11r,12r,13s,22s)-10-[3,5-dihydroxy-4-(3-phenylpropanoyl)phenoxy]-1,11,12,18,19,23,23-heptahydroxy-6,9,14,24-tetraoxapentacyclo[18.3.1.0⁴,²².0⁸,¹³.0¹⁶,²¹]tetracosa-3,16,18,20-tetraene-2,5,15-trione (NP0188481)

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Record Information

Version

2.0

Created at

2022-09-04 04:49:18 UTC

Updated at

2022-09-04 04:49:18 UTC

NP-MRD ID

NP0188481

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(8r,10s,11r,12r,13s,22s)-10-[3,5-dihydroxy-4-(3-phenylpropanoyl)phenoxy]-1,11,12,18,19,23,23-heptahydroxy-6,9,14,24-tetraoxapentacyclo[18.3.1.0⁴,²².0⁸,¹³.0¹⁶,²¹]tetracosa-3,16,18,20-tetraene-2,5,15-trione

Description

(8R,10S,11R,12R,13S,22S)-10-[3,5-dihydroxy-4-(3-phenylpropanoyl)phenoxy]-1,11,12,18,19,23,23-heptahydroxy-6,9,14,24-tetraoxapentacyclo[18.3.1.0⁴,²².0⁸,¹³.0¹⁶,²¹]Tetracosa-3,16,18,20-tetraene-2,5,15-trione 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. Based on a literature review very few articles have been published on (8R,10S,11R,12R,13S,22S)-10-[3,5-dihydroxy-4-(3-phenylpropanoyl)phenoxy]-1,11,12,18,19,23,23-heptahydroxy-6,9,14,24-tetraoxapentacyclo[18.3.1.0⁴,²².0⁸,¹³.0¹⁶,²¹]Tetracosa-3,16,18,20-tetraene-2,5,15-trione.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309042206492D          

 53 59  0  0  1  0            999 V2000
    3.2507    0.1709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6133   -0.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4310   -0.9117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3044   -1.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9761   -0.4875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6853   -0.9091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4049   -0.5057    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1141   -0.9273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1036   -1.7522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8127   -2.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8022   -2.9987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5113   -3.4203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0825   -3.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0720   -4.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7811   -4.6486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3523   -4.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3418   -5.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6221   -5.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6116   -6.6836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8919   -7.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1828   -6.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1933   -5.8404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9130   -5.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3734   -2.9805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6537   -3.3839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3839   -2.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4155    0.3192    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1351    0.7226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7063    0.7408    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7168    1.5657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9866    0.3374    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5688    1.2027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8023    1.8527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4394    2.3768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9568    2.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4404    2.9089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2427    2.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8078    3.3242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4811    1.9222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2848    1.7360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447    1.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0020    1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3278    0.8435    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8165    0.1227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9132   -0.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7443   -0.9157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0017   -1.6995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3466   -0.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9444   -0.7701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9717    0.3817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8232    0.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5826    0.6849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1627    1.1144    0.0000 O   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  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
  9 26  1  0  0  0  0
  7 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
  5 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 35 42  1  0  0  0  0
 43 42  1  6  0  0  0
 43 44  1  0  0  0  0
  2 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 41 50  1  0  0  0  0
 48 51  1  0  0  0  0
 43 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
M  END


  Mrv1652309042206492D          

 53 59  0  0  1  0            999 V2000
    3.2507    0.1709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6133   -0.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4310   -0.9117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3044   -1.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9761   -0.4875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6853   -0.9091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4049   -0.5057    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1141   -0.9273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1036   -1.7522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8127   -2.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8022   -2.9987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5113   -3.4203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0825   -3.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0720   -4.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7811   -4.6486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3523   -4.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3418   -5.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6221   -5.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6116   -6.6836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8919   -7.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1828   -6.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1933   -5.8404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9130   -5.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3734   -2.9805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6537   -3.3839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3839   -2.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4155    0.3192    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1351    0.7226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7063    0.7408    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7168    1.5657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9866    0.3374    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5688    1.2027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8023    1.8527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4394    2.3768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9568    2.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4404    2.9089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2427    2.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8078    3.3242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4811    1.9222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2848    1.7360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447    1.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0020    1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3278    0.8435    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8165    0.1227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9132   -0.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7443   -0.9157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0017   -1.6995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3466   -0.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9444   -0.7701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9717    0.3817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8232    0.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5826    0.6849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1627    1.1144    0.0000 O   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  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
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  9 26  1  0  0  0  0
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  5 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 35 42  1  0  0  0  0
 43 42  1  6  0  0  0
 43 44  1  0  0  0  0
  2 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 41 50  1  0  0  0  0
 48 51  1  0  0  0  0
 43 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0188481

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](O)[C@@H]2OC(=O)C3=CC(O)=C(O)C4=C3[C@H]3C(=CC(=O)C(O)(O4)C3(O)O)C(=O)OC[C@H]2O[C@H]1OC1=CC(O)=C(C(=O)CCC2=CC=CC=C2)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C35H30O18/c36-17(7-6-13-4-2-1-3-5-13)24-18(37)8-14(9-19(24)38)50-33-28(43)27(42)29-21(51-33)12-49-31(44)16-11-22(40)35(48)34(46,47)25(16)23-15(32(45)52-29)10-20(39)26(41)30(23)53-35/h1-5,8-11,21,25,27-29,33,37-39,41-43,46-48H,6-7,12H2/t21-,25-,27-,28-,29-,33-,35?/m1/s1

> <INCHI_KEY>
MPDLAVGCNZQZEL-CLINIECNSA-N

> <FORMULA>
C35H30O18

> <MOLECULAR_WEIGHT>
738.607

> <EXACT_MASS>
738.143214126

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
68.23158813015786

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8R,10S,11R,12R,13S,22S)-10-[3,5-dihydroxy-4-(3-phenylpropanoyl)phenoxy]-1,11,12,18,19,23,23-heptahydroxy-6,9,14,24-tetraoxapentacyclo[18.3.1.0^{4,22}.0^{8,13}.0^{16,21}]tetracosa-3,16,18,20-tetraene-2,5,15-trione

> <JCHEM_LOGP>
3.0370207089999997

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.428413530239206

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.688302870862053

> <JCHEM_PKA_STRONGEST_BASIC>
-4.661635509133082

> <JCHEM_POLAR_SURFACE_AREA>
296.5

> <JCHEM_REFRACTIVITY>
172.13140000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(8R,10S,11R,12R,13S,22S)-10-[3,5-dihydroxy-4-(3-phenylpropanoyl)phenoxy]-1,11,12,18,19,23,23-heptahydroxy-6,9,14,24-tetraoxapentacyclo[18.3.1.0^{4,22}.0^{8,13}.0^{16,21}]tetracosa-3,16,18,20-tetraene-2,5,15-trione

> <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       6.068   0.319   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.878  -0.659   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.404  -1.702   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       8.035  -1.919   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.289  -0.910   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.612  -1.697   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      11.956  -0.944   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      13.280  -1.731   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      13.260  -3.271   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.584  -4.058   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.564  -5.598   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      15.888  -6.385   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      13.221  -6.351   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.201  -7.890   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      14.525  -8.677   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      11.858  -8.643   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.838 -10.183   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.495 -10.936   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.475 -12.476   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.132 -13.229   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.808 -12.442   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.827 -10.902   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.171 -10.149   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.897  -5.564   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.554  -6.317   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      11.917  -4.024   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.976   0.596   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      13.319   1.349   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      10.652   1.383   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.671   2.923   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.308   0.630   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.528   2.245   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.098   3.458   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.287   4.437   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.519   4.188   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.422   5.430   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.920   5.083   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       8.975   6.205   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       8.365   3.588   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       9.865   3.240   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       7.177   2.299   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       5.604   2.694   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.345   1.574   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       3.391   0.229   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       3.571  -1.337   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       5.123  -1.709   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       5.603  -3.172   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       6.247  -0.376   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       7.363  -1.438   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       7.414   0.713   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       5.270   0.677   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       6.688   1.278   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       5.904   2.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   44                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   31                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   27                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   26                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   24                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   13   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    9                                                       
CONECT   27    7   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    5   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   42                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   50                                                  
CONECT   42   41   35   43                                                  
CONECT   43   42   44   51                                                  
CONECT   44   43    2   45                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49   50   51                                             
CONECT   49   48                                                            
CONECT   50   48   41                                                       
CONECT   51   48   43   52   53                                             
CONECT   52   51                                                            
CONECT   53   51                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  118    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₃₀O₁₈

Average Mass

738.6070 Da

Monoisotopic Mass

738.14321 Da

IUPAC Name

(8R,10S,11R,12R,13S,22S)-10-[3,5-dihydroxy-4-(3-phenylpropanoyl)phenoxy]-1,11,12,18,19,23,23-heptahydroxy-6,9,14,24-tetraoxapentacyclo[18.3.1.0^{4,22}.0^{8,13}.0^{16,21}]tetracosa-3,16,18,20-tetraene-2,5,15-trione

Traditional Name

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](O)[C@@H]2OC(=O)C3=CC(O)=C(O)C4=C3[C@H]3C(=CC(=O)C(O)(O4)C3(O)O)C(=O)OC[C@H]2O[C@H]1OC1=CC(O)=C(C(=O)CCC2=CC=CC=C2)C(O)=C1

InChI Identifier

InChI=1S/C35H30O18/c36-17(7-6-13-4-2-1-3-5-13)24-18(37)8-14(9-19(24)38)50-33-28(43)27(42)29-21(51-33)12-49-31(44)16-11-22(40)35(48)34(46,47)25(16)23-15(32(45)52-29)10-20(39)26(41)30(23)53-35/h1-5,8-11,21,25,27-29,33,37-39,41-43,46-48H,6-7,12H2/t21-,25-,27-,28-,29-,33-,35?/m1/s1

InChI Key

MPDLAVGCNZQZEL-CLINIECNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Flavonoid o-glycoside
2'-hydroxy-dihydrochalcone
Linear 1,3-diarylpropanoid
Cinnamylphenol
Phenolic glycoside
Alkyl-phenylketone
Gallic acid or derivatives
Dihydroxybenzoic acid
Butyrophenone
1-benzopyran
Chromane
Benzopyran
Phenylketone
Aryl alkyl ketone
Aryl ketone
Benzoyl
Phenoxy compound
Resorcinol
Phenol ether
Cyclohexenone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Benzenoid
Oxane
Monocyclic benzene moiety
Monosaccharide
Dicarboxylic acid or derivatives
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Ketone
Secondary alcohol
Lactone
Hemiacetal
Carboxylic acid ester
1,2-diol
Polyol
Oxacycle
Organoheterocyclic compound
Carbonyl hydrate
Carboxylic acid derivative
Acetal
1,1-diol
Organooxygen compound
Alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	3.04	ChemAxon
pKa (Strongest Acidic)	5.69	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	296.5 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	172.13 m³·mol⁻¹	ChemAxon
Polarizability	68.23 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

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

163191257

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (8r,10s,11r,12r,13s,22s)-10-[3,5-dihydroxy-4-(3-phenylpropanoyl)phenoxy]-1,11,12,18,19,23,23-heptahydroxy-6,9,14,24-tetraoxapentacyclo[18.3.1.0⁴,²².0⁸,¹³.0¹⁶,²¹]tetracosa-3,16,18,20-tetraene-2,5,15-trione (NP0188481)

MOL for NP0188481 ((8r,10s,11r,12r,13s,22s)-10-[3,5-dihydroxy-4-(3-phenylpropanoyl)phenoxy]-1,11,12,18,19,23,23-heptahydroxy-6,9,14,24-tetraoxapentacyclo[18.3.1.0⁴,²².0⁸,¹³.0¹⁶,²¹]tetracosa-3,16,18,20-tetraene-2,5,15-trione)

3D MOL for NP0188481 ((8r,10s,11r,12r,13s,22s)-10-[3,5-dihydroxy-4-(3-phenylpropanoyl)phenoxy]-1,11,12,18,19,23,23-heptahydroxy-6,9,14,24-tetraoxapentacyclo[18.3.1.0⁴,²².0⁸,¹³.0¹⁶,²¹]tetracosa-3,16,18,20-tetraene-2,5,15-trione)

3D SDF for NP0188481 ((8r,10s,11r,12r,13s,22s)-10-[3,5-dihydroxy-4-(3-phenylpropanoyl)phenoxy]-1,11,12,18,19,23,23-heptahydroxy-6,9,14,24-tetraoxapentacyclo[18.3.1.0⁴,²².0⁸,¹³.0¹⁶,²¹]tetracosa-3,16,18,20-tetraene-2,5,15-trione)

3D-SDF for NP0188481 ((8r,10s,11r,12r,13s,22s)-10-[3,5-dihydroxy-4-(3-phenylpropanoyl)phenoxy]-1,11,12,18,19,23,23-heptahydroxy-6,9,14,24-tetraoxapentacyclo[18.3.1.0⁴,²².0⁸,¹³.0¹⁶,²¹]tetracosa-3,16,18,20-tetraene-2,5,15-trione)

PDB for NP0188481 ((8r,10s,11r,12r,13s,22s)-10-[3,5-dihydroxy-4-(3-phenylpropanoyl)phenoxy]-1,11,12,18,19,23,23-heptahydroxy-6,9,14,24-tetraoxapentacyclo[18.3.1.0⁴,²².0⁸,¹³.0¹⁶,²¹]tetracosa-3,16,18,20-tetraene-2,5,15-trione)

3D PDB for NP0188481 ((8r,10s,11r,12r,13s,22s)-10-[3,5-dihydroxy-4-(3-phenylpropanoyl)phenoxy]-1,11,12,18,19,23,23-heptahydroxy-6,9,14,24-tetraoxapentacyclo[18.3.1.0⁴,²².0⁸,¹³.0¹⁶,²¹]tetracosa-3,16,18,20-tetraene-2,5,15-trione)

SMILES for NP0188481 ((8r,10s,11r,12r,13s,22s)-10-[3,5-dihydroxy-4-(3-phenylpropanoyl)phenoxy]-1,11,12,18,19,23,23-heptahydroxy-6,9,14,24-tetraoxapentacyclo[18.3.1.0⁴,²².0⁸,¹³.0¹⁶,²¹]tetracosa-3,16,18,20-tetraene-2,5,15-trione)

INCHI for NP0188481 ((8r,10s,11r,12r,13s,22s)-10-[3,5-dihydroxy-4-(3-phenylpropanoyl)phenoxy]-1,11,12,18,19,23,23-heptahydroxy-6,9,14,24-tetraoxapentacyclo[18.3.1.0⁴,²².0⁸,¹³.0¹⁶,²¹]tetracosa-3,16,18,20-tetraene-2,5,15-trione)

Structure for NP0188481 ((8r,10s,11r,12r,13s,22s)-10-[3,5-dihydroxy-4-(3-phenylpropanoyl)phenoxy]-1,11,12,18,19,23,23-heptahydroxy-6,9,14,24-tetraoxapentacyclo[18.3.1.0⁴,²².0⁸,¹³.0¹⁶,²¹]tetracosa-3,16,18,20-tetraene-2,5,15-trione)

3D Structure for NP0188481 ((8r,10s,11r,12r,13s,22s)-10-[3,5-dihydroxy-4-(3-phenylpropanoyl)phenoxy]-1,11,12,18,19,23,23-heptahydroxy-6,9,14,24-tetraoxapentacyclo[18.3.1.0⁴,²².0⁸,¹³.0¹⁶,²¹]tetracosa-3,16,18,20-tetraene-2,5,15-trione)