NP-MRD: Showing NP-Card for 1,13,14,15,18,19,20,34,35,39,39-undecahydroxy-2,5,10,23,31-pentaoxo-6,9,24,27,30,40-hexaoxaoctacyclo[34.3.1.0⁴,³⁸.0⁷,²⁶.0⁸,²⁹.0¹¹,¹⁶.0¹⁷,²².0³²,³⁷]tetraconta-3,11(16),12,14,17,19,21,32,34,36-decaen-28-yl 3,4,5-trihydroxybenzoate (NP0230535)

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Record Information

Version

2.0

Created at

2022-09-06 11:00:56 UTC

Updated at

2022-09-06 11:00:56 UTC

NP-MRD ID

NP0230535

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,13,14,15,18,19,20,34,35,39,39-undecahydroxy-2,5,10,23,31-pentaoxo-6,9,24,27,30,40-hexaoxaoctacyclo[34.3.1.0⁴,³⁸.0⁷,²⁶.0⁸,²⁹.0¹¹,¹⁶.0¹⁷,²².0³²,³⁷]tetraconta-3,11(16),12,14,17,19,21,32,34,36-decaen-28-yl 3,4,5-trihydroxybenzoate

Description

Geraniin 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. Geraniin is an extremely weak basic (essentially neutral) compound (based on its pKa). It can also be found in the rind of Nephelium lappaceum (rambutan). Geraniin is a dehydroellagitannin found in geraniums. Chebulagic acid is formed from geraniin through a glutathione-mediated conversion. It mediates apoptosis by cleavage of focal adhesion kinase through up-regulation of Fas ligand expression in human melanoma cells. It is found for instance in Geranium thunbergii, which is one of the most popular folk medicines and also an official antidiarrheic drug in Japan. It is formed with one hexahydroxydiphenic acid unit, one modified hexahydroxydiphenic acid unit (dehydrohexahydroxydiphenic acid or DHHDP) and one gallic acid unit linked to a glucose molecule. 1,13,14,15,18,19,20,34,35,39,39-undecahydroxy-2,5,10,23,31-pentaoxo-6,9,24,27,30,40-hexaoxaoctacyclo[34.3.1.0⁴,³⁸.0⁷,²⁶.0⁸,²⁹.0¹¹,¹⁶.0¹⁷,²².0³²,³⁷]tetraconta-3,11(16),12,14,17,19,21,32,34,36-decaen-28-yl 3,4,5-trihydroxybenzoate is found in Acer tataricum, Bischofia javanica, Cercidiphyllum japonicum, Elaeocarpus sylvestris, Erodium cicutarium, Euphorbia helioscopia, Euphorbia jolkinii, Euphorbia thymifolia, Euphorbia tirucalli, Geranium sibiricum, Heterocentron subtriplinervium, Macaranga tanarius, Mallotus japonicus, Nymphaea tetragona, Phyllanthus amarus, Phyllanthus emblica, Phyllanthus sellowianus, Phyllanthus urinaria, Spondias mombin, Terminalia catappa and Vernicia fordii. It is forming an equilibrium mixture of six-membered hemi-ketal and five-membered hemi-ketal forms.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261514452D          

 68 76  0  0  0  0            999 V2000
    1.8529   -1.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0054   -1.5996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0471   -0.9528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6439   -0.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1950   -0.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3648   -0.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1416   -1.5401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2481   -1.2856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2748   -0.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499    0.5507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3741    0.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3224    0.8786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4165    1.2455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1037    0.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0521   -0.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3132   -0.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9262   -0.0946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8350    1.4212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2015    2.1596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2750   -0.0267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2810   -0.3767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5429    0.6445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9949   -1.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4294   -0.3284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9360    0.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1062    0.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8063   -0.6554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3458   -1.3007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8935   -2.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1787   -2.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4701   -3.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2459   -2.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5344   -2.8077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6967   -1.5538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3559   -1.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8475   -1.2552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1471   -2.7123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0339   -0.7991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0941   -1.0066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1142   -2.7033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2182   -3.5789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6023   -1.9803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6970    1.1651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7352    0.7300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7920    0.7214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3754    1.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1725    2.2001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1669    1.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1922    1.8776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9189    2.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6204    1.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5952    1.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8684    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3451   -0.0842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0365    0.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7720   -0.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8162   -0.8314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1249   -1.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3893   -0.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1375   -1.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4722   -2.5306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4849   -2.2298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5560   -1.2822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6448   -0.0528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8296    0.7773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3468    1.4909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0371    2.6065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9130    3.1449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 15 17  1  0  0  0  0
 14 18  1  0  0  0  0
 13 19  1  0  0  0  0
  5 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 29 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 34 38  1  0  0  0  0
 27 38  1  0  0  0  0
 34 39  1  0  0  0  0
 30 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
  3 42  1  0  0  0  0
 26 43  1  0  0  0  0
 25 44  1  0  0  0  0
  4 45  1  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  2  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
 48 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  2  0  0  0  0
 55 56  1  0  0  0  0
 56 57  2  0  0  0  0
 57 58  1  0  0  0  0
 58 59  2  0  0  0  0
 54 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  2  0  0  0  0
 60 62  1  0  0  0  0
  1 62  1  0  0  0  0
 57 63  1  0  0  0  0
 56 64  1  0  0  0  0
 55 65  1  0  0  0  0
 52 66  1  0  0  0  0
 51 67  1  0  0  0  0
 50 68  1  0  0  0  0
M  END

     RDKit          3D

 96104  0  0  0  0  0  0  0  0999 V2000
   -1.3104   -4.1461   -0.6560 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8360   -3.0014   -0.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0941   -2.4717    0.7391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6458   -1.1520    0.8011 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3074   -0.8055   -0.3145 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6432   -0.7359   -0.0500 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7089   -1.5991   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2666   -1.6624   -1.5227 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3755   -2.5522    0.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9952   -3.8790    0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4398   -4.9588    1.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0361   -6.2382    0.7956 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3176   -4.7284    2.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7960   -5.7795    2.8648 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6066   -3.1575    3.3909 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9523   -1.0512    1.9484 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4039    0.1485    2.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2424    1.2118    2.6593 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6267    1.1549    2.5983 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954    2.2781    2.9364 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1608   -0.0461    2.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5415   -0.1226    2.1302 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3727   -1.1272    1.8758 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0608   -2.2449    1.4857 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9889    0.4520    2.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6902    1.6621    2.1557 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9824   -1.1208    2.7544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2111   -0.5264    2.0402 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.3766    2.6673    0.4488 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5993    3.1504    0.2895 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1703    5.8818   -0.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0796    0.5421   -1.7440 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9949   -2.5405   -1.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1716   -3.4420   -1.6934 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.1588   -1.5101   -2.4868 O   0  0  0  0  0  0  0  0  0  0  0  0
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 46 88  1  6
M  END


  Mrv1533004261514452D          

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 51 67  1  0  0  0  0
 50 68  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0230535

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(=CC(O)=C1O)C(=O)OC1OC2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC3C2OC(=O)C2=CC(=O)C4(O)OC5=C(C2C4(O)O)C(=CC(O)=C5O)C(=O)OC13

> <INCHI_IDENTIFIER>
InChI=1S/C41H28O27/c42-13-1-8(2-14(43)24(13)48)34(54)67-39-33-32-30(64-38(58)12-6-19(47)41(61)40(59,60)23(12)22-11(37(57)66-33)5-17(46)27(51)31(22)68-41)18(63-39)7-62-35(55)9-3-15(44)25(49)28(52)20(9)21-10(36(56)65-32)4-16(45)26(50)29(21)53/h1-6,18,23,30,32-33,39,42-46,48-53,59-61H,7H2

> <INCHI_KEY>
JQQBXPCJFAKSPG-UHFFFAOYSA-N

> <FORMULA>
C41H28O27

> <MOLECULAR_WEIGHT>
952.648

> <EXACT_MASS>
952.081795642

> <JCHEM_ACCEPTOR_COUNT>
22

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
81.24278311455619

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,13,14,15,18,19,20,34,35,39,39-undecahydroxy-2,5,10,23,31-pentaoxo-6,9,24,27,30,40-hexaoxaoctacyclo[34.3.1.0⁴,³⁸.0⁷,²⁶.0⁸,²⁹.0¹¹,¹⁶.0¹⁷,²².0³²,³⁷]tetraconta-3,11,13,15,17,19,21,32,34,36-decaen-28-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
2.2012349269999993

> <ALOGPS_LOGS>
-2.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
7.455759213527221

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.659563140658877

> <JCHEM_PKA_STRONGEST_BASIC>
-5.554812305450288

> <JCHEM_POLAR_SURFACE_AREA>
450.2500000000001

> <JCHEM_REFRACTIVITY>
210.55630000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.66e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,13,14,15,18,19,20,34,35,39,39-undecahydroxy-2,5,10,23,31-pentaoxo-6,9,24,27,30,40-hexaoxaoctacyclo[34.3.1.0⁴,³⁸.0⁷,²⁶.0⁸,²⁹.0¹¹,¹⁶.0¹⁷,²².0³²,³⁷]tetraconta-3,11,13,15,17,19,21,32,34,36-decaen-28-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       3.459  -3.152   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.877  -2.986   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.955  -1.779   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.202  -0.234   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.364  -0.386   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.681  -1.646   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.264  -2.875   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.330  -2.400   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.380  -0.764   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.080   1.028   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.698   0.103   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.602   1.640   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.777   2.325   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.060   1.473   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.964  -0.064   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.585  -0.749   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.596  -0.177   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       3.425   2.653   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.376   4.031   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.380  -0.050   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -4.258  -0.703   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.747   1.203   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -5.591  -1.919   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.402  -0.613   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.481   0.621   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.932   0.435   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.372  -1.223   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.379  -2.428   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.535  -4.271   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.200  -5.504   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.878  -5.795   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.459  -4.139   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.998  -5.241   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.301  -2.900   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.531  -3.623   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -3.449  -2.343   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -4.008  -5.063   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -1.930  -1.492   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       0.176  -1.879   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -0.213  -5.046   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       0.407  -6.681   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       1.124  -3.697   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -3.168   2.175   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -6.972   1.363   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       1.478   1.347   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       2.567   2.461   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       2.189   4.107   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       4.045   1.966   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       4.092   3.505   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       5.449   4.234   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       6.758   3.423   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       6.711   1.884   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       5.354   1.155   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       6.244  -0.157   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       7.535   0.683   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       8.908  -0.014   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       8.990  -1.552   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       7.700  -2.392   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       6.327  -1.695   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       5.857  -3.204   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0       6.481  -4.724   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0       4.638  -4.162   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      10.371  -2.394   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      10.537  -0.099   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0       9.015   1.451   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0       8.114   2.783   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0       7.536   4.865   0.000  0.00  0.00           O+0
HETATM   68  O   UNK     0       5.438   5.871   0.000  0.00  0.00           O+0
CONECT    1    2   62                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4   42                                                  
CONECT    4    3    5   45                                                  
CONECT    5    4    6   20                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   11                                                       
CONECT   17   15                                                            
CONECT   18   14                                                            
CONECT   19   13                                                            
CONECT   20    5   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   44                                                  
CONECT   26   25   27   43                                                  
CONECT   27   26   28   38                                                  
CONECT   28   27   23   29                                                  
CONECT   29   28   30   35                                                  
CONECT   30   29   31   40                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   38   39                                             
CONECT   35   34   29   36   37                                             
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   34   27                                                       
CONECT   39   34                                                            
CONECT   40   30   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40    3                                                       
CONECT   43   26                                                            
CONECT   44   25                                                            
CONECT   45    4   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49   53                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51   68                                                  
CONECT   51   50   52   67                                                  
CONECT   52   51   53   66                                                  
CONECT   53   52   48   54                                                  
CONECT   54   53   55   59                                                  
CONECT   55   54   56   65                                                  
CONECT   56   55   57   64                                                  
CONECT   57   56   58   63                                                  
CONECT   58   57   59                                                       
CONECT   59   58   54   60                                                  
CONECT   60   59   61   62                                                  
CONECT   61   60                                                            
CONECT   62   60    1                                                       
CONECT   63   57                                                            
CONECT   64   56                                                            
CONECT   65   55                                                            
CONECT   66   52                                                            
CONECT   67   51                                                            
CONECT   68   50                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  152    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₁H₂₈O₂₇

Average Mass

952.6480 Da

Monoisotopic Mass

952.08180 Da

IUPAC Name

1,13,14,15,18,19,20,34,35,39,39-undecahydroxy-2,5,10,23,31-pentaoxo-6,9,24,27,30,40-hexaoxaoctacyclo[34.3.1.0⁴,³⁸.0⁷,²⁶.0⁸,²⁹.0¹¹,¹⁶.0¹⁷,²².0³²,³⁷]tetraconta-3,11,13,15,17,19,21,32,34,36-decaen-28-yl 3,4,5-trihydroxybenzoate

Traditional Name

1,13,14,15,18,19,20,34,35,39,39-undecahydroxy-2,5,10,23,31-pentaoxo-6,9,24,27,30,40-hexaoxaoctacyclo[34.3.1.0⁴,³⁸.0⁷,²⁶.0⁸,²⁹.0¹¹,¹⁶.0¹⁷,²².0³²,³⁷]tetraconta-3,11,13,15,17,19,21,32,34,36-decaen-28-yl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

OC1=CC(=CC(O)=C1O)C(=O)OC1OC2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC3C2OC(=O)C2=CC(=O)C4(O)OC5=C(C2C4(O)O)C(=CC(O)=C5O)C(=O)OC13

InChI Identifier

InChI=1S/C41H28O27/c42-13-1-8(2-14(43)24(13)48)34(54)67-39-33-32-30(64-38(58)12-6-19(47)41(61)40(59,60)23(12)22-11(37(57)66-33)5-17(46)27(51)31(22)68-41)18(63-39)7-62-35(55)9-3-15(44)25(49)28(52)20(9)21-10(36(56)65-32)4-16(45)26(50)29(21)53/h1-6,18,23,30,32-33,39,42-46,48-53,59-61H,7H2

InChI Key

JQQBXPCJFAKSPG-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
Acer tataricum	LOTUS Database	35616633
Bischofia javanica	LOTUS Database	35616633
Cercidiphyllum japonicum	LOTUS Database	35616633
Elaeocarpus sylvestris	LOTUS Database	35616633
Erodium cicutarium	LOTUS Database	35616633
Euphorbia helioscopia	LOTUS Database	35616633
Euphorbia jolkini	LOTUS Database	35616633
Euphorbia thymifolia	LOTUS Database	35616633
Euphorbia tirucalli	LOTUS Database	35616633
Geranium sibiricum	LOTUS Database	35616633
Heterocentron subtriplinervium	LOTUS Database	35616633
Macaranga tanarius	LOTUS Database	35616633
Mallotus japonicus	LOTUS Database	35616633
Nymphaea tetragona	LOTUS Database	35616633
Phyllanthus amarus	LOTUS Database	35616633
Phyllanthus emblica	LOTUS Database	35616633
Phyllanthus sellowianus	LOTUS Database	35616633
Phyllanthus urinaria	LOTUS Database	35616633
Spondias mombin	LOTUS Database	35616633
Terminalia catappa	LOTUS Database	35616633
Vernicia fordii	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
Pentacarboxylic acid or derivatives
Macrolide
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Benzopyran
1-benzopyran
Chromane
Benzoate ester
Benzoic acid or derivatives
Pyrogallol derivative
Benzenetriol
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Cyclohexenone
Benzenoid
Monocyclic benzene moiety
Monosaccharide
Oxane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Ketone
Hemiacetal
Lactone
Carboxylic acid ester
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Carbonyl hydrate
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Carbonyl group
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	2.36	ALOGPS
logP	2.2	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	5.66	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	22	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	450.25 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	210.56 m³·mol⁻¹	ChemAxon
Polarizability	81.24 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Geraniin

METLIN ID

Not Available

PubChem Compound

115063

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,13,14,15,18,19,20,34,35,39,39-undecahydroxy-2,5,10,23,31-pentaoxo-6,9,24,27,30,40-hexaoxaoctacyclo[34.3.1.0⁴,³⁸.0⁷,²⁶.0⁸,²⁹.0¹¹,¹⁶.0¹⁷,²².0³²,³⁷]tetraconta-3,11(16),12,14,17,19,21,32,34,36-decaen-28-yl 3,4,5-trihydroxybenzoate (NP0230535)

MOL for NP0230535 (1,13,14,15,18,19,20,34,35,39,39-undecahydroxy-2,5,10,23,31-pentaoxo-6,9,24,27,30,40-hexaoxaoctacyclo[34.3.1.0⁴,³⁸.0⁷,²⁶.0⁸,²⁹.0¹¹,¹⁶.0¹⁷,²².0³²,³⁷]tetraconta-3,11(16),12,14,17,19,21,32,34,36-decaen-28-yl 3,4,5-trihydroxybenzoate)

3D MOL for NP0230535 (1,13,14,15,18,19,20,34,35,39,39-undecahydroxy-2,5,10,23,31-pentaoxo-6,9,24,27,30,40-hexaoxaoctacyclo[34.3.1.0⁴,³⁸.0⁷,²⁶.0⁸,²⁹.0¹¹,¹⁶.0¹⁷,²².0³²,³⁷]tetraconta-3,11(16),12,14,17,19,21,32,34,36-decaen-28-yl 3,4,5-trihydroxybenzoate)

3D SDF for NP0230535 (1,13,14,15,18,19,20,34,35,39,39-undecahydroxy-2,5,10,23,31-pentaoxo-6,9,24,27,30,40-hexaoxaoctacyclo[34.3.1.0⁴,³⁸.0⁷,²⁶.0⁸,²⁹.0¹¹,¹⁶.0¹⁷,²².0³²,³⁷]tetraconta-3,11(16),12,14,17,19,21,32,34,36-decaen-28-yl 3,4,5-trihydroxybenzoate)

3D-SDF for NP0230535 (1,13,14,15,18,19,20,34,35,39,39-undecahydroxy-2,5,10,23,31-pentaoxo-6,9,24,27,30,40-hexaoxaoctacyclo[34.3.1.0⁴,³⁸.0⁷,²⁶.0⁸,²⁹.0¹¹,¹⁶.0¹⁷,²².0³²,³⁷]tetraconta-3,11(16),12,14,17,19,21,32,34,36-decaen-28-yl 3,4,5-trihydroxybenzoate)

PDB for NP0230535 (1,13,14,15,18,19,20,34,35,39,39-undecahydroxy-2,5,10,23,31-pentaoxo-6,9,24,27,30,40-hexaoxaoctacyclo[34.3.1.0⁴,³⁸.0⁷,²⁶.0⁸,²⁹.0¹¹,¹⁶.0¹⁷,²².0³²,³⁷]tetraconta-3,11(16),12,14,17,19,21,32,34,36-decaen-28-yl 3,4,5-trihydroxybenzoate)

3D PDB for NP0230535 (1,13,14,15,18,19,20,34,35,39,39-undecahydroxy-2,5,10,23,31-pentaoxo-6,9,24,27,30,40-hexaoxaoctacyclo[34.3.1.0⁴,³⁸.0⁷,²⁶.0⁸,²⁹.0¹¹,¹⁶.0¹⁷,²².0³²,³⁷]tetraconta-3,11(16),12,14,17,19,21,32,34,36-decaen-28-yl 3,4,5-trihydroxybenzoate)

SMILES for NP0230535 (1,13,14,15,18,19,20,34,35,39,39-undecahydroxy-2,5,10,23,31-pentaoxo-6,9,24,27,30,40-hexaoxaoctacyclo[34.3.1.0⁴,³⁸.0⁷,²⁶.0⁸,²⁹.0¹¹,¹⁶.0¹⁷,²².0³²,³⁷]tetraconta-3,11(16),12,14,17,19,21,32,34,36-decaen-28-yl 3,4,5-trihydroxybenzoate)

INCHI for NP0230535 (1,13,14,15,18,19,20,34,35,39,39-undecahydroxy-2,5,10,23,31-pentaoxo-6,9,24,27,30,40-hexaoxaoctacyclo[34.3.1.0⁴,³⁸.0⁷,²⁶.0⁸,²⁹.0¹¹,¹⁶.0¹⁷,²².0³²,³⁷]tetraconta-3,11(16),12,14,17,19,21,32,34,36-decaen-28-yl 3,4,5-trihydroxybenzoate)

Structure for NP0230535 (1,13,14,15,18,19,20,34,35,39,39-undecahydroxy-2,5,10,23,31-pentaoxo-6,9,24,27,30,40-hexaoxaoctacyclo[34.3.1.0⁴,³⁸.0⁷,²⁶.0⁸,²⁹.0¹¹,¹⁶.0¹⁷,²².0³²,³⁷]tetraconta-3,11(16),12,14,17,19,21,32,34,36-decaen-28-yl 3,4,5-trihydroxybenzoate)

3D Structure for NP0230535 (1,13,14,15,18,19,20,34,35,39,39-undecahydroxy-2,5,10,23,31-pentaoxo-6,9,24,27,30,40-hexaoxaoctacyclo[34.3.1.0⁴,³⁸.0⁷,²⁶.0⁸,²⁹.0¹¹,¹⁶.0¹⁷,²².0³²,³⁷]tetraconta-3,11(16),12,14,17,19,21,32,34,36-decaen-28-yl 3,4,5-trihydroxybenzoate)