NP-MRD: Showing NP-Card for Corilagin (NP0046976)

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Record Information

Version

2.0

Created at

2022-03-17 20:32:36 UTC

Updated at

2022-03-17 20:32:36 UTC

NP-MRD ID

NP0046976

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Corilagin

Description

Corilagin, also known as gallotannin, 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. Corilagin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Corilagin has been detected, but not quantified in, pomegranates. This could make corilagin a potential biomarker for the consumption of these foods. Corilagin is found in Acalypha australis, Acalypha hispida, Acalypha indica, Acer nikoense , Acer spp., Aleurites cordata, Anogeissus latifolia , Arctostaphylos uva-ursi, Bischofia javanica, Carpinus laxiflora, Caryocar villosum, Cercidiphyllum japonicum, Cunonia macrophylla, Euphoria longana , Erodium cicutarium, Erodium moschatum, Erodium stephanianum, Tetradium glabrifolium, Euphorbia fischeriana, Euphorbia helioscopia, Euphorbia humifusa, Euphorbia hyssopifolia, Euphorbia jolkinii, Euphorbia maculata, Euphorbia makinoi, Euphorbia prostrata, Euphorbia thymifolia, Excoecaria agallocha, Geranium sibiricum, Geranium thunbergii, Lotus corniculatus, Lumnitzera racemosa, Macaranga tanarius, Mallotus japonicus, Mallotus repandus, Nephelium lappaceum, Nymphaea alba , Nymphaea nouchali, Nymphaea stellata , Pelargonium reniforme, Phyllanthus amarus, Phyllanthus emblica , Phyllanthus flexuosus, Phyllanthus niruri, Phyllanthus tenellus, Phyllanthus urinaria , Phyllanthus virgatus, Poupartia fordii, Rhus semialata , Ricinus communis , Sapium japonicum, Sapium sebiferum , Terminalia catappa, Terminalia chebula , Terminalia citrina, Triadica sebifera and Vernicia fordii. Corilagin was first documented in 2003 (PMID: 14750026). An ellagitannin with a hexahydroxydiphenoyl group bridging over the 3-O and 6-O of the glucose core (PMID: 18486919).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309272007462D          

 45 49  0  0  0  0            999 V2000
    0.0295   -0.0294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6850   -0.4420    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6850   -1.2669    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0295   -1.6795    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7439   -1.2669    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7439   -0.4420    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4584   -0.0295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0295   -2.5045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5763   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4584   -1.6795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2226   -1.6795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1729   -0.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1729   -1.2669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8873   -0.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6018    1.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8873    0.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6018   -0.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3163   -0.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3163    0.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6018    2.0331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0307    1.2081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0307   -0.4420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5854   -0.4714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5854   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9593   -1.7089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2998   -1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0143   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7288   -1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7288   -2.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0143   -2.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2998   -2.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0143   -3.7714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4432   -2.9464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4432   -1.2964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6850   -2.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3995   -2.5045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6850   -3.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3995   -4.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3995   -4.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6850   -5.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0295   -4.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0295   -4.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6850   -6.2170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1139   -5.3920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7439   -5.3920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  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  1  0  0  0
  4  8  1  1  0  0  0
  2  9  1  1  0  0  0
  5 10  1  6  0  0  0
  3 11  1  6  0  0  0
  7 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 16 14  2  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
 15 19  2  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 15 20  1  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  0  0  0  0
  9 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 31 26  2  0  0  0  0
 27 26  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 29 33  1  0  0  0  0
 28 34  1  0  0  0  0
  8 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 42  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 40 43  1  0  0  0  0
 39 44  1  0  0  0  0
 41 45  1  0  0  0  0
 31 38  1  0  0  0  0
M  END


  Mrv1652309272007462D          

 45 49  0  0  0  0            999 V2000
    0.0295   -0.0294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6850   -0.4420    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6850   -1.2669    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0295   -1.6795    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7439   -1.2669    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7439   -0.4420    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4584   -0.0295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0295   -2.5045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5763   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4584   -1.6795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2226   -1.6795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1729   -0.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1729   -1.2669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8873   -0.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6018    1.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8873    0.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6018   -0.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3163   -0.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3163    0.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6018    2.0331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0307    1.2081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0307   -0.4420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5854   -0.4714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5854   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9593   -1.7089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2998   -1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0143   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7288   -1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7288   -2.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0143   -2.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2998   -2.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0143   -3.7714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4432   -2.9464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4432   -1.2964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6850   -2.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3995   -2.5045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6850   -3.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3995   -4.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3995   -4.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6850   -5.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0295   -4.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0295   -4.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6850   -6.2170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1139   -5.3920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7439   -5.3920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  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  1  0  0  0
  4  8  1  1  0  0  0
  2  9  1  1  0  0  0
  5 10  1  6  0  0  0
  3 11  1  6  0  0  0
  7 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 16 14  2  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
 15 19  2  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 15 20  1  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  0  0  0  0
  9 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 31 26  2  0  0  0  0
 27 26  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 29 33  1  0  0  0  0
 28 34  1  0  0  0  0
  8 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 42  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 40 43  1  0  0  0  0
 39 44  1  0  0  0  0
 41 45  1  0  0  0  0
 31 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046976

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@H]2COC(=O)C3=C(C(O)=C(O)C(O)=C3)C3=C(C=C(O)C(O)=C3O)C(=O)O[C@@H]1[C@@H](O)[C@H](OC(=O)C1=CC(O)=C(O)C(O)=C1)O2

> <INCHI_IDENTIFIER>
InChI=1S/C27H22O18/c28-9-1-6(2-10(29)16(9)32)24(39)45-27-22(38)23-19(35)13(43-27)5-42-25(40)7-3-11(30)17(33)20(36)14(7)15-8(26(41)44-23)4-12(31)18(34)21(15)37/h1-4,13,19,22-23,27-38H,5H2/t13-,19-,22-,23+,27+/m1/s1

> <INCHI_KEY>
TUSDEZXZIZRFGC-XIGLUPEJSA-N

> <FORMULA>
C27H22O18

> <MOLECULAR_WEIGHT>
634.4528

> <EXACT_MASS>
634.0806139

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
55.33839239898596

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,19R,21S,22R,23R)-6,7,8,11,12,13,22,23-octahydroxy-3,16-dioxo-2,17,20-trioxatetracyclo[17.3.1.0^{4,9}.0^{10,15}]tricosa-4,6,8,10,12,14-hexaen-21-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
1.69

> <JCHEM_LOGP>
1.095251979

> <ALOGPS_LOGS>
-2.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.922896497221108

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.408048490818405

> <JCHEM_PKA_STRONGEST_BASIC>
-5.549137490025932

> <JCHEM_POLAR_SURFACE_AREA>
310.65999999999997

> <JCHEM_REFRACTIVITY>
142.29569999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.90e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,19R,21S,22R,23R)-6,7,8,11,12,13,22,23-octahydroxy-3,16-dioxo-2,17,20-trioxatetracyclo[17.3.1.0^{4,9}.0^{10,15}]tricosa-4,6,8,10,12,14-hexaen-21-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0       0.055  -0.055   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.279  -0.825   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.279  -2.365   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.055  -3.135   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.389  -2.365   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.389  -0.825   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.722  -0.055   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.055  -4.675   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.942  -0.165   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.722  -3.135   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -2.282  -3.135   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.056  -0.825   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.056  -2.365   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.390  -0.055   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.723   2.255   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.390   1.485   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.723  -0.825   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.057  -0.055   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.057   1.485   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.723   3.795   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.391   2.255   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       9.391  -0.825   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -4.826  -0.880   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.826  -2.420   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.657  -3.190   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -6.160  -3.190   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -7.493  -2.420   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.827  -3.190   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -8.827  -4.730   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -7.493  -5.500   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -6.160  -4.730   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -7.493  -7.040   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0     -10.161  -5.500   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0     -10.161  -2.420   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.279  -5.445   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.612  -4.675   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -1.279  -6.985   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.612  -7.755   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -2.612  -9.295   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -1.279 -10.065   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.055  -9.295   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       0.055  -7.755   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -1.279 -11.605   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -3.946 -10.065   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       1.389 -10.065   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6   10                                                  
CONECT    6    1    5    7                                                  
CONECT    7    6   12                                                       
CONECT    8    4   35                                                       
CONECT    9    2   23                                                       
CONECT   10    5                                                            
CONECT   11    3                                                            
CONECT   12    7   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   16   17                                                  
CONECT   15   16   19   20                                                  
CONECT   16   14   15                                                       
CONECT   17   14   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   15   18   21                                                  
CONECT   20   15                                                            
CONECT   21   19                                                            
CONECT   22   18                                                            
CONECT   23    9   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   31   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   34                                                  
CONECT   29   28   30   33                                                  
CONECT   30   29   31   32                                                  
CONECT   31   26   30   38                                                  
CONECT   32   30                                                            
CONECT   33   29                                                            
CONECT   34   28                                                            
CONECT   35    8   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   42                                                  
CONECT   38   37   39   31                                                  
CONECT   39   38   40   44                                                  
CONECT   40   39   41   43                                                  
CONECT   41   40   42   45                                                  
CONECT   42   37   41                                                       
CONECT   43   40                                                            
CONECT   44   39                                                            
CONECT   45   41                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   98    0
END

View in JSmol

Synonyms

Value	Source
(beta-1-O-Galloyl-3,6-(R)-hexahydroxydiphenoyl-D-glucose)	ChEBI
1-O-Galloyl-3,6-hexahydroxydiphenic acid-beta-D-glucopyranose	ChEBI
(b-1-O-Galloyl-3,6-(R)-hexahydroxydiphenoyl-D-glucose)	Generator
(Β-1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-D-glucose)	Generator
1-O-Galloyl-3,6-hexahydroxydiphenate-b-D-glucopyranose	Generator
1-O-Galloyl-3,6-hexahydroxydiphenate-beta-D-glucopyranose	Generator
1-O-Galloyl-3,6-hexahydroxydiphenate-β-D-glucopyranose	Generator
1-O-Galloyl-3,6-hexahydroxydiphenic acid-b-D-glucopyranose	Generator
1-O-Galloyl-3,6-hexahydroxydiphenic acid-β-D-glucopyranose	Generator
Corillagin	HMDB
1-O-Galloyl-3,6-(R)-hexahydroxydiphenol-beta-D-glucose	MeSH

Chemical Formula

C₂₇H₂₂O₁₈

Average Mass

634.4528 Da

Monoisotopic Mass

634.08061 Da

IUPAC Name

(1S,19R,21S,22R,23R)-6,7,8,11,12,13,22,23-octahydroxy-3,16-dioxo-2,17,20-trioxatetracyclo[17.3.1.0^{4,9}.0^{10,15}]tricosa-4,6,8,10,12,14-hexaen-21-yl 3,4,5-trihydroxybenzoate

Traditional Name

(1S,19R,21S,22R,23R)-6,7,8,11,12,13,22,23-octahydroxy-3,16-dioxo-2,17,20-trioxatetracyclo[17.3.1.0^{4,9}.0^{10,15}]tricosa-4,6,8,10,12,14-hexaen-21-yl 3,4,5-trihydroxybenzoate

CAS Registry Number

23094-69-1

SMILES

O[C@@H]1[C@H]2COC(=O)C3=C(C(O)=C(O)C(O)=C3)C3=C(C=C(O)C(O)=C3O)C(=O)O[C@@H]1[C@@H](O)[C@H](OC(=O)C1=CC(O)=C(O)C(O)=C1)O2

InChI Identifier

InChI=1S/C27H22O18/c28-9-1-6(2-10(29)16(9)32)24(39)45-27-22(38)23-19(35)13(43-27)5-42-25(40)7-3-11(30)17(33)20(36)14(7)15-8(26(41)44-23)4-12(31)18(34)21(15)37/h1-4,13,19,22-23,27-38H,5H2/t13-,19-,22-,23+,27+/m1/s1

InChI Key

TUSDEZXZIZRFGC-XIGLUPEJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acalypha australis	LOTUS Database	35616633
Acalypha hispida	LOTUS Database	35616633
Acalypha indica	LOTUS Database	35616633
Acer nikoense	Plant	KNApSAcK
Acer spp.	Plant	KNApSAcK
Aleurites cordata	Plant	KNApSAcK
Anogeissus latifolia	Plant	KNApSAcK
Arctostaphylos uva-ursi	LOTUS Database	35616633
Bischofia javanica	LOTUS Database	35616633
Carpinus laxiflora	LOTUS Database	35616633
Caryocar villosum	LOTUS Database	35616633
Cercidiphyllum japonicum	LOTUS Database	35616633
Cunonia macrophylla	Plant	KNApSAcK
Dimocarpus longan	-	KNApSAcK
Erodium cicutarium	LOTUS Database	35616633
Erodium moschatum	LOTUS Database	35616633
Erodium stephanianum	LOTUS Database	35616633
Euodia fargesii	LOTUS Database	35616633
Euphorbia fischeriana	LOTUS Database	35616633
Euphorbia helioscopia	LOTUS Database	35616633
Euphorbia humifusa	LOTUS Database	35616633
Euphorbia hyssopifolia	LOTUS Database	35616633
Euphorbia jolkini	LOTUS Database	35616633
Euphorbia maculata	LOTUS Database	35616633
Euphorbia makinoi	LOTUS Database	35616633
Euphorbia prostrata	LOTUS Database	35616633
Euphorbia thymifolia	LOTUS Database	35616633
Excoecaria agallocha	LOTUS Database	35616633
Geranium sibiricum	LOTUS Database	35616633
Geranium thunbergii	Plant	KNApSAcK
Lotus corniculatus	LOTUS Database	35616633
Lumnitzera racemosa	LOTUS Database	35616633
Macaranga tanarius	LOTUS Database	35616633
Mallotus japonicus	LOTUS Database	35616633
Mallotus repandus	LOTUS Database	35616633
Nephelium lappaceum	LOTUS Database	35616633
Nymphaea alba	Plant	KNApSAcK
Nymphaea nouchali	LOTUS Database	35616633
Nymphaea stellata	Plant	KNApSAcK
Pelargonium reniforme	Plant	KNApSAcK
Phyllanthus amarus	LOTUS Database	35616633
Phyllanthus emblica	Plant	KNApSAcK
Phyllanthus flexuosus	LOTUS Database	35616633
Phyllanthus niruri	LOTUS Database	35616633
Phyllanthus tenellus	LOTUS Database	35616633
Phyllanthus urinaria	Plant	KNApSAcK
Phyllanthus virgatus	LOTUS Database	35616633
Poupartia fordii	Plant	KNApSAcK
Punica granatum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Rhus semialata	Plant	KNApSAcK
Ricinus communis	Plant	KNApSAcK
Sapium japonicum	Plant	KNApSAcK
Sapium sebiferum	Plant	KNApSAcK
Terminalia catappa	LOTUS Database	35616633
Terminalia chebula	Plant	KNApSAcK
Terminalia citrina	LOTUS Database	35616633
Triadica sebifera	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
Macrolide
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Pyrogallol derivative
Tricarboxylic acid or derivatives
Benzenetriol
Benzoic acid or derivatives
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Oxane
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Lactone
Secondary alcohol
Carboxylic acid ester
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

gallate ester (CHEBI:3884 )
ellagitannin (CHEBI:3884 )
Ellagitannins (C10219 )

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	1.69	ALOGPS
logP	1.1	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	7.41	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	310.66 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	142.3 m³·mol⁻¹	ChemAxon
Polarizability	55.34 Å³	ChemAxon
Number of Rings	5	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

HMDB0031457

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Corilagin

METLIN ID

Not Available

PubChem Compound

73568

PDB ID

Not Available

ChEBI ID

3884

Good Scents ID

Not Available

References

General References

Zhao L, Zhang SL, Tao JY, Pang R, Jin F, Guo YJ, Dong JH, Ye P, Zhao HY, Zheng GH: Preliminary exploration on anti-inflammatory mechanism of Corilagin (beta-1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-D-glucose) in vitro. Int Immunopharmacol. 2008 Jul;8(7):1059-64. doi: 10.1016/j.intimp.2008.03.003. Epub 2008 Mar 31. [PubMed:18486919 ]
Shen ZQ, Dong ZJ, Peng H, Liu JK: Modulation of PAI-1 and tPA activity and thrombolytic effects of corilagin. Planta Med. 2003 Dec;69(12):1109-12. doi: 10.1055/s-2003-45191. [PubMed:14750026 ]

Showing NP-Card for Corilagin (NP0046976)

MOL for NP0046976 (Corilagin)

3D MOL for NP0046976 (Corilagin)

3D SDF for NP0046976 (Corilagin)

3D-SDF for NP0046976 (Corilagin)

PDB for NP0046976 (Corilagin)

3D PDB for NP0046976 (Corilagin)

SMILES for NP0046976 (Corilagin)

INCHI for NP0046976 (Corilagin)

Structure for NP0046976 (Corilagin)

3D Structure for NP0046976 (Corilagin)