NP-MRD: Showing NP-Card for (1s,8r,9s,18r,19s,21r,22s)-7,7,8,12,13,22-hexahydroxy-21-(hydroxymethyl)-3,6,16-trioxo-2,17,20,23-tetraoxapentacyclo[16.3.1.1⁸,¹¹.0⁴,⁹.0¹⁰,¹⁵]tricosa-4,10,12,14-tetraen-19-yl 3,4,5-trihydroxybenzoate (NP0218580)

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Record Information

Version

2.0

Created at

2022-09-05 19:17:04 UTC

Updated at

2022-09-05 19:17:04 UTC

NP-MRD ID

NP0218580

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,8r,9s,18r,19s,21r,22s)-7,7,8,12,13,22-hexahydroxy-21-(hydroxymethyl)-3,6,16-trioxo-2,17,20,23-tetraoxapentacyclo[16.3.1.1⁸,¹¹.0⁴,⁹.0¹⁰,¹⁵]tricosa-4,10,12,14-tetraen-19-yl 3,4,5-trihydroxybenzoate

Description

(1S,8R,9S,18R,19S,21R,22S)-7,7,8,12,13,22-hexahydroxy-21-(hydroxymethyl)-3,6,16-trioxo-2,17,20,23-tetraoxapentacyclo[16.3.1.1⁸,¹¹.0⁴,⁹.0¹⁰,¹⁵]Tricosa-4,10,12,14-tetraen-19-yl 3,4,5-trihydroxybenzoate 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. (1s,8r,9s,18r,19s,21r,22s)-7,7,8,12,13,22-hexahydroxy-21-(hydroxymethyl)-3,6,16-trioxo-2,17,20,23-tetraoxapentacyclo[16.3.1.1⁸,¹¹.0⁴,⁹.0¹⁰,¹⁵]tricosa-4,10,12,14-tetraen-19-yl 3,4,5-trihydroxybenzoate is found in Mallotus repandus. Based on a literature review very few articles have been published on (1S,8R,9S,18R,19S,21R,22S)-7,7,8,12,13,22-hexahydroxy-21-(hydroxymethyl)-3,6,16-trioxo-2,17,20,23-tetraoxapentacyclo[16.3.1.1⁸,¹¹.0⁴,⁹.0¹⁰,¹⁵]Tricosa-4,10,12,14-tetraen-19-yl 3,4,5-trihydroxybenzoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052221172D          

 46 51  0  0  1  0            999 V2000
    2.4490   -3.7243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8374   -3.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6241   -2.5769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542   -1.9416    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6150   -1.4204    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0610   -2.0317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4878   -0.6013    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5538   -0.6605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6075   -1.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4385   -0.2251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1278   -1.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5004   -0.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0383   -0.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2280    0.5336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8549   -0.4154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4014    0.2026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1536   -1.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6205   -1.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0724   -2.6996    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9979   -3.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5021   -4.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3065   -4.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748   -4.6154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5198   -3.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2618   -3.5814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0147   -2.5606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8889   -2.5252    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6571   -2.2244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8807   -1.6872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2760   -0.2470    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3175    0.5770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0518    0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7446    0.5050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0934    1.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4006    2.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4422    3.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7494    3.4968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1765    3.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2181    4.2488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8693    2.9768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6036    3.3528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8277    2.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0094   -0.6701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9834   -1.5096    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6938   -1.9291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4123   -1.5236    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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  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  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 11 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
  2 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
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 17 29  1  0  0  0  0
  7 30  1  0  0  0  0
 30 31  1  6  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  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 34 42  1  0  0  0  0
 30 43  1  0  0  0  0
 43 44  1  0  0  0  0
  4 44  1  0  0  0  0
 44 45  1  6  0  0  0
 45 46  1  0  0  0  0
M  END


  Mrv1652309052221172D          

 46 51  0  0  1  0            999 V2000
    2.4490   -3.7243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8374   -3.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6241   -2.5769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542   -1.9416    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6150   -1.4204    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0610   -2.0317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4878   -0.6013    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5538   -0.6605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6075   -1.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4385   -0.2251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1278   -1.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5004   -0.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0383   -0.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2280    0.5336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8549   -0.4154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4014    0.2026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1536   -1.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6205   -1.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0724   -2.6996    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9979   -3.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5021   -4.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3065   -4.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748   -4.6154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5198   -3.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2618   -3.5814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0147   -2.5606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8889   -2.5252    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6571   -2.2244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8807   -1.6872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2760   -0.2470    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3175    0.5770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0518    0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7446    0.5050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0934    1.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4006    2.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4422    3.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7494    3.4968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1765    3.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2181    4.2488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8693    2.9768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6036    3.3528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8277    2.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0094   -0.6701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9834   -1.5096    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6938   -1.9291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4123   -1.5236    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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  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  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 11 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
  2 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
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 17 29  1  0  0  0  0
  7 30  1  0  0  0  0
 30 31  1  6  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  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 34 42  1  0  0  0  0
 30 43  1  0  0  0  0
 43 44  1  0  0  0  0
  4 44  1  0  0  0  0
 44 45  1  6  0  0  0
 45 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0218580

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H22O19/c28-5-12-19-18(35)21(25(42-12)45-22(36)6-1-9(29)16(33)10(30)2-6)44-23(37)7-3-11(31)17(34)20-14(7)15-8(24(38)43-19)4-13(32)26(39,40)27(15,41)46-20/h1-4,12,15,18-19,21,25,28-31,33-35,39-41H,5H2/t12-,15-,18+,19-,21-,25+,27-/m1/s1

> <INCHI_KEY>
CXTMLIMZRPKULL-BOUNHRALSA-N

> <FORMULA>
C27H22O19

> <MOLECULAR_WEIGHT>
650.454

> <EXACT_MASS>
650.075528488

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
55.97920651347172

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,8R,9S,18R,19S,21R,22S)-7,7,8,12,13,22-hexahydroxy-21-(hydroxymethyl)-3,6,16-trioxo-2,17,20,23-tetraoxapentacyclo[16.3.1.1^{8,11}.0^{4,9}.0^{10,15}]tricosa-4,10,12,14-tetraen-19-yl 3,4,5-trihydroxybenzoate

> <JCHEM_LOGP>
-0.24195238633333327

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.996614351393818

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.670100097575421

> <JCHEM_PKA_STRONGEST_BASIC>
-5.549137586734315

> <JCHEM_POLAR_SURFACE_AREA>
316.73

> <JCHEM_REFRACTIVITY>
139.94869999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,8R,9S,18R,19S,21R,22S)-7,7,8,12,13,22-hexahydroxy-21-(hydroxymethyl)-3,6,16-trioxo-2,17,20,23-tetraoxapentacyclo[16.3.1.1^{8,11}.0^{4,9}.0^{10,15}]tricosa-4,10,12,14-tetraen-19-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  O   UNK     0       4.572  -6.952   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.430  -5.919   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.898  -4.810   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.075  -3.624   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.881  -2.651   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.847  -3.792   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.644  -1.122   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.900  -1.233   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.134  -1.928   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.819  -0.420   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.239  -3.007   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.934  -1.630   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.071  -0.462   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.426   0.996   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.596  -0.775   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.616   0.378   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.153  -2.427   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.158  -3.627   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.002  -5.039   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.863  -6.573   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.804  -7.820   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.305  -7.499   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.366  -8.615   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.704  -6.012   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.089  -6.685   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.627  -4.780   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.526  -4.714   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.960  -4.152   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       3.511  -3.149   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.115  -0.461   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.193   1.077   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.563   1.779   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.857   0.943   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       7.641   3.317   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.348   4.153   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.425   5.691   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.132   6.527   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       7.796   6.393   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       7.874   7.931   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       9.089   5.557   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      10.460   6.259   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       9.012   4.019   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       7.484  -1.251   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       7.436  -2.818   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       8.762  -3.601   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      10.103  -2.844   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   44                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   30                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   29                                                  
CONECT   18   17   11   19                                                  
CONECT   19   18   20   27                                                  
CONECT   20   19    2   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   19   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   17                                                       
CONECT   30    7   31   43                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   42                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   34                                                       
CONECT   43   30   44                                                       
CONECT   44   43    4   45                                                  
CONECT   45   44   46                                                       
CONECT   46   45                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  102    0
END

View in JSmol

Synonyms

Value	Source
(1S,8R,9S,18R,19S,21R,22S)-7,7,8,12,13,22-Hexahydroxy-21-(hydroxymethyl)-3,6,16-trioxo-2,17,20,23-tetraoxapentacyclo[16.3.1.1,.0,.0,]tricosa-4,10,12,14-tetraen-19-yl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₂₇H₂₂O₁₉

Average Mass

650.4540 Da

Monoisotopic Mass

650.07553 Da

IUPAC Name

(1S,8R,9S,18R,19S,21R,22S)-7,7,8,12,13,22-hexahydroxy-21-(hydroxymethyl)-3,6,16-trioxo-2,17,20,23-tetraoxapentacyclo[16.3.1.1^{8,11}.0^{4,9}.0^{10,15}]tricosa-4,10,12,14-tetraen-19-yl 3,4,5-trihydroxybenzoate

Traditional Name

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H22O19/c28-5-12-19-18(35)21(25(42-12)45-22(36)6-1-9(29)16(33)10(30)2-6)44-23(37)7-3-11(31)17(34)20-14(7)15-8(24(38)43-19)4-13(32)26(39,40)27(15,41)46-20/h1-4,12,15,18-19,21,25,28-31,33-35,39-41H,5H2/t12-,15-,18+,19-,21-,25+,27-/m1/s1

InChI Key

CXTMLIMZRPKULL-BOUNHRALSA-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
Mallotus repandus	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
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Benzoate ester
Coumaran
Benzoic acid or derivatives
Benzenetriol
Tricarboxylic acid or derivatives
Pyrogallol derivative
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Cyclohexenone
Benzenoid
Monosaccharide
Monocyclic benzene moiety
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic ketone
Ketone
Carboxylic acid ester
Lactone
Secondary alcohol
Hemiacetal
Acetal
Oxacycle
Organoheterocyclic compound
Carbonyl hydrate
Carboxylic acid derivative
1,1-diol
Polyol
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.24	ChemAxon
pKa (Strongest Acidic)	5.67	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	316.73 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	139.95 m³·mol⁻¹	ChemAxon
Polarizability	55.98 Å³	ChemAxon
Number of Rings	6	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

Not Available

METLIN ID

Not Available

PubChem Compound

163054751

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,8r,9s,18r,19s,21r,22s)-7,7,8,12,13,22-hexahydroxy-21-(hydroxymethyl)-3,6,16-trioxo-2,17,20,23-tetraoxapentacyclo[16.3.1.1⁸,¹¹.0⁴,⁹.0¹⁰,¹⁵]tricosa-4,10,12,14-tetraen-19-yl 3,4,5-trihydroxybenzoate (NP0218580)

MOL for NP0218580 ((1s,8r,9s,18r,19s,21r,22s)-7,7,8,12,13,22-hexahydroxy-21-(hydroxymethyl)-3,6,16-trioxo-2,17,20,23-tetraoxapentacyclo[16.3.1.1⁸,¹¹.0⁴,⁹.0¹⁰,¹⁵]tricosa-4,10,12,14-tetraen-19-yl 3,4,5-trihydroxybenzoate)

3D MOL for NP0218580 ((1s,8r,9s,18r,19s,21r,22s)-7,7,8,12,13,22-hexahydroxy-21-(hydroxymethyl)-3,6,16-trioxo-2,17,20,23-tetraoxapentacyclo[16.3.1.1⁸,¹¹.0⁴,⁹.0¹⁰,¹⁵]tricosa-4,10,12,14-tetraen-19-yl 3,4,5-trihydroxybenzoate)

3D SDF for NP0218580 ((1s,8r,9s,18r,19s,21r,22s)-7,7,8,12,13,22-hexahydroxy-21-(hydroxymethyl)-3,6,16-trioxo-2,17,20,23-tetraoxapentacyclo[16.3.1.1⁸,¹¹.0⁴,⁹.0¹⁰,¹⁵]tricosa-4,10,12,14-tetraen-19-yl 3,4,5-trihydroxybenzoate)

3D-SDF for NP0218580 ((1s,8r,9s,18r,19s,21r,22s)-7,7,8,12,13,22-hexahydroxy-21-(hydroxymethyl)-3,6,16-trioxo-2,17,20,23-tetraoxapentacyclo[16.3.1.1⁸,¹¹.0⁴,⁹.0¹⁰,¹⁵]tricosa-4,10,12,14-tetraen-19-yl 3,4,5-trihydroxybenzoate)

PDB for NP0218580 ((1s,8r,9s,18r,19s,21r,22s)-7,7,8,12,13,22-hexahydroxy-21-(hydroxymethyl)-3,6,16-trioxo-2,17,20,23-tetraoxapentacyclo[16.3.1.1⁸,¹¹.0⁴,⁹.0¹⁰,¹⁵]tricosa-4,10,12,14-tetraen-19-yl 3,4,5-trihydroxybenzoate)

3D PDB for NP0218580 ((1s,8r,9s,18r,19s,21r,22s)-7,7,8,12,13,22-hexahydroxy-21-(hydroxymethyl)-3,6,16-trioxo-2,17,20,23-tetraoxapentacyclo[16.3.1.1⁸,¹¹.0⁴,⁹.0¹⁰,¹⁵]tricosa-4,10,12,14-tetraen-19-yl 3,4,5-trihydroxybenzoate)

SMILES for NP0218580 ((1s,8r,9s,18r,19s,21r,22s)-7,7,8,12,13,22-hexahydroxy-21-(hydroxymethyl)-3,6,16-trioxo-2,17,20,23-tetraoxapentacyclo[16.3.1.1⁸,¹¹.0⁴,⁹.0¹⁰,¹⁵]tricosa-4,10,12,14-tetraen-19-yl 3,4,5-trihydroxybenzoate)

INCHI for NP0218580 ((1s,8r,9s,18r,19s,21r,22s)-7,7,8,12,13,22-hexahydroxy-21-(hydroxymethyl)-3,6,16-trioxo-2,17,20,23-tetraoxapentacyclo[16.3.1.1⁸,¹¹.0⁴,⁹.0¹⁰,¹⁵]tricosa-4,10,12,14-tetraen-19-yl 3,4,5-trihydroxybenzoate)

Structure for NP0218580 ((1s,8r,9s,18r,19s,21r,22s)-7,7,8,12,13,22-hexahydroxy-21-(hydroxymethyl)-3,6,16-trioxo-2,17,20,23-tetraoxapentacyclo[16.3.1.1⁸,¹¹.0⁴,⁹.0¹⁰,¹⁵]tricosa-4,10,12,14-tetraen-19-yl 3,4,5-trihydroxybenzoate)

3D Structure for NP0218580 ((1s,8r,9s,18r,19s,21r,22s)-7,7,8,12,13,22-hexahydroxy-21-(hydroxymethyl)-3,6,16-trioxo-2,17,20,23-tetraoxapentacyclo[16.3.1.1⁸,¹¹.0⁴,⁹.0¹⁰,¹⁵]tricosa-4,10,12,14-tetraen-19-yl 3,4,5-trihydroxybenzoate)