NP-MRD: Showing NP-Card for 1-O-galloyl-6-O-cinnamoylglucose (NP0137995)

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Record Information

Version

2.0

Created at

2022-05-31 16:42:23 UTC

Updated at

2022-05-31 16:42:23 UTC

NP-MRD ID

NP0137995

Secondary Accession Numbers

NP0085560

Natural Product Identification

Common Name

1-O-galloyl-6-O-cinnamoylglucose

Description

1-O-Galloyl-6-O-cinnamoylglucose belongs to the class of organic compounds known as tannins. These are naturally occurring polyphenols which be categorized into four main classes: Hydrolyzable tannin (based on ellagic acid or gallic acid), condensed tannins (made of oligomeric or polymeric proanthocyanidins), complex tannins (made of a catechin bound to a gallotannin or elagitannin), and phlorotannins (oligomers of phloroglucinol). Based on a literature review very few articles have been published on 1-O-Galloyl-6-O-cinnamoylglucose.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292208022D          

 33 35  0  0  1  0            999 V2000
   -2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -9.9000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434  -10.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -11.1375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -11.5500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -11.1375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 19 28  2  0  0  0  0
 16 29  1  0  0  0  0
  9 29  1  0  0  0  0
  7 30  2  0  0  0  0
  6 31  1  0  0  0  0
 31 32  2  0  0  0  0
  2 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
   -3.2759    1.5004    1.9053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3606    1.0688    0.7184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6584    0.6045    0.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7458    0.6207    0.9194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0631    0.1901    0.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1474    0.2513    1.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4022   -0.1663    0.9339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5873   -0.6514   -0.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5215   -0.7200   -1.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2580   -0.2972   -0.7620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2169    1.0542   -0.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9543    1.5045    0.4631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0775    1.3529   -0.6352 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2837    1.7743   -0.1858 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3985    1.4441   -0.8717 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2699    0.5427   -0.1965 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5661    0.8452    0.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9994    1.9818   -0.2061 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4745   -0.0670    0.8132 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7715    0.2983    1.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6574   -0.5359    1.7570 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9510   -0.1148    2.0255 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2689   -1.7998    2.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1083   -2.6867    2.8072 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9734   -2.1826    1.8651 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5865   -3.4559    2.2623 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0841   -1.3303    1.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1165    0.8448   -2.2321 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4862    1.7515   -3.0661 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2895   -0.3954   -1.9745 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0809   -1.2708   -1.2336 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0293    0.0017   -1.2655 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0288   -0.0993   -2.1671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7024    0.2467   -0.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6392    1.0006    1.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0548    0.6296    2.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2595   -0.1149    1.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5571   -0.9868   -0.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6709   -1.0979   -2.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4806   -0.3866   -1.4956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0064    2.5599    0.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6908    0.8056    1.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2451    2.0864   -1.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9423    2.4131   -1.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0671    1.3056    0.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6591   -0.6344    2.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0487   -2.4854    3.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6391   -3.7439    2.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0692   -1.6653    0.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1011    0.5018   -2.6278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5584    1.3736   -3.9921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0420   -0.9201   -2.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8308   -1.2952   -0.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1601   -0.7497   -0.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7434   -0.7014   -1.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
 33 32  1  0
 32 13  1  0
 13 12  1  0
 12 11  1  0
 11  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  2  0
 15 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  1  0
 10  5  1  0
 27 19  1  0
 33 55  1  0
 32 54  1  1
 13 43  1  6
 12 41  1  0
 12 42  1  0
  3 34  1  0
  4 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 15 44  1  6
 20 45  1  0
 22 46  1  0
 24 47  1  0
 26 48  1  0
 27 49  1  0
 28 50  1  6
 29 51  1  0
 30 52  1  6
 31 53  1  0
M  END


  Mrv1652304292208022D          

 33 35  0  0  1  0            999 V2000
   -2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -9.9000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434  -10.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -11.1375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -11.5500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -11.1375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 19 28  2  0  0  0  0
 16 29  1  0  0  0  0
  9 29  1  0  0  0  0
  7 30  2  0  0  0  0
  6 31  1  0  0  0  0
 31 32  2  0  0  0  0
  2 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137995

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](COC(=O)\C=C\C2=CC=CC=C2)O[C@@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O11/c23-13-8-12(9-14(24)17(13)26)21(30)33-22-20(29)19(28)18(27)15(32-22)10-31-16(25)7-6-11-4-2-1-3-5-11/h1-9,15,18-20,22-24,26-29H,10H2/b7-6+/t15-,18-,19+,20-,22+/m1/s1

> <INCHI_KEY>
REBRERQNUHGTMS-PCGJYRBUSA-N

> <FORMULA>
C22H22O11

> <MOLECULAR_WEIGHT>
462.407

> <EXACT_MASS>
462.116211528

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
45.11625751139767

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-phenylprop-2-enoyl]oxy}methyl)oxan-2-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
1.24

> <JCHEM_LOGP>
1.685955383666667

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.239171364856418

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.082702010277215

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491129541618603

> <JCHEM_POLAR_SURFACE_AREA>
183.20999999999998

> <JCHEM_REFRACTIVITY>
111.25580000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-phenylprop-2-enoyl]oxy}methyl)oxan-2-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0      -4.001 -10.010   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001 -16.170   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.335 -16.940   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -5.335 -18.480   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001 -19.250   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.667 -18.480   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.001 -20.790   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667 -21.560   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -5.335 -21.560   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.335 -23.100   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -6.668 -20.790   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.002 -21.560   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -9.336 -20.790   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0     -10.669 -21.560   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -10.669 -23.100   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -9.336 -23.870   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -9.336 -25.410   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -8.002 -26.180   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -8.002 -27.720   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -9.336 -28.490   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -10.669 -27.720   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -10.669 -26.180   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -12.003 -20.790   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -6.668 -19.250   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -2.667 -16.940   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -6.668 -11.550   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   31                                                  
CONECT    7    6    8   30                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   29                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   28                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   19                                                            
CONECT   29   16    9                                                       
CONECT   30    7                                                            
CONECT   31    6   32                                                       
CONECT   32   31    2   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₂O₁₁

Average Mass

462.4070 Da

Monoisotopic Mass

462.11621 Da

IUPAC Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-phenylprop-2-enoyl]oxy}methyl)oxan-2-yl 3,4,5-trihydroxybenzoate

Traditional Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-phenylprop-2-enoyl]oxy}methyl)oxan-2-yl 3,4,5-trihydroxybenzoate

CAS Registry Number

115746-69-5

SMILES

O[C@@H]1[C@@H](COC(=O)\C=C\C2=CC=CC=C2)O[C@@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C22H22O11/c23-13-8-12(9-14(24)17(13)26)21(30)33-22-20(29)19(28)18(27)15(32-22)10-31-16(25)7-6-11-4-2-1-3-5-11/h1-9,15,18-20,22-24,26-29H,10H2/b7-6+/t15-,18-,19+,20-,22+/m1/s1

InChI Key

REBRERQNUHGTMS-PCGJYRBUSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tannins. These are naturally occurring polyphenols which be categorized into four main classes: Hydrolyzable tannin (based on ellagic acid or gallic acid), condensed tannins (made of oligomeric or polymeric proanthocyanidins), complex tannins (made of a catechin bound to a gallotannin or elagitannin), and phlorotannins (oligomers of phloroglucinol).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Not Available

Direct Parent

Tannins

Alternative Parents

Substituents

Tannin
Galloyl ester
Cinnamic acid ester
Cinnamic acid or derivatives
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Benzenetriol
Benzoic acid or derivatives
Pyrogallol derivative
Styrene
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Dicarboxylic acid or derivatives
Benzenoid
Monosaccharide
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Acetal
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Polyol
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.24	ALOGPS
logP	1.69	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	8.08	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	183.21 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	111.26 m³·mol⁻¹	ChemAxon
Polarizability	45.12 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00055463

Chemspider ID

22912967

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14034234

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 1-O-galloyl-6-O-cinnamoylglucose (NP0137995)

MOL for NP0137995 (1-O-galloyl-6-O-cinnamoylglucose)

3D MOL for NP0137995 (1-O-galloyl-6-O-cinnamoylglucose)

3D SDF for NP0137995 (1-O-galloyl-6-O-cinnamoylglucose)

3D-SDF for NP0137995 (1-O-galloyl-6-O-cinnamoylglucose)

PDB for NP0137995 (1-O-galloyl-6-O-cinnamoylglucose)

3D PDB for NP0137995 (1-O-galloyl-6-O-cinnamoylglucose)

SMILES for NP0137995 (1-O-galloyl-6-O-cinnamoylglucose)

INCHI for NP0137995 (1-O-galloyl-6-O-cinnamoylglucose)

Structure for NP0137995 (1-O-galloyl-6-O-cinnamoylglucose)

3D Structure for NP0137995 (1-O-galloyl-6-O-cinnamoylglucose)