NP-MRD: Showing NP-Card for pycnalin (NP0040437)

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Record Information

Version

1.0

Created at

2021-06-20 22:36:09 UTC

Updated at

2021-06-30 00:14:20 UTC

NP-MRD ID

NP0040437

Secondary Accession Numbers

None

Natural Product Identification

Common Name

pycnalin

Provided By

JEOL Database JEOL Logo

Description

Ginnalin B belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid. pycnalin is found in Acer pycnanthum and Acer rubrum. It was first documented in 2002 (PMID: 33651529). Based on a literature review a small amount of articles have been published on Ginnalin B (PMID: 31005366) (PMID: 28348624) (PMID: 24960181) (PMID: 20560858).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100363D          

 38 39  0  0  0  0            999 V2000
    0.9904   -2.9926    1.6560 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -1.9010    1.5242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4259   -1.1619    0.3917 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0830   -1.7667   -0.7360 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9489   -0.8586   -1.9672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4456   -0.7733   -2.3227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6702    0.0088   -3.4934 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1965    1.4471   -3.2957 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3717    2.2273   -4.4814 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2874    1.4379   -2.9290 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7342    2.7703   -2.6304 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5381    0.5390   -1.7155 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9478    0.4648   -1.4789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2457   -1.1998    2.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2397   -1.8069    3.9002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8889   -1.1845    4.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9147   -1.7273    6.2149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5397    0.0279    4.7664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1816    0.6480    5.8036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5473    0.6264    3.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1899    1.8163    3.3290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    0.0248    2.4387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1399   -1.9302   -0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6001   -2.7293   -0.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4847   -1.3482   -2.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1795   -0.4603   -4.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7441   -0.0015   -3.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7637    1.9340   -2.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3299    2.2851   -4.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8949    1.1075   -3.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4059    3.3183   -3.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0838    1.0022   -0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2530    1.3950   -1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2725   -2.7555    4.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4215   -2.5671    6.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0405    0.0500    6.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5554    2.0398    4.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9293    0.5125    1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
 20 22  2  0  0  0  0
  8 10  1  0  0  0  0
 22 14  1  0  0  0  0
 10 12  1  0  0  0  0
 14 15  2  0  0  0  0
 12  5  1  0  0  0  0
 15 16  1  0  0  0  0
  5  6  1  0  0  0  0
 16 18  2  0  0  0  0
 18 20  1  0  0  0  0
  6  7  1  0  0  0  0
 14  2  1  0  0  0  0
  8  9  1  0  0  0  0
  2  3  1  0  0  0  0
 12 13  1  0  0  0  0
  2  1  2  0  0  0  0
  3  4  1  0  0  0  0
 10 11  1  0  0  0  0
 18 19  1  0  0  0  0
 16 17  1  0  0  0  0
 20 21  1  0  0  0  0
  5  4  1  0  0  0  0
  9 29  1  0  0  0  0
  7 26  1  0  0  0  0
  7 27  1  0  0  0  0
 12 32  1  1  0  0  0
 13 33  1  0  0  0  0
 10 30  1  6  0  0  0
 11 31  1  0  0  0  0
  8 28  1  1  0  0  0
  4 23  1  0  0  0  0
  4 24  1  0  0  0  0
  5 25  1  6  0  0  0
 22 38  1  0  0  0  0
 15 34  1  0  0  0  0
 19 36  1  0  0  0  0
 17 35  1  0  0  0  0
 21 37  1  0  0  0  0
M  END

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
    0.9904   -2.9926    1.6560 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -1.9010    1.5242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4259   -1.1619    0.3917 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0830   -1.7667   -0.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9489   -0.8586   -1.9672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4456   -0.7733   -2.3227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6702    0.0088   -3.4934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1965    1.4471   -3.2957 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3717    2.2273   -4.4814 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2874    1.4379   -2.9290 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7342    2.7703   -2.6304 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5381    0.5390   -1.7155 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9478    0.4648   -1.4789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2457   -1.1998    2.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2397   -1.8069    3.9002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8889   -1.1845    4.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9147   -1.7273    6.2149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5397    0.0279    4.7664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1816    0.6480    5.8036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5473    0.6264    3.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1899    1.8163    3.3290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    0.0248    2.4387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1399   -1.9302   -0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6001   -2.7293   -0.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4847   -1.3482   -2.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1795   -0.4603   -4.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7441   -0.0015   -3.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7637    1.9340   -2.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3299    2.2851   -4.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8949    1.1075   -3.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4059    3.3183   -3.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0838    1.0022   -0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2530    1.3950   -1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2725   -2.7555    4.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4215   -2.5671    6.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0405    0.0500    6.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5554    2.0398    4.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9293    0.5125    1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
 20 22  2  0
  8 10  1  0
 22 14  1  0
 10 12  1  0
 14 15  2  0
 12  5  1  0
 15 16  1  0
  5  6  1  0
 16 18  2  0
 18 20  1  0
  6  7  1  0
 14  2  1  0
  8  9  1  0
  2  3  1  0
 12 13  1  0
  2  1  2  0
  3  4  1  0
 10 11  1  0
 18 19  1  0
 16 17  1  0
 20 21  1  0
  5  4  1  0
  9 29  1  0
  7 26  1  0
  7 27  1  0
 12 32  1  1
 13 33  1  0
 10 30  1  6
 11 31  1  0
  8 28  1  1
  4 23  1  0
  4 24  1  0
  5 25  1  6
 22 38  1  0
 15 34  1  0
 19 36  1  0
 17 35  1  0
 21 37  1  0
M  END


  Mrv1652306212100363D          

 38 39  0  0  0  0            999 V2000
    0.9904   -2.9926    1.6560 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -1.9010    1.5242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4259   -1.1619    0.3917 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0830   -1.7667   -0.7360 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9489   -0.8586   -1.9672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4456   -0.7733   -2.3227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6702    0.0088   -3.4934 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1965    1.4471   -3.2957 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3717    2.2273   -4.4814 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2874    1.4379   -2.9290 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7342    2.7703   -2.6304 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5381    0.5390   -1.7155 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9478    0.4648   -1.4789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2457   -1.1998    2.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2397   -1.8069    3.9002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8889   -1.1845    4.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9147   -1.7273    6.2149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5397    0.0279    4.7664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1816    0.6480    5.8036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5473    0.6264    3.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1899    1.8163    3.3290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    0.0248    2.4387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1399   -1.9302   -0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6001   -2.7293   -0.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4847   -1.3482   -2.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1795   -0.4603   -4.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7441   -0.0015   -3.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7637    1.9340   -2.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3299    2.2851   -4.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8949    1.1075   -3.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4059    3.3183   -3.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0838    1.0022   -0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2530    1.3950   -1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2725   -2.7555    4.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4215   -2.5671    6.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0405    0.0500    6.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5554    2.0398    4.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9293    0.5125    1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
 20 22  2  0  0  0  0
  8 10  1  0  0  0  0
 22 14  1  0  0  0  0
 10 12  1  0  0  0  0
 14 15  2  0  0  0  0
 12  5  1  0  0  0  0
 15 16  1  0  0  0  0
  5  6  1  0  0  0  0
 16 18  2  0  0  0  0
 18 20  1  0  0  0  0
  6  7  1  0  0  0  0
 14  2  1  0  0  0  0
  8  9  1  0  0  0  0
  2  3  1  0  0  0  0
 12 13  1  0  0  0  0
  2  1  2  0  0  0  0
  3  4  1  0  0  0  0
 10 11  1  0  0  0  0
 18 19  1  0  0  0  0
 16 17  1  0  0  0  0
 20 21  1  0  0  0  0
  5  4  1  0  0  0  0
  9 29  1  0  0  0  0
  7 26  1  0  0  0  0
  7 27  1  0  0  0  0
 12 32  1  1  0  0  0
 13 33  1  0  0  0  0
 10 30  1  6  0  0  0
 11 31  1  0  0  0  0
  8 28  1  1  0  0  0
  4 23  1  0  0  0  0
  4 24  1  0  0  0  0
  5 25  1  6  0  0  0
 22 38  1  0  0  0  0
 15 34  1  0  0  0  0
 19 36  1  0  0  0  0
 17 35  1  0  0  0  0
 21 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040437

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(=C([H])C(O[H])=C1O[H])C(=O)OC([H])([H])[C@@]1([H])OC([H])([H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O9/c14-6-1-5(2-7(15)10(6)17)13(20)22-4-9-12(19)11(18)8(16)3-21-9/h1-2,8-9,11-12,14-19H,3-4H2/t8-,9+,11+,12+/m0/s1

> <INCHI_KEY>
NUVIRDWXIBOJTE-LUTQBAROSA-N

> <FORMULA>
C13H16O9

> <MOLECULAR_WEIGHT>
316.262

> <EXACT_MASS>
316.079432095

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
29.524329552253363

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
-1.14

> <JCHEM_LOGP>
-0.9837113926666664

> <ALOGPS_LOGS>
-1.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.268089663611772

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.107890094294524

> <JCHEM_PKA_STRONGEST_BASIC>
-3.522373766660756

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
70.65820000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.18e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
    0.9904   -2.9926    1.6560 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -1.9010    1.5242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4259   -1.1619    0.3917 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0830   -1.7667   -0.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9489   -0.8586   -1.9672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4456   -0.7733   -2.3227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6702    0.0088   -3.4934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1965    1.4471   -3.2957 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3717    2.2273   -4.4814 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2874    1.4379   -2.9290 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7342    2.7703   -2.6304 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5381    0.5390   -1.7155 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9478    0.4648   -1.4789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2457   -1.1998    2.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2397   -1.8069    3.9002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8889   -1.1845    4.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9147   -1.7273    6.2149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5397    0.0279    4.7664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1816    0.6480    5.8036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5473    0.6264    3.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1899    1.8163    3.3290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    0.0248    2.4387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1399   -1.9302   -0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6001   -2.7293   -0.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4847   -1.3482   -2.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1795   -0.4603   -4.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7441   -0.0015   -3.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7637    1.9340   -2.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3299    2.2851   -4.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8949    1.1075   -3.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4059    3.3183   -3.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0838    1.0022   -0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2530    1.3950   -1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2725   -2.7555    4.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4215   -2.5671    6.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0405    0.0500    6.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5554    2.0398    4.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9293    0.5125    1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
 20 22  2  0
  8 10  1  0
 22 14  1  0
 10 12  1  0
 14 15  2  0
 12  5  1  0
 15 16  1  0
  5  6  1  0
 16 18  2  0
 18 20  1  0
  6  7  1  0
 14  2  1  0
  8  9  1  0
  2  3  1  0
 12 13  1  0
  2  1  2  0
  3  4  1  0
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 18 19  1  0
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 20 21  1  0
  5  4  1  0
  9 29  1  0
  7 26  1  0
  7 27  1  0
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 10 30  1  6
 11 31  1  0
  8 28  1  1
  4 23  1  0
  4 24  1  0
  5 25  1  6
 22 38  1  0
 15 34  1  0
 19 36  1  0
 17 35  1  0
 21 37  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  O   UNK     0       0.990  -2.993   1.656  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.460  -1.901   1.524  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.426  -1.162   0.392  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.083  -1.767  -0.736  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.949  -0.859  -1.967  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.446  -0.773  -2.323  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.670   0.009  -3.493  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.197   1.447  -3.296  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.372   2.227  -4.481  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.287   1.438  -2.929  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.734   2.770  -2.630  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.538   0.539  -1.716  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.948   0.465  -1.479  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.246  -1.200   2.630  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.240  -1.807   3.900  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.889  -1.185   4.961  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.915  -1.727   6.215  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.540   0.028   4.766  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.182   0.648   5.804  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.547   0.626   3.513  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.190   1.816   3.329  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.906   0.025   2.439  0.00  0.00           C+0
HETATM   23  H   UNK     0       2.140  -1.930  -0.496  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.600  -2.729  -0.943  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.485  -1.348  -2.791  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.180  -0.460  -4.355  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.744  -0.002  -3.709  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.764   1.934  -2.493  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.330   2.285  -4.650  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.895   1.107  -3.781  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.406   3.318  -3.371  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.084   1.002  -0.831  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.253   1.395  -1.482  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.273  -2.756   4.040  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.422  -2.567   6.196  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.041   0.050   6.567  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.555   2.040   4.209  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.929   0.513   1.469  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2   14    3    1                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   23   24                                             
CONECT    5   12    6    4   25                                             
CONECT    6    5    7                                                       
CONECT    7    8    6   26   27                                             
CONECT    8    7   10    9   28                                             
CONECT    9    8   29                                                       
CONECT   10    8   12   11   30                                             
CONECT   11   10   31                                                       
CONECT   12   10    5   13   32                                             
CONECT   13   12   33                                                       
CONECT   14   22   15    2                                                  
CONECT   15   14   16   34                                                  
CONECT   16   15   18   17                                                  
CONECT   17   16   35                                                       
CONECT   18   16   20   19                                                  
CONECT   19   18   36                                                       
CONECT   20   22   18   21                                                  
CONECT   21   20   37                                                       
CONECT   22   20   14   38                                                  
CONECT   23    4                                                            
CONECT   24    4                                                            
CONECT   25    5                                                            
CONECT   26    7                                                            
CONECT   27    7                                                            
CONECT   28    8                                                            
CONECT   29    9                                                            
CONECT   30   10                                                            
CONECT   31   11                                                            
CONECT   32   12                                                            
CONECT   33   13                                                            
CONECT   34   15                                                            
CONECT   35   17                                                            
CONECT   36   19                                                            
CONECT   37   21                                                            
CONECT   38   22                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   78    0
END

RDKit          3D

38 39  0  0  0  0  0  0  0  0999 V2000
    0.9904   -2.9926    1.6560 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -1.9010    1.5242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4259   -1.1619    0.3917 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0830   -1.7667   -0.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9489   -0.8586   -1.9672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4456   -0.7733   -2.3227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6702    0.0088   -3.4934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1965    1.4471   -3.2957 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3717    2.2273   -4.4814 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2874    1.4379   -2.9290 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7342    2.7703   -2.6304 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5381    0.5390   -1.7155 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9478    0.4648   -1.4789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2457   -1.1998    2.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2397   -1.8069    3.9002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8889   -1.1845    4.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9147   -1.7273    6.2149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5397    0.0279    4.7664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1816    0.6480    5.8036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5473    0.6264    3.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1899    1.8163    3.3290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    0.0248    2.4387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1399   -1.9302   -0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6001   -2.7293   -0.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4847   -1.3482   -2.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1795   -0.4603   -4.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7441   -0.0015   -3.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7637    1.9340   -2.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3299    2.2851   -4.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8949    1.1075   -3.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4059    3.3183   -3.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0838    1.0022   -0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2530    1.3950   -1.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2725   -2.7555    4.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4215   -2.5671    6.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0405    0.0500    6.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5554    2.0398    4.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9293    0.5125    1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
 20 22  2  0
  8 10  1  0
 22 14  1  0
 10 12  1  0
 14 15  2  0
 12  5  1  0
 15 16  1  0
  5  6  1  0
 16 18  2  0
 18 20  1  0
  6  7  1  0
 14  2  1  0
  8  9  1  0
  2  3  1  0
 12 13  1  0
  2  1  2  0
  3  4  1  0
 10 11  1  0
 18 19  1  0
 16 17  1  0
 20 21  1  0
  5  4  1  0
  9 29  1  0
  7 26  1  0
  7 27  1  0
 12 32  1  1
 13 33  1  0
 10 30  1  6
 11 31  1  0
  8 28  1  1
  4 23  1  0
  4 24  1  0
  5 25  1  6
 22 38  1  0
 15 34  1  0
 19 36  1  0
 17 35  1  0
 21 37  1  0
M  END

View in JSmol

Synonyms

Value	Source
6-O-Galloyl-1,5-anhydro-D-glucitol	MeSH
6-O-Galloyl-1,5-anhydroglucitol	MeSH

Chemical Formula

C₁₃H₁₆O₉

Average Mass

316.2620 Da

Monoisotopic Mass

316.07943 Da

IUPAC Name

[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate

Traditional Name

[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(=C([H])C(O[H])=C1O[H])C(=O)OC([H])([H])[C@@]1([H])OC([H])([H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C13H16O9/c14-6-1-5(2-7(15)10(6)17)13(20)22-4-9-12(19)11(18)8(16)3-21-9/h1-2,8-9,11-12,14-19H,3-4H2/t8-,9+,11+,12+/m0/s1

InChI Key

NUVIRDWXIBOJTE-LUTQBAROSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acer pycnanthum	JEOL database	Ogawa, A., et al., Chem. Pharm. Bull., 59, 672 (2011)
Acer rubrum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Galloyl esters

Alternative Parents

Substituents

Galloyl ester
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Benzenetriol
Pyrogallol derivative
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monosaccharide
Oxane
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Ether
Organoheterocyclic compound
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	-1.1	ALOGPS
logP	-0.98	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	8.11	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	70.66 m³·mol⁻¹	ChemAxon
Polarizability	29.52 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	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

28492748

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44512370

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Curcumin (Curcuma, Turmeric) and Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:33651529 ]
Kato A, Koyama J, Shinzawa K, Imaeda S, Adachi I, Nash RJ, Fleet GWJ, Shintani M, Takeuchi C, Ishikawa F: Ginnalin B induces differentiation markers and modulates the proliferation/differentiation balance via the upregulation of NOTCH1 in human epidermal keratinocytes. Bioorg Med Chem. 2019 Jun 1;27(11):2172-2180. doi: 10.1016/j.bmc.2019.04.008. Epub 2019 Apr 6. [PubMed:31005366 ]
Park KH, Yoon KH, Yin J, Le TT, Ahn HS, Yoon SH, Lee MW: Antioxidative and Anti-Inflammatory Activities of Galloyl Derivatives and Antidiabetic Activities of Acer ginnala. Evid Based Complement Alternat Med. 2017;2017:6945912. doi: 10.1155/2017/6945912. Epub 2017 Mar 2. [PubMed:28348624 ]
Ren Z, He C, Fan Y, Guo L, Si H, Wang Y, Shi Z, Zhang H: Immuno-enhancement effects of ethanol extract from Cyrtomium macrophyllum (Makino) Tagawa on cyclophosphamide-induced immunosuppression in BALB/c mice. J Ethnopharmacol. 2014 Aug 8;155(1):769-75. doi: 10.1016/j.jep.2014.06.021. Epub 2014 Jun 21. [PubMed:24960181 ]
Honma A, Koyama T, Yazawa K: Anti-hyperglycaemic effects of the Japanese red maple Acer pycnanthum and its constituents the ginnalins B and C. J Enzyme Inhib Med Chem. 2011 Apr;26(2):176-80. doi: 10.3109/14756366.2010.486795. Epub 2010 Jun 21. [PubMed:20560858 ]
Ogawa, A., et al. (2011). Ogawa, A., et al., Chem. Pharm. Bull., 59, 672 (2011). Chem. Pharm. Bull..

Showing NP-Card for pycnalin (NP0040437)

MOL for NP0040437 (pycnalin)

3D MOL for NP0040437 (pycnalin)

3D SDF for NP0040437 (pycnalin)

3D-SDF for NP0040437 (pycnalin)

PDB for NP0040437 (pycnalin)

3D PDB for NP0040437 (pycnalin)

SMILES for NP0040437 (pycnalin)

INCHI for NP0040437 (pycnalin)

Structure for NP0040437 (pycnalin)

3D Structure for NP0040437 (pycnalin)