NP-MRD: Showing NP-Card for (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid (NP0243720)

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Record Information

Version

1.0

Created at

2022-09-07 04:19:53 UTC

Updated at

2022-09-07 04:19:53 UTC

NP-MRD ID

NP0243720

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid

Description

4-O-beta-D-glucosyl-trans-caffeic acid, also known as (e)-4-O-(b-D-glucopyranosyl)caffeate or (e)-caffeate 4-O-b-D-glucopyranoside, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid is found in Clematis tashiroi, Picea glauca, Platycodon grandiflorus and Pericallis cruenta. It was first documented in 2001 (PMID: 11042211). 4-O-beta-D-glucosyl-trans-caffeic acid is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 16753780) (PMID: 26222269).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
    7.6892   -0.9339   -0.4171 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2085    0.2089   -0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0700    1.2805   -0.6332 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7589    0.4666   -0.4475 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9685   -0.5611   -0.3172 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5242   -0.4472   -0.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8534    0.7355   -0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4556    0.8058   -0.2671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6801   -0.3100   -0.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6835   -0.3689   -0.0575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5386    0.7324   -0.1279 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1507    0.9523    1.0673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3464    0.3966    1.3427 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3449   -1.0036    1.8821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7890   -1.9488    1.0752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3414    0.5912    0.2221 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5159    1.9793    0.0947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7915    0.1142   -1.1045 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8249   -1.2603   -1.2461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4279    0.7109   -1.3421 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5607    1.9932   -1.8657 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3756   -1.5271   -0.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6685   -2.6983    0.0834 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7288   -1.5891   -0.1158 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8384    2.1304   -0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3979    1.4660   -0.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4154   -1.5630   -0.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4273    1.6632   -0.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0156    1.7755   -0.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8830    1.6420   -0.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7831    1.0159    2.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7594   -0.9802    2.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3728   -1.2784    2.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4767   -2.7207    1.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3208    0.1597    0.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2879    2.2225   -0.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4652    0.5334   -1.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7001   -1.5675   -0.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9149    0.0904   -2.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7118    2.2977   -2.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3346   -2.6710    0.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2497   -2.5352   -0.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  6 24  1  0
 24 22  2  0
 22 23  1  0
 11 20  1  0
 20 21  1  0
 20 18  1  0
 18 19  1  0
 18 16  1  0
 16 17  1  0
 16 13  1  0
 22  9  1  0
 15 34  1  0
 14 32  1  0
 14 33  1  0
 13 31  1  1
 11 30  1  6
  8 29  1  0
  7 28  1  0
  5 27  1  0
  4 26  1  0
  3 25  1  0
 24 42  1  0
 23 41  1  0
 20 39  1  6
 21 40  1  0
 18 37  1  6
 19 38  1  0
 16 35  1  1
 17 36  1  0
M  END


  Mrv1652309272006302D          

 24 25  0  0  0  0            999 V2000
 9994.3701 9994.4306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2292 9996.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9432 9995.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6592 9996.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3730 9995.6682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6592 9996.9063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9407 9996.9063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.2259 9997.3190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9407 9993.6053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.5111 9994.4306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.5111 9996.0809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9407 9996.0805    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9992.2261 9995.6679    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9992.2261 9994.8430    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9992.9407 9994.4306    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9993.6551 9994.8430    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9993.6551 9995.6679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5150 9995.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8007 9996.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.0861 9995.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.0861 9994.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8005 9994.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5150 9994.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8004 9993.6059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  2  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 18  1  0  0  0  0
  1 21  1  0  0  0  0
 18  2  1  0  0  0  0
 16  1  1  1  0  0  0
 12  7  1  1  0  0  0
 13 11  1  6  0  0  0
 14 10  1  1  0  0  0
 15  9  1  6  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0243720

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC=C(\C=C\C(O)=O)C=C2O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O9/c16-6-10-12(20)13(21)14(22)15(24-10)23-9-3-1-7(5-8(9)17)2-4-11(18)19/h1-5,10,12-17,20-22H,6H2,(H,18,19)/b4-2+/t10-,12-,13+,14-,15-/m1/s1

> <INCHI_KEY>
OHEYCHKLBCPRLZ-VHCZEJTMSA-N

> <FORMULA>
C15H18O9

> <MOLECULAR_WEIGHT>
342.3

> <EXACT_MASS>
342.09508216

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
32.741194512517296

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid

> <ALOGPS_LOGP>
-0.59

> <JCHEM_LOGP>
-0.7391124766666665

> <ALOGPS_LOGS>
-1.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.697397559931186

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.462939165953871

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923549038426

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
79.1661

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.92e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid

> <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    8656.1588656.270   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8661.4958659.351   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8662.8278658.581   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8664.1648659.351   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8665.4968658.581   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8664.1648660.892   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8653.4898660.892   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8652.1558661.662   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8653.4898654.730   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8650.8218656.270   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8650.8218659.351   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8653.4898659.350   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8652.1558658.580   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8652.1558657.040   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8653.4898656.270   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8654.8238657.040   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8654.8238658.580   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0    8660.1618658.580   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8658.8288659.350   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8657.4948658.580   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8657.4948657.040   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8658.8288656.270   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8660.1618657.040   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0    8658.8278654.731   0.000  0.00  0.00           O+0
CONECT    1   21   16                                                       
CONECT    2    3   18                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    8   12                                                       
CONECT    8    7                                                            
CONECT    9   15                                                            
CONECT   10   14                                                            
CONECT   11   13                                                            
CONECT   12   13   17    7                                                  
CONECT   13   12   14   11                                                  
CONECT   14   13   15   10                                                  
CONECT   15   14   16    9                                                  
CONECT   16   15   17    1                                                  
CONECT   17   12   16                                                       
CONECT   18   19   23    2                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22    1                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22   18                                                       
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Value	Source
(e)-4-O-(beta-D-Glucopyranosyl)caffeic acid	ChEBI
(e)-Caffeic acid 4-O-beta-D-glucopyranoside	ChEBI
4'-O-beta-D-Glucopyranosylcaffeic acid	ChEBI
4-O-(beta-D-Glucopyranosyl)-e-caffeic acid	ChEBI
4-O-beta-Glucopyranosyl-(e)-caffeic acid	ChEBI
Linocaffein	ChEBI
trans-Caffeic acid 4-O-beta-D-glucopyranoside	ChEBI
trans-Caffeic acid 4-O-beta-D-glucoside	ChEBI
(e)-4-O-(b-D-Glucopyranosyl)caffeate	Generator
(e)-4-O-(b-D-Glucopyranosyl)caffeic acid	Generator
(e)-4-O-(beta-D-Glucopyranosyl)caffeate	Generator
(e)-4-O-(Β-D-glucopyranosyl)caffeate	Generator
(e)-4-O-(Β-D-glucopyranosyl)caffeic acid	Generator
(e)-Caffeate 4-O-b-D-glucopyranoside	Generator
(e)-Caffeate 4-O-beta-D-glucopyranoside	Generator
(e)-Caffeate 4-O-β-D-glucopyranoside	Generator
(e)-Caffeic acid 4-O-b-D-glucopyranoside	Generator
(e)-Caffeic acid 4-O-β-D-glucopyranoside	Generator
4'-O-b-D-Glucopyranosylcaffeate	Generator
4'-O-b-D-Glucopyranosylcaffeic acid	Generator
4'-O-beta-D-Glucopyranosylcaffeate	Generator
4'-O-Β-D-glucopyranosylcaffeate	Generator
4'-O-Β-D-glucopyranosylcaffeic acid	Generator
4-O-(b-D-Glucopyranosyl)-e-caffeate	Generator
4-O-(b-D-Glucopyranosyl)-e-caffeic acid	Generator
4-O-(beta-D-Glucopyranosyl)-e-caffeate	Generator
4-O-(Β-D-glucopyranosyl)-e-caffeate	Generator
4-O-(Β-D-glucopyranosyl)-e-caffeic acid	Generator
4-O-b-Glucopyranosyl-(e)-caffeate	Generator
4-O-b-Glucopyranosyl-(e)-caffeic acid	Generator
4-O-beta-Glucopyranosyl-(e)-caffeate	Generator
4-O-Β-glucopyranosyl-(e)-caffeate	Generator
4-O-Β-glucopyranosyl-(e)-caffeic acid	Generator
trans-Caffeate 4-O-b-D-glucopyranoside	Generator
trans-Caffeate 4-O-beta-D-glucopyranoside	Generator
trans-Caffeate 4-O-β-D-glucopyranoside	Generator
trans-Caffeic acid 4-O-b-D-glucopyranoside	Generator
trans-Caffeic acid 4-O-β-D-glucopyranoside	Generator
trans-Caffeate 4-O-b-D-glucoside	Generator
trans-Caffeate 4-O-beta-D-glucoside	Generator
trans-Caffeate 4-O-β-D-glucoside	Generator
trans-Caffeic acid 4-O-b-D-glucoside	Generator
trans-Caffeic acid 4-O-β-D-glucoside	Generator
4-O-b-D-Glucosyl-trans-caffeate	Generator
4-O-b-D-Glucosyl-trans-caffeic acid	Generator
4-O-beta-D-Glucosyl-trans-caffeate	Generator
4-O-Β-D-glucosyl-trans-caffeate	Generator
4-O-Β-D-glucosyl-trans-caffeic acid	Generator
(2E)-3-[4-(beta-D-Glucopyranosyloxy)-3-hydroxyphenyl]-2-propenoic acid	PhytoBank
(2E)-3-[4-(β-D-Glucopyranosyloxy)-3-hydroxyphenyl]-2-propenoic acid	PhytoBank
(E)-Caffeic acid 4-O-beta-glucopyranoside	PhytoBank
(E)-Caffeic acid 4-O-β-glucopyranoside	PhytoBank
4-O-Glucopyranosylcaffeic acid	PhytoBank
4-O-beta-D-Glucopyranosyl caffeic acid	PhytoBank
4-O-β-D-Glucopyranosyl caffeic acid	PhytoBank
Caffeic acid 4-O-beta-glucopyranoside	PhytoBank
Caffeic acid 4-O-β-glucopyranoside	PhytoBank
Glucocaffeic acid	PhytoBank
Caffeic acid 4-O-beta-D-glucopyranoside	PhytoBank
Caffeic acid 4-O-β-D-glucopyranoside	PhytoBank

Chemical Formula

C₁₅H₁₈O₉

Average Mass

342.3000 Da

Monoisotopic Mass

342.09508 Da

IUPAC Name

(2E)-3-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid

Traditional Name

(2E)-3-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC=C(\C=C\C(O)=O)C=C2O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C15H18O9/c16-6-10-12(20)13(21)14(22)15(24-10)23-9-3-1-7(5-8(9)17)2-4-11(18)19/h1-5,10,12-17,20-22H,6H2,(H,18,19)/b4-2+/t10-,12-,13+,14-,15-/m1/s1

InChI Key

OHEYCHKLBCPRLZ-VHCZEJTMSA-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
Clematis tashiroi	LOTUS Database	35616633
Picea glauca	LOTUS Database	35616633
Platycodon grandiflorus	LOTUS Database	35616633
Senecio cruentus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Cinnamic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hexose monosaccharide
Hydroxycinnamic acid
Hydroxycinnamic acid or derivatives
O-glycosyl compound
Phenoxy compound
Styrene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Acetal
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Primary 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	-0.59	ALOGPS
logP	-0.74	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.46	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	79.17 m³·mol⁻¹	ChemAxon
Polarizability	32.74 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

31129888

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14825516

PDB ID

Not Available

ChEBI ID

142393

Good Scents ID

Not Available

References

General References

Lim EK, Li Y, Parr A, Jackson R, Ashford DA, Bowles DJ: Identification of glucosyltransferase genes involved in sinapate metabolism and lignin synthesis in Arabidopsis. J Biol Chem. 2001 Feb 9;276(6):4344-9. doi: 10.1074/jbc.M007263200. Epub 2000 Oct 20. [PubMed:11042211 ]
Tian JK, Sun F, Cheng YY: Chemical constituents from the roots of Ranunculus ternatus. J Asian Nat Prod Res. 2006 Jan-Mar;8(1-2):35-9. doi: 10.1080/10286020500385663. [PubMed:16753780 ]
Zhang Y, Tian HY, Tan YF, Wong YL, Wu HY, Jia JF, Wang GE, Gao JJ, Li YF, Kurihara H, Shaw PC, Jiang RW: Isolation and identification of polyphenols from Marsilea quadrifolia with antioxidant properties in vitro and in vivo. Nat Prod Res. 2016 Jun;30(12):1404-10. doi: 10.1080/14786419.2015.1062377. Epub 2015 Jul 29. [PubMed:26222269 ]
LOTUS database [Link]

Showing NP-Card for (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid (NP0243720)

MOL for NP0243720 ((2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid)

3D MOL for NP0243720 ((2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid)

3D SDF for NP0243720 ((2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid)

3D-SDF for NP0243720 ((2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid)

PDB for NP0243720 ((2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid)

3D PDB for NP0243720 ((2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid)

SMILES for NP0243720 ((2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid)

INCHI for NP0243720 ((2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid)

Structure for NP0243720 ((2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid)

3D Structure for NP0243720 ((2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid)