NP-MRD: Showing NP-Card for p-coumaric acid glucoside (NP0330724)

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Record Information

Version

1.0

Created at

2022-09-12 16:21:02 UTC

Updated at

2022-09-12 16:21:02 UTC

NP-MRD ID

NP0330724

Secondary Accession Numbers

None

Natural Product Identification

Common Name

p-coumaric acid glucoside

Description

4-O-beta-D-glucosyl-trans-4-coumaric acid, also known as 4-O-b-D-glucosyl-4-hydroxycinnamate or (2E)-3-[4-(b-D-glucopyranosyloxy)phenyl]acrylate, 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. p-coumaric acid glucoside is found in Hypericum sikokumontanum, Lilium mackliniae, Onobrychis viciifolia, Picea abies, Picea glauca, Pinus sylvestris, Ribes rubrum and Rubus chamaemorus. 4-O-beta-D-glucosyl-trans-4-coumaric acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309272007412D          

 23 24  0  0  0  0            999 V2000
 9998.2870 9998.3475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.1461 9999.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8601 9999.5851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5761 9999.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2901 9999.5851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.576110000.8231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.857510000.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.142710001.2359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8575 9997.5220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4279 9998.3475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4279 9999.9978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8575 9999.9974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.1430 9999.5849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.1430 9998.7599    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9996.8575 9998.3475    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.5719 9998.7599    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.5719 9999.5849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.4319 9999.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.7175 9999.9973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0029 9999.5848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0029 9998.7599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.7173 9998.3474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.4319 9998.7599    0.0000 C   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
M  END
> <DATABASE_ID>
NP0330724

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC=C(\C=C\C(O)=O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O8/c16-7-10-12(19)13(20)14(21)15(23-10)22-9-4-1-8(2-5-9)3-6-11(17)18/h1-6,10,12-16,19-21H,7H2,(H,17,18)/b6-3+/t10-,12-,13+,14-,15-/m1/s1

> <INCHI_KEY>
LJFYQZQUAULRDF-FDGSXQGBSA-N

> <FORMULA>
C15H18O8

> <MOLECULAR_WEIGHT>
326.2986

> <EXACT_MASS>
326.100167552

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.93980428791113

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.35

> <JCHEM_LOGP>
-0.43554715499999985

> <ALOGPS_LOGS>
-1.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.200141773335279

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.723397123158301

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343686506

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
77.18520000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.08e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(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    8663.4698663.582   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8668.8068666.663   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8670.1398665.892   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8671.4758666.663   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8672.8088665.892   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8671.4758668.203   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8660.8018668.203   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8659.4668668.974   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8660.8018662.041   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8658.1328663.582   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8658.1328666.663   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8660.8018666.662   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8659.4678665.892   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8659.4678664.352   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8660.8018663.582   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8662.1348664.352   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8662.1348665.892   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0    8667.4738665.892   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8666.1398666.662   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8664.8058665.892   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8664.8058664.352   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8666.1398663.582   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8667.4738664.352   0.000  0.00  0.00           C+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                                                       
CONECT   23   22   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
(2E)-3-[4-(beta-D-Glucopyranosyloxy)phenyl]acrylic acid	ChEBI
3-(4-(beta-D-Glucopyranosyloxy)phenyl)-2-propenoic acid	ChEBI
4-O-[4-(2-Carboxyvinyl)phenyl]-beta-D-glucopyranose	ChEBI
4-O-beta-D-Glucosyl-4-coumaric acid	ChEBI
4-O-beta-D-Glucosyl-4-hydroxycinnamic acid	ChEBI
trans-beta-D-Glucosyl-4-hydroxycinnamic acid	ChEBI
trans-p-Coumaric acid 4-glucoside	ChEBI
(2E)-3-[4-(b-D-Glucopyranosyloxy)phenyl]acrylate	Generator
(2E)-3-[4-(b-D-Glucopyranosyloxy)phenyl]acrylic acid	Generator
(2E)-3-[4-(beta-D-Glucopyranosyloxy)phenyl]acrylate	Generator
(2E)-3-[4-(Β-D-glucopyranosyloxy)phenyl]acrylate	Generator
(2E)-3-[4-(Β-D-glucopyranosyloxy)phenyl]acrylic acid	Generator
3-(4-(b-D-Glucopyranosyloxy)phenyl)-2-propenoate	Generator
3-(4-(b-D-Glucopyranosyloxy)phenyl)-2-propenoic acid	Generator
3-(4-(beta-D-Glucopyranosyloxy)phenyl)-2-propenoate	Generator
3-(4-(Β-D-glucopyranosyloxy)phenyl)-2-propenoate	Generator
3-(4-(Β-D-glucopyranosyloxy)phenyl)-2-propenoic acid	Generator
4-O-[4-(2-Carboxyvinyl)phenyl]-b-D-glucopyranose	Generator
4-O-[4-(2-Carboxyvinyl)phenyl]-β-D-glucopyranose	Generator
4-O-b-D-Glucosyl-4-coumarate	Generator
4-O-b-D-Glucosyl-4-coumaric acid	Generator
4-O-beta-D-Glucosyl-4-coumarate	Generator
4-O-Β-D-glucosyl-4-coumarate	Generator
4-O-Β-D-glucosyl-4-coumaric acid	Generator
4-O-b-D-Glucosyl-4-hydroxycinnamate	Generator
4-O-b-D-Glucosyl-4-hydroxycinnamic acid	Generator
4-O-beta-D-Glucosyl-4-hydroxycinnamate	Generator
4-O-Β-D-glucosyl-4-hydroxycinnamate	Generator
4-O-Β-D-glucosyl-4-hydroxycinnamic acid	Generator
trans-b-D-Glucosyl-4-hydroxycinnamate	Generator
trans-b-D-Glucosyl-4-hydroxycinnamic acid	Generator
trans-beta-D-Glucosyl-4-hydroxycinnamate	Generator
trans-Β-D-glucosyl-4-hydroxycinnamate	Generator
trans-Β-D-glucosyl-4-hydroxycinnamic acid	Generator
trans-p-Coumarate 4-glucoside	Generator
4-O-b-D-Glucosyl-trans-4-coumarate	Generator
4-O-b-D-Glucosyl-trans-4-coumaric acid	Generator
4-O-beta-D-Glucosyl-trans-4-coumarate	Generator
4-O-Β-D-glucosyl-trans-4-coumarate	Generator
4-O-Β-D-glucosyl-trans-4-coumaric acid	Generator
(E)-p-Coumaric acid 4-O-beta-D-glucopyranoside	PhytoBank
(E)-p-Coumaric acid 4-O-β-D-glucopyranoside	PhytoBank
4-O-beta-D-Glucopyranosyl-p-trans-coumaric acid	PhytoBank
4-O-β-D-Glucopyranosyl-p-trans-coumaric acid	PhytoBank
4-O-beta-D-Glucopyranosylcoumaric acid	PhytoBank
4-O-β-D-Glucopyranosylcoumaric acid	PhytoBank
Coumaric acid 4-O-beta-D-glucopyranoside	PhytoBank
Coumaric acid 4-O-β-D-glucopyranoside	PhytoBank
trans-4-O-beta-D-Glucopyranosyl-p-coumaric acid	PhytoBank
trans-4-O-β-D-Glucopyranosyl-p-coumaric acid	PhytoBank
trans-p-Coumaric acid 4-O-beta-D-glucopyranoside	PhytoBank
trans-p-Coumaric acid 4-O-β-D-glucopyranoside	PhytoBank
3-[4-(beta-D-Glucopyranosyloxy)phenyl]-2-propenoic acid	PhytoBank
3-[4-(β-D-Glucopyranosyloxy)phenyl]-2-propenoic acid	PhytoBank
beta-D-p-(2-Carboxyvinyl)phenylglucopyranoside	PhytoBank
β-D-p-(2-Carboxyvinyl)phenylglucopyranoside	PhytoBank
4-(beta-D-Glucopyranosyloxy)cinnamic acid	PhytoBank
4-(β-D-Glucopyranosyloxy)cinnamic acid	PhytoBank
4-O-beta-D-Glucopyranosyl cinnamate	PhytoBank
4-O-β-D-Glucopyranosyl cinnamate	PhytoBank
4-O-beta-D-Glucopyranosyl-p-coumaric acid	PhytoBank
4-O-β-D-Glucopyranosyl-p-coumaric acid	PhytoBank
Glucosido-p-coumaric acid	PhytoBank
p-(Glucosyloxy)cinnamic acid	PhytoBank
p-Coumaric acid 4-O-beta-D-glucopyranoside	PhytoBank
p-Coumaric acid 4-O-β-D-glucopyranoside	PhytoBank
p-Coumaric acid glucoside	PhytoBank
p-Coumaric acid beta-glucoside	PhytoBank
p-Coumaric acid β-glucoside	PhytoBank

Chemical Formula

C₁₅H₁₈O₈

Average Mass

326.2986 Da

Monoisotopic Mass

326.10017 Da

IUPAC Name

(2E)-3-(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-(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=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C15H18O8/c16-7-10-12(19)13(20)14(21)15(23-10)22-9-4-1-8(2-5-9)3-6-11(17)18/h1-6,10,12-16,19-21H,7H2,(H,17,18)/b6-3+/t10-,12-,13+,14-,15-/m1/s1

InChI Key

LJFYQZQUAULRDF-FDGSXQGBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Hypericum sikokumontanum	LOTUS Database	35616633
Lilium mackliniae	LOTUS Database	35616633
Onobrychis viciifolia	LOTUS Database	35616633
Picea abies	LOTUS Database	35616633
Picea glauca	LOTUS Database	35616633
Pinus sylvestris	LOTUS Database	35616633
Ribes rubrum	LOTUS Database	35616633
Rubus chamaemorus	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
Hexose monosaccharide
O-glycosyl compound
Phenoxy compound
Phenol ether
Styrene
Monocyclic benzene moiety
Monosaccharide
Oxane
Benzenoid
Secondary alcohol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
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

4-O-beta-D-glucosyl-4-coumaric acid (CHEBI:83032 )

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	-0.35	ALOGPS
logP	-0.44	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.72	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	77.19 m³·mol⁻¹	ChemAxon
Polarizability	31.94 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C04415

BioCyc ID

CPD-457

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9840292

PDB ID

Not Available

ChEBI ID

83032

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for p-coumaric acid glucoside (NP0330724)

MOL for NP0330724 (p-coumaric acid glucoside)

3D MOL for NP0330724 (p-coumaric acid glucoside)

3D SDF for NP0330724 (p-coumaric acid glucoside)

3D-SDF for NP0330724 (p-coumaric acid glucoside)

PDB for NP0330724 (p-coumaric acid glucoside)

3D PDB for NP0330724 (p-coumaric acid glucoside)

SMILES for NP0330724 (p-coumaric acid glucoside)

INCHI for NP0330724 (p-coumaric acid glucoside)

Structure for NP0330724 (p-coumaric acid glucoside)

3D Structure for NP0330724 (p-coumaric acid glucoside)