NP-MRD: Showing NP-Card for 2-O-p-Coumaroyl-D-glucose (NP0335053)

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Record Information

Version

2.0

Created at

2024-09-10 23:41:25 UTC

Updated at

2024-09-10 23:41:25 UTC

NP-MRD ID

NP0335053

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-O-p-Coumaroyl-D-glucose

Description

2-O-p-Coumaroyl-D-glucose belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. Based on a literature review very few articles have been published on 2-O-p-Coumaroyl-D-glucose.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262302132D          

 23 24  0  0  0  0            999 V2000
    7.5194   -3.1726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5194   -3.9976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2339   -4.4101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2339   -5.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9484   -5.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9484   -6.4726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0905   -3.9976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8050   -4.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8050   -5.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5194   -5.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5194   -6.4726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0905   -5.6476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3760   -5.2351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3760   -4.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6616   -3.9976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9471   -4.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2326   -3.9976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5181   -4.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8037   -3.9976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8037   -3.1726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5181   -2.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2326   -3.1726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0892   -2.7601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  7 14  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 22  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 23  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0335053

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(O)C(OC(=O)\C=C\C2=CC=C(O)C=C2)C(O)C1O

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

> <INCHI_KEY>
ROJVJYZGYUIFEF-ZZXKWVIFNA-N

> <FORMULA>
C15H18O8

> <MOLECULAR_WEIGHT>
326.301

> <EXACT_MASS>
326.10016754

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.766415874379675

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
-0.20221382166666652

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.30689660155507

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.393173120854236

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981079852824804

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
77.47200000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  O   UNK     0      14.036  -5.922   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      14.036  -7.462   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      15.370  -8.232   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      15.370  -9.772   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.704 -10.542   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      16.704 -12.082   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      11.369  -7.462   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      12.703  -8.232   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.703  -9.772   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.036 -10.542   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      14.036 -12.082   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      11.369 -10.542   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      10.035  -9.772   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.035  -8.232   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.702  -7.462   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.368  -8.232   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.034  -7.462   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.700  -8.232   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.367  -7.462   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.367  -5.922   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.700  -5.152   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.034  -5.922   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.033  -5.152   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    8   14                                                       
CONECT    8    2    7    9                                                  
CONECT    9    8   10   12                                                  
CONECT   10    4    9   11                                                  
CONECT   11   10                                                            
CONECT   12    9                                                            
CONECT   13   14                                                            
CONECT   14    7   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   17   21                                                       
CONECT   23   20                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₈

Average Mass

326.3010 Da

Monoisotopic Mass

326.10017 Da

IUPAC Name

2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

OCC1OC(O)C(OC(=O)\C=C\C2=CC=C(O)C=C2)C(O)C1O

InChI Identifier

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

InChI Key

ROJVJYZGYUIFEF-ZZXKWVIFNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acid esters

Alternative Parents

Substituents

Coumaric acid ester
Coumaric acid or derivatives
Hexose monosaccharide
Cinnamic acid ester
Styrene
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Hemiacetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Monocarboxylic acid or derivatives
Organic oxygen compound
Alcohol
Primary alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	-0.2	ChemAxon
pKa (Strongest Acidic)	9.39	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	77.47 m³·mol⁻¹	ChemAxon
Polarizability	31.77 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-O-p-Coumaroyl-D-glucose (NP0335053)

MOL for NP0335053 (2-O-p-Coumaroyl-D-glucose)

3D MOL for NP0335053 (2-O-p-Coumaroyl-D-glucose)

3D SDF for NP0335053 (2-O-p-Coumaroyl-D-glucose)

3D-SDF for NP0335053 (2-O-p-Coumaroyl-D-glucose)

PDB for NP0335053 (2-O-p-Coumaroyl-D-glucose)

3D PDB for NP0335053 (2-O-p-Coumaroyl-D-glucose)

SMILES for NP0335053 (2-O-p-Coumaroyl-D-glucose)

INCHI for NP0335053 (2-O-p-Coumaroyl-D-glucose)

Structure for NP0335053 (2-O-p-Coumaroyl-D-glucose)

3D Structure for NP0335053 (2-O-p-Coumaroyl-D-glucose)