NP-MRD: Showing NP-Card for (2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2r)-2-(4-hydroxyphenyl)propanoate (NP0257325)

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Record Information

Version

2.0

Created at

2022-09-07 22:25:36 UTC

Updated at

2022-09-07 22:25:37 UTC

NP-MRD ID

NP0257325

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2r)-2-(4-hydroxyphenyl)propanoate

Description

(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2R)-2-(4-hydroxyphenyl)propanoate belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. (2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2r)-2-(4-hydroxyphenyl)propanoate is found in Panax ginseng. Based on a literature review very few articles have been published on (2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2R)-2-(4-hydroxyphenyl)propanoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309082200252D          

 23 24  0  0  1  0            999 V2000
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  6  0  0  0
  2 17  1  0  0  0  0
 17 18  2  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 22  1  0  0  0  0
 22 23  2  0  0  0  0
 17 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0257325

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](C(=O)O[C@H]1O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]1O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O8/c1-7(8-2-4-9(17)5-3-8)14(21)23-15-13(20)12(19)11(18)10(6-16)22-15/h2-5,7,10-13,15-20H,6H2,1H3/t7-,10+,11+,12-,13+,15-/m1/s1

> <INCHI_KEY>
XWODHOVNBAEXRX-USYLQRRISA-N

> <FORMULA>
C15H20O8

> <MOLECULAR_WEIGHT>
328.317

> <EXACT_MASS>
328.115817604

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
31.777508655007185

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2R)-2-(4-hydroxyphenyl)propanoate

> <JCHEM_LOGP>
-0.4176530313333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.196914921334475

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.492186597733447

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810936802265635

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
76.3522

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2R)-2-(4-hydroxyphenyl)propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16                                                  
CONECT   16   15                                                            
CONECT   17    2   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
(2R,3S,4R,5R,6S)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl (2R)-2-(4-hydroxyphenyl)propanoic acid	Generator

Chemical Formula

C₁₅H₂₀O₈

Average Mass

328.3170 Da

Monoisotopic Mass

328.11582 Da

IUPAC Name

(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2R)-2-(4-hydroxyphenyl)propanoate

Traditional Name

(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2R)-2-(4-hydroxyphenyl)propanoate

CAS Registry Number

Not Available

SMILES

C[C@@H](C(=O)O[C@H]1O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]1O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C15H20O8/c1-7(8-2-4-9(17)5-3-8)14(21)23-15-13(20)12(19)11(18)10(6-16)22-15/h2-5,7,10-13,15-20H,6H2,1H3/t7-,10+,11+,12-,13+,15-/m1/s1

InChI Key

XWODHOVNBAEXRX-USYLQRRISA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Panax ginseng	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Oxane
Benzenoid
Carboxylic acid ester
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Primary alcohol
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	-0.42	ChemAxon
pKa (Strongest Acidic)	9.49	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	76.35 m³·mol⁻¹	ChemAxon
Polarizability	31.78 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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162943414

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2r)-2-(4-hydroxyphenyl)propanoate (NP0257325)

MOL for NP0257325 ((2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2r)-2-(4-hydroxyphenyl)propanoate)

3D MOL for NP0257325 ((2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2r)-2-(4-hydroxyphenyl)propanoate)

3D SDF for NP0257325 ((2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2r)-2-(4-hydroxyphenyl)propanoate)

3D-SDF for NP0257325 ((2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2r)-2-(4-hydroxyphenyl)propanoate)

PDB for NP0257325 ((2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2r)-2-(4-hydroxyphenyl)propanoate)

3D PDB for NP0257325 ((2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2r)-2-(4-hydroxyphenyl)propanoate)

SMILES for NP0257325 ((2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2r)-2-(4-hydroxyphenyl)propanoate)

INCHI for NP0257325 ((2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2r)-2-(4-hydroxyphenyl)propanoate)

Structure for NP0257325 ((2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2r)-2-(4-hydroxyphenyl)propanoate)

3D Structure for NP0257325 ((2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2r)-2-(4-hydroxyphenyl)propanoate)