NP-MRD: Showing NP-Card for 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 4'-glucuronide (NP0339550)

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Record Information

Version

2.0

Created at

2024-09-11 22:24:02 UTC

Updated at

2024-09-11 22:24:02 UTC

NP-MRD ID

NP0339550

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 4'-glucuronide

Description

5-(3',4'-Dihydroxyphenyl)-gamma-valerolactone-4'-O-glucuronide 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. 5-(3',4'-Dihydroxyphenyl)-gamma-valerolactone-4'-O-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303102016572D          

 33 35  0  0  1  0            999 V2000
    4.1801    5.7134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2272    3.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    6.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821    2.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    4.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    4.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    4.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    3.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    4.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    5.7134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3071    2.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067    5.7134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1067    4.8884    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6078    6.1259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6078    4.4759    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6078    3.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    5.7134    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0367    4.4759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7920    1.7139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    6.1259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    4.4759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    6.9509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    3.2384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067    3.2384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5620    3.1660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    6.1259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    4.8884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6297    4.0254    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    5.3009    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067    4.0634    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    6.5384    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    5.3009    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    5.3009    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  1  0  0  0  0
  7  1  1  0  0  0  0
  7  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  2  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  3  1  0  0  0  0
 10  9  2  0  0  0  0
 11  4  1  0  0  0  0
 13 12  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 15 16  1  6  0  0  0
 17 14  1  0  0  0  0
 18  9  1  0  0  0  0
 19 11  2  0  0  0  0
 12 20  1  1  0  0  0
 13 21  1  6  0  0  0
 14 22  1  6  0  0  0
 23 16  2  0  0  0  0
 24 16  1  0  0  0  0
 25  8  1  0  0  0  0
 25 11  1  0  0  0  0
 26 10  1  0  0  0  0
 17 26  1  1  0  0  0
 27 15  1  0  0  0  0
 27 17  1  0  0  0  0
 28  8  1  0  0  0  0
 12 29  1  6  0  0  0
 13 30  1  1  0  0  0
 14 31  1  1  0  0  0
 15 32  1  6  0  0  0
 17 33  1  6  0  0  0
M  END


  Mrv1652303102016572D          

 33 35  0  0  1  0            999 V2000
    4.1801    5.7134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2272    3.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    6.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821    2.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    4.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    4.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    4.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    3.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    4.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    5.7134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3071    2.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067    5.7134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1067    4.8884    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6078    6.1259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6078    4.4759    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6078    3.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    5.7134    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0367    4.4759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7920    1.7139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    6.1259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    4.4759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    6.9509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    3.2384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067    3.2384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5620    3.1660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    6.1259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    4.8884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6297    4.0254    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    5.3009    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067    4.0634    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    6.5384    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    5.3009    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    5.3009    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  1  0  0  0  0
  7  1  1  0  0  0  0
  7  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  2  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  3  1  0  0  0  0
 10  9  2  0  0  0  0
 11  4  1  0  0  0  0
 13 12  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 15 16  1  6  0  0  0
 17 14  1  0  0  0  0
 18  9  1  0  0  0  0
 19 11  2  0  0  0  0
 12 20  1  1  0  0  0
 13 21  1  6  0  0  0
 14 22  1  6  0  0  0
 23 16  2  0  0  0  0
 24 16  1  0  0  0  0
 25  8  1  0  0  0  0
 25 11  1  0  0  0  0
 26 10  1  0  0  0  0
 17 26  1  1  0  0  0
 27 15  1  0  0  0  0
 27 17  1  0  0  0  0
 28  8  1  0  0  0  0
 12 29  1  6  0  0  0
 13 30  1  1  0  0  0
 14 31  1  1  0  0  0
 15 32  1  6  0  0  0
 17 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0339550

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1(CC2=CC(O)=C(O[C@@]3([H])O[C@@]([H])(C(O)=O)[C@]([H])(O)[C@@]([H])(O)[C@]3([H])O)C=C2)CCC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C17H20O10/c18-9-6-7(5-8-2-4-11(19)25-8)1-3-10(9)26-17-14(22)12(20)13(21)15(27-17)16(23)24/h1,3,6,8,12-15,17-18,20-22H,2,4-5H2,(H,23,24)/t8?,12-,13-,14+,15-,17+/m1/s1

> <INCHI_KEY>
OTBJYBQGMPICIK-GHPVWUPISA-N

> <FORMULA>
C17H20O10

> <MOLECULAR_WEIGHT>
384.3347

> <EXACT_MASS>
384.10564686

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
36.296432526345605

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-{2-hydroxy-4-[(5-oxooxolan-2-yl)methyl]phenoxy}oxane-2-carboxylic acid

> <ALOGPS_LOGP>
-0.22

> <JCHEM_LOGP>
-0.3324715006666663

> <ALOGPS_LOGS>
-1.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.739423147911136

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0598960355045155

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6868279752750155

> <JCHEM_POLAR_SURFACE_AREA>
162.98

> <JCHEM_REFRACTIVITY>
85.3195

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.45e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-{2-hydroxy-4-[(5-oxooxolan-2-yl)methyl]phenoxy}oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0       7.803  10.665   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.891   5.910   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.469  11.435   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.367   4.445   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.137   8.355   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.469   8.355   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.803   9.125   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.137   6.815   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.136   9.125   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.136  10.665   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.907   4.445   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.199  10.665   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.199   9.125   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.135  11.435   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.135   8.355   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.135   6.815   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.468  10.665   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.802   8.355   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      10.812   3.199   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.533  11.435   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.533   8.355   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.135  12.975   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.468   6.045   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.199   6.045   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      10.382   5.910   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       3.802  11.435   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.468   9.125   0.000  0.00  0.00           O+0
HETATM   28  H   UNK     0      10.509   7.514   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.533   9.895   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.199   7.585   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.468  12.205   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.135   9.895   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.802   9.895   0.000  0.00  0.00           H+0
CONECT    1    3    7                                                       
CONECT    2    4    8                                                       
CONECT    3    1   10                                                       
CONECT    4    2   11                                                       
CONECT    5    7    8                                                       
CONECT    6    7    9                                                       
CONECT    7    1    5    6                                                  
CONECT    8    2    5   25   28                                             
CONECT    9    6   10   18                                                  
CONECT   10    3    9   26                                                  
CONECT   11    4   19   25                                                  
CONECT   12   13   14   20   29                                             
CONECT   13   12   15   21   30                                             
CONECT   14   12   17   22   31                                             
CONECT   15   13   16   27   32                                             
CONECT   16   15   23   24                                                  
CONECT   17   14   26   27   33                                             
CONECT   18    9                                                            
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   13                                                            
CONECT   22   14                                                            
CONECT   23   16                                                            
CONECT   24   16                                                            
CONECT   25    8   11                                                       
CONECT   26   10   17                                                       
CONECT   27   15   17                                                       
CONECT   28    8                                                            
CONECT   29   12                                                            
CONECT   30   13                                                            
CONECT   31   14                                                            
CONECT   32   15                                                            
CONECT   33   17                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
5-(3',4'-Dihydroxyphenyl)-g-valerolactone-4'-O-glucuronide	Generator
5-(3',4'-Dihydroxyphenyl)-γ-valerolactone-4'-O-glucuronide	Generator

Chemical Formula

C₁₇H₂₀O₁₀

Average Mass

384.3347 Da

Monoisotopic Mass

384.10565 Da

IUPAC Name

(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-{2-hydroxy-4-[(5-oxooxolan-2-yl)methyl]phenoxy}oxane-2-carboxylic acid

Traditional Name

(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-{2-hydroxy-4-[(5-oxooxolan-2-yl)methyl]phenoxy}oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]C1(CC2=CC(O)=C(O[C@@]3([H])O[C@@]([H])(C(O)=O)[C@]([H])(O)[C@@]([H])(O)[C@]3([H])O)C=C2)CCC(=O)O1

InChI Identifier

InChI=1S/C17H20O10/c18-9-6-7(5-8-2-4-11(19)25-8)1-3-10(9)26-17-14(22)12(20)13(21)15(27-17)16(23)24/h1,3,6,8,12-15,17-18,20-22H,2,4-5H2,(H,23,24)/t8?,12-,13-,14+,15-,17+/m1/s1

InChI Key

OTBJYBQGMPICIK-GHPVWUPISA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Alkyl glycoside
O-glycosyl compound
Phenoxy compound
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Gamma butyrolactone
Hydroxy acid
Monosaccharide
Benzenoid
Oxane
Pyran
Tetrahydrofuran
Lactone
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Acetal
Carboxylic acid derivative
Polyol
Organic oxide
Alcohol
Hydrocarbon derivative
Carbonyl group
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	-0.22	ALOGPS
logP	-0.33	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.06	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.98 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	85.32 m³·mol⁻¹	ChemAxon
Polarizability	36.3 Å³	ChemAxon
Number of Rings	3	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

HMDB0059989

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB093654

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

124202077

PDB ID

Not Available

ChEBI ID

88695

Good Scents ID

Not Available

References

General References

Showing NP-Card for 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 4'-glucuronide (NP0339550)

MOL for NP0339550 (5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 4'-glucuronide)

3D MOL for NP0339550 (5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 4'-glucuronide)

3D SDF for NP0339550 (5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 4'-glucuronide)

3D-SDF for NP0339550 (5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 4'-glucuronide)

PDB for NP0339550 (5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 4'-glucuronide)

3D PDB for NP0339550 (5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 4'-glucuronide)

SMILES for NP0339550 (5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 4'-glucuronide)

INCHI for NP0339550 (5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 4'-glucuronide)

Structure for NP0339550 (5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 4'-glucuronide)

3D Structure for NP0339550 (5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 4'-glucuronide)