NP-MRD: Showing NP-Card for Urolithin a 8-glucuronide (NP0341789)

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Record Information

Version

2.0

Created at

2024-09-12 10:54:45 UTC

Updated at

2024-09-12 10:54:45 UTC

NP-MRD ID

NP0341789

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Urolithin a 8-glucuronide

Description

Urolithin a 8-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. Urolithin a 8-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

<string xmlns="http://www.chemspider.com/">
  Mrv1652304222013462D          

 29 32  0  0  1  0            999 V2000
    5.4624   -2.3635    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7492   -1.9511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0359   -2.3635    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0359   -3.1971    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7492   -3.6096    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4624   -3.1971    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1843   -3.6096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7492   -4.4346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3141   -3.6096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3141   -1.9511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3141   -1.1261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6008   -2.3635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1843   -1.9511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8975   -2.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6108   -1.9511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3326   -2.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3326   -3.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0458   -3.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0458   -4.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3326   -4.8470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6108   -4.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6108   -3.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8975   -3.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8975   -4.8470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7591   -4.8470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4809   -4.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4809   -3.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7591   -3.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1942   -4.8470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1 13  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 10  1  1  0  0  0
  4  5  1  0  0  0  0
  4  9  1  6  0  0  0
  5  6  1  0  0  0  0
  5  8  1  1  0  0  0
  6  7  1  6  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 23  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
 18 19  2  0  0  0  0
 18 28  1  0  0  0  0
 19 20  1  0  0  0  0
 19 25  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 24  2  0  0  0  0
 22 23  2  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 29  1  0  0  0  0
 27 28  2  0  0  0  0
M  END

<string xmlns="http://www.chemspider.com/">
  Mrv1652304222013462D          

 29 32  0  0  1  0            999 V2000
    5.4624   -2.3635    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7492   -1.9511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0359   -2.3635    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0359   -3.1971    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7492   -3.6096    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4624   -3.1971    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1843   -3.6096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7492   -4.4346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3141   -3.6096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3141   -1.9511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3141   -1.1261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6008   -2.3635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1843   -1.9511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8975   -2.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6108   -1.9511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3326   -2.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3326   -3.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0458   -3.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0458   -4.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3326   -4.8470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6108   -4.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6108   -3.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8975   -3.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8975   -4.8470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7591   -4.8470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4809   -4.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4809   -3.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7591   -3.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1942   -4.8470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1 13  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 10  1  1  0  0  0
  4  5  1  0  0  0  0
  4  9  1  6  0  0  0
  5  6  1  0  0  0  0
  5  8  1  1  0  0  0
  6  7  1  6  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 23  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
 18 19  2  0  0  0  0
 18 28  1  0  0  0  0
 19 20  1  0  0  0  0
 19 25  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 24  2  0  0  0  0
 22 23  2  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 29  1  0  0  0  0
 27 28  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0341789

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](O)[C@H](OC2=CC=C3C(=C2)C(=O)OC2=C3C=CC(O)=C2)O[C@@H]([C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H16O10/c20-7-1-3-10-9-4-2-8(6-11(9)18(26)28-12(10)5-7)27-19-15(23)13(21)14(22)16(29-19)17(24)25/h1-6,13-16,19-23H,(H,24,25)/t13-,14-,15+,16-,19+/m0/s1

> <INCHI_KEY>
QMPHAAMUHRNZSL-KSPMYQCISA-N

> <FORMULA>
C19H16O10

> <MOLECULAR_WEIGHT>
404.327

> <EXACT_MASS>
404.074346715

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
37.889452322913506

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({3-hydroxy-6-oxo-6H-benzo[c]chromen-8-yl}oxy)oxane-2-carboxylic acid

> <ALOGPS_LOGP>
0.55

> <JCHEM_LOGP>
0.37040324266666635

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.710984008220984

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0644439291467265

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6868267633008234

> <JCHEM_POLAR_SURFACE_AREA>
162.98000000000002

> <JCHEM_REFRACTIVITY>
92.91270000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.89e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({3-hydroxy-6-oxobenzo[c]chromen-8-yl}oxy)oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: <string xmlns="http://www.chemspider.com/">       
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-20         0                                  
HETATM    1  C   UNK     0      10.197  -4.412   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.865  -3.642   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.534  -4.412   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.534  -5.968   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.865  -6.738   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.197  -5.968   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.544  -6.738   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       8.865  -8.278   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       6.186  -6.738   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.186  -3.642   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.186  -2.102   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.855  -4.412   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      11.544  -3.642   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.875  -4.412   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.207  -3.642   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.554  -4.412   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.554  -5.968   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.886  -6.738   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.886  -8.278   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      15.554  -9.048   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      14.207  -8.278   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.207  -6.738   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.875  -5.968   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.875  -9.048   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      18.217  -9.048   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      19.564  -8.278   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      19.564  -6.738   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      18.217  -5.968   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      20.896  -9.048   0.000  0.00  0.00           O+0
CONECT    1    2    6   13                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    5    7                                                  
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    4                                                            
CONECT   10    3   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    1   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19   28                                                  
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   17   21   23                                                  
CONECT   23   14   22                                                       
CONECT   24   21                                                            
CONECT   25   19   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   18   27                                                       
CONECT   29   26                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
Urolithin a 8-O-beta-D-glucuronide	ChEBI
Urolithin a 8-O-beta-glucuronide	ChEBI
Urolithin a 8-O-b-D-glucuronide	Generator
Urolithin a 8-O-β-D-glucuronide	Generator
Urolithin a 8-O-b-glucuronide	Generator
Urolithin a 8-O-β-glucuronide	Generator
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(3-hydroxy-6-oxobenzo[c]chromen-8-yl)oxyoxane-2-carboxylic acid
3-hydroxy-urolithin-8-glucuronide
urolithin A-8-glucuronide

Chemical Formula

C₁₉H₁₆O₁₀

Average Mass

404.3270 Da

Monoisotopic Mass

404.07435 Da

IUPAC Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({3-hydroxy-6-oxo-6H-benzo[c]chromen-8-yl}oxy)oxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({3-hydroxy-6-oxobenzo[c]chromen-8-yl}oxy)oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](O)[C@H](OC2=CC=C3C(=C2)C(=O)OC2=C3C=CC(O)=C2)O[C@@H]([C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C19H16O10/c20-7-1-3-10-9-4-2-8(6-11(9)18(26)28-12(10)5-7)27-19-15(23)13(21)14(22)16(29-19)17(24)25/h1-6,13-16,19-23H,(H,24,25)/t13-,14-,15+,16-,19+/m0/s1

InChI Key

QMPHAAMUHRNZSL-KSPMYQCISA-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
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Coumarin
Isocoumarin
O-glycosyl compound
2-benzopyran
1-benzopyran
Benzopyran
Pyranone
Beta-hydroxy acid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Pyran
Oxane
Monosaccharide
Hydroxy acid
Heteroaromatic compound
Secondary alcohol
Lactone
Polyol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Acetal
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	0.55	ALOGPS
logP	0.37	ChemAxon
logS	-2.3	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	3	ChemAxon
Refractivity	92.91 m³·mol⁻¹	ChemAxon
Polarizability	37.89 Å³	ChemAxon
Number of Rings	4	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

HMDB0240568

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB093767

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

131708293

PDB ID

Not Available

ChEBI ID

89554

Good Scents ID

Not Available

References

General References

Showing NP-Card for Urolithin a 8-glucuronide (NP0341789)

MOL for NP0341789 (Urolithin a 8-glucuronide)

3D MOL for NP0341789 (Urolithin a 8-glucuronide)

3D SDF for NP0341789 (Urolithin a 8-glucuronide)

3D-SDF for NP0341789 (Urolithin a 8-glucuronide)

PDB for NP0341789 (Urolithin a 8-glucuronide)

3D PDB for NP0341789 (Urolithin a 8-glucuronide)

SMILES for NP0341789 (Urolithin a 8-glucuronide)

INCHI for NP0341789 (Urolithin a 8-glucuronide)

Structure for NP0341789 (Urolithin a 8-glucuronide)

3D Structure for NP0341789 (Urolithin a 8-glucuronide)