NP-MRD: Showing NP-Card for Catechol glucuronide (NP0334479)

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Record Information

Version

2.0

Created at

2024-09-09 23:51:34 UTC

Updated at

2024-09-09 23:51:35 UTC

NP-MRD ID

NP0334479

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Catechol glucuronide

Description

NULL

Structure

MOL SDF PDB SMILES InChI


  Mrv1652310081920572D          

 25 26  0  0  1  0            999 V2000
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000    5.7750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000    4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    6.6000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.3625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.3625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 10 11  1  1  0  0  0
 12  9  1  0  0  0  0
 13  5  1  0  0  0  0
  7 14  1  6  0  0  0
  8 15  1  1  0  0  0
  9 16  1  1  0  0  0
 17 11  2  0  0  0  0
 18 11  1  0  0  0  0
 19  6  1  0  0  0  0
 12 19  1  6  0  0  0
 20 10  1  0  0  0  0
 20 12  1  0  0  0  0
  7 21  1  1  0  0  0
  8 22  1  6  0  0  0
  9 23  1  6  0  0  0
 10 24  1  1  0  0  0
 12 25  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0334479

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(OC2=CC=CC=C2O)O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O8/c13-5-3-1-2-4-6(5)19-12-9(16)7(14)8(15)10(20-12)11(17)18/h1-4,7-10,12-16H,(H,17,18)/t7-,8-,9+,10-,12+/m0/s1

> <INCHI_KEY>
ICPYZFZFSLTYID-GOVZDWNOSA-N

> <FORMULA>
C12H14O8

> <MOLECULAR_WEIGHT>
286.236

> <EXACT_MASS>
286.068867411

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
26.032534264377496

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(2-hydroxyphenoxy)oxane-2-carboxylic acid

> <ALOGPS_LOGP>
-0.64

> <JCHEM_LOGP>
-0.5816783826666665

> <ALOGPS_LOGS>
-0.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.819486048684992

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1547302284280687

> <JCHEM_PKA_STRONGEST_BASIC>
-3.686827975269206

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
62.031600000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.20e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(2-hydroxyphenoxy)oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-OCT-19         0                                  
HETATM    1  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.000  10.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.000   9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.334  13.090   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.334  11.550   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.001  11.550   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.667   9.240   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334   8.470   0.000  0.00  0.00           O+0
HETATM   21  H   UNK     0      -0.000  12.320   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.334  10.010   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       4.001  10.010   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.334  10.010   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.667   7.700   0.000  0.00  0.00           H+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6   13                                                  
CONECT    6    4    5   19                                                  
CONECT    7    8    9   14   21                                             
CONECT    8    7   10   15   22                                             
CONECT    9    7   12   16   23                                             
CONECT   10    8   11   20   24                                             
CONECT   11   10   17   18                                                  
CONECT   12    9   19   20   25                                             
CONECT   13    5                                                            
CONECT   14    7                                                            
CONECT   15    8                                                            
CONECT   16    9                                                            
CONECT   17   11                                                            
CONECT   18   11                                                            
CONECT   19    6   12                                                       
CONECT   20   10   12                                                       
CONECT   21    7                                                            
CONECT   22    8                                                            
CONECT   23    9                                                            
CONECT   24   10                                                            
CONECT   25   12                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Value	Source
2-Hydroxyphenyl beta-D-glucosiduronic acid	ChEBI
2-Hydroxyphenyl beta-D-glucuronide	ChEBI
2-Hydroxyphenyl-beta-D-glucopyranosiduronic acid	ChEBI
Catechol beta-glucuronide	ChEBI
Diphenol glucuronide	ChEBI
2-Hydroxyphenyl b-D-glucosiduronate	Generator
2-Hydroxyphenyl b-D-glucosiduronic acid	Generator
2-Hydroxyphenyl beta-D-glucosiduronate	Generator
2-Hydroxyphenyl β-D-glucosiduronate	Generator
2-Hydroxyphenyl β-D-glucosiduronic acid	Generator
2-Hydroxyphenyl b-D-glucuronide	Generator
2-Hydroxyphenyl β-D-glucuronide	Generator
2-Hydroxyphenyl-b-D-glucopyranosiduronate	Generator
2-Hydroxyphenyl-b-D-glucopyranosiduronic acid	Generator
2-Hydroxyphenyl-beta-D-glucopyranosiduronate	Generator
2-Hydroxyphenyl-β-D-glucopyranosiduronate	Generator
2-Hydroxyphenyl-β-D-glucopyranosiduronic acid	Generator
Catechol b-glucuronide	Generator
Catechol β-glucuronide	Generator
Catechol glucuronide	ChEBI
Catechol b-D-glucuronide	Generator
Catechol β-D-glucuronide	Generator

Chemical Formula

C₁₂H₁₄O₈

Average Mass

286.2360 Da

Monoisotopic Mass

286.06887 Da

IUPAC Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(2-hydroxyphenoxy)oxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(2-hydroxyphenoxy)oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]1(OC2=CC=CC=C2O)O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O

InChI Identifier

InChI=1S/C12H14O8/c13-5-3-1-2-4-6(5)19-12-9(16)7(14)8(15)10(20-12)11(17)18/h1-4,7-10,12-16H,(H,17,18)/t7-,8-,9+,10-,12+/m0/s1

InChI Key

ICPYZFZFSLTYID-GOVZDWNOSA-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
O-glycosyl compound
Phenoxy compound
Phenol ether
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Hydroxy acid
Benzenoid
Pyran
Monosaccharide
Oxane
Monocyclic benzene moiety
Secondary alcohol
Acetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Carbonyl group
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	-0.64	ALOGPS
logP	-0.58	ChemAxon
logS	-0.95	ALOGPS
pKa (Strongest Acidic)	3.15	ChemAxon
pKa (Strongest Basic)	-3.7	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	3	ChemAxon
Refractivity	62.03 m³·mol⁻¹	ChemAxon
Polarizability	26.03 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

HMDB0240490

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB093679

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

75124209

PDB ID

Not Available

ChEBI ID

133689

Good Scents ID

Not Available

References

General References

McMahon TF, Birnbaum LS: Age-related changes in disposition and metabolism of benzene in male C57BL/6N mice. Drug Metab Dispos. 1991 Nov-Dec;19(6):1052-7. [PubMed:1687010 ]

Showing NP-Card for Catechol glucuronide (NP0334479)

MOL for NP0334479 (Catechol glucuronide)

3D MOL for NP0334479 (Catechol glucuronide)

3D SDF for NP0334479 (Catechol glucuronide)

3D-SDF for NP0334479 (Catechol glucuronide)

PDB for NP0334479 (Catechol glucuronide)

3D PDB for NP0334479 (Catechol glucuronide)

SMILES for NP0334479 (Catechol glucuronide)

INCHI for NP0334479 (Catechol glucuronide)

Structure for NP0334479 (Catechol glucuronide)

3D Structure for NP0334479 (Catechol glucuronide)