NP-MRD: Showing NP-Card for Phenylglucuronide (NP0136279)

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Record Information

Version

2.0

Created at

2022-05-12 15:10:27 UTC

Updated at

2022-05-12 15:10:27 UTC

NP-MRD ID

NP0136279

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phenylglucuronide

Description

Phenylglucuronide 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. Phenylglucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa). These are compounds comprising the glucuronic acid linked to another substance via a glycosidic bond.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -4.5913    1.3230    0.7265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3727    1.3062    1.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0480    1.3687    2.3692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2921    1.2225   -0.0193 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0857    1.2229    0.5980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2591    0.1818    0.2199 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9396    0.1083    0.8577 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2248    0.1145    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2928    0.0264    1.2825 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6036    0.0320    0.8383 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8996    0.1267   -0.5043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8438    0.2153   -1.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5196    0.2091   -0.9278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0411   -1.1062    0.5233 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1151   -2.1372    0.5316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0401   -1.2147   -0.5966 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0423   -2.1431   -0.3364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5524    0.1224   -0.9856 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1158    0.5078   -2.2730 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6232    2.1995    2.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3829    2.1935   -0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1284    0.2618   -0.8778 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0708   -0.0481    2.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4493   -0.0377    1.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9284    0.1310   -0.8514 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0817    0.2894   -2.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7423    0.2804   -1.6567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5497   -0.9973    1.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5417   -2.9744    0.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4710   -1.6280   -1.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9494   -2.6055    0.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6740    0.0331   -1.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7206    1.4158   -2.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 14  1  0
 14 15  1  0
 14  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6  5  1  0
  5  4  1  0
  4 18  1  0
 18 19  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
 18 16  1  0
 13  8  1  0
 17 31  1  0
 16 30  1  6
 14 28  1  1
 15 29  1  0
  6 22  1  6
  9 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
  4 21  1  6
 18 32  1  6
 19 33  1  0
  3 20  1  0
M  END


  Mrv1652304062013102D          

 19 20  0  0  0  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  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
  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  6  0  0  0
 12  9  1  0  0  0  0
  7 13  1  6  0  0  0
  8 14  1  1  0  0  0
  9 15  1  1  0  0  0
 16 11  2  0  0  0  0
 17 11  1  0  0  0  0
 18  6  1  0  0  0  0
 18 12  1  0  0  0  0
 19 10  1  0  0  0  0
 19 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136279

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O7/c13-7-8(14)10(11(16)17)19-12(9(7)15)18-6-4-2-1-3-5-6/h1-5,7-10,12-15H,(H,16,17)/t7-,8-,9+,10-,12?/m0/s1

> <INCHI_KEY>
WVHAUDNUGBNUDZ-SDQGTYQYSA-N

> <FORMULA>
C12H14O7

> <MOLECULAR_WEIGHT>
270.2354

> <EXACT_MASS>
270.073952802

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
25.17685048949241

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
-0.78

> <JCHEM_LOGP>
-0.27811306099999966

> <ALOGPS_LOGS>
-0.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.21682142409573

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3626031250011943

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6868267613714494

> <JCHEM_POLAR_SURFACE_AREA>
116.45

> <JCHEM_REFRACTIVITY>
60.050700000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.20e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         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  13.090   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.334  11.550   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.001  11.550   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.667   9.240   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334   8.470   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5   18                                                  
CONECT    7    8    9   13                                                  
CONECT    8    7   10   14                                                  
CONECT    9    7   12   15                                                  
CONECT   10    8   11   19                                                  
CONECT   11   10   16   17                                                  
CONECT   12    9   18   19                                                  
CONECT   13    7                                                            
CONECT   14    8                                                            
CONECT   15    9                                                            
CONECT   16   11                                                            
CONECT   17   11                                                            
CONECT   18    6   12                                                       
CONECT   19   10   12                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
(2S,3S,4S,5R)-3,4,5-Trihydroxy-6-phenoxyoxane-2-carboxylate	Generator
Phenylglucuronide	MeSH

Chemical Formula

C₁₂H₁₄O₇

Average Mass

270.2354 Da

Monoisotopic Mass

270.07395 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H14O7/c13-7-8(14)10(11(16)17)19-12(9(7)15)18-6-4-2-1-3-5-6/h1-5,7-10,12-15H,(H,16,17)/t7-,8-,9+,10-,12?/m0/s1

InChI Key

WVHAUDNUGBNUDZ-SDQGTYQYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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
Beta-hydroxy acid
Monocyclic benzene moiety
Hydroxy acid
Benzenoid
Monosaccharide
Pyran
Oxane
Secondary alcohol
Acetal
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Polyol
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	-0.78	ALOGPS
logP	-0.28	ChemAxon
logS	-0.93	ALOGPS
pKa (Strongest Acidic)	3.36	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	60.05 m³·mol⁻¹	ChemAxon
Polarizability	25.18 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

HMDB0059806

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

119239

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Phenylglucuronide (NP0136279)

MOL for NP0136279 (Phenylglucuronide)

3D MOL for NP0136279 (Phenylglucuronide)

3D SDF for NP0136279 (Phenylglucuronide)

3D-SDF for NP0136279 (Phenylglucuronide)

PDB for NP0136279 (Phenylglucuronide)

3D PDB for NP0136279 (Phenylglucuronide)

SMILES for NP0136279 (Phenylglucuronide)

INCHI for NP0136279 (Phenylglucuronide)

Structure for NP0136279 (Phenylglucuronide)

3D Structure for NP0136279 (Phenylglucuronide)