NP-MRD: Showing NP-Card for Benzoyl glucuronide (NP0090879)

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Record Information

Version

2.0

Created at

2022-05-11 18:24:55 UTC

Updated at

2022-05-11 18:24:55 UTC

NP-MRD ID

NP0090879

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Benzoyl glucuronide

Description

Benzoyl glucuronide (Benzoic acid) belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond. Benzoyl glucuronide (Benzoic acid) is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -1.4480    1.2819    1.0997 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6983    0.5278    0.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6904   -0.1067   -0.5550 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6364    0.0841   -0.1863 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4015    0.6774   -1.1983 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6548    0.9113   -0.6596 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4283    1.9320   -1.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9682    2.5357   -2.3264 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6929    2.2524   -0.8887 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3562   -0.4341   -0.5838 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7211   -0.2979   -0.3633 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6716   -1.1910    0.5359 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1595   -2.4914    0.6448 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2081   -1.2428    0.2442 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5571   -1.5776    1.4533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0789    0.3226   -0.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1249    0.9427    0.4128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4448    0.7650    0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7558   -0.0616   -0.9992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7214   -0.6984   -1.6902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4078   -0.4987   -1.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6849    0.7736    0.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4761    1.2331    0.4077 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7458    2.6713    0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1692   -1.0073   -1.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0901   -0.9929    0.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8361   -0.6128    1.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7071   -3.0720   -0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9245   -2.0410   -0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7189   -0.8723    2.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8650    1.5947    1.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2471    1.2634    0.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7699   -0.2211   -1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9401   -1.3511   -2.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6158   -0.9983   -1.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 14  1  0
 14 15  1  0
 14  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  4  5  1  0
  5  6  1  0
  6 10  1  0
 10 11  1  0
  6  7  1  0
  7  9  1  0
  7  8  2  0
 10 12  1  0
 21 16  1  0
 13 28  1  0
 12 27  1  1
 14 29  1  6
 15 30  1  0
  4 22  1  1
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
  6 23  1  1
 10 25  1  6
 11 26  1  0
  9 24  1  0
M  END


  Mrv0541 02241200502D          

 21 22  0  0  1  0            999 V2000
   18.4500   -5.9221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4500   -8.3972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8790   -7.5721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0210   -5.9221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0210   -7.5721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8790   -5.0971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5934   -6.3346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7355   -4.6846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4500   -7.5721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.1645   -7.1596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.7355   -7.1596    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.1645   -6.3346    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.7355   -6.3346    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.8790   -5.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0210   -5.0971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3065   -4.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5920   -5.0971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3065   -3.8596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8775   -4.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5920   -3.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8775   -3.8596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  9  2  1  6  0  0  0
 10  3  1  1  0  0  0
 13  4  1  6  0  0  0
  4 15  1  0  0  0  0
 11  5  1  1  0  0  0
  6 14  1  0  0  0  0
  7 14  2  0  0  0  0
  8 15  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  2  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0090879

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H14O8/c14-7-8(15)10(11(17)18)20-13(9(7)16)21-12(19)6-4-2-1-3-5-6/h1-5,7-10,13-16H,(H,17,18)/t7-,8-,9+,10-,13-/m0/s1

> <INCHI_KEY>
NLOPFVNXNMEEDI-UNLLLRGISA-N

> <FORMULA>
C13H14O8

> <MOLECULAR_WEIGHT>
298.2455

> <EXACT_MASS>
298.068867424

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
27.295171520276376

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
-0.68

> <JCHEM_LOGP>
-0.11696483133333291

> <ALOGPS_LOGS>
-0.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.212228537569501

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1169568332413657

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6869065379340933

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
65.61280000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.06e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      34.440 -11.055   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      34.440 -15.675   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      37.107 -14.135   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      31.773 -11.055   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      31.773 -14.135   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      37.107  -9.515   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      38.441 -11.825   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      33.106  -8.745   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      34.440 -14.135   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      35.774 -13.365   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      33.106 -13.365   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.774 -11.825   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      33.106 -11.825   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      37.107 -11.055   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      31.773  -9.515   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      30.439  -8.745   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.105  -9.515   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      30.439  -7.205   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      27.771  -8.745   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      29.105  -6.435   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.771  -7.205   0.000  0.00  0.00           C+0
CONECT    1   12   13                                                       
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   13   15                                                       
CONECT    5   11                                                            
CONECT    6   14                                                            
CONECT    7   14                                                            
CONECT    8   15                                                            
CONECT    9    2   10   11                                                  
CONECT   10    3    9   12                                                  
CONECT   11    5    9   13                                                  
CONECT   12    1   10   14                                                  
CONECT   13    1    4   11                                                  
CONECT   14    6    7   12                                                  
CONECT   15    4    8   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   19                                                       
CONECT   18   16   20                                                       
CONECT   19   17   21                                                       
CONECT   20   18   21                                                       
CONECT   21   19   20                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
Benzoyl glucuronide (benzoate)	Generator
Benzoyl glucuronide	HMDB
(2S,3S,4S,5R,6S)-6-(Benzoyloxy)-3,4,5-trihydroxyoxane-2-carboxylate	HMDB

Chemical Formula

C₁₃H₁₄O₈

Average Mass

298.2455 Da

Monoisotopic Mass

298.06887 Da

IUPAC Name

(2S,3S,4S,5R,6S)-6-(benzoyloxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-6-(benzoyloxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C13H14O8/c14-7-8(15)10(11(17)18)20-13(9(7)16)21-12(19)6-4-2-1-3-5-6/h1-5,7-10,13-16H,(H,17,18)/t7-,8-,9+,10-,13-/m0/s1

InChI Key

NLOPFVNXNMEEDI-UNLLLRGISA-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

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glucuronides

Alternative Parents

Substituents

1-o-glucuronide
O-glucuronide
Hexose monosaccharide
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Beta-hydroxy acid
Pyran
Monocyclic benzene moiety
Oxane
Benzenoid
Monosaccharide
Hydroxy acid
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organoheterocyclic compound
Acetal
Polyol
Carboxylic acid
Oxacycle
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	-0.68	ALOGPS
logP	-0.12	ChemAxon
logS	-0.99	ALOGPS
pKa (Strongest Acidic)	3.12	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	65.61 m³·mol⁻¹	ChemAxon
Polarizability	27.3 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

HMDB0010324

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB027476

KNApSAcK ID

Not Available

Chemspider ID

103031

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

115145

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Benzoyl glucuronide (NP0090879)

MOL for NP0090879 (Benzoyl glucuronide)

3D MOL for NP0090879 (Benzoyl glucuronide)

3D SDF for NP0090879 (Benzoyl glucuronide)

3D-SDF for NP0090879 (Benzoyl glucuronide)

PDB for NP0090879 (Benzoyl glucuronide)

3D PDB for NP0090879 (Benzoyl glucuronide)

SMILES for NP0090879 (Benzoyl glucuronide)

INCHI for NP0090879 (Benzoyl glucuronide)

Structure for NP0090879 (Benzoyl glucuronide)

3D Structure for NP0090879 (Benzoyl glucuronide)