NP-MRD: Showing NP-Card for d-glucopyranuronic acid (NP0292599)

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Record Information

Version

2.0

Created at

2022-09-10 00:12:21 UTC

Updated at

2022-09-10 00:12:22 UTC

NP-MRD ID

NP0292599

Secondary Accession Numbers

None

Natural Product Identification

Common Name

d-glucopyranuronic acid

Description

D-glucopyranuronate, also known as glucuronate or glucuronic acid, belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. D-glucopyranuronate is an extremely weak basic (essentially neutral) compound (based on its pKa). D-glucopyranuronate exists in all living organisms, ranging from bacteria to humans. Outside of the human body, D-glucopyranuronate has been detected, but not quantified in, several different foods, such as horseradish tree, dandelions, peachs, almonds, and corns. This could make D-glucopyranuronate a potential biomarker for the consumption of these foods. d-glucopyranuronic acid is found in Astragalus brachycarpus, Chlamydomonas reinhardtii, Codonopsis pilosula, Medicago lupulina, Ramalina fraxinea, Suaeda aegyptiaca, Symplocos tinctoria and Vachellia tortuosa. d-glucopyranuronic acid was first documented in 1974 (PMID: 16658890). A D-glucopyranuronate in cyclic pyranose form (PMID: 1276) (PMID: 17440709) (PMID: 19093370) (PMID: 6814425).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652310111707472D          

 18 18  0  0  1  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  4  5  1  1  0  0  0
  6  3  1  0  0  0  0
  1  7  1  6  0  0  0
  2  8  1  1  0  0  0
  3  9  1  1  0  0  0
 10  5  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  4  1  0  0  0  0
 13  6  1  0  0  0  0
  1 14  1  1  0  0  0
  2 15  1  6  0  0  0
  3 16  1  6  0  0  0
  4 17  1  1  0  0  0
 18  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0292599

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1(O)O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2-,3+,4-,6?/m0/s1

> <INCHI_KEY>
AEMOLEFTQBMNLQ-AQKNRBDQSA-N

> <FORMULA>
C6H10O7

> <MOLECULAR_WEIGHT>
194.1394

> <EXACT_MASS>
194.042652674

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
16.423258944666845

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.30

> <JCHEM_LOGP>
-2.61226468

> <ALOGPS_LOGS>
0.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.309229286068723

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2077910586517073

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6863365702254773

> <JCHEM_POLAR_SURFACE_AREA>
127.45

> <JCHEM_REFRACTIVITY>
35.7908

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.95e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
D-glucopyranuronic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-OCT-17         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  H   UNK     0       2.667   3.080   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0       0.000   3.080   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0      -0.000  -1.540   0.000  0.00  0.00           H+0
CONECT    1    2    3    7   14                                             
CONECT    2    1    4    8   15                                             
CONECT    3    1    6    9   16                                             
CONECT    4    2    5   13   17                                             
CONECT    5    4   10   11                                                  
CONECT    6    3   12   13   18                                             
CONECT    7    1                                                            
CONECT    8    2                                                            
CONECT    9    3                                                            
CONECT   10    5                                                            
CONECT   11    5                                                            
CONECT   12    6                                                            
CONECT   13    4    6                                                       
CONECT   14    1                                                            
CONECT   15    2                                                            
CONECT   16    3                                                            
CONECT   17    4                                                            
CONECT   18    6                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
D-Glucuronic acid	ChEBI
Glucuronate	ChEBI
Glucuronic acid	ChEBI
D-Glucuronate	Generator
D-Glucopyranuronic acid	Generator
Glucuronate, monopotassium	MeSH
Glucuronic acid, monosodium salt	MeSH
Monopotassium glucuronate	MeSH
Glucuronate, monosodium	MeSH
Glucuronic acid, 6-(14)C-labeled, (D)-isomer	MeSH
Glucuronic acid, monopotassium salt	MeSH
Monosodium glucuronate	MeSH

Chemical Formula

C₆H₁₀O₇

Average Mass

194.1394 Da

Monoisotopic Mass

194.04265 Da

IUPAC Name

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

Traditional Name

D-glucopyranuronic acid

CAS Registry Number

Not Available

SMILES

[H]C1(O)O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O

InChI Identifier

InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2-,3+,4-,6?/m0/s1

InChI Key

AEMOLEFTQBMNLQ-AQKNRBDQSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Astragalus brachycarpus	LOTUS Database	35616633
Chlamydomonas reinhardtii	LOTUS Database	35616633
Codonopsis pilosula	LOTUS Database	35616633
Medicago lupulina	LOTUS Database	35616633
Ramalina fraxinea	LOTUS Database	35616633
Suaeda aegyptiaca	LOTUS Database	35616633
Symplocos tinctoria	LOTUS Database	35616633
Vachellia tortuosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Glucuronic acid derivatives

Alternative Parents

Substituents

Glucuronic acid or derivatives
Beta-hydroxy acid
Hydroxy acid
Pyran
Monosaccharide
Oxane
Hemiacetal
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Polyol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-glucuronic acid (CHEBI:47952 )
Uronic acids (C00191 )

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	-2.3	ALOGPS
logP	-2.6	ChemAxon
logS	0.18	ALOGPS
pKa (Strongest Acidic)	3.21	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.45 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	35.79 m³·mol⁻¹	ChemAxon
Polarizability	16.42 Å³	ChemAxon
Number of Rings	1	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

HMDB0187523

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB006716

KNApSAcK ID

C00001123

Chemspider ID

Not Available

KEGG Compound ID

C00191

BioCyc ID

D-Glucopyranuronate

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

94715

PDB ID

Not Available

ChEBI ID

47952

Good Scents ID

Not Available

References

General References

Puhakainen E, Hanninen O: Pyrophosphatase and glucuronosyltransferase in microsomal UDPglucuronic-acid metabolism in the rat liver. Eur J Biochem. 1976 Jan 2;61(1):165-9. doi: 10.1111/j.1432-1033.1976.tb10007.x. [PubMed:1276 ]
Loewus MW, Loewus F: myo-Inositol 1-Phosphate Synthase Inhibition and Control of Uridine Diphosphate-d-glucuronic Acid Biosynthesis in Plants. Plant Physiol. 1974 Sep;54(3):368-71. doi: 10.1104/pp.54.3.368. [PubMed:16658890 ]
Spanikova S, Polakova M, Joniak D, Hirsch J, Biely P: Synthetic esters recognized by glucuronoyl esterase from Schizophyllum commune. Arch Microbiol. 2007 Aug;188(2):185-9. doi: 10.1007/s00203-007-0241-x. Epub 2007 Apr 18. [PubMed:17440709 ]
Danilets MG, Bel'skii IuP, Bel'skaia NF, Trofimova ES, Uchasova EG, Ligacheva AA, Agafonov VI: [Antiallergic effect of D-glucuronic acid]. Eksp Klin Farmakol. 2008 Sep-Oct;71(5):37-9. [PubMed:19093370 ]
Daly AK, Mantle TJ: The kinetic mechanism of the major form of ox kidney aldehyde reductase with D-glucuronic acid. Biochem J. 1982 Aug 1;205(2):381-8. doi: 10.1042/bj2050381. [PubMed:6814425 ]
LOTUS database [Link]

Showing NP-Card for d-glucopyranuronic acid (NP0292599)

MOL for NP0292599 (d-glucopyranuronic acid)

3D MOL for NP0292599 (d-glucopyranuronic acid)

3D SDF for NP0292599 (d-glucopyranuronic acid)

3D-SDF for NP0292599 (d-glucopyranuronic acid)

PDB for NP0292599 (d-glucopyranuronic acid)

3D PDB for NP0292599 (d-glucopyranuronic acid)

SMILES for NP0292599 (d-glucopyranuronic acid)

INCHI for NP0292599 (d-glucopyranuronic acid)

Structure for NP0292599 (d-glucopyranuronic acid)

3D Structure for NP0292599 (d-glucopyranuronic acid)