NP-MRD: Showing NP-Card for beta-D-Glucopyranuronic acid (NP0044226)

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Record Information

Version

1.0

Created at

2022-01-20 19:24:34 UTC

Updated at

2022-01-20 19:31:33 UTC

NP-MRD ID

NP0044226

Secondary Accession Numbers

None

Natural Product Identification

Common Name

beta-D-Glucopyranuronic acid

Description

Beta-D-glucuronic acid is also known as glcab or b-D-glucopyranuronate. Beta-D-glucuronic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. It was first documented in 2018 (PMID: 29497885). Based on a literature review a significant number of articles have been published on beta-D-glucuronic acid (PMID: 33788276) (PMID: 33777530) (PMID: 32961208) (PMID: 32805285).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
   -3.9639   -0.7063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7833    0.2190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9942    1.7041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3917   -0.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0820    1.1268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3440    1.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    2.5176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4601    0.5903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8517    0.0304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1504   -0.8774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3613   -2.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2755   -1.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4562   -2.2682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3858    2.2639    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1847   -1.6142    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3622    2.9158    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3137    4.0027    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2532    1.8635    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0324    0.9556    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6496   -0.9275    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7529   -2.9224    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4306   -2.6664    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2452   -3.7533    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12  4  1  0
  3 14  1  0
  4 15  1  6
  6 16  1  6
  7 17  1  0
  8 18  1  1
  9 19  1  0
 10 20  1  6
 11 21  1  0
 12 22  1  1
 13 23  1  0
M  END
> <DATABASE_ID>
NP0044226

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(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-QIUUJYRFSA-N

> <FORMULA>
C6H10O7

> <MOLECULAR_WEIGHT>
194.1394

> <EXACT_MASS>
194.042652674

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
16.370003221948352

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6R)-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>
3.207791058651709

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6863365702254773

> <JCHEM_POLAR_SURFACE_AREA>
127.45000000000002

> <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-glucuronic 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
beta-D-Glucopyranuronic acid	ChEBI
GlcAb	ChEBI
GlcAbeta	ChEBI
b-D-Glucopyranuronate	Generator
b-D-Glucopyranuronic acid	Generator
beta-D-Glucopyranuronate	Generator
Β-D-glucopyranuronate	Generator
Β-D-glucopyranuronic acid	Generator
b-D-Glucuronate	Generator
b-D-Glucuronic acid	Generator
beta-D-Glucuronate	Generator
Β-D-glucuronate	Generator
Β-D-glucuronic acid	Generator
D-Glucuronate	Generator
beta-D-Glucuronic acid	KEGG
Α-D-glucopyranuronic acid	MeSH
L-Glucopyranuronic acid	MeSH
D-Glucopyranuronic acid	MeSH
Glucopyranuronic acid	MeSH
alpha-D-Glucopyranuronic acid	MeSH

Chemical Formula

C₆H₁₀O₇

Average Mass

194.1394 Da

Monoisotopic Mass

194.04265 Da

IUPAC Name

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

Traditional Name

D-glucuronic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]1(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-QIUUJYRFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, simulated)	Ahselim			2022-01-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, experimental)	Ahselim			2022-01-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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

This compound belongs to the class of organic compounds known as glucuronic acid derivatives. These 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-glucopyranuronic acid (CHEBI:28860 )

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	16.37 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

HMDB0187524

DrugBank ID

DB03156

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Glucuronic_acid

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

28860

Good Scents ID

Not Available

References

General References

Muderrisoglu C, Sargin S, Yesil-Celiktas O: Application of beta-glucuronidase-immobilised silica gel formulation to microfluidic platform for biotransformation of beta-glucuronides. Biotechnol Lett. 2018 May;40(5):773-780. doi: 10.1007/s10529-018-2530-7. Epub 2018 Mar 1. [PubMed:29497885 ]
Ngo NTN, Linares-Pasten JA, Grey C, Adlercreutz P: Synthesis of novel oligomeric anionic alkyl glycosides using laccase/TEMPO oxidation and cyclodextrin glucanotransferase (CGTase)-catalyzed transglycosylation. Biotechnol Bioeng. 2021 Jul;118(7):2548-2558. doi: 10.1002/bit.27770. Epub 2021 May 3. [PubMed:33788276 ]
Liu R, Li H, Wei N, Tan Y: Simultaneous determination of two galangin metabolites from Alpinia Officinarum Hance in rat plasma by UF LC-MS/MS and its application in pharmacokinetics study. PeerJ. 2021 Mar 16;9:e11041. doi: 10.7717/peerj.11041. eCollection 2021. [PubMed:33777530 ]
Hertz MI, Rush A, Nutman TB, Weil GJ, Bennuru S, Budge PJ: Characterization of glycan determinants that mediate recognition of the major Wuchereria bancrofti circulating antigen by diagnostic antibodies. Mol Biochem Parasitol. 2020 Nov;240:111317. doi: 10.1016/j.molbiopara.2020.111317. Epub 2020 Sep 20. [PubMed:32961208 ]
Uhliarikova I, Matulova M, Capek P: Structural features of the bioactive cyanobacterium Nostoc sp. exopolysaccharide. Int J Biol Macromol. 2020 Dec 1;164:2284-2292. doi: 10.1016/j.ijbiomac.2020.08.113. Epub 2020 Aug 15. [PubMed:32805285 ]

Showing NP-Card for beta-D-Glucopyranuronic acid (NP0044226)

MOL for NP0044226 (beta-D-Glucopyranuronic acid)

3D MOL for NP0044226 (beta-D-Glucopyranuronic acid)

3D SDF for NP0044226 (beta-D-Glucopyranuronic acid)

3D-SDF for NP0044226 (beta-D-Glucopyranuronic acid)

PDB for NP0044226 (beta-D-Glucopyranuronic acid)

3D PDB for NP0044226 (beta-D-Glucopyranuronic acid)

SMILES for NP0044226 (beta-D-Glucopyranuronic acid)

INCHI for NP0044226 (beta-D-Glucopyranuronic acid)

Structure for NP0044226 (beta-D-Glucopyranuronic acid)

3D Structure for NP0044226 (beta-D-Glucopyranuronic acid)