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Showing NP-Card for glucuronic acid (NP0160685)

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Record Information
Version2.0
Created at2022-09-02 18:41:26 UTC
Updated at2022-09-02 18:41:26 UTC
NP-MRD IDNP0160685
Secondary Accession NumbersNone
Natural Product Identification
Common Nameglucuronic acid
Description2,3,4,5-Tetrahydroxy-6-oxohexanoic 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. glucuronic acid is found in Abutilon indicum and Afraegle paniculata. 2,3,4,5-Tetrahydroxy-6-oxohexanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0160685 (glucuronic acid)


  Mrv1652305171804082D          

 13 12  0  0  0  0            999 V2000
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 11  1  0  0  0  0
M  END
Download

3D MOL for NP0160685 (glucuronic acid)

     RDKit          3D

 23 22  0  0  0  0  0  0  0  0999 V2000
    2.8265    1.7161    1.1576 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6256    0.6547    0.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9366    0.6193   -0.6745 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6128    1.8879   -1.0991 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7602   -0.3217   -0.7025 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1370   -1.5781   -0.2684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3797    0.1535    0.1615 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8532    1.3885   -0.1590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4278   -0.9296    0.1962 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0785   -1.1211   -0.9875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3671   -0.7493    1.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9852   -0.5611    2.5119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7200   -0.7975    1.0699 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9431   -0.2528    1.0919 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6804    0.1926   -1.4108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4331    2.3485   -1.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3875   -0.3591   -1.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1567   -1.6388    0.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0361    0.2106    1.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8546    1.6218   -1.1123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8701   -1.8826    0.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7492   -0.6279   -1.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2500    0.0262    0.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 13  1  0
 11 12  2  0
  4 16  1  0
  3 15  1  6
  2 14  1  0
  5 17  1  6
  6 18  1  0
  7 19  1  1
  8 20  1  0
  9 21  1  1
 10 22  1  0
 13 23  1  0
M  END
Download

3D SDF for NP0160685 (glucuronic acid)


  Mrv1652305171804082D          

 13 12  0  0  0  0            999 V2000
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0160685

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(C=O)C(O)C(O)C(O)C(O)=O

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

> <INCHI_KEY>
IAJILQKETJEXLJ-UHFFFAOYSA-N

> <FORMULA>
C6H10O7

> <MOLECULAR_WEIGHT>
194.139

> <EXACT_MASS>
194.042652662

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
16.206710780318033

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3,4,5-tetrahydroxy-6-oxohexanoic acid

> <ALOGPS_LOGP>
-2.32

> <JCHEM_LOGP>
-3.248086025

> <ALOGPS_LOGS>
-0.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.262057101736255

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.237887361089809

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6897568428527263

> <JCHEM_POLAR_SURFACE_AREA>
135.29

> <JCHEM_REFRACTIVITY>
37.213

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.00e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glucuronic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0160685 (glucuronic acid)

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PDB for NP0160685 (glucuronic acid)
HEADER    PROTEIN                                 17-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-MAY-18         0                                  
HETATM    1  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.620   1.127   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.953   2.667   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.954   4.977   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.287   1.127   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.621   4.977   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
CONECT    1    2    3    5                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3                                                            
CONECT    5    1    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

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3D PDB for NP0160685 (glucuronic acid)
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SMILES for NP0160685 (glucuronic acid)
OC(C=O)C(O)C(O)C(O)C(O)=O
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INCHI for NP0160685 (glucuronic acid)
InChI=1S/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h1-5,8-11H,(H,12,13)
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View in JSmol
Synonyms
ValueSource
2,3,4,5-Tetrahydroxy-6-oxohexanoateGenerator
Aldehydo-L-iduronic acidGenerator
HexuronateGenerator
(D)-Galacturonic acidMeSH
Galacturonic acid, (alpha-D)-isomerMeSH
DL-Galacturonic acidMeSH
Galacturonic acid, (D)-isomerMeSH
Galacturonic acidMeSH
D-Galacturonic acidMeSH
Galacturonic acid, calcium, sodium salt, (D)-isomerMeSH
Galacturonic acid, monosodium salt, (D)-isomerMeSH
(DL)-Galacturonic acidMeSH
Chemical FormulaC6H10O7
Average Mass194.1390 Da
Monoisotopic Mass194.04265 Da
IUPAC Name2,3,4,5-tetrahydroxy-6-oxohexanoic acid
Traditional Nameglucuronic acid
CAS Registry NumberNot Available
SMILES
OC(C=O)C(O)C(O)C(O)C(O)=O
InChI Identifier
InChI=1S/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h1-5,8-11H,(H,12,13)
InChI KeyIAJILQKETJEXLJ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abutilon indicumLOTUS Database
Afraegle paniculataLOTUS Database
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.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbohydrates and carbohydrate conjugates  
Direct ParentGlucuronic acid derivatives  
Alternative Parents
Substituents
  • Glucuronic acid or derivatives
    • 

  • Hexose monosaccharide
    • 

  • Medium-chain hydroxy acid
    • 

  • Medium-chain fatty acid
    • 

  • Beta-hydroxy acid
    • 

  • Hydroxy fatty acid
    • 

  • Monosaccharide
    • 

  • Fatty acyl
    • 

  • Hydroxy acid
    • 

  • Fatty acid
    • 

  • Alpha-hydroxy acid
    • 

  • Beta-hydroxy aldehyde
    • 

  • Alpha-hydroxyaldehyde
    • 

  • Secondary alcohol
    • 

  • Polyol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Aldehyde
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.3ALOGPS
logP-3.2ChemAxon
logS-0.29ALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area135.29 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.21 m³·mol⁻¹ChemAxon
Polarizability16.21 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0062783  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound152867  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]