Read more...Show more...Show more...
Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-01-17 18:03:20 UTC
NP-MRD IDNP0001332
Secondary Accession NumbersNone
Natural Product Identification
Common NameGluconic acid
Description
Structure
Thumb
Synonyms
Chemical FormulaC6H12O7
Average Mass196.1553 Da
Monoisotopic Mass196.05830 Da
IUPAC Name(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid
Traditional Namegluconate
CAS Registry Number526-95-4
SMILES
OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O
InChI Identifier
InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3-,4+,5-/m1/s1
InChI KeyRGHNJXZEOKUKBD-SQOUGZDYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-01-17View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar acids and derivatives
Alternative Parents
Substituents
  • Gluconic_acid
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Fatty acyl
  • Fatty acid
  • Hydroxy acid
  • Monosaccharide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Polyol
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Carbonyl group
  • Primary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point113 - 118 °CNot Available
Boiling Point673.59 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility316 mg/mL at 25 °CMaynard, R. L. (1997). The Merck Index: 1996. Occupational and Environmental Medicine, 54(4), 288.
LogP-2.116 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility159 g/LALOGPS
logP-2.6ALOGPS
logP-3.4ChemAxon
logS-0.09ALOGPS
pKa (Strongest Acidic)3.39ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area138.45 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.27 m³·mol⁻¹ChemAxon
Polarizability17.15 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000625
DrugBank IDDB13180
Phenol Explorer Compound IDNot Available
FoodDB IDFDB020175
KNApSAcK IDC00007303
Chemspider ID10240
KEGG Compound IDC00257
BioCyc IDGLUCONATE
BiGG IDNot Available
Wikipedia LinkGluconic_acid
METLIN ID345
PubChem Compound10690
PDB IDNot Available
ChEBI ID33198
Good Scents IDrw1233821
References
General References
  1. Harkness RA, Purkiss P, Duffy S, Chalmers RA, Jones M: The effects of fetal energy depletion on amniotic fluid concentrations of amino acids, organic acids and related metabolites. J Inherit Metab Dis. 1988;11(1):103-13. [PubMed:3128683 ]
  2. Marcincinova-Benabdillah K, Boustta M, Coudane J, Vert M: Novel degradable polymers combining D-gluconic acid, a sugar of vegetal origin, with lactic and glycolic acids. Biomacromolecules. 2001 Winter;2(4):1279-84. doi: 10.1021/bm015585j. [PubMed:11777404 ]
  3. Kripal R, Singh P, Govind H: EPR and optical absorption studies of Cr3+ ions in d-gluconic acid monohydrate. Spectrochim Acta A Mol Biomol Spectrosc. 2009 Oct 1;74(2):357-62. doi: 10.1016/j.saa.2009.06.006. Epub 2009 Jun 16. [PubMed:19577953 ]
  4. Rohatgi N, Nielsen TK, Bjorn SP, Axelsson I, Paglia G, Voldborg BG, Palsson BO, Rolfsson O: Biochemical characterization of human gluconokinase and the proposed metabolic impact of gluconic acid as determined by constraint based metabolic network analysis. PLoS One. 2014 Jun 4;9(6):e98760. doi: 10.1371/journal.pone.0098760. eCollection 2014. [PubMed:24896608 ]
  5. Zhang H, Saravanan KM, Yang Y, Hossain MT, Li J, Ren X, Pan Y, Wei Y: Deep Learning Based Drug Screening for Novel Coronavirus 2019-nCov. Interdiscip Sci. 2020 Sep;12(3):368-376. doi: 10.1007/s12539-020-00376-6. Epub 2020 Jun 1. [PubMed:32488835 ]