Record Information
Version1.0
Creation Date2016-05-25 21:06:25 UTC
Update Date2016-11-09 01:17:43 UTC
Accession NumberCHEM023507
Identification
Common NameD-Glucaric acid
ClassSmall Molecule
DescriptionThe D-enantiomer of glucaric acid.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
Synonyms
ValueSource
D-(+)-Saccharic acidChEBI
D-Glucosaccharic acidChEBI
D-Saccharic acidChEBI
L-Gularic acidChEBI
Saccharic acidChEBI
D-Glucaric acidKegg
GlucarateKegg
D-(+)-SaccharateGenerator
D-GlucosaccharateGenerator
D-SaccharateGenerator
L-GularateGenerator
SaccharateGenerator
D-GlucarateGenerator
Acid, saccharicMeSH
Anhydrous calcium glucarateMeSH
Anhydrous calcium saccharateMeSH
Calcium glucarateMeSH
Calcium glucarate, anhydrousMeSH
Calcium saccharateMeSH
Calcium saccharate anhydrousMeSH
Calcium saccharate tetrahydrateMeSH
Calcium saccharate, anhydrousMeSH
D Glucaric acidMeSH
D Saccharic acidMeSH
Glucarate, anhydrous calciumMeSH
Glucarate, calciumMeSH
Glucosaccharic acidMeSH
L Gularic acidMeSH
Levo gularic acidMeSH
Levo-gularic acidMeSH
Saccharate tetrahydrate, calciumMeSH
Saccharate, anhydrous calciumMeSH
Saccharate, calciumMeSH
Tetrahydrate, calcium saccharateMeSH
Tetrahydroxyadipic acidMeSH
(2R,3S,4S,5S)-2,3,4,5-TetrahydroxyhexanedioateHMDB
(2R,3S,4S,5S)-2,3,4,5-Tetrahydroxyhexanedioic acidHMDB
D-TetrahydroxyadipateHMDB
D-Tetrahydroxyadipic acidHMDB
DL-Glucaric acidHMDB
GKRHMDB
Chemical FormulaC6H10O8
Average Molecular Mass210.139 g/mol
Monoisotopic Mass210.038 g/mol
CAS Registry Number87-73-0
IUPAC Name(2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioic acid
Traditional Namesaccharic acid
SMILESOC(C(O)C(O)C(O)=O)C(O)C(O)=O
InChI IdentifierInChI=1S/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14)
InChI KeyDSLZVSRJTYRBFB-UHFFFAOYSA-N
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
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Hydroxy fatty acid
  • Monosaccharide
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Alpha-hydroxy acid
  • Fatty acyl
  • Fatty acid
  • Secondary alcohol
  • Polyol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility63.1 g/LALOGPS
logP-1.8ALOGPS
logP-3.1ChemAxon
logS-0.52ALOGPS
pKa (Strongest Acidic)2.83ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area155.52 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.14 m³·mol⁻¹ChemAxon
Polarizability16.8 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00kb-0951000000-900f03a7c305b77327a7Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0931000000-0b5da9d9795e377e2131Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-000w-0934000000-065f1d82bf37b3646812Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-000t-0933000000-88564b1ce0ddb6a8ab41Spectrum
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-001l-0988100000-b295a3efe00c6ac42fb9Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000w-0934000000-065f1d82bf37b3646812Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001l-0988100000-b295a3efe00c6ac42fb9Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000t-0923000000-6490a1c6d0dfb83df0a3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05bf-9400000000-5d870077c657dc484d46Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (6 TMS) - 70eV, Positivesplash10-00b9-6011394000-83b916b3001ad13cf34dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_14) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_5_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_6_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Glucaric acid,4TBDMS,#14" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-4290000000-dff4fd55a904d215586aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0abi-9000000000-178202e29014c0d1d594Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0ab9-9000000000-c6d132cfd1374248952dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4i-0390000000-f3fdb1545009312f6a25Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9620000000-1bde5d31aa638eab1df1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-052r-9000000000-fcfaa9b35c8d204ab0ecSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0ab9-9000000000-20e03e65e2d34a86ffbaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0ab9-9000000000-dd03e436136ea5ad38c4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0390000000-f3fdb1545009312f6a25Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9620000000-1bde5d31aa638eab1df1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-052r-9000000000-fcfaa9b35c8d204ab0ecSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0ab9-9000000000-20e03e65e2d34a86ffbaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0ab9-9000000000-dd03e436136ea5ad38c4Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-000i-9310000000-bd910793555bb11fd037Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-2960000000-b147e30a08581da98464Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-059i-9000000000-613b85fa3c0d461986b3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-9310000000-ede1713559571675b04dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-9530000000-87fcd3003f686bddb999Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-05fu-9000000000-7fa748efe187f8a95a86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-2950000000-4213fb06e5d54a446f19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a70-8900000000-1c5b1e57a901b2c85510Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9200000000-3d6d232455d3bf96a461Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-8920000000-a1393eb5fa869e7c23f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9600000000-8c43d68278949dbece7fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ar9-9300000000-98861fb518fdc09acc58Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB03603
HMDB IDHMDB0000663
FooDB IDFDB022169
Phenol Explorer IDNot Available
KNApSAcK IDC00052287
BiGG ID35926
BioCyc IDD-GLUCARATE
METLIN ID5633
PDB IDNot Available
Wikipedia LinkSaccharic_acid
Chemspider ID30577
ChEBI ID16002
PubChem Compound ID33037
Kegg Compound IDC00818
YMDB IDNot Available
ECMDB IDECMDB24171
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=18384797
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21269605
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24333274
4. Bamba, K.; Kokoh, K. B.; Servat, K.; Leger, J.-M. Electrocatalytic oxidation of monosaccharides on platinum electrodes modified by thallium adatoms in carbonate buffered medium. Journal of Applied Electrochemistry (2006), 36(2), 233-238.
5. Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.
6. Bamba, K.; Kokoh, K. B.; Servat, K.; Leger, J.-M. Electrocatalytic oxidation of monosaccharides on platinum electrodes modified by thallium adatoms in carbonate buffered medium. Journal of Applied Electrochemistry (2006), 36(2), 233-238.
7. Matsushiro T, Suzuki N, Sato T, Maki T: Effects of diet on glucaric acid concentration in bile and the formation of calcium bilirubinate gallstones. Gastroenterology. 1977 Apr;72(4 Pt 1):630-3.
8. Roth B, Heimann G, Gladtke E: [Excretion of D-glucaric-acid in newborns with non-hemolytic hyperbilirubinemia after phenobarbital treatment (author's transl)]. Padiatr Padol. 1977;12(4):385-93.
9. Sorrell MF, Burnett DA, Tuma DJ, Barak AJ: Paradoxical urinary excretion of D-glucaric acid in acute viral hepatitis. Clin Pharmacol Ther. 1976 Sep;20(3):365-8.
10. Levy G, Khanna NN, Soda DM, Tsuzuki O, Stern L: Pharmacokinetics of acetaminophen in the human neonate: formation of acetaminophen glucuronide and sulfate in relation to plasma bilirubin concentration and D-glucaric acid excretion. Pediatrics. 1975 Jun;55(6):818-25.
11. Traeger A, Horvath T, Rechenbach C, Javor T: Beta-adrenoceptor blocking drugs and cytochrome P-450: the influence of propranolol treatment on caffeine, antipyrine, D-glucaric acid and indocyanine green elimination in patients with hepatic disorders. Int J Clin Pharmacol Res. 1986;6(3):235-9.
12. Herzberg M, Tenenbaum E, Fishel B, Wiener MH: D-Glucaric acid and gamma-glutamyltransferase as indices of hepatic enzyme induction in pregnancy. Clin Chem. 1977 Mar;23(3):596-8.
13. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762.
14. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.