Record Information
Version1.0
Created at2020-03-18 23:22:26 UTC
Updated at2020-11-18 16:34:39 UTC
CannabisDB IDCDB006171
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameGlucaric acid
DescriptionGlucaric acid, also known as D-saccharic 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. Glucaric acid is very soluble in water, and relatively neutral. Glucaric acid exists in all living organisms, ranging from bacteria to humans. In mammals, D-glucaric acid is an end product of the D-glucuronic acid pathway. The glucuronic acid pathway catalyzes the conversion of glucose to glucuronic acid, ascorbic acid, and pentoses. Like the pentose phosphate pathway, this pathway provides biosynthetic precursors and inter-converts some less common sugars to ones that can be metabolized. D-glucaric acid is particularly abundant in fruits and vegetables, with the highest concentrations found in grapefruits, apples, oranges, and cruciferous vegetables. The D-glucaric acid content in fruits and vegetables ranges from about 0.1 g/kg in grapes and lettuce to about 3.5 g/kg in apples and broccoli. Glucaric acid is available as a dietary supplement in the form of calcium D-glucarate and has been studied for therapeutic purposes including cholesterol reduction and cancer chemotherapy (PMID: 12747003 ; PMID: 18772850 ). Industrially, D-glucaric acid produced from oxidizing D-glucose has been successfully utilized to produce a hydroxylated nylon, resulting in a presumably biodegradable nylon fiber. Glucaric acid’s sodium salt is used in dishwasher detergents. The acid acts as a chelating agent that ties up the hard-water calcium and magnesium ions to make the detergents more efficient. Glucaric acid is also a powerful corrosion inhibitor and is used in many applications where water contacts metal surfaces.
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 Weight210.14
Monoisotopic Molecular Weight210.0376
IUPAC Name(2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioic acid
Traditional Namesaccharic acid
CAS Registry Number25525-21-7
SMILES
O[C@@H]([C@H](O)[C@@H](O)C(O)=O)[C@H](O)C(O)=O
InChI Identifier
InChI=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)/t1-,2-,3-,4+/m0/s1
InChI KeyDSLZVSRJTYRBFB-LLEIAEIESA-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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point125-126 °CWikipedia
Boiling PointNot AvailableNot Available
Water Solubility912 mg/mLNot Available
logP6.1Wikipedia
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSGlucaric acid, non-derivatized, GC-MS Spectrumsplash10-00kb-0951000000-900f03a7c305b77327a7Spectrum
GC-MSGlucaric acid, non-derivatized, GC-MS Spectrumsplash10-0002-0931000000-0b5da9d9795e377e2131Spectrum
GC-MSGlucaric acid, non-derivatized, GC-MS Spectrumsplash10-000w-0934000000-065f1d82bf37b3646812Spectrum
GC-MSGlucaric acid, non-derivatized, GC-MS Spectrumsplash10-000t-0933000000-88564b1ce0ddb6a8ab41Spectrum
GC-MSGlucaric acid, 6 TMS, GC-MS Spectrumsplash10-001l-0988100000-b295a3efe00c6ac42fb9Spectrum
GC-MSGlucaric acid, non-derivatized, GC-MS Spectrumsplash10-000w-0934000000-065f1d82bf37b3646812Spectrum
GC-MSGlucaric acid, non-derivatized, GC-MS Spectrumsplash10-001l-0988100000-b295a3efe00c6ac42fb9Spectrum
GC-MSGlucaric acid, non-derivatized, GC-MS Spectrumsplash10-000t-0923000000-6490a1c6d0dfb83df0a3Spectrum
Predicted GC-MSGlucaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05bf-9400000000-5d870077c657dc484d46Spectrum
Predicted GC-MSGlucaric acid, 6 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00b9-6011394000-83b916b3001ad13cf34dSpectrum
Predicted GC-MSGlucaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, TBDMS_4_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, TBDMS_5_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, TBDMS_6_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, "Glucaric acid,4TBDMS,#14" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-4290000000-dff4fd55a904d215586a2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0abi-9000000000-178202e29014c0d1d5942012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0ab9-9000000000-c6d132cfd1374248952d2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4i-0390000000-f3fdb1545009312f6a252012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9620000000-1bde5d31aa638eab1df12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-052r-9000000000-fcfaa9b35c8d204ab0ec2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0ab9-9000000000-20e03e65e2d34a86ffba2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0ab9-9000000000-dd03e436136ea5ad38c42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0390000000-f3fdb1545009312f6a252017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9620000000-1bde5d31aa638eab1df12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-052r-9000000000-fcfaa9b35c8d204ab0ec2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0ab9-9000000000-20e03e65e2d34a86ffba2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0ab9-9000000000-dd03e436136ea5ad38c42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-000i-9310000000-bd910793555bb11fd0372017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-2960000000-b147e30a08581da984642017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-059i-9000000000-613b85fa3c0d461986b32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-9310000000-ede1713559571675b04d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-9530000000-87fcd3003f686bddb9992021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-05fu-9000000000-7fa748efe187f8a95a862021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-2950000000-4213fb06e5d54a446f192017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a70-8900000000-1c5b1e57a901b2c855102017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9200000000-3d6d232455d3bf96a4612017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-8920000000-a1393eb5fa869e7c23f32017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9600000000-8c43d68278949dbece7f2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ar9-9300000000-98861fb518fdc09acc582017-07-26View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, 5%_DMSO, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
4-trimethylaminobutyraldehyde dehydrogenaseALDH9A11q23.1P49189 details
Alpha-aminoadipic semialdehyde dehydrogenaseALDH7A15q31P49419 details
Aldehyde dehydrogenase, mitochondrialALDH212q24.2P05091 details
Fatty aldehyde dehydrogenaseALDH3A217p11.2P51648 details
Aldehyde dehydrogenase X, mitochondrialALDH1B19p11.1P30837 details
UDP-glucuronosyltransferase 2B4UGT2B44q13P06133 details
UDP-glucuronosyltransferase 1-4UGT1A42q37P22310 details
UDP-glucuronosyltransferase 2B7UGT2B74q13P16662 details
UDP-glucuronosyltransferase 1-1UGT1A12q37P22309 details
UDP-glucuronosyltransferase 1-9UGT1A92q37O60656 details
UDP-glucuronosyltransferase 1-6UGT1A62q37P19224 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000663
DrugBank IDDB03603
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022169
KNApSAcK IDC00052287
Chemspider ID30577
KEGG Compound IDC00818
BioCyc IDD-GLUCARATE
BiGG ID35926
Wikipedia LinkSaccharic_acid
METLIN ID5633
PubChem Compound33037
PDB IDNot Available
ChEBI ID16002
References
General References
  1. Zoltaszek R, Hanausek M, Kilianska ZM, Walaszek Z: [The biological role of D-glucaric acid and its derivatives: potential use in medicine]. Postepy Hig Med Dosw (Online). 2008 Sep 5;62:451-62. [PubMed:18772850 ]
  2. Singh J, Gupta KP: Calcium glucarate prevents tumor formation in mouse skin. Biomed Environ Sci. 2003 Mar;16(1):9-16. [PubMed:12747003 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Molecular weight:
56291.485
General function:
Involved in oxidoreductase activity
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:
UGT2B4
Uniprot ID:
P06133
Molecular weight:
60512.035
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:
UGT1A4
Uniprot ID:
P22310
Molecular weight:
60024.535
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular weight:
60720.15
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular weight:
59940.495

Only showing the first 10 proteins. There are 11 proteins in total.