Human Metabolome Database: Showing metabocard for D-Glucaric acid (HMDB0029881)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

enzymes (6) Show 6 proteins

Record Information

Version

4.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:33:13 UTC

Update Date

2018-03-12 21:56:48 UTC

HMDB ID

HMDB0029881

Secondary Accession Numbers

HMDB29881

Metabolite Identification

Common Name

D-Glucaric acid

Description

Galactaric acid, also known as mucic acid or galactarate, 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. Galactaric acid exists as a solid, soluble (in water), and a moderately acidic compound (based on its pKa). Galactaric acid has been detected in multiple biofluids, such as saliva, urine, and blood. Within the cell, galactaric acid is primarily located in the cytoplasm. Galactaric acid is also a parent compound for other transformation products, including but not limited to, 2-(e)-O-feruloyl-D-galactaric acid, O-feruloylgalactaric acid, and galactaric acid derivative.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
acido Galactarico	ChEBI
acido Mucico	ChEBI
Galactarsaeure	ChEBI
Galactosaccharic acid	ChEBI
Galaktarsaeure	ChEBI
Mucic acid	ChEBI
Mucinsaeure	ChEBI
Saccharolactic acid	ChEBI
Schleimsaeure	ChEBI
Galactarate	Generator
Galactosaccharate	Generator
Mucate	Generator
Saccharolactate	Generator
(2R,3S,4R,5S)-2,3,4,5-Tetrahydroxyhexanedioate	HMDB
(2R,3S,4R,5S)-2,3,4,5-Tetrahydroxyhexanedioic acid	HMDB
D-Galactaric acid	HMDB
Hexaric acid	HMDB
meso-Galactaric acid	HMDB
Schleimsaure	HMDB
Strontium galactarate mono-hydrate	MeSH
Galactaric acid, sodium salt	MeSH

Chemical Formula

C₆H₁₀O₈

Average Molecular Weight

210.1388

Monoisotopic Molecular Weight

210.037567296

IUPAC Name

(2R,3S,4R,5S)-2,3,4,5-tetrahydroxyhexanedioic acid

Traditional Name

mucin

CAS Registry Number

87-73-0

SMILES

OC(C(O)C(O)C(O)=O)C(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)

InChI Key

DSLZVSRJTYRBFB-UHFFFAOYSA-N

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
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 Framework

Aliphatic acyclic compounds

External Descriptors

hexaric acid (CHEBI:30852 )
Dicarboxylic acids (LMFA01170107 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	125 - 126 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	63.1 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-3.1	ChemAxon
logS	-0.52	ALOGPS
pKa (Strongest Acidic)	2.83	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	155.52 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	38.14 m³·mol⁻¹	ChemAxon
Polarizability	17.14 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (6 TMS)	splash10-001l-0987000000-76d3c6748cb8a79adc39	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001l-0987000000-76d3c6748cb8a79adc39	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05bf-9400000000-b80ffbca6c943091f16e	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (6 TMS) - 70eV, Positive	splash10-00b9-6011394000-83b916b3001ad13cf34d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-052r-9260000000-16fac7d5f0f85285824d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0abi-9000000000-80a4d5a9910d243f2e48	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0abc-9000000000-144a5e96a20e3c66ca9d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0a4i-0190000000-53cb6532b098f7615896	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-052r-9430000000-7bc8b56c9c00f7aed59f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9000000000-34bca663662f41b51683	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-05fr-9000000000-c1a4fdc6f3d7d8e237aa	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-05fr-9000000000-f2f36dc0c7eca0f78710	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-052r-9240000000-c24ca4338feeca20c7f5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0190000000-53cb6532b098f7615896	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-052r-9430000000-7bc8b56c9c00f7aed59f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-34bca663662f41b51683	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-05fr-9000000000-c1a4fdc6f3d7d8e237aa	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-05fr-9000000000-f2f36dc0c7eca0f78710	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-052r-9240000000-c24ca4338feeca20c7f5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-1940000000-66a37b8eabfbc367df77	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-9700000000-ae255ce964e55a9644c5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9100000000-fa70d3c1751580028d65	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0adr-9820000000-19f2dbe53ca43b0a1195	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-9500000000-e0ce27927a6119cf1489	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ap0-9100000000-0c338926a15f642737e1	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001205

KNApSAcK ID

Not Available

Chemspider ID

2301286

KEGG Compound ID

C00879

BioCyc ID

D-GALACTARATE

BiGG ID

Not Available

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 2B4

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

Enzyme Details

2. UDP-glucuronosyltransferase 1-4

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

Enzyme Details

3. UDP-glucuronosyltransferase 2B7

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

Enzyme Details

4. UDP-glucuronosyltransferase 1-1

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

Enzyme Details

5. UDP-glucuronosyltransferase 1-9

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

Enzyme Details

6. UDP-glucuronosyltransferase 1-6

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:: UGT1A6
Uniprot ID:: P19224
Molecular weight:: 60750.215

Showing metabocard for D-Glucaric acid (HMDB0029881)

Structure for HMDB0029881 (D-Glucaric acid)

Enzymes