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| Record Information |
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| Version | 4.0 |
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| Status | Detected and Quantified |
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| Creation Date | 2005-11-16 15:48:42 UTC |
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| Update Date | 2020-02-26 21:21:52 UTC |
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| HMDB ID | HMDB0000127 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | D-Glucuronic acid |
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| Description | Glucuronic acid is a carboxylic acid that has the structure of a glucose molecule that has had its sixth carbon atom (of six total) oxidized. The salts of glucuronic acid are known as glucuronates. Glucuronic acid is highly soluble in water. In humans, glucuronic acid is often linked to toxic or poisonous substances to allow for subsequent elimination, and to hormones to allow for easier transport. These linkages involve O-glycosidic bonds. The process is known as glucuronidation, and the resulting substances are known as glucuronides (or glucuronosides). Glucuronidation uses UDP-glucuronic acid (glucuronic acid linked via a glycosidic bond to uridine diphosphate) as an intermediate. UDP-glucuronic acid is formed in the liver of all animals. |
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| Structure | |
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| Synonyms | | Value | Source |
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| GlcAa | ChEBI | | GlcAalpha | ChEBI | | D-Glucuronate | Generator | | alpha-D-Glucopyranuronic acid | HMDB | | alpha-D-Glucuronic acid | HMDB | | alpha-delta-Glucopyranuronic acid | HMDB | | alpha-delta-Glucuronic acid | HMDB | | D-(+)-Glucuronate | HMDB | | D-(+)-Glucuronic acid | HMDB | | delta-(+)-Glucuronate | HMDB | | delta-(+)-Glucuronic acid | HMDB | | delta-Glucuronate | HMDB | | GCU | HMDB | | Glucosiduronate | HMDB | | Glucosiduronic acid | HMDB | | Glucuronate | HMDB | | Glucuronic acid | HMDB |
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| Chemical Formula | C6H10O7 |
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| Average Molecular Weight | 194.1394 |
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| Monoisotopic Molecular Weight | 194.042652674 |
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| IUPAC Name | (2S,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid |
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| Traditional Name | glucuronic acid |
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| CAS Registry Number | 6556-12-3 |
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| SMILES | O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O |
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| InChI Identifier | InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2-,3+,4-,6-/m0/s1 |
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| InChI Key | AEMOLEFTQBMNLQ-WAXACMCWSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organic oxygen compounds |
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| Class | Organooxygen compounds |
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| Sub Class | Carbohydrates and carbohydrate conjugates |
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| Direct Parent | Glucuronic acid derivatives |
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| Alternative Parents | |
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| Substituents | - Glucuronic acid or derivatives
- Beta-hydroxy acid
- Hydroxy acid
- Pyran
- Monosaccharide
- Oxane
- Hemiacetal
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Polyol
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Alcohol
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Disposition | Route of exposure: Source: Biological location: |
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| Process | Naturally occurring process: |
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| Role | Biological role: |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 143 - 144 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 485 mg/mL | Not Available | | LogP | -2.57 | HANSCH,C ET AL. (1995) |
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| Predicted Properties | |
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| Spectra |
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| | Spectrum Type | Description | Splash Key | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a6s-5900000000-4145d7dbe91803d8047f | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive | splash10-000l-6242950000-7b610ed98440b47c2a32 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-0h9c-7900000000-36121a46a2890d86232e | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-0ab9-9000000000-8c30084b43ecb0cf7818 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004j-0900000000-580b96de2b78621ac645 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-056s-1900000000-5b29218582cf3ee829fd | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4r-9400000000-2aa876e0cbcc0ef3bddf | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0007-0900000000-5e77c9eef959f8dfe0bf | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0035-3900000000-97b32d589162947b3a11 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9100000000-23aa5a5d3545ff8b0f90 | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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| Biological Properties |
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| Cellular Locations | - Cytoplasm
- Lysosome
- Endoplasmic reticulum
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| Biospecimen Locations | |
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| Tissue Locations | |
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| Pathways | |
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| Normal Concentrations |
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| Blood | Detected and Quantified | 165.0 +/- 32.0 uM | Adult (>18 years old) | Male | Normal | | details | | Blood | Detected and Quantified | 165.0 +/- 23.0 uM | Adult (>18 years old) | Female | Normal | | details | | Feces | Detected but not Quantified | | Infant (0-1 year old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Not Specified | Not Specified | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Not Specified | Not Specified | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 9.7 (3.7-20.6) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 36.07-453.51 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 125.0 +/- 30.0 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | | Urine | Detected and Quantified | 3.0 (1.38-5.00) umol/mmol creatinine | Children (1-13 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 33.82 +/- 20.95 umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | | Urine | Detected and Quantified | 5.9 umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | | Urine | Detected and Quantified | 30.5 umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | | Urine | Detected and Quantified | 144.7 +/- 27.0 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details |
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| Abnormal Concentrations |
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| Feces | Detected but not Quantified | | Not Specified | Not Specified | Cryptosporidium infection | | details | | Urine | Detected but not Quantified | | Adult (>18 years old) | Both | Bladder cancer | | details |
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| Associated Disorders and Diseases |
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| Disease References | None |
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| Associated OMIM IDs | None |
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| External Links |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FoodDB ID | FDB021897 |
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| KNApSAcK ID | C00001123 |
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| Chemspider ID | 392615 |
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| KEGG Compound ID | C00191 |
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| BioCyc ID | Not Available |
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| BiGG ID | 34196 |
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| Wikipedia Link | Glucuronic acid |
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| METLIN ID | 161 |
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| PubChem Compound | 444791 |
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| PDB ID | Not Available |
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| ChEBI ID | 42717 |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| References |
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| Synthesis Reference | Hamayasu, Kenichi; Tadokoro, Hiroki; Kishino, Eriko; Ito, Tetsuya; Fujita, Koki; Hara, Kozo. Preparation of glucuronic acid and/or glucuronolactone from sucrose. PCT Int. Appl. (2006), 21pp. |
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| Material Safety Data Sheet (MSDS) | Download (PDF) |
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| General References | - Jowett TP, Slater JD: A radioimmunoassay for the measurement of tetrahydroaldosterone 3-glucosiduronic acid in human plasma. Clin Chim Acta. 1981 Jan 22;109(2):133-44. [PubMed:7193539 ]
- Schmitt G, Aderjan R, Keller T, Wu M: Ethyl glucuronide: an unusual ethanol metabolite in humans. Synthesis, analytical data, and determination in serum and urine. J Anal Toxicol. 1995 Mar-Apr;19(2):91-4. [PubMed:7769794 ]
- Karasawa E: [Supplementary findings on urinary glucuronic acid excretion in pediatrics. I. Total glucuronic acid in 24-hour urine of normal infants determined by the modified Fishman's method with NaBH4]. Nihon Shonika Gakkai Zasshi. 1968 Aug 1;72(8):1122-7. [PubMed:5755643 ]
- Carpenter PC, Mattox VR: Isolation, determination of structure and synthesis of the acid-labile conjugate of aldosterone. Biochem J. 1976 Jul 1;157(1):1-14. [PubMed:962850 ]
- Raju U, Sklarew RJ, Post J, Levitz M: Steroid metabolism in human breast cancer cell lines. Steroids. 1978 Dec;32(5):669-80. [PubMed:734701 ]
- Stearns RA, Miller RR, Doss GA, Chakravarty PK, Rosegay A, Gatto GJ, Chiu SH: The metabolism of DuP 753, a nonpeptide angiotensin II receptor antagonist, by rat, monkey, and human liver slices. Drug Metab Dispos. 1992 Mar-Apr;20(2):281-7. [PubMed:1352222 ]
- Little JM, St Pyrek J, Lester R: Hepatic metabolism of 3 alpha-hydroxy-5 beta-etianic acid (3 alpha-hydroxy-5 beta-androstan-17 beta-carboxylic acid) in the adult rat. J Clin Invest. 1983 Jan;71(1):73-80. [PubMed:6848561 ]
- Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
- Pfeiffer E, Graf E, Gerstner S, Metzler M: Stimulation of estradiol glucuronidation: a protective mechanism against estradiol-mediated carcinogenesis? Mol Nutr Food Res. 2006 Apr;50(4-5):385-9. [PubMed:16598814 ]
- McDonagh AF, Palma LA, Lauff JJ, Wu TW: Origin of mammalian biliprotein and rearrangement of bilirubin glucuronides in vivo in the rat. J Clin Invest. 1984 Sep;74(3):763-70. [PubMed:6470139 ]
- Murano PS, Robichaud VY, Webb RE: Urinary excretion of sulfate and glucuronate conjugates in a free living population of adult males. Bull Environ Contam Toxicol. 1989 Jul;43(1):13-6. [PubMed:2758129 ]
- Nishida T, Gatmaitan Z, Roy-Chowdhry J, Arias IM: Two distinct mechanisms for bilirubin glucuronide transport by rat bile canalicular membrane vesicles. Demonstration of defective ATP-dependent transport in rats (TR-) with inherited conjugated hyperbilirubinemia. J Clin Invest. 1992 Nov;90(5):2130-5. [PubMed:1430236 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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