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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 | 2020-11-09 23:13:22 UTC |
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HMDB ID | HMDB0000355 |
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Secondary Accession Numbers | - HMDB00355
- HMDB0059737
- HMDB59737
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Metabolite Identification |
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Common Name | 3-Hydroxymethylglutaric acid |
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Description | 3-Hydroxymethylglutaric acid is an "off-product" intermediate in the leucine degradation process. It is produced by defective or inefficient versions of 3-hydroxy-3-methylglutaryl-CoA lyase, an enzyme that normally catalyzes the conversion of 3-hydroxy-3-methylglutaryl-CoA to acetyl-CoA and acetoacetate. If this enzyme is defective, 3-hydroxy-3-methylglutaryl-CoA will accumulate in the mitochondria. Increased concentrations of 3-hydroxy-3-methylglutaryl-CoA can lead to a disruption of the esterified CoA:free CoA ratio and ultimately to mitochondrial toxicity. Detoxification of these CoA end products occurs via the transfer of the 3-hydroxymethylglutaryl moiety to carnitine, forming 3-hydroxymethylglutaric-carnitine, which is then transferred across the inner mitochondrial membrane where 3-hydroxymethylglutaric acid is released as the free acid. 3-Hydroxymethylglutaric acid has been found to accumulate in the urine of patients affected by 3-Hydroxy-3-methylglutaric aciduria, a rare inborn error of metabolism (OMIM: 246450 ). 3-Hydroxy-3-methylglutaric aciduria is caused by significantly reduced enzyme activity of the intramitochondrial 3-hydroxy-3-methylglutaryl-CoA lyase (EC 4.1.3.4), the enzyme that catalyzes the final step of leucine degradation. This enzyme also plays a key role in ketone body formation. The profile of urinary organic acids for individuals with 3-hydroxy-3-methylglutaric aciduria is different from that of the other identified defects of leucine degradation, such as maple syrup urine disease (OMIM: 248600 ), isovaleric acidemia (OMIM: 243500 ), and methylcrotonylglycinemia (OMIM: 210200 ). The urinary organic acid profile of 3-hydroxy-3-methylglutaric aciduria includes elevated concentrations of 3-hydroxy-3-isovaleric, 3-hydroxy-3-methylglutaric, 3-methylglutaconic, and 3-methylglutaric acids (PMID: 10916782 , 9658458 , 3063529 ). Clinical manifestations of 3-hydroxy-3-methylglutaric aciduria include hepatomegaly, lethargy, coma, and apnea. Biochemically, there is a characteristic absence of ketosis with hypoglycemia, acidosis, hypertransaminasemia, and variable hyperammonemia. Therefore, when present in sufficiently high concentrations, 3-hydroxymethylglutaric acid can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. As noted above, chronically high levels of 3-hydroxymethylglutaric acid are associated with the inborn error of metabolism 3-hydroxy-3-methylglutaryl-CoA lyase deficiency. 3-Hydroxymethylglutaric acid is an organic acid. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of the untreated IEMs mentioned above. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures. |
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Structure | |
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Synonyms | Value | Source |
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(S)-3-Hydroxy-3-methylglutaric acid | ChEBI | (S)-Meglutol | ChEBI | 3-HYDROXY-3-methyl-glutarIC ACID | ChEBI | 3-Hydroxy-3-methylpentanedioic acid | ChEBI | beta-Hydroxy-beta-methylglutaric acid | ChEBI | Dicrotalic acid | ChEBI | Meglutol | ChEBI | Meglutolum | ChEBI | 3-Hydorxy-3-methylglutaric acid | Kegg | (S)-3-Hydroxy-3-methylglutarate | Generator | 3-HYDROXY-3-methyl-glutarate | Generator | 3-Hydroxy-3-methylpentanedioate | Generator | b-Hydroxy-b-methylglutarate | Generator | b-Hydroxy-b-methylglutaric acid | Generator | beta-Hydroxy-beta-methylglutarate | Generator | Β-hydroxy-β-methylglutarate | Generator | Β-hydroxy-β-methylglutaric acid | Generator | Dicrotalate | Generator | 3-Hydorxy-3-methylglutarate | Generator | 3-Hydroxymethylglutarate | Generator | 3-Hydroxy-3-methylglutarate | HMDB | 3-Hydroxy-3-methylglutaric acid | HMDB | 3-Methyl-3-hydroxyglutarate | HMDB | 3-Methyl-3-hydroxyglutaric acid | HMDB | CB 337 | HMDB | 3 Hydroxy 3 methylpentanedioic acid | HMDB | Acid, 3-hydroxy-3-methylglutaric | HMDB | Acid, 3-hydroxy-3-methylpentanedioic | HMDB | beta Hydroxy beta methylglutarate | HMDB | 3 Hydroxy 3 methylglutaric acid | HMDB | 3-Methyl-3-hydroxypentanedioate | HMDB | 3-Methyl-3-hydroxypentanedioic acid | HMDB | HMG | HMDB | HMGA | HMDB | Lipoglutaren | HMDB | Medroglutarate | HMDB | Medroglutaric acid | HMDB |
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Chemical Formula | C6H10O5 |
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Average Molecular Weight | 162.1406 |
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Monoisotopic Molecular Weight | 162.05282343 |
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IUPAC Name | 3-hydroxy-3-methylpentanedioic acid |
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Traditional Name | meglutol |
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CAS Registry Number | 503-49-1 |
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SMILES | CC(O)(CC(O)=O)CC(O)=O |
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InChI Identifier | InChI=1S/C6H10O5/c1-6(11,2-4(7)8)3-5(9)10/h11H,2-3H2,1H3,(H,7,8)(H,9,10) |
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InChI Key | NPOAOTPXWNWTSH-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acids and conjugates |
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Direct Parent | Hydroxy fatty acids |
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Alternative Parents | |
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Substituents | - Methyl-branched fatty acid
- Short-chain hydroxy acid
- Hydroxy fatty acid
- Branched fatty acid
- Dicarboxylic acid or derivatives
- Tertiary alcohol
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic 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 | Indirect biological role: Biological role: Industrial application: |
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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 | 105 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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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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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0002-0930000000-67cdb23f1a51498bb80d | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (3 TMS) | splash10-05nb-2950000000-10da019551eceff729ec | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0002-0960000000-75a1f0bc3ffb60117676 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-0930000000-67cdb23f1a51498bb80d | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-05nb-2950000000-10da019551eceff729ec | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-0920000000-77008c8c7fb6eb798e79 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0udi-4900000000-ae0329f185525bab6028 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-0079-9253000000-af0bf7551c9147193ed4 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-05fr-2900000000-d5b3d7ccc3617f392a63 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-004i-9800000000-1a510972071bf02a23f7 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0kdi-9300000000-6afee652d0eb18e589c3 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-03di-0900000000-ae679b03ae8cdbc1cc40 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-0002-9300000000-8d7565d3b9cbed5d13ac | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0a4i-9000000000-d06ad8ce44567793a49d | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0a4i-9000000000-f3c4c2c0cb3ff49db482 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0a4i-9000000000-98c0337e0bebe4fefe6c | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-01qa-2900000000-182405b2867309ab7df8 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-03dj-5900000000-d9ffa79e6b62296f2626 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-03di-0900000000-2847ca367167b7cf107b | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0002-9300000000-f9ab44912911fd1e9ec7 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-9000000000-589bf77ae5f575911b64 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-9000000000-f3c4c2c0cb3ff49db482 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-9000000000-98c0337e0bebe4fefe6c | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-03dj-5900000000-d9ffa79e6b62296f2626 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-01qa-2900000000-182405b2867309ab7df8 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0900000000-a3631689983e6d6a3be7 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-002b-2900000000-54e16eaede819dea2bdc | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-9600000000-31a4e319505eebd3d1d1 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03xr-2900000000-405383db70ec0564b916 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-07bg-5900000000-dfc057320722ae1d926c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4m-9300000000-e5a720c14cbc5de82d4d | Spectrum | 1D NMR | 1H 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 (predicted from logP)
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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 but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 0.0201 +/- 0.0639 uM | Adult (>18 years old) | Not Specified | Normal | | details | Saliva | Detected and Quantified | 0.0917 +/- 0.0851 uM | Adult (>18 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | <200 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 2.6-4.5 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 6.788 +/- 4.222 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 27.0 (6.0-73.0) umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | Urine | Detected and Quantified | 1.4 (0.7-3.0) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 3 (0-10) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | <50 umol/mmol creatinine | Not Specified | Not Specified | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 2.4-3.6 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | <31.61 umol/mmol creatinine | Children (1 - 18 years old) | Both | Normal | | details | Urine | Detected and Quantified | <200 umol/mmol creatinine | Not Specified | Not Specified | Normal | | details | Urine | Detected and Quantified | 2.8 (1.1 -5.8) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 28.1 (10.7-57.5) umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | Urine | Detected and Quantified | 10.3 (4.3-31.4) umol/mmol creatinine | Children (1-13 years old) | Both | Normal | | details | Urine | Detected and Quantified | 9.9 (5.7-14.4) umol/mmol creatinine | Children (1-13 years old) | Both | Normal | | details | Urine | Detected and Quantified | 51.7 (13.1-101.1) umol/mmol creatinine | Infant (0-1 year old) | Female | Normal | | details | Urine | Detected and Quantified | 7.1 (2.2-24.5) umol/mmol creatinine | Adolescent (13-18 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 0.025 +/- 0.001 umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | Urine | Detected and Quantified | 3.2(1.1-5.2) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 12.098 +/- 6.49 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 0-110 umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details |
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Abnormal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Urine | Detected and Quantified | 481 umol/mmol creatinine | Adult (>18 years old) | Female | 3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency | | details | Urine | Detected and Quantified | 1028.4 umol/mmol creatinine | Newborn (0-30 days old) | Male | 3-hydroxy-3-methylglutaric- coenzyme A lyase deficiency | | details | Urine | Detected and Quantified | 10.581 +/- 10.628 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | Urine | Detected and Quantified | 1028.4 umol/mmol creatinine | Newborn (0-30 days old) | Male | 3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Bladder cancer | | details | Urine | Detected and Quantified | 481 umol/mmol creatinine | Adult (>18 years old) | Female | 3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency | | details | Urine | Detected and Quantified | 137.4 umol/mmol creatinine | Infant (0-1 year old) | Not Specified | Metabolic acidosis | | details | Urine | Detected and Quantified | 17.227 +/- 8.202 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | Urine | Detected and Quantified | 31.947 +/- 39.294 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Gastroesophageal reflux disease | | details |
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Associated Disorders and Diseases |
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Disease References | Colorectal cancer |
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- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
| Eosinophilic esophagitis |
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- (). Mordechai, Hien, and David S. Wishart. .
| 3-Hydroxy-3-methylglutaryl-CoA lyase deficiency |
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- Bischof F, Nagele T, Wanders RJ, Trefz FK, Melms A: 3-hydroxy-3-methylglutaryl-CoA lyase deficiency in an adult with leukoencephalopathy. Ann Neurol. 2004 Nov;56(5):727-30. [PubMed:15505778 ]
- Santarelli F, Cassanello M, Enea A, Poma F, D'Onofrio V, Guala G, Garrone G, Puccinelli P, Caruso U, Porta F, Spada M: A neonatal case of 3-hydroxy-3-methylglutaric-coenzyme A lyase deficiency. Ital J Pediatr. 2013 May 24;39:33. doi: 10.1186/1824-7288-39-33. [PubMed:23705938 ]
- G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
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Associated OMIM IDs | - 114500 (Colorectal cancer)
- 610247 (Eosinophilic esophagitis)
- 246450 (3-Hydroxy-3-methylglutaryl-CoA lyase deficiency)
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External Links |
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DrugBank ID | DB04377 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB004207 |
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KNApSAcK ID | C00001187 |
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Chemspider ID | 1600 |
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KEGG Compound ID | C03761 |
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BioCyc ID | CPD-547 |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | 5344 |
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PubChem Compound | 1662 |
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PDB ID | Not Available |
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ChEBI ID | 16831 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | MDB00000152 |
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References |
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Synthesis Reference | Klosterman, Harold J.; Smith, F. The isolation of b-hydroxy-b-methylglutaric acid from the seed of flax (Linum usitatissimum). Journal of the American Chemical Society (1954), 76 1229-30. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Mitchell GA, Jakobs C, Gibson KM, Robert MF, Burlina A, Dionisi-Vici C, Dallaire L: Molecular prenatal diagnosis of 3-hydroxy-3-methylglutaryl CoA lyase deficiency. Prenat Diagn. 1995 Aug;15(8):725-9. [PubMed:7479590 ]
- Fu Z, Runquist JA, Forouhar F, Hussain M, Hunt JF, Miziorko HM, Kim JJ: Crystal structure of human 3-hydroxy-3-methylglutaryl-CoA Lyase: insights into catalysis and the molecular basis for hydroxymethylglutaric aciduria. J Biol Chem. 2006 Mar 17;281(11):7526-32. Epub 2005 Dec 5. [PubMed:16330550 ]
- Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
- Wysocki SJ, Wilkinson SP, Hahnel R, Wong CY, Panegyres PK: 3-Hydroxy-3-methylglutaric aciduria, combined with 3-methylglutaconic aciduria. Clin Chim Acta. 1976 Aug 2;70(3):399-406. [PubMed:947633 ]
- Tuchman M, McCann MT, Johnson PE, Lemieux B: Screening newborns for multiple organic acidurias in dried filter paper urine samples: method development. Pediatr Res. 1991 Oct;30(4):315-21. [PubMed:1956713 ]
- Truscott RJ, Halpern B, Wysocki SJ, Hahnel R, Wilcken B: Studies on a child suspected of having a dficiency in 3-hydroxy-3-methylglutaryl-Co A lyase. Clin Chim Acta. 1979 Jul 2;95(1):11-16. [PubMed:509721 ]
- Koling S, Kalhoff H, Schauerte P, Lehnert W, Diekmann L: [3-hydroxy-3-methylglutaraciduria (case report of a female Turkish sisters with 3-hydroxy-3- methylglutaryl-Coenzyme A lyase deficiency]. Klin Padiatr. 2000 May-Jun;212(3):113-6. [PubMed:10916782 ]
- Eiris J, Ribes A, Fernandez-Prieto R, Rodriguez-Garcia J, Rodriguez-Segade S, Castro-Gago M: [3-hydroxy-3-methylglutaric aciduria and recurrent Reye-like syndrome]. Rev Neurol. 1998 Jun;26(154):911-4. [PubMed:9658458 ]
- Gibson KM, Breuer J, Nyhan WL: 3-Hydroxy-3-methylglutaryl-coenzyme A lyase deficiency: review of 18 reported patients. Eur J Pediatr. 1988 Dec;148(3):180-6. [PubMed:3063529 ]
- Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- 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 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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