Record Information |
---|
Version | 5.0 |
---|
Status | Detected but not Quantified |
---|
Creation Date | 2012-09-11 17:43:47 UTC |
---|
Update Date | 2022-03-07 02:53:00 UTC |
---|
HMDB ID | HMDB0031518 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | D-Malic acid |
---|
Description | D-Malic acid, also known as D-malate, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. D-Malic acid exists in all living organisms, ranging from bacteria to humans. D-Malic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on D-Malic acid. |
---|
Structure | InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m1/s1 |
---|
Synonyms | Value | Source |
---|
(+)-D-Malic acid | ChEBI | (R)-2-Hydroxybutanedioic acid | ChEBI | 2-HYDROXY-succinIC ACID | ChEBI | D-Malate | Kegg | (+)-D-Malate | Generator | (R)-2-Hydroxybutanedioate | Generator | 2-HYDROXY-succinate | Generator | (R)-Malate | HMDB | (R)-Hydroxybutanedioic acid | HMDB | D-(+)-Malic acid | HMDB | D-Hydroxybutanedioic acid | HMDB | Hydroxy-(R)-butanedioic acid | HMDB | R-Malic acid | HMDB | D-Malic acid | ChEBI |
|
---|
Chemical Formula | C4H6O5 |
---|
Average Molecular Weight | 134.0874 |
---|
Monoisotopic Molecular Weight | 134.021523302 |
---|
IUPAC Name | (2R)-2-hydroxybutanedioic acid |
---|
Traditional Name | .+-.-malic acid |
---|
CAS Registry Number | 636-61-3 |
---|
SMILES | O[C@H](CC(O)=O)C(O)=O |
---|
InChI Identifier | InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m1/s1 |
---|
InChI Key | BJEPYKJPYRNKOW-UWTATZPHSA-N |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic acids and derivatives |
---|
Class | Hydroxy acids and derivatives |
---|
Sub Class | Beta hydroxy acids and derivatives |
---|
Direct Parent | Beta hydroxy acids and derivatives |
---|
Alternative Parents | |
---|
Substituents | - Short-chain hydroxy acid
- Beta-hydroxy acid
- Fatty acid
- Dicarboxylic acid or derivatives
- Alpha-hydroxy acid
- Secondary alcohol
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | |
---|
Role | |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | 101 °C | Not Available | Boiling Point | 306.00 to 307.00 °C. @ 760.00 mm Hg (est) | The Good Scents Company Information System | Water Solubility | 364 mg/mL at 20 °C | Not Available | LogP | -1.26 | Not Available |
|
---|
Experimental Chromatographic Properties | Experimental Collision Cross Sections |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
D-Malic acid,1TMS,isomer #1 | C[Si](C)(C)O[C@H](CC(=O)O)C(=O)O | 1317.5 | Semi standard non polar | 33892256 | D-Malic acid,1TMS,isomer #2 | C[Si](C)(C)OC(=O)C[C@@H](O)C(=O)O | 1311.4 | Semi standard non polar | 33892256 | D-Malic acid,1TMS,isomer #3 | C[Si](C)(C)OC(=O)[C@H](O)CC(=O)O | 1279.0 | Semi standard non polar | 33892256 | D-Malic acid,2TMS,isomer #1 | C[Si](C)(C)OC(=O)C[C@@H](O[Si](C)(C)C)C(=O)O | 1404.0 | Semi standard non polar | 33892256 | D-Malic acid,2TMS,isomer #2 | C[Si](C)(C)OC(=O)[C@@H](CC(=O)O)O[Si](C)(C)C | 1376.6 | Semi standard non polar | 33892256 | D-Malic acid,2TMS,isomer #3 | C[Si](C)(C)OC(=O)C[C@@H](O)C(=O)O[Si](C)(C)C | 1382.5 | Semi standard non polar | 33892256 | D-Malic acid,3TMS,isomer #1 | C[Si](C)(C)OC(=O)C[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1498.5 | Semi standard non polar | 33892256 | D-Malic acid,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@H](CC(=O)O)C(=O)O | 1572.3 | Semi standard non polar | 33892256 | D-Malic acid,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)C[C@@H](O)C(=O)O | 1571.3 | Semi standard non polar | 33892256 | D-Malic acid,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)CC(=O)O | 1555.1 | Semi standard non polar | 33892256 | D-Malic acid,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O | 1851.7 | Semi standard non polar | 33892256 | D-Malic acid,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CC(=O)O)O[Si](C)(C)C(C)(C)C | 1836.9 | Semi standard non polar | 33892256 | D-Malic acid,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)C[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C | 1825.4 | Semi standard non polar | 33892256 | D-Malic acid,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2116.5 | Semi standard non polar | 33892256 |
|
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Experimental GC-MS | GC-MS Spectrum - D-Malic acid GC-EI-TOF (Non-derivatized) | splash10-0002-0930000000-53a536e3bc82b8e91612 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - D-Malic acid GC-EI-TOF (Non-derivatized) | splash10-00di-9610000000-883e07f52319a029b9f9 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - D-Malic acid GC-EI-TOF (Non-derivatized) | splash10-0002-0930000000-53a536e3bc82b8e91612 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - D-Malic acid GC-EI-TOF (Non-derivatized) | splash10-00di-9610000000-883e07f52319a029b9f9 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - D-Malic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9100000000-add08efe51cfe6d9243c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - D-Malic acid GC-MS (3 TMS) - 70eV, Positive | splash10-02j9-7191000000-b78c78194b39deee0ca4 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - D-Malic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Experimental LC-MS/MS | LC-MS/MS Spectrum - D-Malic acid LC-ESI-QTOF , negative-QTOF | splash10-0159-3900000000-b601107a03ca7060bc56 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - D-Malic acid 10V, Negative-QTOF | splash10-01b9-7900000000-7e16d13cd13953520b72 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - D-Malic acid 20V, Negative-QTOF | splash10-00di-9000000000-ed4a8a4776b51e62327c | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - D-Malic acid 40V, Negative-QTOF | splash10-0006-9000000000-22c9ebc50090b4cd6671 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Malic acid 10V, Positive-QTOF | splash10-014i-6900000000-3b7d14a7ed7bb42627e4 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Malic acid 20V, Positive-QTOF | splash10-01bj-9300000000-20f68e610aeba32d1947 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Malic acid 40V, Positive-QTOF | splash10-00dl-9000000000-044292489a383c81ae1d | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Malic acid 10V, Negative-QTOF | splash10-00m0-8900000000-9da4062d3c439ed2f7eb | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Malic acid 20V, Negative-QTOF | splash10-00ri-9200000000-c4d019ab4961e5b1a1ae | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Malic acid 40V, Negative-QTOF | splash10-05fu-9000000000-bc073c2d0e1a2f8a82e3 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Malic acid 10V, Negative-QTOF | splash10-00y0-9400000000-b346287170f4b47937d9 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Malic acid 20V, Negative-QTOF | splash10-00du-9000000000-94fcc5032bed94eae77e | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Malic acid 40V, Negative-QTOF | splash10-052f-9000000000-43c40f8a7715a996c55b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Malic acid 10V, Positive-QTOF | splash10-00ri-9400000000-a20ca040dba0bb25ae2b | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Malic acid 20V, Positive-QTOF | splash10-0095-9000000000-90064952bc6def150ecc | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Malic acid 40V, Positive-QTOF | splash10-0006-9000000000-4dd1a07ea5d3aab2c6ea | 2021-09-23 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
---|
Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum |
|
---|
Disease References | Colorectal cancer |
---|
- Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
- 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 ]
|
|
---|