Record Information |
---|
Version | 1.0 |
---|
Creation date | 2011-09-21 00:25:22 UTC |
---|
Update date | 2024-11-29 22:26:07 UTC |
---|
Primary ID | FDB023149 |
---|
Secondary Accession Numbers | |
---|
Chemical Information |
---|
FooDB Name | L-Dihydroorotic acid |
---|
Description | L-Dihydroorotic acid, also known as (S)-4,5-dihydroorotate or dihydro-L-orotate, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. L-Dihydroorotic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). The (S)-enantiomer of dihydroorotic acid that is an intermediate in the metabolism of pyridine. L-Dihydroorotic acid exists in all living species, ranging from bacteria to humans. Within humans, L-dihydroorotic acid participates in a number of enzymatic reactions. In particular, L-dihydroorotic acid can be biosynthesized from ureidosuccinic acid through the action of the enzyme cad protein. In addition, L-dihydroorotic acid and quinone can be converted into orotic acid through the action of the enzyme dihydroorotate dehydrogenase (quinone), mitochondrial. In humans, L-dihydroorotic acid is involved in pyrimidine metabolism. Outside of the human body, L-Dihydroorotic acid has been detected, but not quantified in, several different foods, such as american pokeweeds, prunus (cherry, plum), red huckleberries, white lupines, and shallots. This could make L-dihydroorotic acid a potential biomarker for the consumption of these foods. |
---|
CAS Number | 5988-19-2 |
---|
Structure | |
---|
Synonyms | |
---|
Predicted Properties | |
---|
Chemical Formula | C5H6N2O4 |
---|
IUPAC name | (4S)-2,6-dioxo-1,3-diazinane-4-carboxylic acid |
---|
InChI Identifier | InChI=1S/C5H6N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h2H,1H2,(H,9,10)(H2,6,7,8,11)/t2-/m0/s1 |
---|
InChI Key | UFIVEPVSAGBUSI-REOHCLBHSA-N |
---|
Isomeric SMILES | OC(=O)[C@@H]1CC(=O)NC(=O)N1 |
---|
Average Molecular Weight | 158.1121 |
---|
Monoisotopic Molecular Weight | 158.03275669 |
---|
Classification |
---|
Description | Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic acids and derivatives |
---|
Class | Carboxylic acids and derivatives |
---|
Sub Class | Amino acids, peptides, and analogues |
---|
Direct Parent | Alpha amino acids and derivatives |
---|
Alternative Parents | |
---|
Substituents | - Alpha-amino acid or derivatives
- N-acyl urea
- Pyrimidone
- Ureide
- 1,3-diazinane
- Pyrimidine
- Dicarboximide
- Urea
- Carbonic acid derivative
- Azacycle
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Organic oxygen compound
- Carbonyl group
- Organic nitrogen compound
- Aliphatic heteromonocyclic compound
|
---|
Molecular Framework | Aliphatic heteromonocyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Disposition | Route of exposure: Biological location: Source: |
---|
Role | Industrial application: |
---|
Physico-Chemical Properties |
---|
Physico-Chemical Properties - Experimental | |
---|
Spectra |
---|
Spectra | |
---|
EI-MS/GC-MS | Type | Description | Splash Key | View |
---|
GC-MS | L-Dihydroorotic acid, non-derivatized, GC-MS Spectrum | splash10-0zfs-1920000000-6e853bcb65fafce1f25e | Spectrum | GC-MS | L-Dihydroorotic acid, non-derivatized, GC-MS Spectrum | splash10-000j-1900000000-4c364adc386eb5db027b | Spectrum | GC-MS | L-Dihydroorotic acid, non-derivatized, GC-MS Spectrum | splash10-0zfs-0930000000-373786ac89c19f0cbc6b | Spectrum | GC-MS | L-Dihydroorotic acid, 3 TMS, GC-MS Spectrum | splash10-0pb9-2951000000-9975cf569acb6854865d | Spectrum | GC-MS | L-Dihydroorotic acid, 4 TMS, GC-MS Spectrum | splash10-005a-5938000000-6f622577780cd53385eb | Spectrum | GC-MS | L-Dihydroorotic acid, non-derivatized, GC-MS Spectrum | splash10-0zfs-1920000000-6e853bcb65fafce1f25e | Spectrum | GC-MS | L-Dihydroorotic acid, non-derivatized, GC-MS Spectrum | splash10-0pb9-2951000000-9975cf569acb6854865d | Spectrum | GC-MS | L-Dihydroorotic acid, non-derivatized, GC-MS Spectrum | splash10-005a-5938000000-6f622577780cd53385eb | Spectrum | Predicted GC-MS | L-Dihydroorotic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-000f-9400000000-248b8d6d703ba73c2058 | Spectrum | Predicted GC-MS | L-Dihydroorotic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-03di-3900000000-b0776f22820e6e570a09 | Spectrum | Predicted GC-MS | L-Dihydroorotic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
|
---|
MS/MS | Type | Description | Splash Key | View |
---|
MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-059i-9700000000-681989bb70419ccf0e26 | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00di-9000000000-c08746cfe4c476aff942 | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-006x-9000000000-c59db6f9b23380c30e8c | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , negative | splash10-001i-2920000000-1c8b06ed77517a0e8606 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-03k9-4900000000-5b6e94f06ce0c97ad751 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-03dl-9800000000-933d1487bcb4d23e2a5a | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-0006-9000000000-34d46a3aa973f0412a45 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-00di-9100000000-0004fe5f5bbd6b1f1a41 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-05fr-9000000000-9accaaec3ae3b41f55a9 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-00di-9000000000-41686c36ddb271856b65 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-074u-9500000000-c4e4ed6470c8ad78afec | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-8214c2f0d9df1ac7c79c | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-022i-9400000000-257f9838bad9d558822c | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-2e8bea71938b0c3ee548 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0006-9100000000-8cda59dcc275524136f4 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0900000000-2ddb498acc970a567f6b | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03dl-5900000000-4b73ae512e57466dd4e6 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9100000000-d6c31a36d6fe5c68d9e1 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-1900000000-c84801951eaa1da750f7 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-9000000000-4ae1d11ab20f903606c3 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-aec3a40befb20e60f21b | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0900000000-b0c5e687f246809cdae9 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01ox-6900000000-cb60b796898e6ca4336d | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-fccf5d7216b23cffed7a | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-06r6-0900000000-86736ae769db7bc83c23 | 2021-09-22 | View Spectrum |
|
---|
NMR | Type | Description | | View |
---|
1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
|
---|
External Links |
---|
ChemSpider ID | Not Available |
---|
ChEMBL ID | Not Available |
---|
KEGG Compound ID | Not Available |
---|
Pubchem Compound ID | 439216 |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | 17025 |
---|
Phenol-Explorer ID | Not Available |
---|
DrugBank ID | Not Available |
---|
HMDB ID | HMDB03349 |
---|
CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
---|
EAFUS ID | Not Available |
---|
Dr. Duke ID | Not Available |
---|
BIGG ID | Not Available |
---|
KNApSAcK ID | Not Available |
---|
HET ID | Not Available |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
Flavornet ID | Not Available |
---|
GoodScent ID | Not Available |
---|
SuperScent ID | Not Available |
---|
Wikipedia ID | Not Available |
---|
Phenol-Explorer Metabolite ID | Not Available |
---|
Duplicate IDS | Not Available |
---|
Old DFC IDS | Not Available |
---|
Associated Foods |
---|
|
Biological Effects and Interactions |
---|
Health Effects / Bioactivities | Not Available |
---|
Enzymes | Not Available |
---|
Pathways | |
---|
Metabolism | Not Available |
---|
Biosynthesis | Not Available |
---|
Organoleptic Properties |
---|
Flavours | Not Available |
---|
Files |
---|
MSDS | show |
---|
References |
---|
Synthesis Reference | Not Available |
---|
General Reference | Not Available |
---|
Content Reference | |
---|