Metabolite Card
Formula: C5H8N2O2 (128.0586)
SMILES: C[C@H]1CNC(=O)NC1=O
Synonyms [en]
Dihydrothymine; 5,6-dihydrothymine; 5,6-Dihydro-5-methyluracil; 5-Methyldihydropyrimidine-2,4(1H,3H)-dione; 5-Methyl-5,6-dihydrouracil; AI3-25480
Last reviewed on 2024-06-28.
Cite this Page
5,6-Dihydrothymine. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China.
https://biocad_registry.innovation.ac.cn/s/(-)-arctiin
(retrieved
2026-01-03) (CAD Registry RN: BioCAD00000004970). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
Dihydrothymine (CAS: 696-04-8) is an intermediate breakdown product of thymine. Dihydropyrimidine dehydrogenase catalyzes the reduction of thymine into 5,6-dihydrothymine; then dihydropyrimidinase hydrolyzes 5,6-dihydrothymine into N-carbamyl-beta-alanine. Finally, beta-ureidopropionase catalyzes the conversion of N-carbamyl-beta-alanine into beta-alanine. When present at abnormally high levels, dihydrothymine can be toxic, although the mechanism of toxicity is not clear. In particular, patients with dihydropyrimidinase deficiency exhibit highly increased concentrations of 5,6-dihydrouracil and 5,6-dihydrothymine; and moderately increased concentrations of uracil and thymine can be detected in urine. Dihydropyrimidinase deficiency is a disorder that can cause neurological and gastrointestinal problems in some affected individuals. The most common neurological abnormalities that occur are intellectual disability, seizures, weak muscle tone (hypotonia), abnormally small head size (microcephaly), and autistic behaviours that affect communication and social interaction. Gastrointestinal problems that occur in dihydropyrimidinase deficiency include the backflow of acidic stomach contents into the esophagus (gastroesophageal reflux) and recurrent episodes of vomiting.
DBLinks
- CAS Registry Number: 696-04-8
- PubChem CID: 676414
- ChEBI: 27468
- HMDB: HMDB0000079
- LipidMaps:
- KEGG: C00906
- BioCyc: DIHYDRO-THYMINE
- NCBI MeSH: 5,6-dihydrothymine
- Wikipedia: Dihydrothymine
Other DBLinks
- CAS Registry Number: 19140-80-8
- CAS Registry Number: 696-04-8
- CAS Registry Number: 7307-02-0
- CAS Registry Number: 7307-03-1
- PubChem: 676414
- PubChem: 93556
- ChEBI: ChEBI:27468
- HMDB: HMDB0000079
- HMDB: HMDB0304210
- KEGG: C00906
- BioCyc: DIHYDRO-THYMINE
- NCBI MeSH: 5,6-dihydrothymine
- Wikipedia: Dihydrothymine
- RefMet: RM0135880
- MoNA: FiehnHILIC001696
- MoNA: HMDB0000079_c_ms_1166
- MoNA: HMDB0000079_c_ms_1172
- MoNA: HMDB0000079_ms_ms_129
- MoNA: HMDB0000079_ms_ms_130
- MoNA: HMDB0000079_ms_ms_131
- Metlin: METLIN_291
- Coconut NaturalProduct: CNP0050073.1
- Coconut NaturalProduct: CNP0053056.0
- Coconut NaturalProduct: CNP0109827.0
- Coconut NaturalProduct: CNP0124346.0
- Coconut NaturalProduct: CNP0349997.0
- Coconut NaturalProduct: CNP0351307.0
- Coconut NaturalProduct: CNP0441019.0
Class / Ontology
- WishartLab ClassyFire: [Pyrimidines and pyrimidine derivatives] Pyrimidines and pyrimidine derivatives
- RefMet: [Ureides] Ureides
- ChEBI: [CHEBI:27468] 5,6-dihydrothymine
- Coconut NaturalProduct: [Lysine alkaloids] Lysine alkaloids
- Coconut NaturalProduct: [Oxygenated hydrocarbons] Oxygenated hydrocarbons
- Coconut NaturalProduct: [Unsaturated fatty acids] Unsaturated fatty acids
| ID | EC Number | Name |
|---|---|---|
| KEGG:R01414 | 1.3.1.1 | 5,6-dihydrothymine:NAD+ oxidoreductase |
| BioCyc:RXN0-6565 | 1.3.1.1 | DIHYDRO-THYMINE + NAD<=>THYMINE + NADH + PROTON |
| Rhea:RHEA:28792 | 1.3.1.1 | 5,6-dihydrothymine + NAD+ => thymine + NADH + H+ |
| Rhea:RHEA:28793 | 1.3.1.1 | thymine + NADH + H+ => 5,6-dihydrothymine + NAD+ |
| Rhea:RHEA:28794 | 1.3.1.1 | 5,6-dihydrothymine + NAD+ <=> thymine + NADH + H+ |
| Rhea:RHEA:37336 | 3.5.2.2 | 5,6-dihydrothymine + H2O => 3-(carbamoylamino)-2-methylpropanoate + H+ |
| Rhea:RHEA:37337 | 3.5.2.2 | 3-(carbamoylamino)-2-methylpropanoate + H+ => 5,6-dihydrothymine + H2O |
| Rhea:RHEA:37338 | 3.5.2.2 | 5,6-dihydrothymine + H2O <=> 3-(carbamoylamino)-2-methylpropanoate + H+ |
| Rhea:RHEA:58285 | 1.3.1.2 | 5,6-dihydrothymine + NADP+ => thymine + NADPH + H+ |
| Rhea:RHEA:58286 | 1.3.1.2 | thymine + NADPH + H+ => 5,6-dihydrothymine + NADP+ |
| Rhea:RHEA:58287 | 1.3.1.2 | 5,6-dihydrothymine + NADP+ <=> thymine + NADPH + H+ |
| BioCyc:RXN-11211 | 3.5.2.2 | DIHYDRO-THYMINE + WATER<=>3-UREIDO-ISOBUTYRATE + PROTON |
| BioCyc:RXN-11209 | 1.3.1.2 | DIHYDRO-THYMINE + NADP<=>THYMINE + NADPH + PROTON |
Taxonomy Source
- Homo sapiens [ncbi taxid: 9606]
- Mus musculus [ncbi taxid: 10090]
- Ligusticum chuanxiong [ncbi taxid: 2689076]
Pathway Synthetic
| pathway id | name |
|---|---|
| PlantCyc:BSTRICTA_PWY-6430 | thymine degradation |
| PlantCyc:CASSAVA_PWY-6430 | thymine degradation |
| PlantCyc:CASTORBEAN_PWY-6430 | thymine degradation |
| PlantCyc:CCAMPESTRIS_PWY-6430 | thymine degradation |
| PlantCyc:BREADWHEAT_PWY-6430 | thymine degradation |
| PlantCyc:BLACKPEPPER_PWY-6430 | thymine degradation |
| PlantCyc:BOLERACEA_CAPITATA_PWY-6430 | thymine degradation |
| PlantCyc:CARNATION_PWY-6430 | thymine degradation |
| PlantCyc:CCAPSULARIS_PWY-6430 | thymine degradation |
| PlantCyc:ARA_PWY-6430 | thymine degradation |
| PlantCyc:CORN_PWY-6430 | thymine degradation |
| PlantCyc:AMBORELLA_PWY-6430 | thymine degradation |
| PlantCyc:BARLEY_PWY-6430 | thymine degradation |
| PlantCyc:BRACHYPODIUM_PWY-6430 | thymine degradation |
| PlantCyc:BRAPA_FPSC_PWY-6430 | thymine degradation |
| PlantCyc:CARIETINUM_ICC4958_PWY-6430 | thymine degradation |
| PlantCyc:CASHEW_PWY-6430 | thymine degradation |
| PlantCyc:LER_PWY-6430 | thymine degradation |
| PlantCyc:PLANT_PWY-6430 | thymine degradation |
| PlantCyc:ACOERULEA_PWY-6430 | thymine degradation |