L-Dihydroorotic acid - 10mM in DMSO , CAS No.5988-19-2

CAS: 5988-19-2 Cat. No.: L424981 Molecular Weight: 158.11 EC Number: 624-952-7

GRADE & PURITY 10mM in DMSO

Synonyms

2,6-Dioxohexahydro-4-pyrimidinecarboxylic acid | bmse000342 | Hydroorotic acid, L- | (S)-dihydroorotic acid | UNII-4LPL64ZNA5 | L-4,5-dihydroorotic acid | 1,2,3,4-tetrahydro-2-quinolinylcarboxylic acid methyl ester | 2,6-Dioxohexahydro-4-pyrimidinecarboxy

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Application：

L-Dihydroorotic acid has been used as a substrate in dihydroorotate dehydrogenase (DHODH) assay.

Specifications

Synonyms

2, 6-Dioxohexahydro-4-pyrimidinecarboxylic acid | bmse000342 | Hydroorotic acid, L- | (S)-dihydroorotic acid | UNII-4LPL64ZNA5 | L-4, 5-dihydroorotic acid | 1, 2, 3, 4-tetrahydro-2-quinolinylcarboxylic acid methyl ester | 2, 6-Dioxohexahydro-4-pyrimidinecarboxy

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

L-Dihydroorotic acid (DHO) serves as a substrate for dihydroorotate dehydrogenase (DHODH), an enzyme in the de novo synthesis of pyrimidine. Inhibition of DHOH by its inhibitors causes a large accumulation of upstream metabolite DHO and a reduction in the

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

• Canonical Smiles: C1C(NC(=O)NC1=O)C(=O)O
• IUPAC Name: (4S)-2,6-dioxo-1,3-diazinane-4-carboxylic acid
• InChIKey: UFIVEPVSAGBUSI-REOHCLBHSA-N
• 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
• Isomeric SMILES: C1[C@H](NC(=O)NC1=O)C(=O)O
• WGK Germany: 3
• Molecular Weight: 158.11
• Reaxy-Rn: 83959
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=83959&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives
• Direct Parent: Alpha amino acids and derivatives
• Alternative Parents: Pyrimidones N-acyl ureas Diazinanes Dicarboximides Monocarboxylic acids and derivatives Carboxylic acids Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• 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
• Description: This compound 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.
• External Descriptors: dihydroorotic acid

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Melt Point(°C): 254-255°C
• Molecular Weight: 158.110 g/mol
• XLogP3: -1.500
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 158.033 Da
• Monoisotopic Mass: 158.033 Da
• Topological Polar Surface Area: 95.500 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 225.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Yiming Liu, Mingrui Zhang, Jingjing Zhao, Yongshuo Ren, Shubin Li, Weichen Wang, Wei Mu, Xiaojun Han.  (2025)  Construction of a De Novo Nucleotide Biosynthesis Pathway in Artificial Cells for RNA Transcription.  Journal of the American Chemical Society,      [PMID:40708544] [10.1021/jacs.5c09375]