2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid

• ChemBase编号: 2011
• 分子式: C5H4N2O4
• 平均质量: 156.09626
• 单一同位素质量: 156.01710662
• SMILES: OC(=O)c1cc(=O)[nH]c(=O)[nH]1
• Canonical SMILES: O=c1[nH]c(=O)[nH]c(c1)C(=O)O
• InChI: InChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)
• InChIKey: PXQPEWDEAKTCGB-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
• IUPAC传统名: orotic acid
• 别名: 无水乳清酸; 乳清酸; 6-Carboxyuracil; Orodin; Oropur; Orotonin; Orotonsan; 1,2,3,6-Tetrahydro-2,6-dioxopyrimidine-4-carboxylic acid; Uracil-4-carboxylic acid; Orotic acid, anhydrous; Orotic acid; 6-Carboxy-2,4-dihydroxypyrimidine; 2,6-Dihydroxypyrimidine-4-carboxylic acid; Uracil-6-carboxylic acid; Orotic Acid; Orotic acid; 2,6-Dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid; 2,6-Dioxo-1,2,3,6-tetrahydro-4-pyrimidinecarboxylic acid

登记号

• CAS号: 65-86-1
• EC号: 200-619-8
• MDL号: MFCD00006027
• Beilstein号: 383901
• PubChem SID: 24897967; 46508903; 160965466
• PubChem CID: 967
• Chemspider ID: 942
• DrugBank ID: DB02262
• KEGG ID: C00295
• 美国药典/FDA物质标识码: 61H4T033E5
• 维基百科标题: Orotic_acid

理论计算性质

JChem

• Acid pKa: 2.8272662
• 质子受体: 4
• 质子供体: 3
• LogD (pH = 5.5): -3.8449886
• LogD (pH = 7.4): -4.736972
• Log P: -1.2276645
• 摩尔折射率: 33.2746 cm^3
• 极化性: 12.221098 Å^3
• 极化表面积: 95.5 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.89
• LOG S: -1.54
• 溶解度: 4.51e+00 g/l

分子性质

理化性质

• 溶解度: 1.82 mg/mL at 18 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
• 熔点: ≥300 °C; 300-347°C; 344-347°C; 345-346°C
• 疏水性(logP): -0.83 [SANGSTER (1994)]

安全信息

• 保存条件: -20°C; Room Temperature (15-30°C)
• 保存注意事项: Harmful/Irritant
• RTECS编号: RM3180000
• 欧盟危险性物质标志: X; 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22-36/37/38; 22-36/38
• 安全公开号: 26; 26-36/37
• TSCA收录: 是
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H315-H319; H302-H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338; P280-P305+P351+P338-P302+P352-P321-P362-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

• 纯度: ≥98% (titration); ≥98.0% (T); 97%
• 级别: anhydrous
• 成盐信息: Free Base
• 适用性: plant cell culture tested
• 杂质: ≤1% water
• Empirical Formula (Hill Notation): C5H4N2O4

详细说明

MP Biomedicals - 05215251

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02151790

Anhydrous
Crystalline
Free Acid

DrugBank - DB02262

Drug information: experimental

Selleck Chemicals - S2336

Research Area: Metabolic Disease
Biological Activity:
Orotic acid(6-Carboxyuracil) is a heterocyclic compound and an acid. It was once believed to be part of the vitamin B complex and was called vitamin B13, but it is now known that it is not a vitamin but is instead manufactured in the body by intestinal flora. Its salts, known as orotates, are sometimes used as mineral carriers in some dietary supplements, to increase their bioavailability.Lithium orotate is the most frequently used in this manner. [1]

Sigma Aldrich - O2750

Application
Orotic acid (OA) is an intermediate in de novo pyrimidine biosynthesis that may be used to study the specificity and kinetics of orotate phosphoribosyltransferase (OPRT) which catalyzes the reversible phosphoribosyl transfer from 5′-phospho-α-d-ribose 1′-diphosphate (PRPP) to orotic acid (OA), forming pyrophosphate and orotidine 5′-monophosphate (OMP). Orotic acid is used as a starting material for the potential commercial bioproduction of uridine 5′-monophosphate (UMP) by microbes such as Corynebacterium ammoniagenes (ATCC 6872) or Saccharomyces cerevisiae. OA may be used to study the AMPK/SREBP-1 dependent cell signaling pathway and transcription regulation mechanisms that induce hepatic lipogenesis.

参考文献

• http://en.wikipedia.org/wiki/Orotic_acid