(2S)-2-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

• ChemBase编号: 44
• 分子式: C19H19N7O6
• 平均质量: 441.39746
• 单一同位素质量: 441.13968136
• SMILES: OC(=O)[C@@H](NC(=O)c1ccc(NCc2nc3c([nH]c(nc3=O)N)nc2)cc1)CCC(=O)O
• Canonical SMILES: OC(=O)CC[C@@H](C(=O)O)NC(=O)c1ccc(cc1)NCc1cnc2c(n1)c(=O)nc([nH]2)N
• InChI: InChI=1S/C19H19N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,8,12,21H,5-7H2,(H,24,29)(H,27,28)(H,31,32)(H3,20,22,25,26,30)/t12-/m0/s1
• InChIKey: OVBPIULPVIDEAO-LBPRGKRZSA-N

名称和登记号

名称

• IUPAC标准名: (2S)-2-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
• IUPAC传统名: folic acid; folate
• 商标名: Acifolic; Apo-Folic; Cytofol; Dosfolat B activ; Folacid; Folacin; Folbal; Folcidin; Foldine; Folettes; Foliamin; Folicet; Folipac; Folsan; Folsaure; Folsav; Folvite; Folvron; Incafolic; Millafol
• 别名: N-4-[(2-氨基-4-氧代-1,4-二氢-6-喋啶)甲氨基苯甲酰基]-L-谷氨酸; 维生素 M; 叶酸; 叶酸; Pteroylglutamic acid; Pteroylmonoglutamic acid; Vitamin M; Vitamin Be; Vitamin Bc; Vitamin B9; Folic Acid; Folate; PGA; Pteroyl-L-glutamic acid; Pteroyl-L-monoglutamic acid; N-​(4-​{[(2-​amino-​4-​oxo-​1,​4-​dihydropteridin-​6-​yl)​methyl]​amino}​benzoyl)-​L-​glutamic acid; Vitamin B₉; Vitamin B_c; Folacin; PteGlu; Folic acid; Acidum folicum; Folic acid

登记号

• CAS号: 59-30-3
• EC号: 200-419-0
• MDL号: MFCD00079305
• Beilstein号: 100781
• PubChem SID: 24845192; 24894979; 24894973; 24871538; 24894977; 160963507; 24871220; 24894950; 46508092
• PubChem CID: 6037
• CHEBI ID: 27470
• ATC码: B03BB01
• CHEMBL: 1622
• Chemspider ID: 5815
• DrugBank ID: DB00158
• KEGG ID: C00504
• 美国药典/FDA物质标识码: 935E97BOY8
• 维基百科标题: Folic_acid

理论计算性质

JChem

• Acid pKa: 3.3738735
• 质子受体: 12
• 质子供体: 6
• LogD (pH = 5.5): -3.942576
• LogD (pH = 7.4): -7.12074
• Log P: -0.68225247
• 摩尔折射率: 111.0112 cm^3
• 极化性: 40.461403 Å^3
• 极化表面积: 208.99 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: -0.04
• LOG S: -3.76
• 溶解度: 7.61e-02 g/l

分子性质

理化性质

• 溶解度: 1.6 mg/L (25 °C) in water; Slight
• 外观: yellow-orange crystalline powder
• 熔点: 250 °C (523 K), decomp.
• 比旋光度: [α]20/D +20±2°, c = 1% in 0.1 M NaOH
• 疏水性(logP): -2.5
• pKa: 1^st: 4.65, 2^nd: 6.75, 3^rd: 9.00

安全信息

• RTECS编号: LP5425000
• 德国WGK号: 1; 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥97%; ≥97.0% (HPLC)
• 级别: analytical standard; Ph Eur
• 包装: ampule of 500 mg
• 适用性: meets USP testing specifications; plant cell culture tested; suitable for cell culture; suitable for insect cell culture; suitable for plant cell culture
• 燃烧残渣: ≤0.1% (as SO4)
• 杂质: ~8% water
• 痕量阳离子: Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤1500 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• 产品质量级别: PREMIUM
• 特征: standard type water soluble vitamin
• 药典: testing & handling conforms to Pharmacopeia
• Pharmacopeia Traceability: traceable to PhEur F0300000; traceable to USP 1286005
• Empirical Formula (Hill Notation): C19H19N7O6

详细说明

DrugBank - DB00158

• Drug Groups: approved; nutraceutical
• Description: A member of the vitamin B family that stimulates the hematopoietic system. It is present in the liver and kidney and is found in mushrooms, spinach, yeast, green leaves, and grasses (poaceae). Folic acid is used in the treatment and prevention of folate deficiencies and megaloblastic anemia. [PubChem]
• Indication: For treatment of folic acid deficiency, megaloblastic anemia and in anemias of nutritional supplements, pregnancy, infancy, or childhood.
• Pharmacology: Folic acid, a water-soluble B-complex vitamin, is found in foods such as liver, kidneys, yeast, and leafy, green vegetables. Folic acid is used to diagnose folate deficiency and to treat topical sprue and megaloblastic and macrocytic anemias, hematologic complications resulting from a deficiency in folic acid.
• Toxicity: IPR-MUS LD₅₀ 85 mg/kg,IVN-GPG LD₅₀ 120 mg/kg, IVN-MUS LD₅₀ 239 mg/kg, IVN-RAT LD₅₀ 500 mg/kg, IVN-RBT LD₅₀ 410 mg/kg
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Protein Binding: Very high to plasma protein
• Elimination: Folic Acid is metabolized in the liver to 7, 8-dihydrofolic acid and eventually to 5,6,7,8-tetrahydrofolic acid with the aid of reduced diphosphopyridine nucleotide (DPNH) and folate reductases. A majority of the metabolic products appeared in the urine after 6 hours; excretion was generally complete within 24 hours. Folic Acid is also excreted in the milk of lactating mothers.
• References: Kamen B: Folate and antifolate pharmacology. Semin Oncol. 1997 Oct;24(5 Suppl 18):S18-30-S18-39. [Pubmed] ; Fenech M, Aitken C, Rinaldi J: Folate, vitamin B12, homocysteine status and DNA damage in young Australian adults. Carcinogenesis. 1998 Jul;19(7):1163-71. [Pubmed] ; Zittoun J: [Anemias due to disorder of folate, vitamin B12 and transcobalamin metabolism] Rev Prat. 1993 Jun 1;43(11):1358-63. [Pubmed] ; Alaimo K, McDowell MA, Briefel RR, Bischof AM, Caughman CR, Loria CM, Johnson CL: Dietary intake of vitamins, minerals, and fiber of persons ages 2 months and over in the United States: Third National Health and Nutrition Examination Survey, Phase 1, 1988-91. Adv Data. 1994 Nov 14;(258):1-28. [Pubmed] ; Raiten DJ, Fisher KD: Assessment of folate methodology used in the Third National Health and Nutrition Examination Survey (NHANES III, 1988-1994). J Nutr. 1995 May;125(5):1371S-1398S. [Pubmed]
• External Links: Wikipedia; PDRhealth; Drugs.com

Sigma Aldrich - F7876

包装
1, 10, 25, 100 g in glass bottle
Biochem/physiol Actions
Folic acid (FA) and dihydrofolic acid (FAH2) are substrates of dihydrofolate reductase(s) which reduce them to tetrahydrofolate (THF), which in turn supports ‘one carbon’ transfer. Tetrahydrofolates are required for de novo synthesis of purines, thymidylic acid and various amino acids and for post-translational methylation (epigenetics).

Sigma Aldrich - F8890

General description
Folic acid is a vitamin that is reduced to dihydrofolate in vivo. Dihydrofolate is further reduced tetrahydrofolate, a methyl group shuttle required for the de novo synthesis of purines, thymidylic acid, and certain amino acids.

Sigma Aldrich - F8758

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
A nutritional delivery form of folate. Folic acid and its derivatives are essential mediators of one-carbon metabolism within cells.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. F8758.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 47620

Other Notes
The biochemistry of folates. Reviews1,2

参考文献

• Raiten DJ, Fisher KD: Assessment of folate methodology used in the Third National Health and Nutrition Examination Survey (NHANES III, 1988-1994). J Nutr. 1995 May;125(5):1371S-1398S. Pubmed
• Fenech M, Aitken C, Rinaldi J: Folate, vitamin B12, homocysteine status and DNA damage in young Australian adults. Carcinogenesis. 1998 Jul;19(7):1163-71. Pubmed
• Zittoun J: [Anemias due to disorder of folate, vitamin B12 and transcobalamin metabolism] Rev Prat. 1993 Jun 1;43(11):1358-63. Pubmed
• Alaimo K, McDowell MA, Briefel RR, Bischof AM, Caughman CR, Loria CM, Johnson CL: Dietary intake of vitamins, minerals, and fiber of persons ages 2 months and over in the United States: Third National Health and Nutrition Examination Survey, Phase 1, 1988-91. Adv Data. 1994 Nov 14;(258):1-28. Pubmed
• Kamen B: Folate and antifolate pharmacology. Semin Oncol. 1997 Oct;24(5 Suppl 18):S18-30-S18-39. Pubmed