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

• ChemBase ID: 44
• Molecular Formular: C19H19N7O6
• Molecular Mass: 441.39746
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
• IUPAC Traditional name: folic acid; folate
• Brand Name: Acifolic; Apo-Folic; Cytofol; Dosfolat B activ; Folacid; Folacin; Folbal; Folcidin; Foldine; Folettes; Foliamin; Folicet; Folipac; Folsan; Folsaure; Folsav; Folvite; Folvron; Incafolic; Millafol
• Synonyms: 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; 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

Database IDs

• CAS Number: 59-30-3
• EC Number: 200-419-0
• MDL Number: MFCD00079305
• Beilstein Number: 100781
• PubChem SID: 24894977; 24871220; 24871538; 24845192; 24894979; 24894973; 160963507; 24894950; 46508092
• PubChem CID: 6037
• CHEBI ID: 27470
• ATC CODE: B03BB01
• CHEMBL: 1622
• Chemspider ID: 5815
• DrugBank ID: DB00158
• KEGG ID: C00504
• Unique Ingredient Identifier: 935E97BOY8
• Wikipedia Title: Folic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.3738735
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -3.942576
• LogD (pH = 7.4): -7.12074
• Log P: -0.68225247
• Molar Refractivity: 111.0112 cm^3
• Polarizability: 40.461403 Å^3
• Polar Surface Area: 208.99 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.04
• LOG S: -3.76
• Solubility (Water): 7.61e-02 g/l

PROPERTIES

Physical Property

• Solubility: 1.6 mg/L (25 °C) in water; Slight
• Apperance: yellow-orange crystalline powder
• Melting Point: 250 °C (523 K), decomp.
• Optical Rotation: [α]20/D +20±2°, c = 1% in 0.1 M NaOH
• Hydrophobicity(logP): -2.5
• pKa: 1^st: 4.65, 2^nd: 6.75, 3^rd: 9.00

Safety Information

• RTECS: LP5425000
• German water hazard class: 1; 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97%; ≥97.0% (HPLC)
• Grade: analytical standard; Ph Eur
• Packaging: ampule of 500 mg
• Suitability: meets USP testing specifications; plant cell culture tested; suitable for cell culture; suitable for insect cell culture; suitable for plant cell culture
• Ignition Residue: ≤0.1% (as SO4)
• Impurities: ~8% water
• Cation Traces: 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
• Quality Level: PREMIUM
• Feature: standard type water soluble vitamin
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Pharmacopeia Traceability: traceable to PhEur F0300000; traceable to USP 1286005
• Empirical Formula (Hill Notation): C19H19N7O6

DETAILS

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

REFERENCES

• 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