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59-30-3 分子结构
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(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和InChIs

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

引用这个纪录

CBID:44 http://www.chembase.cn/molecule-44.html

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名称和登记号

名称和登记号

名称 登记号
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
Folate
PGA
Pteroyl-L-glutamic acid
Pteroyl-L-monoglutamic acid
Pteroylglutamic acid
Pteroylmonoglutamic acid
Vitamin M
Vitamin Be
Vitamin Bc
Vitamin B9
Folic Acid
N-​(4-​{[(2-​amino-​4-​oxo-​1,​4-​dihydropteridin-​6-​yl)​methyl]​amino}​benzoyl)-​L-​glutamic acid
Vitamin B9
Vitamin Bc
PteGlu
Folic acid
Acidum folicum
Folic acid
Folacin
CAS号
59-30-3
EC号
200-419-0
MDL号
MFCD00079305
Beilstein号
100781
PubChem SID
24871220
24894950
24845192
24894977
46508092
24894979
24894973
160963507
24871538
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

理论计算性质

JChem ALOGPS 2.1
Acid pKa 3.3738735  质子受体 12 
质子供体 LogD (pH = 5.5) -3.942576 
LogD (pH = 7.4) -7.12074  Log P -0.68225247 
摩尔折射率 111.0112 cm3 极化性 40.461403 Å3
极化表面积 208.99 Å2 可自由旋转的化学键
里宾斯基五规则 false 
Log P -0.04  LOG S -3.76 
溶解度 7.61e-02 g/l 

分子性质

分子性质

理化性质 安全信息 产品相关信息 生物活性(PubChem)
溶解度
1.6 mg/L (25 °C) in water expand 查看数据来源
Slight expand 查看数据来源
外观
yellow-orange crystalline powder expand 查看数据来源
熔点
250 °C (523 K), decomp. expand 查看数据来源
比旋光度
[α]20/D +20±2°, c = 1% in 0.1 M NaOH expand 查看数据来源
疏水性(logP)
-2.5 expand 查看数据来源
pKa
1st: 4.65, 2nd: 6.75, 3rd: 9.00 expand 查看数据来源
RTECS编号
LP5425000 expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
1 expand 查看数据来源
3 expand 查看数据来源
个人保护装置
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand 查看数据来源
保存温度
2-8°C expand 查看数据来源
纯度
≥97% expand 查看数据来源
≥97.0% (HPLC) expand 查看数据来源
级别
analytical standard expand 查看数据来源
Ph Eur expand 查看数据来源
包装
ampule of 500 mg expand 查看数据来源
适用性
meets USP testing specifications expand 查看数据来源
plant cell culture tested expand 查看数据来源
suitable for cell culture expand 查看数据来源
suitable for insect cell culture expand 查看数据来源
suitable for plant cell culture expand 查看数据来源
燃烧残渣
≤0.1% (as SO4) expand 查看数据来源
杂质
~8% water expand 查看数据来源
痕量阳离子
Ca: ≤10 mg/kg expand 查看数据来源
Cd: ≤5 mg/kg expand 查看数据来源
Co: ≤5 mg/kg expand 查看数据来源
Cr: ≤5 mg/kg expand 查看数据来源
Cu: ≤5 mg/kg expand 查看数据来源
Fe: ≤5 mg/kg expand 查看数据来源
K: ≤50 mg/kg expand 查看数据来源
Mg: ≤5 mg/kg expand 查看数据来源
Mn: ≤5 mg/kg expand 查看数据来源
Na: ≤1500 mg/kg expand 查看数据来源
Ni: ≤5 mg/kg expand 查看数据来源
Pb: ≤5 mg/kg expand 查看数据来源
Zn: ≤5 mg/kg expand 查看数据来源
产品质量级别
PREMIUM expand 查看数据来源
特征
standard type water soluble vitamin expand 查看数据来源
药典
testing & handling conforms to Pharmacopeia expand 查看数据来源
Pharmacopeia Traceability
traceable to PhEur F0300000 expand 查看数据来源
traceable to USP 1286005 expand 查看数据来源
Empirical Formula (Hill Notation)
C19H19N7O6 expand 查看数据来源

详细说明

详细说明

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich DrugBank DrugBank
Sigma Aldrich -  F8890 external link
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 external link
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 external link
Other Notes
The biochemistry of folates. Reviews1,2
Sigma Aldrich -  F7876 external link
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).
DrugBank -  DB00158 external link
Item Information
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

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • 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
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