CAS 59-30-3|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|(2S)-2-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid|维生素 M|PteG...

基本信息

化学结构

分子式

C₁₉H₁₉N₇O₆

分子量

441.39746

精确质量

441.13968136

电荷

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

Canonic Smiles

OC(=O)CC[C@@H](C(=O)O)NC(=O)c1ccc(cc1)NCc1cnc2c(n1)c(=O)nc([nH]2)N

Isomeric Smiles

OC(=O)[C@@H](NC(=O)c1ccc(NCc2nc3c([nH]c(nc3=O)N)nc2)cc1)CCC(=O)O

计算属性

JChem

Acid pKa

3.3738735

质子受体

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

极化性

40.461403

极化表面积

208.99

可自由旋转的化学键

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

数据来源

名称和标识

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Folic acid维生素 MPteGlu叶酸Vitamin MPteroyl-L-glutamic acid叶酸Acidum folicumFolic acidFolic AcidN-(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acidVitamin B₉Vitamin B_cFolacinFolateVitamin BePteroyl-L-monoglutamic acidPteroylmonoglutamic acidPteroylglutamic acidVitamin BcVitamin B9PGA

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

folate folic acid

商标名

FoliaminFolviteFolbalFolicetFolipacIncafolicMillafolFolacidFolacinFolettesFolvronFolsavAcifolicApo-FolicFolcidinFoldineFolsaureFolsanDosfolat B activCytofol

名称和标识

数据登录号

PubChem CID

CAS号

美国药典/FDA物质标识码

DrugBank ID

ATC码

MDL号

维基百科标题

Beilstein号

PubChem SID

2487153824894950248949734650809224894977248712201609635072489497924845192

KEGG ID

CHEMBL

CHEBI ID

EC号

Chemspider ID

数据登录号

化合物性质

理化性质

疏水性(logP)

-2.5

溶解度

Slight

1.6 mg/L (25 °C) in water

p𝘒ₐ

1^st: 4.65, 2^nd: 6.75, 3^rd: 9.00

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

化合物性质

分子相关蛋白质

暂无数据

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分子图谱

暂无数据

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描述信息

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]

Wikipedia

Folic_acid

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).

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.

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.

47620

Other Notes
The biochemistry of folates. Reviews1,2

描述信息

参考文献

PubChem文献

数据源提供

• 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

• 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

• Zittoun J: [Anemias due to disorder of folate, vitamin B12 and transcobalamin metabolism] Rev Prat. 1993 Jun 1;43(11):1358-63. Pubmed

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

别名

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

folate folic acid

商标名

FoliaminFolviteFolbalFolicetFolipacIncafolicMillafolFolacidFolacinFolettesFolvronFolsavAcifolicApo-FolicFolcidinFoldineFolsaureFolsanDosfolat B activCytofol

数据登录号

PubChem CID

CAS号

美国药典/FDA物质标识码

DrugBank ID

ATC码

MDL号

维基百科标题

Beilstein号

PubChem SID

2487153824894950248949734650809224894977248712201609635072489497924845192

KEGG ID

CHEMBL

CHEBI ID

EC号

Chemspider ID

描述信息

DB00158

Drug Groups

approved; nutraceutical

Description

Indication

For treatment of folic acid deficiency, megaloblastic anemia and in anemias of nutritional supplements, pregnancy, infancy, or childhood.

Pharmacology

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

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]

• 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]

Wikipedia

Folic_acid

Sigma Aldrich

F7876

F8758

F8890

47620

Other Notes
The biochemistry of folates. Reviews1,2

参考文献

PubChem文献

数据源提供

• 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

• 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

• Zittoun J: [Anemias due to disorder of folate, vitamin B12 and transcobalamin metabolism] Rev Prat. 1993 Jun 1;43(11):1358-63. Pubmed

生物活性

PubChem BioAssay

化合物性质

理化性质

疏水性(logP)

-2.5

溶解度

Slight

1.6 mg/L (25 °C) in water

p𝘒ₐ

1^st: 4.65, 2^nd: 6.75, 3^rd: 9.00

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

化合物信息

ID:44