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...

General Information

Structure

Molecular Formula

C₁₉H₁₉N₇O₆

Molecular Mass

441.39746

Exact Mass

441.13968136

Charge

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

Calculated Properties

JChem

Acid pKa

3.3738735

H Acceptors

H Donor

LogD (pH = 5.5)

-3.942576

LogD (pH = 7.4)

-7.12074

Log P

-0.68225247

Molar Refractivity

111.0112

Polarizability

40.461403

Polar Surface Area

208.99

Rotatable Bonds

Lipinski's Rule of Five

false

ALOGPS 2.1

Log P

-0.04

LOG S

-3.76

Solubility (Water)

7.61e-02 g/l

Data Source

Names and Identifiers

Synonyms

Folic acidN-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 MPteGlu叶酸Vitamin MPteroyl-L-glutamic acidAcidum folicum叶酸Folic acidFolacinVitamin B₉Vitamin B_cN-(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acidFolic AcidPteroyl-L-monoglutamic acidVitamin BeVitamin BcPteroylmonoglutamic acidVitamin B9Pteroylglutamic acidFolatePGA

IUPAC name

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

IUPAC Traditional name

folate folic acid

Brand Name

FolcidinFoldineIncafolicDosfolat B activFolacidFolbalMillafolFolacinFolettesFolsavCytofolFoliaminFolvronFolicetFolviteFolsaureFolsanAcifolicApo-FolicFolipac

Names and Identifiers

Registration numbers

CAS Number

59-30-3

PubChem CID

6037

Unique Ingredient Identifier

ATC CODE

DrugBank ID

MDL Number

Beilstein Number

Wikipedia Title

PubChem SID

2487153824894950248949734650809224894977248712201609635072489497924845192

KEGG ID

CHEMBL

Chemspider ID

CHEBI ID

EC Number

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

-2.5

Solubility

Slight

1.6 mg/L (25 °C) in water

p𝘒ₐ

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

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

Safety Information

RTECS

LP5425000

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

German water hazard class

Storage Temperature

2-8°C

MSDS Link

Download link

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule 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]

Molecule Details

References

PubChem Literature

From Data Sources

• 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

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC name

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

IUPAC Traditional name

folate folic acid

Brand Name

FolcidinFoldineIncafolicDosfolat B activFolacidFolbalMillafolFolacinFolettesFolsavCytofolFoliaminFolvronFolicetFolviteFolsaureFolsanAcifolicApo-FolicFolipac

Registration numbers

CAS Number

59-30-3

PubChem CID

6037

Unique Ingredient Identifier

ATC CODE

DrugBank ID

MDL Number

Beilstein Number

Wikipedia Title

PubChem SID

2487153824894950248949734650809224894977248712201609635072489497924845192

KEGG ID

CHEMBL

Chemspider ID

CHEBI ID

EC Number

References

PubChem Literature

From Data Sources

• 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

Bioactivity

PubChem BioAssay

Properties

Physical Property

Hydrophobicity(logP)

-2.5

Solubility

Slight

1.6 mg/L (25 °C) in water

p𝘒ₐ

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

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

Safety Information

RTECS

LP5425000

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

German water hazard class

Storage Temperature

2-8°C

MSDS Link

Download link

Molecule Details

DrugBank

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]

Molecule

ID:44