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59-30-3 molecular structure
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(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 and 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

Cite this record

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

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
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
Folacin
Folic acid
Folic acid
Acidum folicum
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
CAS Number
59-30-3
EC Number
200-419-0
MDL Number
MFCD00079305
Beilstein Number
100781
PubChem SID
24894979
24871538
24871220
24894977
24894950
46508092
24845192
24894973
160963507
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.3738735  H Acceptors 12 
H Donor LogD (pH = 5.5) -3.942576 
LogD (pH = 7.4) -7.12074  Log P -0.68225247 
Molar Refractivity 111.0112 cm3 Polarizability 40.461403 Å3
Polar Surface Area 208.99 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P -0.04  LOG S -3.76 
Solubility (Water) 7.61e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
1.6 mg/L (25 °C) in water expand Show data source
Slight expand Show data source
Apperance
yellow-orange crystalline powder expand Show data source
Melting Point
250 °C (523 K), decomp. expand Show data source
Optical Rotation
[α]20/D +20±2°, c = 1% in 0.1 M NaOH expand Show data source
Hydrophobicity(logP)
-2.5 expand Show data source
pKa
1st: 4.65, 2nd: 6.75, 3rd: 9.00 expand Show data source
RTECS
LP5425000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥97% expand Show data source
≥97.0% (HPLC) expand Show data source
Grade
analytical standard expand Show data source
Ph Eur expand Show data source
Packaging
ampule of 500 mg expand Show data source
Suitability
meets USP testing specifications expand Show data source
plant cell culture tested expand Show data source
suitable for cell culture expand Show data source
suitable for insect cell culture expand Show data source
suitable for plant cell culture expand Show data source
Ignition Residue
≤0.1% (as SO4) expand Show data source
Impurities
~8% water expand Show data source
Cation Traces
Ca: ≤10 mg/kg expand Show data source
Cd: ≤5 mg/kg expand Show data source
Co: ≤5 mg/kg expand Show data source
Cr: ≤5 mg/kg expand Show data source
Cu: ≤5 mg/kg expand Show data source
Fe: ≤5 mg/kg expand Show data source
K: ≤50 mg/kg expand Show data source
Mg: ≤5 mg/kg expand Show data source
Mn: ≤5 mg/kg expand Show data source
Na: ≤1500 mg/kg expand Show data source
Ni: ≤5 mg/kg expand Show data source
Pb: ≤5 mg/kg expand Show data source
Zn: ≤5 mg/kg expand Show data source
Quality Level
PREMIUM expand Show data source
Feature
standard type water soluble vitamin expand Show data source
Pharmacopeia
testing & handling conforms to Pharmacopeia expand Show data source
Pharmacopeia Traceability
traceable to PhEur F0300000 expand Show data source
traceable to USP 1286005 expand Show data source
Empirical Formula (Hill Notation)
C19H19N7O6 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich Wikipedia Wikipedia
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
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).
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

REFERENCES

REFERENCES

From Suppliers 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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