(2S)-2-[(4-{[(2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

• ChemBase ID: 3
• Molecular Formular: C19H23N7O6
• Molecular Mass: 445.42922
• Monoisotopic Mass: 445.17098149
• SMILES: O=c1nc([nH]c2NCC(Nc12)CNc1ccc(cc1)C(=O)N[C@@H](CCC(=O)O)C(=O)O)N
• 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/C19H23N7O6/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/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11?,12-/m0/s1
• InChIKey: MSTNYGQPCMXVAQ-KIYNQFGBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(4-{[(2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
• IUPAC Traditional name: @tetrahydrofolic acid; tetrahydrofolic acid
• Synonyms: tetrahydropteroylglutamate; tetrahydropteroyl mono-L-glutamate; tetrahydrafolate; tetra-H-folate; tetrahydrofolate; N-(4-(((2-Amino-1,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)methyl)amino)benzoyl)glutamic acid; H4PteGlu; th-folate; THF; folate-H4; FH4; 5,6,7,8-tetrahydrofolic acid; 5,6,7,8-tetrahydrofolate; (6S)-tetrahydrofolate; Tetrahydrofolic acid; N-[4-[[(2-Amino-3,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic Acid; (-)-L-5,6,7,8-Tetrahydrofolic Acid; THFA; Tetrahydropteroylglutamic Acid; L-Tetrahydrofolic Acid, synthesized on receipt of order. 95% minimum purity when shipped.

Database IDs

• CAS Number: 29347-89-5; 135-16-0
• PubChem SID: 160963466; 46504756
• PubChem CID: 91443
• CHEBI ID: 20506
• Chemspider ID: 82572
• DrugBank ID: DB00116
• KEGG ID: C00101
• MeSH Name: 5,6,7,8-tetrahydrofolic+acid
• Wikipedia Title: Tetrahydrofolic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.4210246
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -5.826242
• LogD (pH = 7.4): -8.4603615
• Log P: -2.6668603
• Molar Refractivity: 121.3866 cm^3
• Polarizability: 41.3385 Å^3
• Polar Surface Area: 207.27 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.96
• LOG S: -3.22
• Solubility (Water): 2.69e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -2.7

Safety Information

• Storage Warning: We have observed that this material decomposes steadily over

DETAILS

DrugBank - DB00116

• Drug Groups: approved; nutraceutical
• Description: Tetrahydrofolic acid is a folic acid derivative. It is produced from dihydrofolic acid by dihydrofolate reductase.; It is converted into 5,10-methylenetetrahydrofolate by serine hydroxymethyltransferase. It is a coenzyme in many reactions, especially in the metabolism of amino acids and nucleic acids. It acts as a donor of a group with one carbon atom. It gets this carbon atom by sequestering formaldehyde produced in other processes.
• Indication: For nutritional supplementation, also for treating dietary shortage or imbalance.
• Pharmacology: Tetrahydrofolate is the main active metabolite of dietary folate. It is vital as a coenzyme in reactions involving transfers of single carbon groups. Tetrahydrofolate has a role in nucleic and amino acid synthesis. As nucleic and amino acid synthesis is affected by a deficiency of tetrahydrofolate, actively dividing and growing cells tend to be the first affected. Tetrahydrofolate is used to treat topical sprue and megaloblastic and macrocytic anemias, hematologic complications resulting from a deficiency in folic acid.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia

Toronto Research Chemicals - T293515

A folic acid derivative and coenzyme involved in the metabolism of amino and nucleic acids. We have observed that this material decomposes steadily over time. Use immediately upon receipt.

REFERENCES

• Prinz-Langenohl, R., et al.: Brit. J. Pharmacol., 158, 2014 (2009)
• Martin, H., et al.: Anal. Biochem., 402, 137 (2009)
• Dasarathy, J., et al.: Am. J. Clin. Nut., 91, 357 (2009)
• Karas-Kuzelicki, N., et al.: Clin. Biochem., 43, 37 (2009)