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

• ChemBase ID: 127031
• Molecular Formular: C19H21N7O6
• Molecular Mass: 443.41334
• Monoisotopic Mass: 443.15533143
• SMILES: O=C(O)[C@@H](NC(=O)c1ccc(cc1)NCC1=Nc2c(=O)nc([nH]c2NC1)N)CCC(=O)O
• Canonical SMILES: OC(=O)CC[C@@H](C(=O)O)NC(=O)c1ccc(cc1)NCC1=Nc2c(NC1)[nH]c(nc2=O)N
• InChI: InChI=1S/C19H21N7O6/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/h1-4,12,21H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t12-/m0/s1
• InChIKey: OZRNSSUDZOLUSN-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(4-{[(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
• IUPAC Traditional name: dihydrofolic acid
• Synonyms: H₂folate; DH; Dihydrofolic acid; 7,8-Dihydropteroyl-L-glutamic acid; Dihydropteroyl-L-glutamic acid; FAH2; Dihydrofolic acid; 二氢叶酸

Database IDs

• CAS Number: 4033-27-6
• MDL Number: MFCD00083619
• Beilstein Number: 69017
• PubChem SID: 162221354; 24894068
• PubChem CID: 98792
• CHEBI ID: 15633
• CHEMBL: 46294
• Chemspider ID: 89228
• MeSH Name: dihydrofolate
• Wikipedia Title: Dihydrofolic_acid

CALCULATED PROPERTIES

• Acid pKa: 3.381581
• H Acceptors: 12
• H Donor: 7
• LogD (pH = 5.5): -5.0415783
• LogD (pH = 7.4): -8.116197
• Log P: -1.8052275
• Molar Refractivity: 120.9914 cm^3
• Polarizability: 40.931744 Å^3
• Polar Surface Area: 207.6 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 0.1 M NaOH: soluble10 mg/mL, slightly hazy, orange

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... DHFRP1(573971)mouse ... Dhfr(13361)

Product Information

• Purity: ≥88% (enzymatic); ≥90%
• Impurities: ≤12% water
• Empirical Formula (Hill Notation): C19H21N7O6

DETAILS

Sigma Aldrich - D7006

General description
Intermediate in mammalian conversion of dietary folic acid to tetrahydrofolate by dihydrofolate reductase (DHFR). In bacteria, dihydrofolic acid is generated from 7,8-dihydropteroate by dihydrofolate synthetase.
包装
Sealed ampule.
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).
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D7006.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 37296

General description
Intermediate in mammalian conversion of dietary folic acid to tetrahydrofolate by dihydrofolate reductase (DHFR). In bacteria, dihydrofolic acid is generated from 7,8-dihydropteroate by dihydrofolate synthetase.
Other Notes
Assay of dihydrofolate reductase1