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

• ChemBase编号: 127031
• 分子式: C19H21N7O6
• 平均质量: 443.41334
• 单一同位素质量: 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

名称和登记号

名称

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

登记号

• CAS号: 4033-27-6
• MDL号: MFCD00083619
• Beilstein号: 69017
• PubChem SID: 162221354; 24894068
• PubChem CID: 98792
• CHEBI ID: 15633
• CHEMBL: 46294
• Chemspider ID: 89228
• 医学主题词(MeSH): dihydrofolate
• 维基百科标题: Dihydrofolic_acid

理论计算性质

• Acid pKa: 3.381581
• 质子受体: 12
• 质子供体: 7
• LogD (pH = 5.5): -5.0415783
• LogD (pH = 7.4): -8.116197
• Log P: -1.8052275
• 摩尔折射率: 120.9914 cm^3
• 极化性: 40.931744 Å^3
• 极化表面积: 207.6 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: false

分子性质

理化性质

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

安全信息

• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: -20°C

药理学性质

• 相关基因信息: human ... DHFRP1(573971)mouse ... Dhfr(13361)

产品相关信息

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

详细说明

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