(2S)-2-[(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}phenyl)formamido]pentanedioic acid hydrate

• ChemBase编号: 130867
• 分子式: C20H24N8O6
• 平均质量: 472.45456
• 单一同位素质量: 472.18188053
• SMILES: CN(Cc1cnc2c(n1)c(nc(n2)N)N)c1ccc(cc1)C(=O)N[C@@H](CCC(=O)O)C(=O)O.O
• Canonical SMILES: OC(=O)CC[C@@H](C(=O)O)NC(=O)c1ccc(cc1)N(Cc1cnc2c(n1)c(N)nc(n2)N)C.O
• InChI: InChI=1S/C20H22N8O5.H2O/c1-28(9-11-8-23-17-15(24-11)16(21)26-20(22)27-17)12-4-2-10(3-5-12)18(31)25-13(19(32)33)6-7-14(29)30;/h2-5,8,13H,6-7,9H2,1H3,(H,25,31)(H,29,30)(H,32,33)(H4,21,22,23,26,27);1H2/t13-;/m0./s1
• InChIKey: FPJYMUQSRFJSEW-ZOWNYOTGSA-N

名称和登记号

名称

• IUPAC标准名: (2S)-2-[(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}phenyl)formamido]pentanedioic acid hydrate
• IUPAC传统名: hydrate methotrexate
• 别名: L-氨甲喋呤 水合物; 甲氨蝶呤 水合物; 对-[(2,4-二氨基喋啶-6)-N-甲基甲氨基]苯甲酰谷氨酸 水合物; L-氨甲喋呤 水合物; MTX 水合物; 氟安定 水合物; 氨甲叶酸 水合物; 氨甲喋呤 水合物; 甲氨蝶呤 水合物; 甲氨蝶呤; 4-Amino-10-methylfolic acid hydrate; L-4-Amino-N10-methylpteroylglutamic acid hydrate; L-Amethopterin hydrate; Antifolan hydrate; MTX hydrate; Methotrexate hydrate; Methylaminopterin hydrate; L-Amethopterin hydrate; Methotrexate hydrate; Methotrexate

登记号

• CAS号: 133073-73-1
• EC号: 200-413-8
• MDL号: MFCD00150847
• PubChem SID: 162225145; 24853414; 24278233; 24897252; 24897373
• PubChem CID: 165528

理论计算性质

• Acid pKa: 3.2608879
• 质子受体: 12
• 质子供体: 5
• LogD (pH = 5.5): -3.640823
• LogD (pH = 7.4): -6.5636883
• Log P: -0.23654379
• 摩尔折射率: 119.2108 cm^3
• 极化性: 43.521362 Å^3
• 极化表面积: 210.54 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: H2O: insoluble
• 外观: powder; yellow powder
• 比旋光度: [α]25/D +17°, c = 1 in 0.05 M Na2CO3

安全信息

• RTECS编号: MA1225000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 1544
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 46-61-25-36/38; 61-25-36/38
• 安全公开号: 53-26-36/37-45; 53-26-36-45
• GHS危险品标识: GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H301-H315-H319-H340-H360; H301-H315-H319-H360
• GHS警示性声明: P201-P301 + P310-P305 + P351 + P338-P308 + P313
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1544 6.1/PG 3
• 保存温度: -20°C

药理学性质

• 相关基因信息: human ... DHFRP1(573971), FPGS(2356), SLC19A1(6573), TYMS(7298)mouse ... Dhfr(13361)rat ... Dhfr(24312)

产品相关信息

• 纯度: ≥98% (HPLC); 85%; 98%
• 适用性: meets EP, USP testing specifications; meets USP testing specifications; suitable for cell culture; suitable for insect cell culture
• Empirical Formula (Hill Notation): C20H22N8O5 · xH2O

详细说明

Sigma Aldrich - A6770

Application
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.2,3 Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also effective in treatment of pyrimethamine-resistant Plasmodium vivax malaria parasites.4
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.2,3 Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also shows immunosuppressive effects in, e.g., rheumatoid arthritis.

Sigma Aldrich - M8407

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
Recommended for use in cell culture and molecular biology applications at 0.01-300 μM in nucleoside-free cell culture medium to select for DHFR expression.
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.2,3 Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also effective in treatment of pyrimethamine-resistant Plasmodium vivax malaria parasites.4
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.2,3 Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also shows immunosuppressive effects in, e.g., rheumatoid arthritis.
Biochem/physiol Actions
Methotrexate used to inhibit dihyrofolate reductase and select for DHFR overexpresssion.

Sigma Aldrich - M4010

Application
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.2,3 Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also effective in treatment of pyrimethamine-resistant Plasmodium vivax malaria parasites.4
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.2,3 Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also shows immunosuppressive effects in, e.g., rheumatoid arthritis.

Sigma Aldrich - 223948

包装
100 mg in glass bottle
Application
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.2,3 Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also effective in treatment of pyrimethamine-resistant Plasmodium vivax malaria parasites.
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.2,3 Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also shows immunosuppressive effects in, e.g., rheumatoid arthritis.
二氢叶酸还原酶的强效抑制剂1，以及用于抗癌抗菌素研究的试剂。2,3

Sigma Aldrich - 06564

Application
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.2,3 Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also effective in treatment of pyrimethamine-resistant Plasmodium vivax malaria parasites.4
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.2,3 Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also shows immunosuppressive effects in, e.g., rheumatoid arthritis.

Sigma Aldrich - M9929

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Methotrexate is an allosteric inhibititor of dihydrofolate reductase (DHFR), the enzyme that catalyzes the conversion of dihydrofolate to tetrahydrofolate. Since tetrahydrolfolate is required for purine and pyrimidine synthesis, methotrexate treatment results in the inhibition of DNA and RNA synthesis.
Application
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.2,3 Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also effective in treatment of pyrimethamine-resistant Plasmodium vivax malaria parasites.4
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.2,3 Use to inhibit dihydrofolate reductase in DHFR-based protein expression systems. Also shows immunosuppressive effects in, e.g., rheumatoid arthritis.