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

• ChemBase ID: 130867
• Molecular Formular: C20H24N8O6
• Molecular Mass: 472.45456
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}phenyl)formamido]pentanedioic acid hydrate
• IUPAC Traditional name: hydrate methotrexate
• Synonyms: 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; 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

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 3.2608879
• H Acceptors: 12
• H Donor: 5
• LogD (pH = 5.5): -3.640823
• LogD (pH = 7.4): -6.5636883
• Log P: -0.23654379
• Molar Refractivity: 119.2108 cm^3
• Polarizability: 43.521362 Å^3
• Polar Surface Area: 210.54 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: insoluble
• Apperance: powder; yellow powder
• Optical Rotation: [α]25/D +17°, c = 1 in 0.05 M Na2CO3

Safety Information

• RTECS: MA1225000
• European Hazard Symbols: Toxic (T)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 46-61-25-36/38; 61-25-36/38
• Safety Statements: 53-26-36/37-45; 53-26-36-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H340-H360; H301-H315-H319-H360
• GHS Precautionary statements: P201-P301 + P310-P305 + P351 + P338-P308 + P313
• Personal Protective Equipment: 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
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... DHFRP1(573971), FPGS(2356), SLC19A1(6573), TYMS(7298)mouse ... Dhfr(13361)rat ... Dhfr(24312)

Product Information

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

DETAILS

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

Packaging
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.
Potent inhibitor of dihydrofolate reductase1 and agent for antitumor studies.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.