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

• ChemBase ID: 132374
• Molecular Formular: C19H20N8O5
• Molecular Mass: 440.4127
• Monoisotopic Mass: 440.15566578
• SMILES: c1cc(ccc1C(=O)N[C@@H](CCC(=O)O)C(=O)O)NCc1cnc2c(n1)c(nc(n2)N)N
• Canonical SMILES: OC(=O)CC[C@@H](C(=O)O)NC(=O)c1ccc(cc1)NCc1cnc2c(n1)c(N)nc(n2)N
• InChI: InChI=1S/C19H20N8O5/c20-15-14-16(27-19(21)26-15)23-8-11(24-14)7-22-10-3-1-9(2-4-10)17(30)25-12(18(31)32)5-6-13(28)29/h1-4,8,12,22H,5-7H2,(H,25,30)(H,28,29)(H,31,32)(H4,20,21,23,26,27)/t12-/m0/s1
• InChIKey: TVZGACDUOSZQKY-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(4-{[(2,4-diaminopteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
• IUPAC Traditional name: 4-aminopteroylglutamic acid
• Synonyms: Aminopterin; N-[4-[[(2,4-Diamino-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic Acid; 4-Aminofolic Acid, 4-Aminopteroyl-L-glutamic Acid, 4-Amino-PGA; NSC 739; Aminopterin; 4-Amino-PGA; 4-Aminofolic acid; 4-Aminopteroyl-L-glutamic acid; 4-氨基-PGA; 4-氨基叶酸; N-[4-[[(2,4-二氨基-6-蝶啶)甲基]氨基]苯甲酰]-L-谷氨酸; 氨基蝶呤

Database IDs

• CAS Number: 54-62-6
• EC Number: 200-209-9
• MDL Number: MFCD00036692
• Beilstein Number: 69045
• PubChem SID: 24846313; 24890768; 24278186; 24890950; 162226651
• PubChem CID: 169371

CALCULATED PROPERTIES

• Acid pKa: 3.3831797
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -4.1830673
• LogD (pH = 7.4): -7.1697493
• Log P: -0.9509029
• Molar Refractivity: 114.976 cm^3
• Polarizability: 41.69816 Å^3
• Polar Surface Area: 219.33 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 2 M NaOH: soluble50 mg/mL; 2 M NaOH: soluble50 mg/mL (Solutions may be stored for 1-2 days at 4°C.); DMF; DMSO; DMSO: soluble; DMSO: soluble (Solutions may be stored for 1-2 days at 4°C.)
• Apperance: Dark Yellow Solid; lyophilized powder; yellow powder
• Melting Point: 208-213°C (dec.); 228-235 °C (dec.)
• Optical Rotation: [α]20/D +18±2°, c = 1% in 0.1 M NaOH
• Absorption Wavelength: ε1M/261 nm, 0.1 M NaOH 25,700; ε1M/282 nm, 0.1 M NaOH 24,500; ε1M/373 nm, 0.1 M NaOH 8,100

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: MA1050000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 61-28
• Safety Statements: 53-28-36/37-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H360
• GHS Precautionary statements: P201-P264-P301 + P310-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 2811 6.1/PG 1
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Gene Information: human ... FPGS(2356)mouse ... Fpgs(14287)

Product Information

• Purity: ~98%; ~98% (TLC); ≥96.0% (UV)
• Concentration: 50 ×
• Grade: Hybri-Max™
• Suitability: suitable for cell culture; suitable for hybridoma
• Impurities: endotoxin, tested
• Sterility: γ-irradiated
• Shipped in: dry ice
• abs.: ε1M/261 nm, 0.1 M NaOH 25,700; ε1M/282 nm, 0.1 M NaOH 24,500; ε1M/373 nm, 0.1 M NaOH 8,100
• Empirical Formula (Hill Notation): C19H20N8O5

DETAILS

Sigma Aldrich - A5159

Application
用于杂交瘤细胞培养应用的氨基蝶呤浓缩物添加剂。
Linkage
比甲氨喋呤更有效，但毒性也更强。
Reconstitution
10mL 无菌细胞培养基可复原一小瓶本品。储备液足以制备 500mL 培养基。最终工作浓度：0.4μM 氨基蝶呤。
Biochem/physiol Actions
叶酸拮抗剂。氨基蝶呤是由叶酸转运蛋白运输至细胞内的。在细胞内，它被叶酰聚谷氨酸合酶转化为一种高分子量的聚谷氨酸盐代谢物，该产物又与二氢叶酸还原酶结合并抑制其活性。氨基蝶呤-聚谷氨酸盐经 γ-谷氨酰基水解酶作用发生细胞内降解。
法律信息
Hybri-Max 商标 Sigma-Aldrich Co. LLC
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A5159.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - A1784

Linkage
比甲氨喋呤更有效，但毒性也更强。
Biochem/physiol Actions
叶酸拮抗剂。氨基蝶呤是由叶酸转运蛋白运输至细胞内的。在细胞内，它被叶酰聚谷氨酸合酶转化为一种高分子量的聚谷氨酸盐代谢物，该产物又与二氢叶酸还原酶结合并抑制其活性。氨基蝶呤-聚谷氨酸盐经 γ-谷氨酰基水解酶作用发生细胞内降解。

Sigma Aldrich - A3411

Linkage
比甲氨喋呤更有效，但毒性也更强。
Biochem/physiol Actions
叶酸拮抗剂。氨基蝶呤是由叶酸转运蛋白运输至细胞内的。在细胞内，它被叶酰聚谷氨酸合酶转化为一种高分子量的聚谷氨酸盐代谢物，该产物又与二氢叶酸还原酶结合并抑制其活性。氨基蝶呤-聚谷氨酸盐经 γ-谷氨酰基水解酶作用发生细胞内降解。

Sigma Aldrich - 09328

Linkage
More potent, but more toxic, than methotrexate.
Other Notes
Folic acid antagonist.; Potent competitive inhibitor of dihydrofolate reductase1
Biochem/physiol Actions
Folic acid antagonist. Aminopterin is actively transported into cells by the folate transporter. In the cell, it is converted to a high molecular weight polyglutamate metabolite by folylpolyglutamate synthase that, in turn, binds to dihydrofolate reductase and inhibits its activity. Aminopterin-polyglutamate is degraded intracellularly by γ-glutamyl hydrolase.

Toronto Research Chemicals - A628850

A folic acid antagonist. Its actively transported into cells by thefolate transporter. In the cell, its converted to a high molecular weight polyglutamate metabolite by folylpolyglutamate synthase, that, in turn, binds to dihydrofolate reductase and inh

REFERENCES

• Matherly, L.H., et al.: Cancer Res., 45, 1073 (1985)
• Rumberger, B.G., et al.: Cancer Res., 50, 4639 (1985)
• Roy, K., et al.: J. Biol. Chem., 273, 2526 (1985)