(2S)-2-{[4-({[(6S)-2-amino-4-oxo-4,4a,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}-5-hydroperoxypentanoic acid; 4-methylbenzene-1-sulfonic acid

• ChemBase ID: 178350
• Molecular Formular: C26H33N7O9S
• Molecular Mass: 619.64672
• Monoisotopic Mass: 619.20604667
• SMILES: N1=C(N=C2C(C1=O)N[C@H](CN2)CNc1ccc(cc1)C(=O)N[C@@H](CCCOO)C(=O)O)N.c1(ccc(cc1)C)S(=O)(=O)O
• Canonical SMILES: Cc1ccc(cc1)S(=O)(=O)O.OOCCC[C@@H](C(=O)O)NC(=O)c1ccc(cc1)NC[C@H]1CNC2=NC(=NC(=O)C2N1)N
• InChI: InChI=1S/C19H25N7O6.C7H8O3S/c20-19-25-15-14(17(28)26-19)23-12(9-22-15)8-21-11-5-3-10(4-6-11)16(27)24-13(18(29)30)2-1-7-32-31;1-6-2-4-7(5-3-6)11(8,9)10/h3-6,12-14,21,23,31H,1-2,7-9H2,(H,24,27)(H,29,30)(H3,20,22,25,26,28);2-5H,1H3,(H,8,9,10)/t12-,13-,14?;/m0./s1
• InChIKey: AKJZWWRVQRFAFG-HLMYEFCQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[4-({[(6S)-2-amino-4-oxo-4,4a,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}-5-hydroperoxypentanoic acid; 4-methylbenzene-1-sulfonic acid
• IUPAC Traditional name: (2S)-2-{[4-({[(6S)-2-amino-4-oxo-5,6,7,8-tetrahydro-4aH-pteridin-6-yl]methyl}amino)phenyl]formamido}-5-hydroperoxypentanoic acid; toluenesulfonic acid
• Synonyms: (S)-N-[4-[[(2-Amino-1,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic Acid Mono(4-methylbenzenesulfonate); (6S)-Tetrahydrofolic Acid p-Toluenesulfonate Salt

Database IDs

• CAS Number: 144077-69-0
• PubChem SID: 164234260
• PubChem CID: 71752455

CALCULATED PROPERTIES

• Acid pKa: 2.4669065
• H Acceptors: 12
• H Donor: 7
• LogD (pH = 5.5): -4.8309937
• LogD (pH = 7.4): -6.9467096
• Log P: -3.6548111
• Molar Refractivity: 111.6196 cm^3
• Polarizability: 42.31737 Å^3
• Polar Surface Area: 199.76 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide
• Apperance: Beige Solid

Safety Information

• Storage Condition: Refrigerator, under inert atmosphere

DETAILS

Toronto Research Chemicals - T293590

Folic Acid (F680300) derivative. Has been shown to increase methotrexalate metabolism in humans.

REFERENCES

• Jolivet, J. et al.; Biochem. Phamacol. 36, 3310 (1987).