(2S)-2-[(4-{[(2,4-diamino-7-hydroxypteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

• ChemBase ID: 170105
• Molecular Formular: C19H20N8O6
• Molecular Mass: 456.4121
• Monoisotopic Mass: 456.1505804
• SMILES: c12c(nc(c(n1)CNc1ccc(cc1)C(=O)N[C@@H](CCC(=O)O)C(=O)O)O)nc(nc2N)N
• Canonical SMILES: OC(=O)CC[C@@H](C(=O)O)NC(=O)c1ccc(cc1)NCc1nc2c(N)nc(nc2nc1O)N
• InChI: InChI=1S/C19H20N8O6/c20-14-13-15(27-19(21)25-14)26-17(31)11(23-13)7-22-9-3-1-8(2-4-9)16(30)24-10(18(32)33)5-6-12(28)29/h1-4,10,22H,5-7H2,(H,24,30)(H,28,29)(H,32,33)(H5,20,21,25,26,27,31)/t10-/m0/s1
• InChIKey: KTRAZHHNSREJAS-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(4-{[(2,4-diamino-7-hydroxypteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
• IUPAC Traditional name: (2S)-2-[(4-{[(2,4-diamino-7-hydroxypteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
• Synonyms: N-[4-[[(2,4-Diamino-7,8-dihydro-7-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic Acid; N-[p-[[(2,4-Diamino-7-hydroxy-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic Acid; N-[4-[[(2,4-Diamino-1,7-dihydro-7-oxo-6-pteridinyl)methyl]amino]benzoyl]- L-Glutamic Acid; 7-Hydroxy Aminopterin

Database IDs

• CAS Number: 97772-99-1
• PubChem SID: 164226015
• PubChem CID: 71748806

CALCULATED PROPERTIES

• Acid pKa: 3.372709
• H Acceptors: 13
• H Donor: 7
• LogD (pH = 5.5): -3.8924708
• LogD (pH = 7.4): -6.895036
• Log P: -0.63925046
• Molar Refractivity: 117.2704 cm^3
• Polarizability: 42.37041 Å^3
• Polar Surface Area: 239.56 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Red Solid
• Melting Point: >165°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H797250

The 7-hydroxy metabolite of Aminopterin (A628850) as substrate for folylpolyglutamate synthetase (FPGS).

REFERENCES

• Schoo, M.M.J., et al.: Cancer Res., 45, 3034 (1985)