N-{4-[(2S)-2-amino-2-carboxyethyl]phenyl}-2-chloro-N-(2-chloroethyl)ethanamine oxide

• ChemBase ID: 172625
• Molecular Formular: C13H18Cl2N2O3
• Molecular Mass: 321.19962
• Monoisotopic Mass: 320.06944781
• SMILES: c1c(ccc(c1)C[C@@H](C(=O)O)N)[N+](CCCl)(CCCl)[O-]
• Canonical SMILES: ClCC[N+](c1ccc(cc1)C[C@@H](C(=O)O)N)(CCCl)[O-]
• InChI: InChI=1S/C13H18Cl2N2O3/c14-5-7-17(20,8-6-15)11-3-1-10(2-4-11)9-12(16)13(18)19/h1-4,12H,5-9,16H2,(H,18,19)/t12-/m0/s1
• InChIKey: GSKQMLGAUOTSKT-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{4-[(2S)-2-amino-2-carboxyethyl]phenyl}-2-chloro-N-(2-chloroethyl)ethanamine oxide
• IUPAC Traditional name: N-{4-[(2S)-2-amino-2-carboxyethyl]phenyl}-2-chloro-N-(2-chloroethyl)ethanamine oxide
• Synonyms: 4-[Bis(2-chloroethyl)oxidoamino]-L-phenylalanine; Melphalan N-OxideDISCONTINUED

Database IDs

• CAS Number: 685847-78-3
• PubChem SID: 164228535
• PubChem CID: 11234795

CALCULATED PROPERTIES

• Acid pKa: 1.3097694
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -4.721641
• LogD (pH = 7.4): -4.7247586
• Log P: -4.721523
• Molar Refractivity: 89.1704 cm^3
• Polarizability: 30.645395 Å^3
• Polar Surface Area: 90.2 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M216920

A derivative of Melphalan for treating diseased states associated with hypoxia-inducible factor; antitumor PX478 inhibitor hypoxia inducible factor.

REFERENCES

• Isaacs, J., et al.: J. Biol. Chem., 277, 29936 (2002)
• Bachtiary, B., et al.: Clin. Cancer Res., 9, 2234 (2002)
• Koukourakis, M., et al.: J. Clin. Oncol., 24, 727 (2002)