methyl (2S)-3-[3-(acetyloxy)-4-(benzyloxy)phenyl]-2-{[(benzyloxy)carbonyl]amino}propanoate

• ChemBase ID: 172759
• Molecular Formular: C27H27NO7
• Molecular Mass: 477.50578
• Monoisotopic Mass: 477.17875221
• SMILES: c1c(c(ccc1C[C@H](NC(=O)OCc1ccccc1)C(=O)OC)OCc1ccccc1)OC(=O)C
• Canonical SMILES: COC(=O)[C@H](Cc1ccc(c(c1)OC(=O)C)OCc1ccccc1)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C27H27NO7/c1-19(29)35-25-16-22(13-14-24(25)33-17-20-9-5-3-6-10-20)15-23(26(30)32-2)28-27(31)34-18-21-11-7-4-8-12-21/h3-14,16,23H,15,17-18H2,1-2H3,(H,28,31)/t23-/m0/s1
• InChIKey: RLCZEHPOGOWNMU-QHCPKHFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-3-[3-(acetyloxy)-4-(benzyloxy)phenyl]-2-{[(benzyloxy)carbonyl]amino}propanoate
• IUPAC Traditional name: methyl (2S)-3-[3-(acetyloxy)-4-(benzyloxy)phenyl]-2-{[(benzyloxy)carbonyl]amino}propanoate
• Synonyms: 3-Acetyloxy-N-[(phenylmethoxy)carbonyl]-O-(phenylmethyl)-L-tyrosine Methyl Ester; 4-O-Benzyl-N-[(benzyloxy)carbonyl]-3-O-acetyl-L-DOPA Methyl Ester

Database IDs

• PubChem SID: 164228669
• PubChem CID: 71750012

CALCULATED PROPERTIES

• Acid pKa: 12.885779
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.5601826
• LogD (pH = 7.4): 4.5601816
• Log P: 4.5601826
• Molar Refractivity: 127.7736 cm^3
• Polarizability: 50.183456 Å^3
• Polar Surface Area: 100.16 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: Off-white Solid

DETAILS

Toronto Research Chemicals - M232895

Intermediate in the preparation of a L-DOPA (D533751) metabolite.