(2S,4S)-4-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)pentanedioic acid

• ChemBase ID: 128435
• Molecular Formular: C14H16N2O5
• Molecular Mass: 292.28724
• Monoisotopic Mass: 292.10592162
• SMILES: O[C@](C(=O)O)(C[C@H](N)C(=O)O)Cc1c[nH]c2ccccc12
• Canonical SMILES: OC(=O)[C@H](C[C@](C(=O)O)(Cc1c[nH]c2c1cccc2)O)N
• InChI: InChI=1S/C14H16N2O5/c15-10(12(17)18)6-14(21,13(19)20)5-8-7-16-11-4-2-1-3-9(8)11/h1-4,7,10,16,21H,5-6,15H2,(H,17,18)(H,19,20)/t10-,14-/m0/s1
• InChIKey: RMLYXMMBIZLGAQ-HZMBPMFUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S)-4-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)pentanedioic acid
• IUPAC Traditional name: (2S,4S)-4-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)pentanedioic acid
• Synonyms: 2-Hydroxy-2-(indol-3-ylmethyl)-4-aminoglutaric acid; (S)-4-Hydroxy-4-(1H-indol-3-ylmethyl)-L-glutamic acid; Monatin

Database IDs

• CAS Number: 146142-94-1
• PubChem SID: 162222742
• PubChem CID: 9860847
• Wikipedia Title: Monatin

CALCULATED PROPERTIES

• Acid pKa: 2.084255
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -3.511222
• LogD (pH = 7.4): -5.146133
• Log P: -2.0324674
• Molar Refractivity: 73.1551 cm^3
• Polarizability: 29.774973 Å^3
• Polar Surface Area: 136.64 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true