(2S)-2-[(2S)-2-{[hydroxy({[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphoryl]amino}-4-methylpentanamido]-3-(1H-indol-3-yl)propanoic acid

• ChemBase ID: 129689
• Molecular Formular: C23H34N3O10P
• Molecular Mass: 543.503921
• Monoisotopic Mass: 543.19818093
• SMILES: O=C(O)[C@@H](NC(=O)[C@H](CC(C)C)NP(=O)(O[C@@H]1O[C@@H](C)[C@@H](O)[C@@H](O)[C@H]1O)O)Cc1c[nH]c2c1cccc2
• Canonical SMILES: CC(C[C@@H](C(=O)N[C@H](C(=O)O)Cc1c[nH]c2c1cccc2)NP(=O)(O[C@@H]1O[C@@H](C)[C@H]([C@H]([C@H]1O)O)O)O)C
• InChI: InChI=1S/C23H34N3O10P/c1-11(2)8-16(26-37(33,34)36-23-20(29)19(28)18(27)12(3)35-23)21(30)25-17(22(31)32)9-13-10-24-15-7-5-4-6-14(13)15/h4-7,10-12,16-20,23-24,27-29H,8-9H2,1-3H3,(H,25,30)(H,31,32)(H2,26,33,34)/t12-,16-,17-,18+,19+,20+,23-/m0/s1
• InChIKey: ZPHBZEQOLSRPAK-XVOJFHBISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-{[hydroxy({[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphoryl]amino}-4-methylpentanamido]-3-(1H-indol-3-yl)propanoic acid
• IUPAC Traditional name: talopeptin
• Synonyms: N-[N-[[(6-deoxy-α-L-talopyranosyl)oxy]hydroxyphosphinyl]-L-leucyl]-L-tryptophan; Talopeptin

Database IDs

• CAS Number: 84235-60-9
• PubChem SID: 162223978
• PubChem CID: 134712
• Wikipedia Title: Talopeptin

CALCULATED PROPERTIES

• Acid pKa: 2.48479
• H Acceptors: 9
• H Donor: 8
• LogD (pH = 5.5): -3.6547024
• LogD (pH = 7.4): -5.3870897
• Log P: 0.15903191
• Molar Refractivity: 128.9397 cm^3
• Polarizability: 52.45724 Å^3
• Polar Surface Area: 210.67 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false