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

• ChemBase ID: 2286
• Molecular Formular: C23H34N3O10P
• Molecular Mass: 543.503921
• Monoisotopic Mass: 543.19818093
• SMILES: CC(C)C[C@@H](N[P@@](=O)(O)O[C@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@@H]1O)C(=O)N[C@H](Cc1c[nH]c2ccccc12)C(=O)O
• Canonical SMILES: CC(C[C@H](C(=O)N[C@@H](C(=O)O)Cc1c[nH]c2c1cccc2)N[P@](=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-AYVHNPTNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[(2R)-2-{[hydroxy({[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphoryl]amino}-4-methylpentanamido]-3-(indol-3-yl)propanoic acid
• IUPAC Traditional name: @phosphoramidon
• Synonyms: Phosphoramidon

Database IDs

• CAS Number: 36357-77-4
• PubChem SID: 160965739; 46506179
• PubChem CID: 46936424

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.4754798
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -3.9842014
• LogD (pH = 7.4): -5.6396165
• Log P: -1.973471
• Molar Refractivity: 127.4315 cm^3
• Polarizability: 52.152042 Å^3
• Polar Surface Area: 207.77 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.04
• LOG S: -2.81
• Solubility (Water): 8.39e-01 g/l

DETAILS

DrugBank - DB02557

Drug information: experimental