[(3S)-3-[(2-{[2-(hexanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy]phosphonic acid

• ChemBase ID: 6193
• Molecular Formular: C17H33N2O8PS
• Molecular Mass: 456.491281
• Monoisotopic Mass: 456.16952366
• SMILES: OP(=O)(O)OCC(C)(C)[C@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCC
• Canonical SMILES: CCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](C(COP(=O)(O)O)(C)C)O
• InChI: InChI=1S/C17H33N2O8PS/c1-4-5-6-7-14(21)29-11-10-18-13(20)8-9-19-16(23)15(22)17(2,3)12-27-28(24,25)26/h15,22H,4-12H2,1-3H3,(H,18,20)(H,19,23)(H2,24,25,26)/t15-/m1/s1
• InChIKey: KGMBPSVUBJAAEN-OAHLLOKOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(3S)-3-[(2-{[2-(hexanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy]phosphonic acid
• IUPAC Traditional name: (3S)-3-[(2-{[2-(hexanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxyphosphonic acid
• Synonyms: S-[2-({N-[(2S)-2-hydroxy-3,3-dimethyl-4-(phosphonooxy)butanoyl]-beta-alanyl}amino)ethyl] hexanethioate

Database IDs

• PubChem SID: 160969618; 99445056
• PubChem CID: 25220903

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.7938627
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -2.158969
• LogD (pH = 7.4): -2.8347628
• Log P: 0.21800163
• Molar Refractivity: 109.4755 cm^3
• Polarizability: 43.363216 Å^3
• Polar Surface Area: 162.26 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.52
• LOG S: -3.32
• Solubility (Water): 2.20e-01 g/l

DETAILS

DrugBank - DB08585

Drug information: experimental