(2S)-2-{[4-(2-{2-amino-4-oxo-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}-3-methylbutanoic acid

• ChemBase ID: 5758
• Molecular Formular: C20H23N5O4
• Molecular Mass: 397.42772
• Monoisotopic Mass: 397.17500424
• SMILES: c1c(ccc(c1)C(=O)N[C@@H](C(C)C)C(=O)O)CCc1c[nH]c2c1c(=O)[nH]c(n2)N
• Canonical SMILES: CC([C@@H](C(=O)O)NC(=O)c1ccc(cc1)CCc1c[nH]c2c1c(=O)[nH]c(n2)N)C
• InChI: InChI=1S/C20H23N5O4/c1-10(2)15(19(28)29)23-17(26)12-6-3-11(4-7-12)5-8-13-9-22-16-14(13)18(27)25-20(21)24-16/h3-4,6-7,9-10,15H,5,8H2,1-2H3,(H,23,26)(H,28,29)(H4,21,22,24,25,27)/t15-/m0/s1
• InChIKey: MYENGRJSPURSQB-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[4-(2-{2-amino-4-oxo-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}-3-methylbutanoic acid
• IUPAC Traditional name: (2S)-2-{[4-(2-{2-amino-4-oxo-3H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}-3-methylbutanoic acid
• Synonyms: 2-{4-[2-(2-AMINO-4-OXO-4,7-DIHYDRO-3H-PYRROLO[2,3-D]PYRIMIDIN-5-YL)-ETHYL]-BENZOYLAMINO}-3-METHYL-BUTYRIC ACID

Database IDs

• PubChem SID: 160969185; 99444602
• PubChem CID: 446560

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.4025052
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): 0.3797771
• LogD (pH = 7.4): -1.1009666
• Log P: 1.428292
• Molar Refractivity: 108.0882 cm^3
• Polarizability: 39.5887 Å^3
• Polar Surface Area: 149.67 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.69
• LOG S: -4.09
• Solubility (Water): 3.21e-02 g/l

DETAILS

DrugBank - DB08131

Drug information: experimental