(2S)-4-{[(1S)-5-{[(benzyloxy)carbonyl]amino}-1-{[(1S)-1-(dihydroxyboranyl)ethyl]carbamoyl}pentyl]carbamoyl}-2-{[(tert-butoxy)carbonyl]amino}butanoic acid

• ChemBase ID: 4207
• Molecular Formular: C26H41BN4O10
• Molecular Mass: 580.43554
• Monoisotopic Mass: 580.29157393
• SMILES: C[C@@H](NC(=O)[C@H](CCCCNC(=O)OCc1ccccc1)NC(=O)CC[C@H](NC(=O)OC(C)(C)C)C(=O)O)B(O)O
• Canonical SMILES: OB([C@H](NC(=O)[C@@H](NC(=O)CC[C@@H](C(=O)O)NC(=O)OC(C)(C)C)CCCCNC(=O)OCc1ccccc1)C)O
• InChI: InChI=1S/C26H41BN4O10/c1-17(27(38)39)29-22(33)19(12-8-9-15-28-24(36)40-16-18-10-6-5-7-11-18)30-21(32)14-13-20(23(34)35)31-25(37)41-26(2,3)4/h5-7,10-11,17,19-20,38-39H,8-9,12-16H2,1-4H3,(H,28,36)(H,29,33)(H,30,32)(H,31,37)(H,34,35)/t17-,19+,20+/m1/s1
• InChIKey: OTTYWVUOPWENAJ-HOJAQTOUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-4-{[(1S)-5-{[(benzyloxy)carbonyl]amino}-1-{[(1S)-1-(dihydroxyboranyl)ethyl]carbamoyl}pentyl]carbamoyl}-2-{[(tert-butoxy)carbonyl]amino}butanoic acid
• IUPAC Traditional name: (2S)-4-{[(1S)-5-{[(benzyloxy)carbonyl]amino}-1-{[(1S)-1-(dihydroxyboranyl)ethyl]carbamoyl}pentyl]carbamoyl}-2-[(tert-butoxycarbonyl)amino]butanoic acid
• Synonyms: BOC-GAMMA-D-GLU-L-LYS(CBZ)-D-BOROALA

Database IDs

• PubChem SID: 46508422; 160967639
• PubChem CID: 5287824

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.7243729
• H Acceptors: 8
• H Donor: 7
• LogD (pH = 5.5): -0.086591385
• LogD (pH = 7.4): -1.6864777
• Log P: 1.6909
• Molar Refractivity: 141.6057 cm^3
• Polarizability: 57.297955 Å^3
• Polar Surface Area: 212.62 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 1.17
• LOG S: -4.39
• Solubility (Water): 2.37e-02 g/l

DETAILS

DrugBank - DB04647

Drug information: experimental