(2S)-2-{[(2S)-1-[(2S)-1-[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}propanamide

• ChemBase ID: 3714
• Molecular Formular: C23H33N5O5
• Molecular Mass: 459.53862
• Monoisotopic Mass: 459.24816918
• SMILES: C[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)[C@@H](O)[C@H](N)Cc1ccccc1)C(=O)N
• Canonical SMILES: C[C@@H](C(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)[C@H]([C@@H](Cc1ccccc1)N)O
• InChI: InChI=1S/C23H33N5O5/c1-14(20(25)30)26-21(31)17-9-5-11-27(17)22(32)18-10-6-12-28(18)23(33)19(29)16(24)13-15-7-3-2-4-8-15/h2-4,7-8,14,16-19,29H,5-6,9-13,24H2,1H3,(H2,25,30)(H,26,31)/t14-,16+,17-,18-,19-/m0/s1
• InChIKey: YVUUZAPYLPWFHE-HXFGRODQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S)-1-[(2S)-1-[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}propanamide
• IUPAC Traditional name: (2S)-2-{[(2S)-1-[(2S)-1-[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}propanamide
• Synonyms: Apstatin

Database IDs

• PubChem SID: 160967152; 46504972
• PubChem CID: 447280

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.109403
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -4.0546503
• LogD (pH = 7.4): -2.415373
• Log P: -1.4238883
• Molar Refractivity: 120.1714 cm^3
• Polarizability: 47.224045 Å^3
• Polar Surface Area: 159.06 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.41
• LOG S: -2.38
• Solubility (Water): 1.92e+00 g/l

DETAILS

DrugBank - DB04092

Drug information: experimental