(2S)-2-[(2S)-2-[(2S)-2-[(2R,3R)-3-amino-2-hydroxy-5-methylhexanamido]-3-methylbutanamido]-3-methylbutanamido]butanedioic acid hydrochloride

• ChemBase ID: 133781
• Molecular Formular: C21H39ClN4O8
• Molecular Mass: 511.00936
• Monoisotopic Mass: 510.24564191
• SMILES: CC(C)C[C@H]([C@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(=O)O)C(=O)O)O)N.Cl
• Canonical SMILES: CC(C[C@H]([C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)CC(=O)O)C(C)C)C(C)C)O)N)C.Cl
• InChI: InChI=1S/C21H38N4O8.ClH/c1-9(2)7-12(22)17(28)20(31)25-16(11(5)6)19(30)24-15(10(3)4)18(29)23-13(21(32)33)8-14(26)27;/h9-13,15-17,28H,7-8,22H2,1-6H3,(H,23,29)(H,24,30)(H,25,31)(H,26,27)(H,32,33);1H/t12-,13+,15+,16+,17-;/m1./s1
• InChIKey: GBDUPCKQTDKNLS-TXUMRZAQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2S)-2-[(2R,3R)-3-amino-2-hydroxy-5-methylhexanamido]-3-methylbutanamido]-3-methylbutanamido]butanedioic acid hydrochloride
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2S)-2-[(2R,3R)-3-amino-2-hydroxy-5-methylhexanamido]-3-methylbutanamido]-3-methylbutanamido]butanedioic acid hydrochloride
• Synonyms: [(2R,3R)-3-Amino-2-hydroxy-5-methylhexanoyl]-Val-Val-Asp hydrochloride; Epiamastatin hydrochloride

Database IDs

• CAS Number: 100992-59-4
• MDL Number: MFCD00070396
• PubChem SID: 24894512; 162228058
• PubChem CID: 24203251

CALCULATED PROPERTIES

• Acid pKa: 3.2423563
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -3.2634552
• LogD (pH = 7.4): -5.019427
• Log P: -2.7815282
• Molar Refractivity: 116.0522 cm^3
• Polarizability: 46.411858 Å^3
• Polar Surface Area: 208.15 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - E3389

Biochem/physiol Actions
Epimer of amastatin at the 2-position. There are no reports of aminopeptidase inhibition by this epimer; on the contrary, there are suggestions that a 2S-hydroxyl group is important for the stability of an initial collision complex with the enzyme.