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

• ChemBase ID: 134167
• Molecular Formular: C21H41ClN4O9
• Molecular Mass: 529.02464
• Monoisotopic Mass: 528.25620659
• 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.O.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.O.Cl
• InChI: InChI=1S/C21H38N4O8.ClH.H2O/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;1H2/t12-,13+,15+,16+,17+;;/m1../s1
• InChIKey: WBYDQJQQTMJMQH-AFROIDPFSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 100938-10-1
• MDL Number: MFCD00150636
• Beilstein Number: 8888370
• PubChem SID: 162228444; 24890521
• PubChem CID: 16218848

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

Physical Property

• Solubility: methanol: soluble1 mM (Stock solution stable for 1 month at -20 °C. Working solution stable for 1 day.)

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 - A1276

Biochem/physiol Actions
It inhibits cytosolic leucine aminopeptidase (EC.3.4.11.1), microsomal aminopeptidase M (EC.3.4.11.2) and bacterial leucine aminopeptidase (EC.3.4.11.10). It is less effective against aminopeptidase A (EC 3.4.11.7), the enzyme that converts angiotensin II to angiotensin III. Potentiates the CNS effects of vasopressin and oxytocin in vivo.1Effective concentration: 1-10 μM.
It inhibits cytosolic leucine aminopeptidase (EC.3.4.11.1), microsomal aminopeptidase M (EC.3.4.11.2) and bacterial leucine aminopeptidase (EC.3.4.11.10). It is less effective against aminopeptidase A (EC 3.4.11.7), the enzyme that converts angiotensin II to angiotensin III. Potentiates the CNS effects of vasopressin and oxytocin in vivo.1Effective concentration: 1-10 μM.