(2S)-2-({[(S)-{[(1S)-3-carbamoyl-1-{[(2S)-1-oxopropan-2-yl]carbamoyl}propyl]carbamoyl}[(4S)-2-imino-1,3-diazinan-4-yl]methyl]carbamoyl}amino)-4-methylpentanoic acid

• ChemBase ID: 132499
• Molecular Formular: C21H36N8O7
• Molecular Mass: 512.55994
• Monoisotopic Mass: 512.27069553
• SMILES: C[C@@H](C=O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H]([C@@H]1CCNC(=N)N1)NC(=O)N[C@@H](CC(C)C)C(=O)O
• Canonical SMILES: O=C[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@@H]1CCNC(=N)N1)NC(=O)N[C@H](C(=O)O)CC(C)C)CCC(=O)N)C
• InChI: InChI=1S/C21H36N8O7/c1-10(2)8-14(19(34)35)28-21(36)29-16(12-6-7-24-20(23)27-12)18(33)26-13(4-5-15(22)31)17(32)25-11(3)9-30/h9-14,16H,4-8H2,1-3H3,(H2,22,31)(H,25,32)(H,26,33)(H,34,35)(H3,23,24,27)(H2,28,29,36)/t11-,12-,13-,14-,16-/m0/s1
• InChIKey: IJWCGVPEDDQUDE-YGJAXBLXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-({[(S)-{[(1S)-3-carbamoyl-1-{[(2S)-1-oxopropan-2-yl]carbamoyl}propyl]carbamoyl}[(4S)-2-imino-1,3-diazinan-4-yl]methyl]carbamoyl}amino)-4-methylpentanoic acid
• IUPAC Traditional name: (2S)-2-({[(S)-{[(1S)-3-carbamoyl-1-{[(2S)-1-oxopropan-2-yl]carbamoyl}propyl]carbamoyl}[(4S)-2-imino-1,3-diazinan-4-yl]methyl]carbamoyl}amino)-4-methylpentanoic acid
• Synonyms: (2S)-2-[(4S)-2-Amino-1,4,5,6-tetrahydro4-pyrimidinyl]-N-[[[(1S)-1-carboxy-3-methylbutyl]amino]carbonyl]glycyl-N1-[(1S)-1-methyl-2-oxoethyl-L-glutamamide; Elastatinal

Database IDs

• CAS Number: 51798-45-9
• EC Number: 257-426-7
• Beilstein Number: 873543
• PubChem SID: 162226776; 24894375
• PubChem CID: 91645

CALCULATED PROPERTIES

• Acid pKa: 3.7571263
• H Acceptors: 10
• H Donor: 9
• LogD (pH = 5.5): -4.873753
• LogD (pH = 7.4): -4.8674173
• Log P: -4.867457
• Molar Refractivity: 135.3056 cm^3
• Polarizability: 48.542145 Å^3
• Polar Surface Area: 244.7 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: LZ9600000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Biological Source: microbial

DETAILS

Sigma Aldrich - E0881

Biochem/physiol Actions
Potent, irreversible elastase inhibitor. Elastatinal is a much stronger inhibitor of elastase from pancreas than from leucocytes.1