(2S)-2-[(2S)-2-{[(2S)-1-[(2S,3R)-2-[(2S)-2-amino-3-phenylpropanamido]-3-hydroxybutanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanamido]-4-methylpentanamide

• ChemBase ID: 131873
• Molecular Formular: C30H49N9O6
• Molecular Mass: 631.76676
• Monoisotopic Mass: 631.38058033
• SMILES: C[C@H]([C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC(C)C)C(=O)N)NC(=O)[C@H](Cc1ccccc1)N)O
• Canonical SMILES: CC(C[C@@H](C(=O)N)NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@H]([C@H](O)C)NC(=O)[C@H](Cc1ccccc1)N)CCCNC(=N)N)C
• InChI: InChI=1S/C30H49N9O6/c1-17(2)15-22(25(32)41)37-27(43)21(11-7-13-35-30(33)34)36-28(44)23-12-8-14-39(23)29(45)24(18(3)40)38-26(42)20(31)16-19-9-5-4-6-10-19/h4-6,9-10,17-18,20-24,40H,7-8,11-16,31H2,1-3H3,(H2,32,41)(H,36,44)(H,37,43)(H,38,42)(H4,33,34,35)/t18-,20+,21+,22+,23+,24+/m1/s1
• InChIKey: UWKNDYISLPTEKG-RMCGQVEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-{[(2S)-1-[(2S,3R)-2-[(2S)-2-amino-3-phenylpropanamido]-3-hydroxybutanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanamido]-4-methylpentanamide
• IUPAC Traditional name: (2S)-2-[(2S)-2-{[(2S)-1-[(2S,3R)-2-[(2S)-2-amino-3-phenylpropanamido]-3-hydroxybutanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanamido]-4-methylpentanamide
• Synonyms: Phe-Thr-Pro-Arg-Leu-NH2; Leucopyrokinin fragment 4-8

Database IDs

• CAS Number: 104191-78-8
• MDL Number: MFCD00133454
• PubChem SID: 24896385; 162226150
• PubChem CID: 16219572

CALCULATED PROPERTIES

• Acid pKa: 12.021108
• H Acceptors: 10
• H Donor: 9
• LogD (pH = 5.5): -6.45536
• LogD (pH = 7.4): -4.780189
• Log P: -2.3798053
• Molar Refractivity: 176.8791 cm^3
• Polarizability: 65.0857 Å^3
• Polar Surface Area: 258.85 Å^2
• Rotatable Bonds: 17
• 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

DETAILS

Sigma Aldrich - L5018

Biochem/physiol Actions
The C-terminal pentapeptide of leucopyrokinin, retaining 30% of the activity of the parent.