(2S)-2-amino-N-[(1S)-4-carbamimidamido-1-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}butyl]hexanamide

• ChemBase ID: 133821
• Molecular Formular: C21H35N7O3
• Molecular Mass: 433.5477
• Monoisotopic Mass: 433.28013802
• SMILES: CCCC[C@@H](C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc1ccccc1)C(=O)N)N
• Canonical SMILES: CCCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)Cc1ccccc1)CCCNC(=N)N)N
• InChI: InChI=1S/C21H35N7O3/c1-2-3-10-15(22)19(30)27-16(11-7-12-26-21(24)25)20(31)28-17(18(23)29)13-14-8-5-4-6-9-14/h4-6,8-9,15-17H,2-3,7,10-13,22H2,1H3,(H2,23,29)(H,27,30)(H,28,31)(H4,24,25,26)/t15-,16-,17-/m0/s1
• InChIKey: XPMYDYSYRCLZEG-ULQDDVLXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-N-[(1S)-4-carbamimidamido-1-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}butyl]hexanamide
• IUPAC Traditional name: (2S)-2-amino-N-[(1S)-4-carbamimidamido-1-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}butyl]hexanamide
• Synonyms: Nle-Arg-Phe amide

Database IDs

• CAS Number: 104809-29-2
• MDL Number: MFCD00079487
• PubChem SID: 162228098
• PubChem CID: 71308722

CALCULATED PROPERTIES

• Acid pKa: 12.501713
• H Acceptors: 7
• H Donor: 7
• LogD (pH = 5.5): -5.1898856
• LogD (pH = 7.4): -3.4995766
• Log P: -0.6226906
• Molar Refractivity: 128.6851 cm^3
• Polarizability: 46.12863 Å^3
• Polar Surface Area: 189.21 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: ≥95% (HPLC)

DETAILS

Sigma Aldrich - N3637

Linkage
FMRF amide analog; molluscan cardioexcitatory neuropeptide analog
Biochem/physiol Actions
Nle-Arg-Phe amide is a molluscan cardioexcitatory neuropeptide analog.