2-[2-(2-amino-3-phenylpropanamido)-4-(methylsulfanyl)butanamido]-5-carbamimidamido-N-(1-carbamoyl-2-phenylethyl)pentanamide

• ChemBase ID: 103410
• Molecular Formular: C29H42N8O4S
• Molecular Mass: 598.75998
• Monoisotopic Mass: 598.30497286
• SMILES: CSCCC(NC(=O)C(N)Cc1ccccc1)C(=O)NC(CCCNC(=N)N)C(=O)NC(Cc1ccccc1)C(=O)N
• Canonical SMILES: CSCCC(C(=O)NC(C(=O)NC(C(=O)N)Cc1ccccc1)CCCNC(=N)N)NC(=O)C(Cc1ccccc1)N
• InChI: InChI=1S/C29H42N8O4S/c1-42-16-14-23(35-26(39)21(30)17-19-9-4-2-5-10-19)28(41)36-22(13-8-15-34-29(32)33)27(40)37-24(25(31)38)18-20-11-6-3-7-12-20/h2-7,9-12,21-24H,8,13-18,30H2,1H3,(H2,31,38)(H,35,39)(H,36,41)(H,37,40)(H4,32,33,34)
• InChIKey: WCSPDMCSKYUFBX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[2-(2-amino-3-phenylpropanamido)-4-(methylsulfanyl)butanamido]-5-carbamimidamido-N-(1-carbamoyl-2-phenylethyl)pentanamide
• IUPAC Traditional name: 2-[2-(2-amino-3-phenylpropanamido)-4-(methylsulfanyl)butanamido]-5-carbamimidamido-N-(1-carbamoyl-2-phenylethyl)pentanamide
• Synonyms: [D-Arg3]-Molluscan cardioexcitatory neuropeptide; Phe-Met-D-Arg-Phe amide; [D-Phe4]-Molluscan cardioexcitatory neuropeptide; Phe-Met-Arg-D-Phe amide; FMRF amide; Molluscan cardioexcitatory neuropeptide; Phe-Met-Arg-Phe amide; Phe-Met-Arg-Phe-NH₂; MOLLUSCAN CARDIOEXCITATORY NEUROPEPTIDE; [D-Phe1]-Molluscan cardioexcitatory neuropeptide; D-Phe-Met-Arg-Phe-NH2

Database IDs

• CAS Number: 84413-35-4; 84313-44-0; 84313-42-8; 64190-70-1
• MDL Number: MFCD00076625; MFCD00076628; MFCD00076626
• PubChem SID: 162103126; 24898566
• PubChem CID: 4418610

CALCULATED PROPERTIES

• Acid pKa: 12.185034
• H Acceptors: 8
• H Donor: 8
• LogD (pH = 5.5): -4.5075803
• LogD (pH = 7.4): -2.8334837
• Log P: -0.34954396
• Molar Refractivity: 173.9642 cm^3
• Polarizability: 63.67307 Å^3
• Polar Surface Area: 218.31 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: 0°C
• 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); ≥97% (HPLC)
• Compostion: Peptide content, ~65%; Peptide content, ~70%
• Empirical Formula (Hill Notation): C29H42N8O4S

DETAILS

MP Biomedicals - 02151703

Phe-Met-Arg-Phe-NH2

Sigma Aldrich - P4898

Amino Acid Sequence
Phe-Met-Arg-Phe-NH2

REFERENCES

• Price, Science, 197: 670 (1977).