(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido]-5-carbamimidamidopentanamido]acetamido}-4-methylpentanoic acid

• ChemBase ID: 131560
• Molecular Formular: C41H61N11O10S
• Molecular Mass: 900.05574
• Monoisotopic Mass: 899.43235821
• SMILES: CC(C)C[C@@H](C(=O)O)NC(=O)CNC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCSC)NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@H](Cc1ccc(cc1)O)N
• Canonical SMILES: CSCC[C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)O)CC(C)C)CCCNC(=N)N)NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@H](Cc1ccc(cc1)O)N
• InChI: InChI=1S/C41H61N11O10S/c1-24(2)18-32(40(61)62)50-35(56)23-48-37(58)29(10-7-16-45-41(43)44)51-38(59)30(15-17-63-3)52-39(60)31(20-25-8-5-4-6-9-25)49-34(55)22-46-33(54)21-47-36(57)28(42)19-26-11-13-27(53)14-12-26/h4-6,8-9,11-14,24,28-32,53H,7,10,15-23,42H2,1-3H3,(H,46,54)(H,47,57)(H,48,58)(H,49,55)(H,50,56)(H,51,59)(H,52,60)(H,61,62)(H4,43,44,45)/t28-,29-,30-,31-,32-/m0/s1
• InChIKey: NVWLPCPCSZOUCO-XDIGFQIYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido]-5-carbamimidamidopentanamido]acetamido}-4-methylpentanoic acid
• IUPAC Traditional name: (2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido]-5-carbamimidamidopentanamido]acetamido}-4-methylpentanoic acid
• Synonyms: MERGL; Tyr-Gly-Gly-Phe-Met-Arg-Gly-Leu; Methionine Enkephalin-Arg-Gly-Leu

Database IDs

• CAS Number: 80501-44-6
• PubChem SID: 162225838
• PubChem CID: 123791

CALCULATED PROPERTIES

• Acid pKa: 3.481424
• H Acceptors: 14
• H Donor: 13
• LogD (pH = 5.5): -5.8577895
• LogD (pH = 7.4): -4.183649
• Log P: -3.8225832
• Molar Refractivity: 243.5044 cm^3
• Polarizability: 90.6824 Å^3
• Polar Surface Area: 349.15 Å^2
• Rotatable Bonds: 28
• 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 - E6515

Preparation Note
Originally extracted from bovine adrenal medulla