2-{[1-(2-{2-[2-({1-[2-amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-2-yl}formamido)-3-phenylpropanamido]-3-methylbutanamido}-4-carboxybutanoyl)pyrrolidin-2-yl]formamido}-3-methylpentanoic acid

• ChemBase ID: 104069
• Molecular Formular: C44H61N7O11
• Molecular Mass: 863.99544
• Monoisotopic Mass: 863.44290581
• SMILES: CCC(C)C(NC(=O)C1CCCN1C(=O)C(CCC(=O)O)NC(=O)C(NC(=O)C(Cc1ccccc1)NC(=O)C1CCCN1C(=O)C(N)Cc1ccc(O)cc1)C(C)C)C(=O)O
• Canonical SMILES: CCC(C(C(=O)O)NC(=O)C1CCCN1C(=O)C(NC(=O)C(C(C)C)NC(=O)C(Cc1ccccc1)NC(=O)C1CCCN1C(=O)C(Cc1ccc(cc1)O)N)CCC(=O)O)C
• InChI: InChI=1S/C44H61N7O11/c1-5-26(4)37(44(61)62)49-40(57)34-14-10-22-51(34)43(60)31(19-20-35(53)54)46-41(58)36(25(2)3)48-38(55)32(24-27-11-7-6-8-12-27)47-39(56)33-13-9-21-50(33)42(59)30(45)23-28-15-17-29(52)18-16-28/h6-8,11-12,15-18,25-26,30-34,36-37,52H,5,9-10,13-14,19-24,45H2,1-4H3,(H,46,58)(H,47,56)(H,48,55)(H,49,57)(H,53,54)(H,61,62)
• InChIKey: ADBHAJDGVKLXHK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[1-(2-{2-[2-({1-[2-amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-2-yl}formamido)-3-phenylpropanamido]-3-methylbutanamido}-4-carboxybutanoyl)pyrrolidin-2-yl]formamido}-3-methylpentanoic acid
• IUPAC Traditional name: 2-{[1-(2-{2-[2-({1-[2-amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-2-yl}formamido)-3-phenylpropanamido]-3-methylbutanamido}-4-carboxybutanoyl)pyrrolidin-2-yl]formamido}-3-methylpentanoic acid
• Synonyms: β-Casomorphin human; β-CASOMORPHIN

Database IDs

• CAS Number: 102029-74-3
• MDL Number: MFCD00076324
• PubChem SID: 24892274; 162091576
• PubChem CID: 4424653

CALCULATED PROPERTIES

• Acid pKa: 3.4282382
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -2.0885503
• LogD (pH = 7.4): -3.9202418
• Log P: -0.9462115
• Molar Refractivity: 224.2614 cm^3
• Polarizability: 87.954796 Å^3
• Polar Surface Area: 277.87 Å^2
• Rotatable Bonds: 21
• 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

Pharmacology Properties

• Gene Information: human ... CSN1S1(1446), CSN3(1448)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

MP Biomedicals - 02154498

H2N-Tyr-Pro-Phe-Val- Glu-Pro-Ile-OH Source/Species: Human

Sigma Aldrich - C0783

Amino Acid Sequence
Tyr-Pro-Phe-Val-Glu-Pro-Ile
Biochem/physiol Actions
Opioid peptide first isolated from an enzymatic digest of casein that is an agonist at μ opioid receptors. Casomorphin 1-7 stimulates fat intake in rats.

REFERENCES

• Greenberg, R., et al., J. Biol. Chem., 259: 132, (1984).