(2S)-2-{[(2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-2-yl]formamido}-N-[(1S)-1-carbamoyl-2-phenylethyl]-3-(1H-indol-3-yl)propanamide

• ChemBase ID: 133968
• Molecular Formular: C34H38N6O5
• Molecular Mass: 610.70272
• Monoisotopic Mass: 610.29036835
• SMILES: c1ccc(cc1)C[C@@H](C(=O)N)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@@H]1CCCN1C(=O)[C@H](Cc1ccc(cc1)O)N
• Canonical SMILES: Oc1ccc(cc1)C[C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N)Cc1ccccc1)Cc1c[nH]c2c1cccc2)N
• InChI: InChI=1S/C34H38N6O5/c35-26(17-22-12-14-24(41)15-13-22)34(45)40-16-6-11-30(40)33(44)39-29(19-23-20-37-27-10-5-4-9-25(23)27)32(43)38-28(31(36)42)18-21-7-2-1-3-8-21/h1-5,7-10,12-15,20,26,28-30,37,41H,6,11,16-19,35H2,(H2,36,42)(H,38,43)(H,39,44)/t26-,28-,29-,30-/m0/s1
• InChIKey: ZEXLJFNSKAHNFH-SYKYGTKKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-2-yl]formamido}-N-[(1S)-1-carbamoyl-2-phenylethyl]-3-(1H-indol-3-yl)propanamide
• IUPAC Traditional name: (2S)-2-{[(2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-2-yl]formamido}-N-[(1S)-1-carbamoyl-2-phenylethyl]-3-(1H-indol-3-yl)propanamide
• Synonyms: Endomorphin 1

Database IDs

• CAS Number: 189388-22-5
• MDL Number: MFCD01321063
• PubChem SID: 162228245
• PubChem CID: 5311080

CALCULATED PROPERTIES

• Acid pKa: 9.510391
• H Acceptors: 6
• H Donor: 6
• LogD (pH = 5.5): -0.12443423
• LogD (pH = 7.4): 1.5450934
• Log P: 1.9019808
• Molar Refractivity: 168.8252 cm^3
• Polarizability: 66.733345 Å^3
• Polar Surface Area: 183.64 Å^2
• Rotatable Bonds: 12
• 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 ... OPRM1(4988)mouse ... OPRM1(18390)rat ... OPRM1(25601)

DETAILS

Sigma Aldrich - E3273

Amino Acid Sequence
Tyr-Pro-Trp-Phe-NH2
Biochem/physiol Actions
Potent, selective endogenous μ opioid receptor agonist.
Legal Information
Sold under license to US patent number 6,303,578
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. E3273.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.