(3S)-4-[(2S)-2-{[(1R)-1-{[(1R)-1-carbamoyl-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}pyrrolidin-1-yl]-4-oxo-3-{[(2S)-5-oxopyrrolidin-2-yl]formamido}butanamide

• ChemBase ID: 154404
• Molecular Formular: C34H40N8O8
• Molecular Mass: 688.7302
• Monoisotopic Mass: 688.29691028
• SMILES: c1ccc2c(c1)c(c[nH]2)C[C@H](C(=O)N)NC(=O)[C@@H](Cc1ccc(cc1)O)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CC(=O)N)NC(=O)[C@@H]1CCC(=O)N1
• Canonical SMILES: NC(=O)C[C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N)Cc1c[nH]c2c1cccc2)Cc1ccc(cc1)O)NC(=O)[C@@H]1CCC(=O)N1
• InChI: InChI=1S/C34H40N8O8/c35-28(44)16-26(41-31(47)23-11-12-29(45)38-23)34(50)42-13-3-6-27(42)33(49)40-25(14-18-7-9-20(43)10-8-18)32(48)39-24(30(36)46)15-19-17-37-22-5-2-1-4-21(19)22/h1-2,4-5,7-10,17,23-27,37,43H,3,6,11-16H2,(H2,35,44)(H2,36,46)(H,38,45)(H,39,48)(H,40,49)(H,41,47)/t23-,24+,25+,26-,27-/m0/s1
• InChIKey: SZQSOKVXBMULDL-VQHLWIOESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-4-[(2S)-2-{[(1R)-1-{[(1R)-1-carbamoyl-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}pyrrolidin-1-yl]-4-oxo-3-{[(2S)-5-oxopyrrolidin-2-yl]formamido}butanamide
• IUPAC Traditional name: (3S)-4-[(2S)-2-{[(1R)-1-{[(1R)-1-carbamoyl-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}pyrrolidin-1-yl]-4-oxo-3-{[(2S)-5-oxopyrrolidin-2-yl]formamido}butanamide
• Synonyms: JAK4D; Glp-Asn-Pro-d-Tyr-d-Trp-NH2

Database IDs

• CAS Number: 882400-49-9
• MDL Number: MFCD11114385
• PubChem SID: 162248543
• PubChem CID: 11621732

CALCULATED PROPERTIES

• Acid pKa: 9.4922285
• H Acceptors: 8
• H Donor: 8
• LogD (pH = 5.5): -1.9109716
• LogD (pH = 7.4): -1.9143959
• Log P: -1.9109279
• Molar Refractivity: 176.9517 cm^3
• Polarizability: 69.6668 Å^3
• Polar Surface Area: 258.91 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: >2 mg/mL
• Apperance: white solid

Safety Information

• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: rat ... TRH(7200), TRHDE(29953), TRHR(7201)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C34H40N8O8

DETAILS

Sigma Aldrich - G5297

Amino Acid Sequence
Glp-Asn-Pro-Tyr-Trp-NH2
Biochem/physiol Actions
The synthetic peptide Glp-Asn-Pro-d-Tyr-d-Trp-NH2 mimics and amplifies central actions of TRH in rat without releasing TSH. Glp-Asn-Pro-d-Tyr-d-Trp-NH2 has dual pharmacological activities: it inhibits TRH-DE and binds to central TRH receptors with nM affinity in rat hippocampus and cortex but not pituitary or heterologous cells expressing TRH receptor 1 (TRHR1) or TRH receptor 2 (TRHR2). The peptide can be a potent tool for probing the role of TRH actions in the CNS and a platform for development of novel TRH-based therapeutics for neuro diseases.