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

• ChemBase ID: 132512
• Molecular Formular: C27H32N6O5
• Molecular Mass: 520.58018
• Monoisotopic Mass: 520.24341815
• SMILES: c1ccc2c(c1)c(c[nH]2)C[C@@H](C(=O)NCC(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](Cc1ccc(cc1)O)N
• Canonical SMILES: NC(=O)CNC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@@H]1CCCN1C(=O)[C@H](Cc1ccc(cc1)O)N
• InChI: InChI=1S/C27H32N6O5/c28-20(12-16-7-9-18(34)10-8-16)27(38)33-11-3-6-23(33)26(37)32-22(25(36)31-15-24(29)35)13-17-14-30-21-5-2-1-4-19(17)21/h1-2,4-5,7-10,14,20,22-23,30,34H,3,6,11-13,15,28H2,(H2,29,35)(H,31,36)(H,32,37)/t20-,22-,23-/m0/s1
• InChIKey: HWGSOAJXZHSMGE-PMVMPFDFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)-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-(carbamoylmethyl)-3-(1H-indol-3-yl)propanamide
• Synonyms: Tyr-W-MIF-I; [Tyr0, Trp2]-MIF-I; Tyr-[Trp2]-Melanocyte Stimulating Hormone Release Inhibiting Factor trifluoroacetate salt

Database IDs

• CAS Number: 144450-13-5
• PubChem SID: 162226789
• PubChem CID: 132632

CALCULATED PROPERTIES

• Acid pKa: 9.510491
• H Acceptors: 6
• H Donor: 6
• LogD (pH = 5.5): -2.349525
• LogD (pH = 7.4): -0.67999685
• Log P: -0.32308045
• Molar Refractivity: 139.7123 cm^3
• Polarizability: 55.3103 Å^3
• Polar Surface Area: 183.64 Å^2
• Rotatable Bonds: 10
• 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 - M8009

Amino Acid Sequence
Tyr-Pro-Trp-Gly-NH2
Biochem/physiol Actions
Mixed agonist/antagonist at opiate receptors
Other Notes
Originally isolated from human frontal cortex and from bovine hypothalamus