(2S)-1-(2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-4-(methylsulfanyl)butanamido]-4-carboxybutanamido]-3-(1H-imidazol-4-yl)propanamido]-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}acetyl)pyrrolidine-2-carboxylic acid; trifluoroacetic acid

• ChemBase ID: 154926
• Molecular Formular: C39H52F3N9O12S
• Molecular Mass: 927.9434896
• Monoisotopic Mass: 927.34082381
• SMILES: CSCC[C@@H](C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)NCC(=O)N1CCC[C@H]1C(=O)O)N.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.CSCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)NCC(=O)N1CCC[C@H]1C(=O)O)Cc1ccccc1)Cc1nc[nH]c1)CCC(=O)O)N
• InChI: InChI=1S/C37H51N9O10S.C2HF3O2/c1-57-16-13-24(38)32(50)42-25(11-12-31(48)49)33(51)43-26(18-23-19-39-21-41-23)34(52)44-27(17-22-7-3-2-4-8-22)36(54)46-15-5-9-28(46)35(53)40-20-30(47)45-14-6-10-29(45)37(55)56;3-2(4,5)1(6)7/h2-4,7-8,19,21,24-29H,5-6,9-18,20,38H2,1H3,(H,39,41)(H,40,53)(H,42,50)(H,43,51)(H,44,52)(H,48,49)(H,55,56);(H,6,7)/t24-,25-,26-,27-,28-,29-;/m0./s1
• InChIKey: UAXRUQRHZBYPHF-IGCYJKAMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-(2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-4-(methylsulfanyl)butanamido]-4-carboxybutanamido]-3-(1H-imidazol-4-yl)propanamido]-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}acetyl)pyrrolidine-2-carboxylic acid; trifluoroacetic acid
• IUPAC Traditional name: (2S)-1-(2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-4-(methylsulfanyl)butanamido]-4-carboxybutanamido]-3-(1H-imidazol-4-yl)propanamido]-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}acetyl)pyrrolidine-2-carboxylic acid; trifluoroacetic acid
• Synonyms: ACTH (4-7), Pro-Gly-Pro trifluoroacetate salt; L-Methionyl-L-a-glutamyl-L-histidyl-L-phenylalanyl-L-prolylglycyl-L-proline trifluoroacetate salt; Met-Glu-His-Phe-Pro-Gly-Pro; Semax

Database IDs

• CAS Number: 80714-61-0(freebase)
• MDL Number: MFCD04113563
• PubChem SID: 162249064
• PubChem CID: 71312027

CALCULATED PROPERTIES

• Acid pKa: 3.1460676
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -6.9395056
• LogD (pH = 7.4): -7.824588
• Log P: -6.6502047
• Molar Refractivity: 204.6601 cm^3
• Polarizability: 79.96144 Å^3
• Polar Surface Area: 286.32 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: >2 mg/mL
• Apperance: white to tan powder

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C37H51N9O10S · xC2HF3O2

DETAILS

Sigma Aldrich - S8826

Biochem/physiol Actions
Semax (Met-Glu-His-Phe-Pro-Gly-Pro) is an analog of the adrenocorticotropin fragment (4-10). It activates the transcription of neurotrophins and has neuroprotective and nootropic activity.