(2S)-6-amino-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]-N-[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-carbamoyl-3-(methylsulfanyl)propyl]carbamoyl}-2-methylpropyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]hexanamide; trifluoroacetic acid

• ChemBase ID: 154972
• Molecular Formular: C43H62F3N9O9S2
• Molecular Mass: 970.1324896
• Monoisotopic Mass: 969.40640127
• SMILES: CC(C)[C@@H](C(=O)N[C@@H](CCSC)C(=O)N)NC(=O)[C@H](CCSC)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)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)CCSC)C(C)C)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@@H](NC(=O)[C@H](Cc1c[nH]c2c1cccc2)N)CCCCN
• InChI: InChI=1S/C41H61N9O7S2.C2HF3O2/c1-24(2)35(41(57)46-31(36(44)52)16-19-58-3)50-39(55)33(17-20-59-4)48-40(56)34(21-25-12-14-27(51)15-13-25)49-38(54)32(11-7-8-18-42)47-37(53)29(43)22-26-23-45-30-10-6-5-9-28(26)30;3-2(4,5)1(6)7/h5-6,9-10,12-15,23-24,29,31-35,45,51H,7-8,11,16-22,42-43H2,1-4H3,(H2,44,52)(H,46,57)(H,47,53)(H,48,56)(H,49,54)(H,50,55);(H,6,7)/t29-,31-,32-,33-,34-,35-;/m0./s1
• InChIKey: MYVYQWVNXDVTBW-CZPFDPCBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-6-amino-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]-N-[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-carbamoyl-3-(methylsulfanyl)propyl]carbamoyl}-2-methylpropyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]hexanamide; trifluoroacetic acid
• IUPAC Traditional name: (2S)-6-amino-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]-N-[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-carbamoyl-3-(methylsulfanyl)propyl]carbamoyl}-2-methylpropyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]hexanamide; trifluoroacetic acid
• Synonyms: Trp-Lys-Tyr-Met-Val-L-Met NH2 trifluoroacetate salt; WKYMVM trifluoroacetate salt

Database IDs

• CAS Number: 187986-11-4(freebase)
• MDL Number: MFCD19443869
• PubChem SID: 162249110
• PubChem CID: 71312038

CALCULATED PROPERTIES

• Acid pKa: 9.429101
• H Acceptors: 9
• H Donor: 10
• LogD (pH = 5.5): -4.0279965
• LogD (pH = 7.4): -1.8300647
• Log P: 0.25215942
• Molar Refractivity: 231.5971 cm^3
• Polarizability: 91.89581 Å^3
• Polar Surface Area: 276.65 Å^2
• Rotatable Bonds: 27
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: >2 mg/mL
• Apperance: white to off-white 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): C41H61N9O7S2 · xC2HF3O2

DETAILS

Sigma Aldrich - W4270

Amino Acid Sequence
Trp-Lys-Tyr-Met-Val-L-Met NH2
Biochem/physiol Actions
WKYMVM is a peptide agonist of formyl peptide receptors. WKYMVM binds to and stimulates FPRL family members 1, 2 with EC50 values of 2 and 80 nM, respectively. The peptide is a potent activator of neutrophils.