(3S)-3-[(2S)-2-[(2S,3S)-2-amino-3-methylpentanamido]-4-(methylsulfanyl)butanamido]-3-{[(1S)-3-carbamoyl-1-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(1S)-1-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-phenylethyl]carbamoyl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamoyl}propyl]carbamoyl}propanoic acid

• ChemBase ID: 155667
• Molecular Formular: C47H74N10O14S
• Molecular Mass: 1035.21406
• Monoisotopic Mass: 1034.5106681
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N[C@@H](C(C)C)C(=O)O)N
• Canonical SMILES: 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)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)C(C)C)CO)Cc1ccccc1)C(C)C)CCC(=O)N)CC(=O)O)NC(=O)[C@H]([C@H](CC)C)N
• InChI: InChI=1S/C47H74N10O14S/c1-8-26(6)36(49)45(68)51-29(18-20-72-7)39(62)52-31(22-35(60)61)42(65)50-28(16-17-34(48)59)40(63)55-37(24(2)3)46(69)57-19-12-15-33(57)44(67)53-30(21-27-13-10-9-11-14-27)41(64)54-32(23-58)43(66)56-38(25(4)5)47(70)71/h9-11,13-14,24-26,28-33,36-38,58H,8,12,15-23,49H2,1-7H3,(H2,48,59)(H,50,65)(H,51,68)(H,52,62)(H,53,67)(H,54,64)(H,55,63)(H,56,66)(H,60,61)(H,70,71)/t26-,28-,29-,30-,31-,32-,33-,36-,37-,38-/m0/s1
• InChIKey: BDQMCYCLZBSYJZ-BBXCZNCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-[(2S)-2-[(2S,3S)-2-amino-3-methylpentanamido]-4-(methylsulfanyl)butanamido]-3-{[(1S)-3-carbamoyl-1-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(1S)-1-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-phenylethyl]carbamoyl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamoyl}propyl]carbamoyl}propanoic acid
• IUPAC Traditional name: (3S)-3-[(2S)-2-[(2S,3S)-2-amino-3-methylpentanamido]-4-(methylsulfanyl)butanamido]-3-{[(1S)-3-carbamoyl-1-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(1S)-1-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-phenylethyl]carbamoyl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamoyl}propyl]carbamoyl}propanoic acid
• Synonyms: [Met53]-Melanocyte Protein PMEL 17 fragment 52-60 bovine; [Met210]-Melanocyte Protein PMEL 17 Fragment 209-217 human, mouse

Database IDs

• MDL Number: MFCD03093433
• PubChem SID: 162249805
• PubChem CID: 657090

CALCULATED PROPERTIES

• Acid pKa: 3.2220893
• H Acceptors: 15
• H Donor: 12
• LogD (pH = 5.5): -5.9695024
• LogD (pH = 7.4): -7.603123
• Log P: -4.705341
• Molar Refractivity: 260.0528 cm^3
• Polarizability: 102.54273 Å^3
• Polar Surface Area: 387.95 Å^2
• Rotatable Bonds: 31
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: solid

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 ... SILV(6490)

Product Information

• Purity: >98% (HPLC)
• Empirical Formula (Hill Notation): C47H74N10O14S

DETAILS

Sigma Aldrich - M0563

Amino Acid Sequence
Ile-Met-Asp-Gln-Val-Pro-Phe-Ser-Val
Biochem/physiol Actions
Modification of the melanoma differentiation antigen gp100/PMEL 17 fragment 209-217 sequence with greater affinity for the HLA-A2 molecule than the unmodified peptide. Has an increased ability to generate melanoma-reactive cytotoxic T lymphocytes in vitro.