(4S)-4-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-carboxyethyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}pentyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}ethyl]carbamoyl}-4-[(2S)-2-[(2S)-6-amino-2-{[(2S)-1-[(2S)-6-amino-2-[(2S)-2-amino-4-carboxybutanamido]hexanoyl]pyrrolidin-2-yl]formamido}hexanamido]-3-methylbutanamido]butanoic acid; trifluoroacetic acid

• ChemBase ID: 154062
• Molecular Formular: C72H115F3N18O23
• Molecular Mass: 1657.7855096
• Monoisotopic Mass: 1656.83345669
• SMILES: C[C@@H](C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C)C(=O)O)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@H](C)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(=O)O)N.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.NCCCC[C@@H](C(=O)N[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)O)C)C)C)C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@H](CCC(=O)O)N)CCCCN)CCCCN)CCC(=O)O)C)Cc1ccc(cc1)O
• InChI: InChI=1S/C70H114N18O21.C2HF3O2/c1-36(2)55(86-63(101)47(18-10-13-31-72)82-66(104)52-21-16-34-88(52)69(107)49(19-11-14-32-73)84-60(98)45(74)26-28-53(90)91)67(105)83-48(27-29-54(92)93)62(100)78-40(6)59(97)85-50(35-43-22-24-44(89)25-23-43)64(102)81-46(17-9-12-30-71)61(99)77-39(5)57(95)75-37(3)56(94)76-38(4)58(96)79-41(7)68(106)87-33-15-20-51(87)65(103)80-42(8)70(108)109;3-2(4,5)1(6)7/h22-25,36-42,45-52,55,89H,9-21,26-35,71-74H2,1-8H3,(H,75,95)(H,76,94)(H,77,99)(H,78,100)(H,79,96)(H,80,103)(H,81,102)(H,82,104)(H,83,105)(H,84,98)(H,85,97)(H,86,101)(H,90,91)(H,92,93)(H,108,109);(H,6,7)/t37-,38-,39-,40-,41-,42-,45-,46-,47-,48-,49-,50-,51-,52-,55-;/m0./s1
• InChIKey: JHPGEXWNFDTTLX-RMOYKTNBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-carboxyethyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}pentyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}ethyl]carbamoyl}-4-[(2S)-2-[(2S)-6-amino-2-{[(2S)-1-[(2S)-6-amino-2-[(2S)-2-amino-4-carboxybutanamido]hexanoyl]pyrrolidin-2-yl]formamido}hexanamido]-3-methylbutanamido]butanoic acid; trifluoroacetic acid
• IUPAC Traditional name: (4S)-4-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-carboxyethyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}pentyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}ethyl]carbamoyl}-4-[(2S)-2-[(2S)-6-amino-2-{[(2S)-1-[(2S)-6-amino-2-[(2S)-2-amino-4-carboxybutanamido]hexanoyl]pyrrolidin-2-yl]formamido}hexanamido]-3-methylbutanamido]butanoic acid; trifluoroacetic acid
• Synonyms: MBP (85-99) peptide antagonist trifluoroacetate salt; MBP (85-99) peptide antagonist

Database IDs

• CAS Number: 444305-16-2(freebase)
• PubChem SID: 162248201
• PubChem CID: 71311785

CALCULATED PROPERTIES

• Acid pKa: 3.1238158
• H Acceptors: 25
• H Donor: 20
• LogD (pH = 5.5): -15.700263
• LogD (pH = 7.4): -14.006149
• Log P: -13.431802
• Molar Refractivity: 387.152 cm^3
• Polarizability: 152.44333 Å^3
• Polar Surface Area: 626.03 Å^2
• Rotatable Bonds: 49
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: >1 mg/mL
• Apperance: lyophilized powder

Safety Information

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

Product Information

• Purity: 95% (HPLC)
• Compostion: Peptide content, 63% HPLC
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C70H114N18O21 · xC2HF3O2

DETAILS

Sigma Aldrich - M0571

Amino Acid Sequence
Glu-Lys-Pro-Lys-Val-Glu-Ala-Tyr-Lys-Ala- Ala- Ala- Ala-Pro-Ala
Biochem/physiol Actions
MBP (85-99) peptide antagonist inhibits the binding of MBP 85-99 to HLA-DR2 and IL-2 and is a tool for MS research. The peptide antagonist is a 15-mer peptide that competes with Myelin Basic Protein MBP (85-99), the immunodominant epitope of MBP and major candidate autoantigen in multiple sclerosis (MS).