(3S)-3-amino-3-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-({2-[(2S)-2-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamoyl}ethyl]carbamoyl}pyrrolidin-1-yl]-2-oxoethyl}carbamoyl)ethyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}propanoic acid

• ChemBase ID: 153594
• Molecular Formular: C51H81N13O16
• Molecular Mass: 1132.26634
• Monoisotopic Mass: 1131.59242358
• SMILES: C[C@@H](C(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H]1CCCN1C(=O)[C@H](C)NC(=O)[C@H](CC(=O)O)N
• Canonical SMILES: OC(=O)C[C@@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)NCC(=O)N1CCC[C@H]1C(=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)C)C)C)C)C)C)N
• InChI: InChI=1S/C51H81N13O16/c1-24(2)38(50(78)64-21-13-17-35(64)47(75)60-39(25(3)4)51(79)80)59-42(70)28(7)56-44(72)32-14-10-18-61(32)36(65)23-53-40(68)26(5)54-45(73)33-15-11-19-62(33)48(76)29(8)57-41(69)27(6)55-46(74)34-16-12-20-63(34)49(77)30(9)58-43(71)31(52)22-37(66)67/h24-35,38-39H,10-23,52H2,1-9H3,(H,53,68)(H,54,73)(H,55,74)(H,56,72)(H,57,69)(H,58,71)(H,59,70)(H,60,75)(H,66,67)(H,79,80)/t26-,27-,28-,29-,30-,31-,32-,33-,34-,35-,38-,39-/m0/s1
• InChIKey: WGEFWMRJXQRWOR-CHXQDLIVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-amino-3-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-({2-[(2S)-2-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamoyl}ethyl]carbamoyl}pyrrolidin-1-yl]-2-oxoethyl}carbamoyl)ethyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}propanoic acid
• IUPAC Traditional name: (3S)-3-amino-3-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-({2-[(2S)-2-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-carboxy-2-methylpropyl]carbamoyl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamoyl}ethyl]carbamoyl}pyrrolidin-1-yl]-2-oxoethyl}carbamoyl)ethyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}propanoic acid
• Synonyms: β-Sheet Breaker Peptide

Database IDs

• MDL Number: MFCD03093422
• PubChem SID: 162247733
• PubChem CID: 9812209

CALCULATED PROPERTIES

• Acid pKa: 3.1666727
• H Acceptors: 17
• H Donor: 11
• LogD (pH = 5.5): -9.355649
• LogD (pH = 7.4): -10.956388
• Log P: -7.9480257
• Molar Refractivity: 278.3552 cm^3
• Polarizability: 109.33639 Å^3
• Polar Surface Area: 414.66 Å^2
• Rotatable Bonds: 25
• 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

Product Information

• Purity: >95% (HPLC)
• Empirical Formula (Hill Notation): C51H81N13O16

DETAILS

Sigma Aldrich - S7563

Amino Acid Sequence
Asp-Ala-Pro-Ala-Ala-Pro-Ala-Gly-Pro-Ala-Val-Pro-Val
Biochem/physiol Actions
Reverses prion protein (PrP) conformational changes implicated in the pathogenesis of spongiform encephalopathies.