(4S)-4-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]-4-{[(1S)-1-{[(1S,2S)-1-{[(1S)-4-carbamimidamido-1-{[(1S,2S)-1-[({[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(1S)-3-carbamoyl-1-carboxypropyl]carbamoyl}-2-hydroxyethyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}-2-methylpropyl]carbamoyl}methyl)carbamoyl]-2-methylbutyl]carbamoyl}butyl]carbamoyl}-2-methylbutyl]carbamoyl}-2-hydroxyethyl]carbamoyl}butanoic acid; trifluoroacetic acid

• ChemBase ID: 154938
• Molecular Formular: C60H95F3N16O21
• Molecular Mass: 1433.4861096
• Monoisotopic Mass: 1432.6809788
• SMILES: CC[C@H](C)[C@@H](C(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(=O)N)C(=O)O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](Cc1ccc(cc1)O)N.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.CC[C@@H]([C@@H](C(=O)NCC(=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)O)CCC(=O)N)CO)C)C(C)C)NC(=O)[C@@H](NC(=O)[C@H]([C@H](CC)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](Cc1ccc(cc1)O)N)CCC(=O)O)CO)CCCNC(=N)N)C
• InChI: InChI=1S/C58H94N16O19.C2HF3O2/c1-8-29(5)45(53(88)64-25-42(79)71-44(28(3)4)54(89)65-31(7)56(91)74-23-11-13-40(74)52(87)70-38(26-75)50(85)68-37(57(92)93)18-20-41(60)78)72-49(84)35(12-10-22-63-58(61)62)67-55(90)46(30(6)9-2)73-51(86)39(27-76)69-48(83)36(19-21-43(80)81)66-47(82)34(59)24-32-14-16-33(77)17-15-32;3-2(4,5)1(6)7/h14-17,28-31,34-40,44-46,75-77H,8-13,18-27,59H2,1-7H3,(H2,60,78)(H,64,88)(H,65,89)(H,66,82)(H,67,90)(H,68,85)(H,69,83)(H,70,87)(H,71,79)(H,72,84)(H,73,86)(H,80,81)(H,92,93)(H4,61,62,63);(H,6,7)/t29-,30-,31-,34-,35-,36-,37-,38-,39-,40-,44-,45-,46-;/m0./s1
• InChIKey: UVRSGFIIMHKCQD-ASTQSYHGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]-4-{[(1S)-1-{[(1S,2S)-1-{[(1S)-4-carbamimidamido-1-{[(1S,2S)-1-[({[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(1S)-3-carbamoyl-1-carboxypropyl]carbamoyl}-2-hydroxyethyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}-2-methylpropyl]carbamoyl}methyl)carbamoyl]-2-methylbutyl]carbamoyl}butyl]carbamoyl}-2-methylbutyl]carbamoyl}-2-hydroxyethyl]carbamoyl}butanoic acid; trifluoroacetic acid
• IUPAC Traditional name: (4S)-4-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]-4-{[(1S)-1-{[(1S,2S)-1-{[(1S)-4-carbamimidamido-1-{[(1S,2S)-1-[({[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(1S)-3-carbamoyl-1-carboxypropyl]carbamoyl}-2-hydroxyethyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}-2-methylpropyl]carbamoyl}methyl)carbamoyl]-2-methylbutyl]carbamoyl}butyl]carbamoyl}-2-methylbutyl]carbamoyl}-2-hydroxyethyl]carbamoyl}butanoic acid; trifluoroacetic acid
• Synonyms: L-Tyrosyl-L-a-glutamyl-L-seryl-L-isoleucyl-L-arginyl-L-isoleucylglycyl-L-valyl-L-alanyl-L-prolyl-L-seryl-L-glutamine trifluoroacetate salt; YESIRIGVAPSQ trifluoroacetate salt; D12-116 trifluoroacetate salt

Database IDs

• PubChem SID: 162249076
• PubChem CID: 71312033

CALCULATED PROPERTIES

• Acid pKa: 3.0152886
• H Acceptors: 23
• H Donor: 20
• LogD (pH = 5.5): -10.297541
• LogD (pH = 7.4): -10.446678
• Log P: -10.298211
• Molar Refractivity: 336.6688 cm^3
• Polarizability: 127.85712 Å^3
• Polar Surface Area: 577.61 Å^2
• Rotatable Bonds: 42
• 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)
• Empirical Formula (Hill Notation): C58H94N16O19 · xC2HF3O2

DETAILS

Sigma Aldrich - D0447

Biochem/physiol Actions
D12-116 is a specific allosteric modulator of the glycine receptor (GlyR). The peptide D12-116 produces a marked enhancement of GlyR function while not affecting a1b2g2S GABAA receptors.