(2S)-1-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-5-carbamimidamido-2-{[(2S)-1-[(2S)-2-[(2R)-2-[(2S)-3-(1H-imidazol-4-yl)-2-[(2S)-pyrrolidin-2-ylformamido]propanamido]-3-sulfanylpropanamido]-3-methylbutanoyl]pyrrolidin-2-yl]formamido}pentanamido]-3-carboxypropanamido]-4-methylpentanamido]-3-hydroxypropanamido]-3-(1H-indol-3-yl)propanamido]-4-methylpentanamido]-3-carboxypropanamido]-4-methylpentanamido]-4-carboxybutanamido]propanamido]-3-carbamoylpropanamido]-4-(methylsulfanyl)butanamido]-3-sulfanylpropanamido]-4-methylpentanoyl]pyrrolidine-2-carboxylic acid; trifluoroacetic acid

• ChemBase ID: 153269
• Molecular Formular: C103H158F3N27O31S3
• Molecular Mass: 2423.7091296
• Monoisotopic Mass: 2422.07312907
• SMILES: C[C@@H](C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(C)C)C(=O)N1CCC[C@H]1C(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](C(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@@H]1CCCN1.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)N1CCC[C@H]1C(=O)O)CC(C)C)CS)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1)Cc1nc[nH]c1)CS)CCCNC(=N)N)CC(=O)O)CC(C)C)CO)CC(C)C)CC(=O)O)CC(C)C)CCC(=O)O)C)CC(=O)N
• InChI: InChI=1S/C101H157N27O29S3.C2HF3O2/c1-48(2)33-62(86(142)111-60(25-26-77(131)132)83(139)110-53(11)81(137)114-67(39-76(102)130)91(147)112-61(27-32-160-12)85(141)124-72(45-158)95(151)122-70(36-51(7)8)98(154)128-31-18-24-75(128)100(156)157)116-93(149)69(41-79(135)136)121-87(143)63(34-49(3)4)115-89(145)65(37-54-42-108-57-20-14-13-19-56(54)57)118-94(150)71(44-129)123-88(144)64(35-50(5)6)117-92(148)68(40-78(133)134)120-84(140)59(22-16-29-107-101(103)104)113-97(153)74-23-17-30-127(74)99(155)80(52(9)10)126-96(152)73(46-159)125-90(146)66(38-55-43-105-47-109-55)119-82(138)58-21-15-28-106-58;3-2(4,5)1(6)7/h13-14,19-20,42-43,47-53,58-75,80,106,108,129,158-159H,15-18,21-41,44-46H2,1-12H3,(H2,102,130)(H,105,109)(H,110,139)(H,111,142)(H,112,147)(H,113,153)(H,114,137)(H,115,145)(H,116,149)(H,117,148)(H,118,150)(H,119,138)(H,120,140)(H,121,143)(H,122,151)(H,123,144)(H,124,141)(H,125,146)(H,126,152)(H,131,132)(H,133,134)(H,135,136)(H,156,157)(H4,103,104,107);(H,6,7)/t53-,58-,59-,60-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-,80-;/m0./s1
• InChIKey: RLMYFUMCZYJMNX-KIXMOXNVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-5-carbamimidamido-2-{[(2S)-1-[(2S)-2-[(2R)-2-[(2S)-3-(1H-imidazol-4-yl)-2-[(2S)-pyrrolidin-2-ylformamido]propanamido]-3-sulfanylpropanamido]-3-methylbutanoyl]pyrrolidin-2-yl]formamido}pentanamido]-3-carboxypropanamido]-4-methylpentanamido]-3-hydroxypropanamido]-3-(1H-indol-3-yl)propanamido]-4-methylpentanamido]-3-carboxypropanamido]-4-methylpentanamido]-4-carboxybutanamido]propanamido]-3-carbamoylpropanamido]-4-(methylsulfanyl)butanamido]-3-sulfanylpropanamido]-4-methylpentanoyl]pyrrolidine-2-carboxylic acid; trifluoroacetic acid
• IUPAC Traditional name: (2S)-1-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-5-carbamimidamido-2-{[(2S)-1-[(2S)-2-[(2R)-2-[(2S)-3-(1H-imidazol-4-yl)-2-[(2S)-pyrrolidin-2-ylformamido]propanamido]-3-sulfanylpropanamido]-3-methylbutanoyl]pyrrolidin-2-yl]formamido}pentanamido]-3-carboxypropanamido]-4-methylpentanamido]-3-hydroxypropanamido]-3-(1H-indol-3-yl)propanamido]-4-methylpentanamido]-3-carboxypropanamido]-4-methylpentanamido]-4-carboxybutanamido]propanamido]-3-carbamoylpropanamido]-4-(methylsulfanyl)butanamido]-3-sulfanylpropanamido]-4-methylpentanoyl]pyrrolidine-2-carboxylic acid; trifluoroacetic acid
• Synonyms: PHCVPRDLSWLDLEANMCLP trifluoroacetate; Pro-His-Cys-Val-Pro-Arg-Asp-Leu-Ser-Trp-Leu-Asp-Leu-Glu-Ala-Asn-Met-Cys-Leu-Pro trifluoroacetate; R18 trifluoroacetate; L-Prolyl-L-histidyl-L-cysteinyl-L-valyl-L-prolyl-L-arginyl-L-a-aspartyl-L-leucyl-L-seryl-L-tryptophyl-L-leucyl-L-a-aspartyl-L-leucyl-L-a-glutamyl-L-alanyl-L-asparaginyl-L-methionyl-L-cysteinyl-L-leucyl-L-proline trifluoroacetate

Database IDs

• CAS Number: 211364-78-2(freebase)
• MDL Number: MFCD20527319
• PubChem SID: 162247408
• PubChem CID: 71311628

CALCULATED PROPERTIES

• Acid pKa: 3.054352
• H Acceptors: 34
• H Donor: 31
• LogD (pH = 5.5): -14.580811
• LogD (pH = 7.4): -17.248695
• Log P: -12.486633
• Molar Refractivity: 586.7142 cm^3
• Polarizability: 226.84221 Å^3
• Polar Surface Area: 866.24 Å^2
• Rotatable Bonds: 70
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: white to off-white powder

Safety Information

• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C101H157N27O29S3

DETAILS

Sigma Aldrich - SML0108

Biochem/physiol Actions
R18 is a competitive inhibitor of the 14-3-3 scaffolding proteins. It binds to the general binding groove of 14-3-3. R18 blocks 14-3-3 interaction with most or all of its client proteins.