trifluoroacetic acid amino (2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-5-carbamimidamido-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-5-carbamimidamido-2-[(2S)-2-[(2S)-5-carbamimidamido-2-[(2S)-2-acetamido-4-methylpentanamido]pentanamido]-3-methylbutanamido]pentanamido]-4-methylpentanamido]propanamido]-3-hydroxypropanamido]-3-(1H-imidazol-5-yl)propanamido]-4-methylpentanamido]pentanamido]hexanamido]-4-methylpentanamido]-5-carbamimidamidopentanamido]hexanamido]-5-carbamimidamidopentanamido]-4-methylpentanamido]-4-methylpentanoate

• ChemBase ID: 154872
• Molecular Formular: C99H182F3N37O22
• Molecular Mass: 2299.7342896
• Monoisotopic Mass: 2298.42122531
• SMILES: C[C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)ON)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)C.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)N[C@H](C(=O)N[C@H](C(=O)ON)CC(C)C)CC(C)C)CCCNC(=N)N)CCCCN)CCCNC(=N)N)CC(C)C)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](NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C)CC(C)C)CCCNC(=N)N)CCCNC(=N)N)CC(C)C)C)CO)Cc1[nH]cnc1)CC(C)C)CCCNC(=N)N
• InChI: InChI=1S/C97H181N37O20.C2HF3O2/c1-50(2)40-67(119-58(16)136)85(146)125-66(32-25-39-116-97(108)109)83(144)134-75(56(13)14)91(152)126-65(31-24-38-115-96(106)107)82(143)127-68(41-51(3)4)84(145)118-57(15)76(137)133-74(48-135)90(151)131-72(46-59-47-111-49-117-59)89(150)130-70(43-53(7)8)87(148)124-63(29-22-36-113-94(102)103)79(140)121-61(27-18-20-34-99)80(141)128-69(42-52(5)6)86(147)123-62(28-21-35-112-93(100)101)78(139)120-60(26-17-19-33-98)77(138)122-64(30-23-37-114-95(104)105)81(142)129-71(44-54(9)10)88(149)132-73(45-55(11)12)92(153)154-110;3-2(4,5)1(6)7/h47,49-57,60-75,135H,17-46,48,98-99,110H2,1-16H3,(H,111,117)(H,118,145)(H,119,136)(H,120,139)(H,121,140)(H,122,138)(H,123,147)(H,124,148)(H,125,146)(H,126,152)(H,127,143)(H,128,141)(H,129,142)(H,130,150)(H,131,151)(H,132,149)(H,133,137)(H,134,144)(H4,100,101,112)(H4,102,103,113)(H4,104,105,114)(H4,106,107,115)(H4,108,109,116);(H,6,7)/t57-,60-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-;/m0./s1
• InChIKey: SIAUOBGYBRMVPH-BGJGLIJFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: trifluoroacetic acid amino (2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-5-carbamimidamido-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-5-carbamimidamido-2-[(2S)-2-[(2S)-5-carbamimidamido-2-[(2S)-2-acetamido-4-methylpentanamido]pentanamido]-3-methylbutanamido]pentanamido]-4-methylpentanamido]propanamido]-3-hydroxypropanamido]-3-(1H-imidazol-5-yl)propanamido]-4-methylpentanamido]pentanamido]hexanamido]-4-methylpentanamido]-5-carbamimidamidopentanamido]hexanamido]-5-carbamimidamidopentanamido]-4-methylpentanamido]-4-methylpentanoate
• IUPAC Traditional name: trifluoroacetic acid amino (2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-5-carbamimidamido-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-5-carbamimidamido-2-[(2S)-2-[(2S)-5-carbamimidamido-2-[(2S)-2-acetamido-4-methylpentanamido]pentanamido]-3-methylbutanamido]pentanamido]-4-methylpentanamido]propanamido]-3-hydroxypropanamido]-3-(3H-imidazol-4-yl)propanamido]-4-methylpentanamido]pentanamido]hexanamido]-4-methylpentanamido]-5-carbamimidamidopentanamido]hexanamido]-5-carbamimidamidopentanamido]-4-methylpentanamido]-4-methylpentanoate
• Synonyms: Ac- LRVRLASHLRKLRKRLL-NH2; Ac-Leu-Arg-Val-Arg-Leu-Ala-Ser-His-Leu- Arg-Lys-Leu-Arg-Lys-Arg-Leu-Leu-NH2; COG133; N-acetyl-L-leucyl-L-arginyl-L-valyl-L-arginyl-L-leucyl-L-alanyl-L-seryl-L-histidyl-L-leucyl-L-arginyl-L-lysyl-L-leucyl-L-arginyl-L-lysyl-L-arginyl-L-leucyl-L-Leucinamide; apoE(133-149); COG 133 trifluoroacetate salt

Database IDs

• CAS Number: 514200-66-9(freebase)
• MDL Number: MFCD18432706
• PubChem SID: 162249010
• PubChem CID: 71312012

CALCULATED PROPERTIES

• H Acceptors: 38
• H Donor: 37
• LogD (pH = 5.5): -26.591232
• LogD (pH = 7.4): -25.269226
• Log P: -7.939026
• Molar Refractivity: 622.952 cm^3
• Polarizability: 222.29204 Å^3
• Polar Surface Area: 957.47 Å^2
• Rotatable Bonds: 80
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

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

Safety Information

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

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C97H181N37O19 · xC2HF3O2

DETAILS

Sigma Aldrich - C8624

Biochem/physiol Actions
COG 1333 or apoE(133-149) is a fragment of Apolipoprotein E (APOE) that mimics the functional anti-inflammatory and neuroprotective effects of the intact apoE protein. It was suggested that neuroprotective functions of the mimetic results from binding to the low-density lipoprotein receptor-related protein (LRP) or LDL receptors, and such binding results in inhibition of the N-methyl-D-aspartate (NMDA) receptor.