bihelical apoA-I mimetic peptide 5A   Click here for help

GtoPdb Ligand ID: 9183

Synonyms: 5A peptide
Immunopharmacology Ligand
Compound class: Peptide or derivative
Comment: The initial 2008 study looked at the effect of asymmetry in the lipid affinity of amphipathic helices in bihelical apoA-I mimetic peptides. The 5A sequence was able to solubilize phospholipid vesicles and stimulated cholesterol and phospholipid efflux by the ABCA1 transporter with high specificity [3]. A later 2010 study showed that, like apoA-I, the 5A peptide inhibits acute inflammation and oxidative stress in rabbit carotids and human coronary artery endothelial cells. In vitro, the 5A peptide exerts these beneficial effects through interaction with ABCA1 [4]. Data and peptide analogues related to the latter publication also appeared in patent US8148323 [2]. A 2016 study indicates 5A peptide ameliorated murine colitis by preventing intestinal monocyte infiltration and activation, implying potential for IBD treatment [1] (n.b. there are InChIKey missmatch and submission splitting issues with the current PubChem CID 121231406 entry that we hope to resolve).
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES [NH3]CCCCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1CCCC1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)O)C)C)CCC(=O)O)CCCC[NH3])C)CCCC[NH3])CCC(=O)O)C)C)CCCC[NH3])CC(=O)O)Cc1ccc(cc1)O)C)C)CCCC[NH3])C)Cc1c[nH]c2c1cccc2)CC(=O)O)Cc1ccccc1)C)CCC(=O)O)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(C(C)C)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)C(CC(=O)O)N)CC(C)C)CCCC[NH3])C)Cc1ccccc1)Cc1ccc(cc1)O)CC(=O)O)CCCC[NH3])C)CCC(=O)O)CCCC[NH3])CC(C)C
Isomeric SMILES [NH3]CCCC[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)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)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)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)O)C)C)CCC(=O)O)CCCC[NH3])C)CCCC[NH3])CCC(=O)O)C)C)CCCC[NH3])CC(=O)O)Cc1ccc(cc1)O)C)C)CCCC[NH3])C)Cc1c[nH]c2c1cccc2)CC(=O)O)Cc1ccccc1)C)CCC(=O)O)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@@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](CC(=O)O)N)CC(C)C)CCCC[NH3])C)Cc1ccccc1)Cc1ccc(cc1)O)CC(=O)O)CCCC[NH3])C)CCC(=O)O)CCCC[NH3])CC(C)C
InChI InChI=1S/C197H303N47O56/c1-101(2)87-140(235-180(282)134(59-34-42-84-204)225-182(284)139(73-77-155(253)254)223-167(269)113(16)218-195(297)160(103(5)6)243-183(285)135(60-35-43-85-205)229-192(294)148(97-158(259)260)240-189(291)144(91-118-64-68-122(246)69-65-118)237-187(289)142(89-115-45-20-18-21-46-115)232-169(271)111(14)215-175(277)130(55-30-38-80-200)226-186(288)141(88-102(3)4)236-190(292)146(234-171(273)125(206)95-156(255)256)94-120-100-208-127-52-27-25-50-124(120)127)185(287)228-133(58-33-41-83-203)179(281)231-137(71-75-153(249)250)177(279)216-112(15)170(272)242-150(92-116-47-22-19-23-48-116)196(298)244-86-44-61-151(244)194(296)241-149(98-159(261)262)193(295)238-145(93-119-99-207-126-51-26-24-49-123(119)126)184(286)217-110(13)166(268)220-128(53-28-36-78-198)172(274)211-104(7)162(264)210-108(11)168(270)233-143(90-117-62-66-121(245)67-63-117)188(290)239-147(96-157(257)258)191(293)227-131(56-31-39-81-201)174(276)212-105(8)161(263)209-107(10)164(266)222-138(72-76-154(251)252)181(283)224-129(54-29-37-79-199)173(275)214-109(12)165(267)221-132(57-32-40-82-202)178(280)230-136(70-74-152(247)248)176(278)213-106(9)163(265)219-114(17)197(299)300/h18-27,45-52,62-69,99-114,125,128-151,160,207-208,245-246H,28-44,53-61,70-98,206H2,1-17,198-205H3,(H,209,263)(H,210,264)(H,211,274)(H,212,276)(H,213,278)(H,214,275)(H,215,277)(H,216,279)(H,217,286)(H,218,297)(H,219,265)(H,220,268)(H,221,267)(H,222,266)(H,223,269)(H,224,283)(H,225,284)(H,226,288)(H,227,293)(H,228,287)(H,229,294)(H,230,280)(H,231,281)(H,232,271)(H,233,270)(H,234,273)(H,235,282)(H,236,292)(H,237,289)(H,238,295)(H,239,290)(H,240,291)(H,241,296)(H,242,272)(H,243,285)(H,247,248)(H,249,250)(H,251,252)(H,253,254)(H,255,256)(H,257,258)(H,259,260)(H,261,262)(H,299,300)/t104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,125-,128-,129-,130-,131-,132-,133-,134-,135-,136-,137-,138-,139-,140-,141-,142-,143-,144-,145-,146-,147-,148-,149-,150-,151-,160-/m0/s1
InChI Key FOIYDQXBMQZAML-GNGNDROBSA-N
References
1. Nowacki TM, Remaley AT, Bettenworth D, Eisenblätter M, Vowinkel T, Becker F, Vogl T, Roth J, Tietge UJ, Lügering A et al.. (2016)
The 5A apolipoprotein A-I (apoA-I) mimetic peptide ameliorates experimental colitis by regulating monocyte infiltration.
Br J Pharmacol, 173 (18): 2780-92. [PMID:27425846]
2. Remaley AT et al.. (2012)
Method of treating or inhibiting inflammation by multi-domain amphipathic helical peptides.
Patent number: US8148323. Assignee: US Government. Priority date: 15/10/2004. Publication date: 03/04/2012.
3. Sethi AA, Stonik JA, Thomas F, Demosky SJ, Amar M, Neufeld E, Brewer HB, Davidson WS, D'Souza W, Sviridov D et al.. (2008)
Asymmetry in the lipid affinity of bihelical amphipathic peptides. A structural determinant for the specificity of ABCA1-dependent cholesterol efflux by peptides.
J Biol Chem, 283 (47): 32273-82. [PMID:18805791]
4. Tabet F, Remaley AT, Segaliny AI, Millet J, Yan L, Nakhla S, Barter PJ, Rye KA, Lambert G. (2010)
The 5A apolipoprotein A-I mimetic peptide displays antiinflammatory and antioxidant properties in vivo and in vitro.
Arterioscler Thromb Vasc Biol, 30 (2): 246-52. [PMID:19965776]