bihelical apoA-I mimetic peptide 5A   

GtoPdb Ligand ID: 9183

Synonyms: 5A peptide
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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SMILES / InChI / InChIKey
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
Bioactivity Comments
In vitro, the 5A peptide was able to solubilize phospholipid vesicles and stimulated cholesterol and phospholipid efflux by the ABCA1 transporter with high specificity but no affinity data has yet been reported [4].
Selectivity at transporters
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
ABCA1 Hs None Binding - - - 3
The 5A sequence was able to solubilize phospholipid vesicles and stimulated cholesterol and phospholipid efflux by the ABCA1 transporter with high specificity but no specific binding data was reported [3]