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fulipiftide   Click here for help

GtoPdb Ligand ID: 14377

Synonyms: BR 21001 | BR21001 | BRM-421 | BRM421 | PSP 29-mer
Compound class: Peptide
Comment: Fulipiftide (BRM421; BRIM Biotechnology) is a synthetic analogue of pigment epithelium-derived factor (PEDF). The peptide induces regenerative effects (via ERK2 and STAT3 signalling) and has anti-inflammatory activity. It has been used in the study of tendon repair [3], but has been repurposed for dry eye disease [4] where it is reported to stimulate corneal limbal stem cell proliferation/differentiation and increase mucin secretion from goblet cells. Like full-length PEDF, fulipiftide may act through patatin-like phospholipase domain-containing protein 2 (PNPLA2), which is involved in mitogenic signalling in human embryonic and neural stem cells, and other progenitor cells [1-2,5].
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC[C@H](C)[C@@H](C(=O)N[C@@H](CC1=CN=CN1)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N)NC(=O)[C@H](CC(=O)O)NC(=O)[C@@H]2CCCN2C(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CC3=CC=C(C=C3)O)NC(=O)[C@H](CC4=CC=C(C=C4)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC5=CN=CN5)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)C
Isomeric SMILES C(N[C@H](C(N[C@H](C(N[C@@H](CC1=CN=CN1)C(NCC(N[C@@H]([C@@H](C)O)C(N)=O)=O)=O)=O)[C@H](CC)C)=O)CC(O)=O)(=O)[C@H]2N(C([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@H](CC3=CC=C(O)C=C3)NC([C@H](CC4=CC=C(O)C=C4)NC([C@@H](NC([C@@H](NC([C@@H](NC([C@H](CC5=CN=CN5)NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC(CNC([C@@H](NC([C@@H](NC(C)=O)CO)=O)CC(C)C)=O)=O)C)=O)CCC(O)=O)=O)CCC(N)=O)=O)CCCNC(=N)N)=O)[C@@H](C)O)=O)CCC(O)=O)=O)CO)=O)[C@H](CC)C)=O)[C@H](CC)C)=O)=O)CCCNC(=N)N)=O)C)=O)CC(C)C)=O)=O)=O)CC(O)=O)=O)CC(C)C)=O)[C@H](CC)C)=O)CO)=O)CO)=O)CCC2
InChI InChI=1S/C144H227N41O47/c1-20-69(11)110(137(227)174-94(52-80-56-151-64-157-80)120(210)156-59-105(197)179-114(75(17)190)116(146)206)181-132(222)97(55-109(204)205)173-136(226)102-29-26-46-185(102)142(232)101(63-189)178-134(224)99(61-187)177-139(229)111(70(12)21-2)180-131(221)91(49-68(9)10)169-130(220)96(54-108(202)203)172-128(218)93(51-79-32-36-83(194)37-33-79)171-127(217)92(50-78-30-34-82(193)35-31-78)170-126(216)90(48-67(7)8)167-118(208)74(16)160-121(211)84(27-24-44-153-143(147)148)164-129(219)95(53-81-57-152-65-158-81)175-138(228)112(71(13)22-3)183-140(230)113(72(14)23-4)182-135(225)100(62-188)176-124(214)88(40-43-107(200)201)166-141(231)115(76(18)191)184-125(215)85(28-25-45-154-144(149)150)163-122(212)86(38-41-103(145)195)165-123(213)87(39-42-106(198)199)162-117(207)73(15)159-104(196)58-155-119(209)89(47-66(5)6)168-133(223)98(60-186)161-77(19)192/h30-37,56-57,64-76,84-102,110-115,186-191,193-194H,20-29,38-55,58-63H2,1-19H3,(H2,145,195)(H2,146,206)(H,151,157)(H,152,158)(H,155,209)(H,156,210)(H,159,196)(H,160,211)(H,161,192)(H,162,207)(H,163,212)(H,164,219)(H,165,213)(H,166,231)(H,167,208)(H,168,223)(H,169,220)(H,170,216)(H,171,217)(H,172,218)(H,173,226)(H,174,227)(H,175,228)(H,176,214)(H,177,229)(H,178,224)(H,179,197)(H,180,221)(H,181,222)(H,182,225)(H,183,230)(H,184,215)(H,198,199)(H,200,201)(H,202,203)(H,204,205)(H4,147,148,153)(H4,149,150,154)/t69-,70-,71-,72-,73-,74-,75+,76+,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,110-,111-,112-,113-,114-,115-/m0/s1
InChI Key WKXNKQZYGSNBDJ-VGQQASIRSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Castro-Garcia P, Díaz-Moreno M, Gil-Gas C, Fernández-Gómez FJ, Honrubia-Gómez P, Álvarez-Simón CB, Sánchez-Sánchez F, Cano JC, Almeida F, Blanco V et al.. (2015)
Defects in subventricular zone pigmented epithelium-derived factor niche signaling in the senescence-accelerated mouse prone-8.
FASEB J, 29 (4): 1480-92. [PMID:25636741]
2. Gonzalez R, Jennings LL, Knuth M, Orth AP, Klock HE, Ou W, Feuerhelm J, Hull MV, Koesema E, Wang Y et al.. (2010)
Screening the mammalian extracellular proteome for regulators of embryonic human stem cell pluripotency.
Proc Natl Acad Sci U S A, 107 (8): 3552-7. [PMID:20133595]
3. Ho TC, Tsai SH, Yeh SI, Chen SL, Tung KY, Chien HY, Lu YC, Huang CH, Tsao YP. (2019)
PEDF-derived peptide promotes tendon regeneration through its mitogenic effect on tendon stem/progenitor cells.
Stem Cell Res Ther, 10 (1): 2. [PMID:30606221]
4. Patil S, Sawale G, Ghuge S, Sathaye S. (2025)
Quintessence of currently approved and upcoming treatments for dry eye disease.
Graefes Arch Clin Exp Ophthalmol, 263 (2): 269-278. [PMID:39215848]
5. Shih SC, Ho TC, Chen SL, Tsao YP. (2017)
Pigment epithelium-derived factor (PEDF) peptide promotes the expansion of hepatic stem/progenitor cells via ERK and STAT3-dependent signaling.
Am J Transl Res, 9 (3): 1114-1126. [PMID:28386338]