CHEBI:131850 - PR-39

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ChEBI Name PR-39
ChEBI ID CHEBI:131850
Definition A 39 amino acid porcine cathelicidin that is rich in proline and arginine residues. It plays a pivotal role in the innate immune defence of the pig against infections and exhibits antimicrobial and immunomodulatory activities.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information eMolecules:29542986, ZINC000000119839
Download Molfile XML SDF
Formula C229H345N69O41
Net Charge 0
Average Mass 4720.721
Monoisotopic Mass 4717.70324
InChI InChI=1S/C229H345N69O41/c1-7-135(6)181(218(337)297-122-50-89-178(297)216(335)283-108-33-72-161(283)190(309)261-132-180(300)262-157(128-137-54-15-9-16-55-137)206(325)293-118-46-84-173(293)212(331)284-109-37-77-166(284)192(311)265-146(65-26-98-254-223(237)238)185(304)276-158(129-138-56-17-10-18-57-138)207(326)294-119-47-85-174(294)213(332)286-111-39-78-167(286)193(312)266-147(66-27-99-255-224(239)240)186(305)277-160(131-140-60-21-12-22-61-140)209(328)298-123-51-90-179(298)219(338)339)279-187(306)148(67-28-100-256-225(241)242)267-194(313)168-79-40-112-287(168)211(330)172-83-45-117-292(172)205(324)156(125-134(4)5)274-184(303)145(64-25-97-253-222(235)236)264-191(310)165-76-38-110-285(165)214(333)175-86-48-120-295(175)208(327)159(130-139-58-19-11-20-59-139)278-189(308)153(126-136-52-13-8-14-53-136)272-198(317)170-81-42-114-289(170)215(334)177-88-49-121-296(177)217(336)176-87-44-116-291(176)203(322)152(71-32-104-260-229(249)250)271-196(315)163-74-35-106-281(163)201(320)150(69-30-102-258-227(245)246)269-197(316)164-75-36-107-282(164)204(323)155(124-133(2)3)275-188(307)154(127-141-91-93-142(299)94-92-141)273-199(318)169-80-41-113-288(169)210(329)171-82-43-115-290(171)202(321)151(70-31-103-259-228(247)248)270-195(314)162-73-34-105-280(162)200(319)149(68-29-101-257-226(243)244)268-183(302)144(63-24-96-252-221(233)234)263-182(301)143(230)62-23-95-251-220(231)232/h8-22,52-61,91-94,133-135,143-179,181,299H,7,23-51,62-90,95-132,230H2,1-6H3,(H,261,309)(H,262,300)(H,263,301)(H,264,310)(H,265,311)(H,266,312)(H,267,313)(H,268,302)(H,269,316)(H,270,314)(H,271,315)(H,272,317)(H,273,318)(H,274,303)(H,275,307)(H,276,304)(H,277,305)(H,278,308)(H,279,306)(H,338,339)(H4,231,232,251)(H4,233,234,252)(H4,235,236,253)(H4,237,238,254)(H4,239,240,255)(H4,241,242,256)(H4,243,244,257)(H4,245,246,258)(H4,247,248,259)(H4,249,250,260)/t135-,143-,144-,145-,146-,147-,148-,149-,150-,151-,152-,153-,154-,155-,156-,157-,158-,159-,160-,161-,162-,163-,164-,165-,166-,167-,168-,169-,170-,171-,172-,173-,174-,175-,176-,177-,178-,179-,181-/m0/s1
InChIKey JTJJGVCUEGCBHL-IWDHFESKSA-N
SMILES CC[C@H](C)[C@H](NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CC(C)C)NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](N)CCCNC(N)=N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N1CCC[C@H]1C(O)=O
Metabolite of Species Details
Sus scrofa domesticus (NCBI:txid9825) Found in blood (UBERON:0000178). See: PubMed
Sus scrofa domesticus (NCBI:txid9825) Found in small intestine (BTO:0000651). See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
apoptosis inhibitor
Any substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.
mammalian metabolite
Any animal metabolite produced during a metabolic reaction in mammals.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via peptide antibiotic )
Application(s): anti-inflammatory agent
Any compound that has anti-inflammatory effects.
immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing PR-39 (CHEBI:131850) has role anti-inflammatory agent (CHEBI:67079)
PR-39 (CHEBI:131850) has role antibacterial agent (CHEBI:33282)
PR-39 (CHEBI:131850) has role antifungal agent (CHEBI:35718)
PR-39 (CHEBI:131850) has role apoptosis inhibitor (CHEBI:68494)
PR-39 (CHEBI:131850) has role immunomodulator (CHEBI:50846)
PR-39 (CHEBI:131850) has role mammalian metabolite (CHEBI:75768)
PR-39 (CHEBI:131850) is a cathelicidin (CHEBI:81578)
IUPAC Name
L-arginyl-L-arginyl-L-arginyl-L-prolyl-L-arginyl-L-prolyl-L-prolyl-L-tyrosyl-L-leucyl-L-prolyl-L-arginyl-L-prolyl-L-arginyl-L-prolyl-L-prolyl-L-prolyl-L-phenylalanyl-L-phenylalanyl-L-prolyl-L-prolyl-L-arginyl-L-leucyl-L-prolyl-L-prolyl-L-arginyl-L-isoleucyl-L-prolyl-L-prolylglycyl-L-phenylalanyl-L-prolyl-L-prolyl-L-arginyl-L-phenylalanyl-L-prolyl-L-prolyl-L-arginyl-L-phenylalanyl-L-prolinamide
Synonyms Sources
H-Arg-Arg-Arg-Pro-Arg-Pro-Pro-Tyr-Leu-Pro-Arg-Pro-Arg-Pro-Pro-Pro-Phe-Phe-Pro-Pro-Arg-Leu-Pro-Pro-Arg-Ile-Pro-Pro-Gly-Phe-Pro-Pro-Arg-Phe-Pro-Pro-Arg-Phe-Pro-OH ChEBI
H-L-Arg-L-Arg-L-Arg-L-Pro-L-Arg-L-Pro-L-Pro-L-Tyr-L-Leu-L-Pro-L-Arg-L-Pro-L-Arg-L-Pro-L-Pro-L-Pro-L-Phe-L-Phe-L-Pro-L-Pro-L-Arg-L-Leu-L-Pro-L-Pro-L-Arg-L-Ile-L-Pro-L-Pro-Gly-L-Phe-L-Pro-L-Pro-L-Arg-L-Phe-L-Pro-L-Pro-L-Arg-L-Phe-L-Pro-NH2 ChEBI
L-Arg-L-Arg-L-Arg-L-Pro-L-Arg-L-Pro-L-Pro-L-Tyr-L-Leu-L-Pro-L-Arg-L-Pro-L-Arg-L-Pro-L-Pro-L-Pro-L-Phe-L-Phe-L-Pro-L-Pro-L-Arg-L-Leu-L-Pro-L-Pro-L-Arg-L-Ile-L-Pro-L-Pro-Gly-L-Phe-L-Pro-L-Pro-L-Arg-L-Phe-L-Pro-L-Pro-L-Arg-L-Phe-L-Pro ChEBI
PR 39 ChemIDplus
RRRPRPPYLPRPRPPPFFPPRLPPRIPPGFPPRFPPRFP ChEBI
Registry Number Type Source
139637-11-9 CAS Registry Number ChemIDplus
Citations Types Sources
12969801 PubMed citation Europe PMC
17081280 PubMed citation Europe PMC
1765098 PubMed citation Europe PMC
17683376 PubMed citation Europe PMC
18519732 PubMed citation Europe PMC
19505806 PubMed citation Europe PMC
20573563 PubMed citation Europe PMC
23016650 PubMed citation Europe PMC
23078400 PubMed citation Europe PMC
24755622 PubMed citation Europe PMC
24929581 PubMed citation Europe PMC
26331932 PubMed citation Europe PMC
27353320 PubMed citation Europe PMC
27865272 PubMed citation Europe PMC
28043357 PubMed citation Europe PMC
28093715 PubMed citation Europe PMC
28539918 PubMed citation Europe PMC
29913265 PubMed citation Europe PMC
30003470 PubMed citation Europe PMC
30641213 PubMed citation Europe PMC
31935447 PubMed citation Europe PMC
8988856 PubMed citation Europe PMC
IND43668597 Agricola citation Europe PMC
Last Modified
24 February 2021