PR-39 (CHEBI:131850)

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CHEBI:131850 - PR-39

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ChEBI ID	CHEBI:131850
ChEBI Name	PR-39
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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.
Last Modified	24 February 2021
Submitter	Gareth Owen
Downloads	Molfile

Formula	C229H345N69O41
Net Charge	0
Average Mass	4720.721
Monoisotopic Mass	4717.70324
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](Cc1ccccc1)NC(=O)[C@H](Cc1ccccc1)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](Cc1ccc(O)cc1)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](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)O
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

Species of Metabolite	Component	Source	Comments
Sus scrofa domesticus (ncbitaxon:9825)
	blood (UBERON:0000178)	PubMed (26331932)
	small intestine (BTO:0000651)	PubMed (8514403)

Roles Classification

Chemical Roles:	Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid). Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:	immunomodulator Biologically active substance whose activity affects or plays a role in the functioning of the immune system. antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. 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. antibacterial agent A substance (or active part thereof) that kills or slows the growth of bacteria. antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Applications:	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.

ChEBI Ontology

Outgoing Relation(s)
	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	Source
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
PR 39	ChemIDplus
RRRPRPPYLPRPRPPPFFPPRLPPRIPPGFPPRFPPRFP	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

Registry Numbers	Sources
CAS:139637-11-9	ChemIDplus

Citations