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(+)-alpha-tocopherol +   
(12R)-hydroxy-10,11-dihydroleukotriene E4 
(2R)-2-ammonio-2-carboxylatoethyl-disulfanyl-oxopropanoate 
(2S)-2-amino-4-phosphonobutanoic acid 
(2S)-3-(3-pyridyl)propyl 1-(3,3-dimethyl-1,2-dioxopentyl)pyrrolidine-2-carboxylate 
(2S)-amino[(4R)-2-iminohexahydropyrimidin-4-yl]acetic acid 
(2S,3R)-capreomycidine 
(2S,3S)-beta-methylphenylalanine 
(2S,4R)-1-acetyl-N-[(1S)-4-[(aminoiminomethyl)amino]-1-(benzothiazol-2-ylcarbonyl)butyl]-4-hydroxypyrrolidine-2-carboxamide 
(2S,4R)-hypoglycin A +  
(2S,4S)-hypoglycin A +  
(3S)-3-hydroxy-L-asparagine 
(3S)-3-hydroxy-L-enduracididine 
(3S)-3-hydroxy-L-lysine 
(3S,4S)-3,4-dihydroxy-L-proline 
(4R)-5-oxo-L-leucine 
(4S)-4-hydroxy-L-isoleucine 
(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoic acid +   
(5S)-5-(carboxymethyl)-L-proline 
(5Z,9Z,12Z,15Z)-octadecatetraenoic acid +  
(6Z,9Z,12Z,15Z)-henicosa-1,6,9,12,15-pentaene 
(6Z,9Z,12Z,15Z)-tricosa-1,6,9,12,15-pentaene 
(7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid +  
(9Z)-hexadecenoic acid +   
(N(omega)-L-arginino)succinic acid  
(R)-2-hydroxyglutaric acid 
(R)-4-hydroxy-1-methyl-L-proline 
(S)-2-amino-6-boronohexanoic acid 
(S)-3,5-dihydroxyphenylglycine  
(S)-ATPA 
1,2-dibromoethane  
1-(L-norleucin-6-yl)pyrraline 
1-(L-norvalin-5-yl)pyrraline 
1-[(2R)-2-amino-2-cyclohexylacetyl]-N-\{5-chloro-2-[2-(ethylamino)-2-oxoethoxy]benzyl\}-L-prolinamide 
1-[3,3-dimethyl-2-(2-2-methylaminopropionylamino)butyryl]-4-phenoxypyrrolidine-2-[N-(1,2,3,4-tetrahydronaphthalen-1-yl)]carboxamide 
1-\{[1-(2-amino-3-phenylpropionyl)pyrrolidine-2-carbonyl]amino\}-2-(3-cyanophenyl)ethaneboronic acid 
1-monopalmitoylglycerol +  
1-monostearoylglycerol +  
1-naphthyl beta-D-glucoside 
11(R)-HEPE 
11(R)-HEPE(1-) 
14-carboxy-15,16,17,18,19,20-hexanor-leukotriene E3 
16-carboxy-17,18,19,20-tetranor-leukotriene E3 
16-carboxy-Delta(13)-17,18,19,20-tetranor-leukotriene E4 +  
18-carboxy-19,20-dinor-leukotriene E4 
1D-myo-inositol 4-phosphate 
2'-(S-L-cysteinyl)-L-histidine 
2,5-dihydrophenyl-L-alanine 
2,5-diiodo-L-histidine 
2-(3-amino-3-carboxypropyl)-L-histidine +  
2-(\{3-[(2S)-2-amino-2-carboxyethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl\}methyl)benzoic acid 
2-[3-carboxy-3-(dimethylamino)propyl]-L-histidine 
2-[3-carboxylato-3-(trimethylammonio)propyl]-L-histidine +  
2-hydroxy-5-[(1E)-(2-phenylethylidene)amino]-L-tyrosine 
2-hydroxy-L-tryptophan 
2-hydroxybutyric acid +  
2-hydroxypentanoic acid +  
2-hydroxypropanoic acid +   
2-L-bromohistidine 
2-methyl-L-glutamine 
2-methyl-L-serine +  
2-oxoglutarate(2-) 
2-palmitoylglycerol 
20-carboxyleukotriene E4 
20-hydroxy-leukotriene E4 
20-oxoleukotriene E4 
3'-L-prolyl-AMP 
3,5-dibromo-L-tyrosine 
3,5-dibromocatechol 
3,5-dichloro-L-tyrosine 
3,5-diiodo-L-tyrosine +  
3,5-dinitro-L-tyrosine 
3-(2,4-dioxo-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-1-yl)-L-alanine 
3-(5-bromouracil-1-yl)-L-alanine 
3-(5-fluorouracil-1-yl)-L-alanine  
3-(5-iodouracil-1-yl)-L-alanine 
3-(5-oxoisoxazolin-2-yl)-L-alanine 
3-(5-oxoisoxazolin-4-yl)-L-alanine 
3-(\{3-[(2S)-2-amino-2-carboxyethyl]-5-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl\}methyl)thiophene-2-carboxylic acid 
3-(N(tele)-L-histidino)-L-tyrosine residue 
3-(pyrazol-1-yl)-L-alanine 
3-(uracil-1-yl)-L-alanine 
3-[(3R)-1-carbamimidoylpiperidin-3-yl]-L-alanine 
3-[(3S)-1-carbamimidoylpiperidin-3-yl]-L-alanine 
3-\{(3E)-4-hydroxy-6-oxo-3-[(2-phenylethyl)imino]cyclohexa-1,4-dien-1-yl\}-L-alanine 
3-amino-L-alanine +  
3-bromo-4,5-dihydroxybenzoic acid 
3-bromo-4-hydroxybenzoic acid 
3-bromo-L-tyrosine 
3-chloro-L-phenylalanine 
3-chloro-L-tyrosine 
3-cyano-L-alanine +  
3-fluoro-L-tyrosine 
3-hydroxy-L-aspartic acid +  
3-hydroxy-L-glutamic acid +  
3-hydroxy-L-proline +  
3-hydroxy-L-tryptophan +  
3-hydroxy-L-valine +  
3-hydroxy-O,5-dimethyl-L-tyrosine 
3-iodo-L-tyrosine +  
3-mercaptopropanoic acid  
3-mercaptopropionate 
3-methyl-L-lanthionine 
3-methyl-L-tyrosine 
3-Methylamino-L-alanine 
3-methylthioaspartic acid +  
3-nitro-L-tyrosine 
3-O-(N-acetyl-beta-D-glucosaminyl)-L-serine +  
3-O-(N-acetyl-beta-D-glucosaminyl)-L-threonine +  
3-O-methyldopa 
3-phosphoglyceric acid +   
3-selenino-L-alanine +  
3-thio-L-aspartic acid +  
4-(3-methylbut-2-enyl)-L-tryptophan 
4-chloro-L-phenylalanine 
4-chloro-L-threonine +  
4-fluoro-L-phenylalanine 
4-fluoro-L-threonine 
4-fluorophenyl-L-alanine 
4-hydroxy-4-methylglutamate 
4-hydroxy-4-methylglutamic acid 
4-hydroxy-L-glutamic acid +  
4-hydroxy-L-lysine +  
4-hydroxy-L-proline +  
4-hydroxy-L-threonine 
4-hydroxy-L-tryptophan 
4-hydroxybenzoic acid +   
4-methyl-2-oxopentanoic acid  
4-Methyl-L-glutamate 
4-methyl-L-glutamic acid 
4-methylene-L-glutamic acid 
4-methylene-L-glutamine 
4-O-(beta-L-Araf)-cis-L-Hyp 
4-O-(beta-L-Araf-(1->2)-beta-L-Araf-(1->2)-beta-L-Araf)-cis-L-Hyp 
4-oxo-L-proline 
4-phospho-L-aspartic acid +  
5'-(N(6)-L-lysine)-L-tyrosylquinone +  
5'-S-methyl-5'-thioadenosine  
5-chloro-L-tryptophan 
5-hydroxy-L-kynurenine +  
5-hydroxy-L-tryptophan 
5-iodo-L-histidine 
5-methyl-L-arginine +  
5-oxo-D-proline 
5-oxo-L-proline +   
An optically active form of 5-oxoproline having L-configuration.
5-oxo-L-proline 2-naphthylamide 
6,7-dichloro-L-tryptophan 
6-chloro-L-tryptophan 
6-diazo-5-oxo-L-norleucine 
6-fluoro-L-dopa +  
6-hydroxy-L-dopa 
7-(3-methylbut-2-enyl)-L-tryptophan 
7-chloro-L-tryptophan 
7-hydroxy-L-tryptophan +  
[(R)-1-L-prolylpyrrolidin-2-yl]boronic acid 
\{(2S,3S,4S)-2-carboxy-4-[(1Z,3E,5R)-5-carboxy-1-methylhexa-1,3-dienyl]pyrrolidin-3-yl\}acetic acid 
acetohydroxamic acid  
acivicin  
adonixanthin 
agar 
agaritine 
agaropectin +  
all-cis-docosa-4,7,10,13,16,19-hexaenoic acid +   
all-cis-docosa-7,10,13,16-tetraenoic acid +   
alpha-Allokainic acid 
alpha-D-GlcNAc-(1->4)-beta-D-GlcA-(1->4)-alpha-D-GlcNAc-(1->4)-beta-D-GlcA-(1->3)-beta-D-Gal-(1->3)-beta-D-Gal-(1->4)-beta-D-Xyl-(1->3)-L-Ser 
alpha-D-xylose +  
alpha-methyl-L-dopa +   
alpha-methyl-L-tyrosine 
anticapsin 
aplysiatoxin 
asparagine +   
azaserine 
benzoic acid +   
beta-(N(pros)-L-histidino)-L-tyrosine 
beta-guanidino-L-alanine 
beta-L-aspartylhydroxamic acid 
beta-phenyl-D-phenylalanyl-N-(2,5-dichlorobenzyl)-L-prolinamide 
biocytin +  
brassicasterol +  
bromomethane  
butyl octadecanoate 
CANALINE 
captopril +  
carboxynorspermidine 
carrageenan +   
cholesterol +   
cilastatin  
cis-14-hydroxy-10,13-dioxo-7-heptadecenoic acid L-aspartate ester 
cis-4-hydroxy-L-proline +  
citramalic acid +  
coprine 
D-altritol 
D-galactose 6-phosphate +  
D-glucopyranuronic acid +   
D-glycerate 
debromoaplysiatoxin 
decanoic acid +   
deoxyhypusine +  
dibromomethane  
dimethyl sulfide +  
dinoflagellate luciferin 
discadenine 
disodium maleate 
dodecanoic acid +   
domoic acid  
DP-987 
erythro-5-phosphonooxy-L-lysine 
felinine 
filiforminol 
FMN-L-threonine +  
fosinopril  
fosinoprilat +   
fructoselysine 6-phosphate 
fucoxanthin  
furanomycin 
gadoleic acid +  
galacturonic acid +  
gamma-carboxy-L-glutamic acid +  
gamma-glutamyl-beta-aminopropiononitrile 
gamma-glutamyl-gamma-aminobutyraldehyde 
gamma-hydroxy-L-arginine +  
gamma-L-glutamylputrescine 
gamma-tocopherol +   
glycerol +   
glycerol 1-phosphate +   
glycerol 1-phosphoserine +  
glycolate +  
glyoxal-lysine dimer 
guanine +   
harmalol  
hepoxilin B3 
heptacosan-1-ol 
heptadecanoic acid +   
hexadecan-1-ol +  
hexadecanoic acid +   
homoserine +  
hydroxylamine +   
hypusine +  
indole-4-carbaldehyde 
inulobiose 
isoglutamic acid 
isonicotinic acid +   
isonocardicin A 
isonocardicin C 
kainic acid +   
L-2,4,6-trimethylphenylalanine +  
L-2-amino-3-oxobutanoic acid 
L-2-amino-4-(hydroxymethylphosphinoyl)butanoic acid 
L-2-amino-4-chloropent-4-enoic acid 
L-2-aminopimelic acid 
L-3-oxoalanine +  
L-6'-bromotryptophan +  
L-Albizziine 
L-alloisoleucine +  
L-allysine +  
L-alpha-(methylidenecyclopropyl)glycine 
L-alpha-aminobutyric acid +  
L-arabinose +  
L-beta-carboxyaspartic acid 
L-beta-ethynylserine 
L-beta-methylthioasparagine 
L-beta-methylthioaspartic acid 
L-BMAA 
L-canavanine 
L-cysteic acid 
L-cystine +   
L-dihydroanticapsin 
L-djenkolic acid 
L-dopa +  
L-enduracididine 
L-erythro-beta-hydroxyasparagine 
L-gamma-carboxyglutamic acid 
L-glutamic acid 5-methyl ester 
L-histidine +   
L-homoarginine 
L-homocitrulline +  
L-homolanthionine 
L-homophenylalanine 
L-homoserine +  
L-hydroxyproline 2-naphthylamide 
L-indospicine 
L-isoleucine +  
L-kynurenine +  
L-lanthionine 
L-Lathyrine 
L-leucine +   
L-lupinic acid 
L-lysine +   
L-m-tyrosine 
L-methionine sulfone 
L-methionine sulfoximine +  
L-mimosine  
L-norleucine +  
L-O,2,3-trimethyltyrosine +  
L-ornithine +   
L-phenylalanine +   
L-polyhomomethionine +  
L-prolinamide 
L-proline +   
L-proline 2-naphthylamide 
L-propargylglycine +  
L-serine +   
L-serine O-sulfate 
L-sorbose 1-phosphate 
L-thialysine 
L-threitol 
L-threonic acid +  
L-threonine +  
L-thyroxine +  
L-topaquinone +  
L-valine +   
L-vinylglycine 
laurebiphenyl 
leukotriene E3 +  
leukotriene E4 +   
lincomycin +   
linoleic acid +   
linolenic acid +   
lysidine +  
lysidine monophosphate +  
m-fluoro-L-phenylalanine 
maleic acid +   
mannopine 
melphalan  
methionine +   
methyl 1-methyl-5-oxo-L-prolinate 
methyl cis-10-pentadecenoate 
methyl dihydrogen phosphate  
methylglyoxal-lysine dimer 
microthecin 
N(3)-fumaroyl-(S)-2,3-diaminopropanoic acid 
N(4)-glycosyl-L-asparagine +  
N(5)-methyl-L-arginine 
N(6),N(6)-dimethyl-L-lysine +  
N(6)-(1-carboxyethyl)-L-lysine 
N(6)-(glycylglycyl)-L-lysine +  
N(6)-[(indol-3-yl)acetyl]-L-lysine +  
N(6)-acetimidoyl-L-lysine 
N(6)-carboxy-L-lysine +  
N(6)-carboxymethyl-L-lysine +  
N(6)-dansyl-L-lysine 
N(6)-formyl-L-lysine 
N(6)-glycyl-L-lysine 
N(6)-methyl-L-lysine +  
N(delta)-hydroxy-L-arginine 
N(delta)-hydroxy-N(omega)-hydroxy-N(omega)-methyl-L-arginine zwitterion 
N(delta)-hydroxy-N(omega)-methyl-L-argininium 
N(delta)-hydroxy-N(omega)-methyl-L-citrulline zwitterion 
N(delta)-hydroxy-N(omega)-methyl-N(omega)-nitroso-L-citrulline zwitterion 
N(gamma)-nitro-L-arginine 
N(omega),N'(omega)-dimethyl-L-arginine +  
N(omega),N(omega)-dimethyl-L-arginine +  
N(omega)-hydroxy-L-arginine +  
N(omega)-methyl-L-arginine 
N(omega)-phospho-L-arginine 
N(pros)-methyl-L-histidine +  
N(pros)-methyl-L-histidine zwitterion 
N(pros)-phospho-L-histidine +  
N(tele)-methyl-L-histidine +  
N-(2,4-dinitrophenyl)-L-proline 
N-(5'-phosphopyridoxyl)-L-alanine 
N-[4-(morpholin-4-ylcarbonyl)benzoyl]-L-valyl-N-[(3S)-5,5,6,6,6-pentafluoro-2-methyl-4-oxohexan-3-yl]-L-prolinamide 
N-acetyl-L-proline +  
N-benzyloxycarbonyl-L-prolyl-L-prolinal 
N-carboxy-L-methionine +  
N-ethoxycarbonyl-D-phenylalanylprolyl-2-(4-aminobutyl)hydrazine 
N-ethyl-L-asparagine 
N-formyl-L-kynurenine +  
N-methyl-L-alpha-amino acid +  
N-methylproline 
N-Nitrosohydroxyproline 
N-Nitrosoproline 
N4-hydroxymethyl-L-asparagine 
nonanoic acid +   
O(4)-phospho-L-tyrosine +  
O-(2-aminoethyl)-L-serine 
O-(3-O-beta-D-galactosyl-N-acetyl-alpha-D-galactosaminyl)-L-serine +  
O-(3-O-D-galactosyl-N-acetyl-beta-D-galactosaminyl)-L-serine 
O-(alpha-D-mannosyl)-L-serine +  
O-(N-acetyl-alpha-D-galactosaminyl)-L-serine +  
O-(N-acetyl-alpha-D-galactosaminyl)-L-threonine +  
O-(pantetheine-4'-phosphoryl)serine +  
O-(S-acylpantetheine-4'-phosphoryl)serine +  
O-[N-acetyl-alpha-neuraminyl-(2->6)-N-acetyl-alpha-D-galactosaminyl]-L-serine +  
O-[N-acetyl-alpha-neuraminyl-(2->6)-N-acetyl-alpha-D-galactosaminyl]-L-threonine +  
O-carbamoyl-L-serine 
O-methylserine 
O-phospho-L-threonine +  
O-phosphoethanolamine +  
O-ureido-L-serine 
octadecan-1-ol +   
octadecanoic acid +   
ornithine +   
ovothiol A 
ovothiol A disulfide 
oxalic acid +   
oxidized dinoflagellate luciferin 
pantothenate +  
pentadecanoic acid +  
pentosidine 
phloroglucinol +   
phlorotannin +   
Phosphoallohydroxy-L-lysine 
phosphoric acid +   
phytol +   
psicosyllysine 
ribofuranose +   
S-(1,2-dichlorovinyl)-L-cysteine +   
S-(2-boronoethyl)-L-cysteine 
S-(4-Methylthiobutylthiohydroximoyl)-L-cysteine 
S-(5-histidyl)cysteine sulfoxide 
S-(Hydroxyphenylacetothiohydroximoyl)-L-cysteine 
S-(Indolylmethylthiohydroximoyl)-L-cysteine 
S-(Phenylacetothiohydroximoyl)-L-cysteine 
S-alkyl-L-cysteine S-oxide +  
S-anthraniloyl-L-cysteine +  
S-carboxymethyl-L-cysteine 
S-farnesyl-L-cysteine +  
S-hydrocarbyl-L-cysteine +   
S-hydroxy-L-cysteine +  
S-methyl-L-thiocitrulline  
S-octanoyl-L-cysteine 
S-oxy-L-cysteine +  
salicylic acid +   
Se-methyl-L-selenocysteine +   
sodium 4-hydroxybenzoate 
sodium benzoate +   
spirolaurenone 
sucrose +   
tetradecanoic acid +   
tetradecyl tetradecanoate 
Thalassemine 
threo-3-methyl-L-aspartic acid 
Tnp-Gln 
trifluoro-L-methionine 
tryptophan N-glucoside 
tyrosine-4-azobenzenearsonate 
xylitol +   
zofenopril 
zofenoprilat 

Synonyms
Exact Synonyms: (2S)-5-oxopyrrolidine-2-carboxylic acid
Related Synonyms: (S)-(-)-2-pyrrolidone-5-carboxylic acid ;   (S)-pyroglutamic acid ;   5-Pyrrolidone-2-carboxylic acid ;   Formula=C5H7NO3 ;   InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1 ;   InChIKey=ODHCTXKNWHHXJC-VKHMYHEASA-N ;   L-5-Pyrrolidone-2-carboxylic acid ;   L-Pyroglutamic acid ;   PYROGLUTAMIC ACID ;   Pyroglutamate ;   SMILES=OC(=O)[C@@H]1CCC(=O)N1 ;   pidolic acid
Alternate IDs: CHEBI:12153 ;   CHEBI:20619 ;   CHEBI:2113 ;   CHEBI:44704
Xrefs: Beilstein:5251861 "Beilstein" ;   Beilstein:82132 "Beilstein" ;   CAS:98-79-3 "ChemIDplus" ;   CAS:98-79-3 "KEGG COMPOUND" ;   CAS:98-79-3 "NIST Chemistry WebBook" ;   DrugBank:DB03088 ;   Gmelin:1125330 "Gmelin" ;   HMDB:HMDB0000267 ;   KEGG:C01879 ;   KNApSAcK:C00007403
Xref Mesh: MESH:D011761
Xrefs: MetaCyc:5-OXOPROLINE ;   PDBeChem:PCA ;   PMID:17439666 "Europe PMC" ;   PMID:22560249 "Europe PMC" ;   PMID:22619187 "Europe PMC" ;   Reaxys:82132 "Reaxys" ;   Wikipedia:Pyroglutamic_acid ;   YMDB:YMDB00107
Cyclic Relationships: is_conjugate_acid_of CHEBI:58402 ;   is_enantiomer_of CHEBI:16924

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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.