CHEBI:17203 - L-proline

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ChEBI Name L-proline
ChEBI ID CHEBI:17203
ChEBI ASCII Name L-proline
Definition Pyrrolidine in which the pro-S hydrogen at position 2 is substituted by a carboxylic acid group. L-Proline is the only one of the twenty DNA-encoded amino acids which has a secondary amino group α to the carboxyl group. It is an essential component of collagen and is important for proper functioning of joints and tendons. It also helps maintain and strengthen heart muscles.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:45159, CHEBI:45100, CHEBI:45040, CHEBI:42067, CHEBI:184637, CHEBI:6286, CHEBI:13154, CHEBI:21373
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Formula C5H9NO2
Net Charge 0
Average Mass 115.13050
Monoisotopic Mass 115.06333
InChI InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1
InChIKey ONIBWKKTOPOVIA-BYPYZUCNSA-N
SMILES OC(=O)[C@@H]1CCCN1
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Chlamydomonas reinhardtii (NCBI:txid3055) See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932) Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Homo sapiens (NCBI:txid9606) Found in blood serum (BTO:0000133). See: MetaboLights Study
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
micronutrient
Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions.
algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
compatible osmolytes

human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(via proline )
Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
(via proline )
Application(s): nutraceutical
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing L-proline (CHEBI:17203) has role Escherichia coli metabolite (CHEBI:76971)
L-proline (CHEBI:17203) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
L-proline (CHEBI:17203) has role algal metabolite (CHEBI:84735)
L-proline (CHEBI:17203) has role compatible osmolytes (CHEBI:23366)
L-proline (CHEBI:17203) has role micronutrient (CHEBI:27027)
L-proline (CHEBI:17203) has role mouse metabolite (CHEBI:75771)
L-proline (CHEBI:17203) has role nutraceutical (CHEBI:50733)
L-proline (CHEBI:17203) is a L-α-amino acid (CHEBI:15705)
L-proline (CHEBI:17203) is a glutamine family amino acid (CHEBI:24318)
L-proline (CHEBI:17203) is a proline (CHEBI:26271)
L-proline (CHEBI:17203) is a proteinogenic amino acid (CHEBI:83813)
L-proline (CHEBI:17203) is conjugate acid of L-prolinate (CHEBI:32862)
L-proline (CHEBI:17203) is conjugate base of L-prolinium (CHEBI:32864)
L-proline (CHEBI:17203) is enantiomer of D-proline (CHEBI:16313)
L-proline (CHEBI:17203) is tautomer of L-proline zwitterion (CHEBI:60039)
Incoming (2S,5S)-5-amino-4-oxo-1,2,4,5,6,7-hexahydroazepino[3,2,1-hi]indole-2-carboxylic acid (CHEBI:42941) has functional parent L-proline (CHEBI:17203)
(E)-nesocodin (alcohol-form) zwitterion (CHEBI:191394) has functional parent L-proline (CHEBI:17203)
(E)-nesocodin (oxo-form) zwitterion (CHEBI:191393) has functional parent L-proline (CHEBI:17203)
L-proline derivative (CHEBI:84186) has functional parent L-proline (CHEBI:17203)
acromelic acid A (CHEBI:134690) has functional parent L-proline (CHEBI:17203)
Ala-Ala-Pro (CHEBI:73323) has functional parent L-proline (CHEBI:17203)
Ala-Ala-Pro-Pro (CHEBI:73324) has functional parent L-proline (CHEBI:17203)
Ala-Asn-Asn-Pro (CHEBI:73326) has functional parent L-proline (CHEBI:17203)
Ala-Asn-Asp-Pro (CHEBI:73329) has functional parent L-proline (CHEBI:17203)
Ala-Asp-Pro (CHEBI:73342) has functional parent L-proline (CHEBI:17203)
Ala-Gln-Pro (CHEBI:73347) has functional parent L-proline (CHEBI:17203)
Ala-Gly-Pro (CHEBI:73349) has functional parent L-proline (CHEBI:17203)
Ala-Leu-Ala-Pro (CHEBI:73353) has functional parent L-proline (CHEBI:17203)
Ala-Leu-Thr-Pro (CHEBI:73292) has functional parent L-proline (CHEBI:17203)
Ala-Pro (CHEBI:73393) has functional parent L-proline (CHEBI:17203)
Ala-Thr-Ala-Pro (CHEBI:73381) has functional parent L-proline (CHEBI:17203)
Ala-Val-Asp-Pro (CHEBI:73384) has functional parent L-proline (CHEBI:17203)
Ala-Val-Pro-Pro (CHEBI:73392) has functional parent L-proline (CHEBI:17203)
Arg-Pro (CHEBI:141419) has functional parent L-proline (CHEBI:17203)
Arg-Trp-Pro (CHEBI:156080) has functional parent L-proline (CHEBI:17203)
Asn-Asn-Pro-Ser (CHEBI:73407) has functional parent L-proline (CHEBI:17203)
Asn-Gly-Pro-His (CHEBI:176851) has functional parent L-proline (CHEBI:17203)
Asn-Met-Gln-Pro (CHEBI:138505) has functional parent L-proline (CHEBI:17203)
Asn-Pro (CHEBI:73425) has functional parent L-proline (CHEBI:17203)
Asp-Gly-Pro (CHEBI:73291) has functional parent L-proline (CHEBI:17203)
Asp-Met-Thr-Pro (CHEBI:73436) has functional parent L-proline (CHEBI:17203)
Asp-Pro-Ser-Ser (CHEBI:73439) has functional parent L-proline (CHEBI:17203)
Asp-Val-Gly-Pro (CHEBI:73441) has functional parent L-proline (CHEBI:17203)
Asp-Val-Pro-Pro (CHEBI:73443) has functional parent L-proline (CHEBI:17203)
cyclo(L-His-L-Pro) (CHEBI:90039) has functional parent L-proline (CHEBI:17203)
Cys-Pro (CHEBI:73461) has functional parent L-proline (CHEBI:17203)
Gln-Leu-Leu-Pro (CHEBI:73463) has functional parent L-proline (CHEBI:17203)
Glu-Pro (CHEBI:73508) has functional parent L-proline (CHEBI:17203)
Gly-Arg-Pro (CHEBI:144473) has functional parent L-proline (CHEBI:17203)
Gly-Pro (CHEBI:70744) has functional parent L-proline (CHEBI:17203)
Gly-Pro-Hyp (CHEBI:74135) has functional parent L-proline (CHEBI:17203)
Ile-Leu-Pro (CHEBI:158558) has functional parent L-proline (CHEBI:17203)
Leu-Gly-Pro (CHEBI:6414) has functional parent L-proline (CHEBI:17203)
Leu-Pro (CHEBI:73580) has functional parent L-proline (CHEBI:17203)
Leu-Pro-Tyr (CHEBI:73581) has functional parent L-proline (CHEBI:17203)
Lys-Thr-Pro-Pro (CHEBI:73596) has functional parent L-proline (CHEBI:17203)
maculosin (CHEBI:6631) has functional parent L-proline (CHEBI:17203)
Met-Pro (CHEBI:73612) has functional parent L-proline (CHEBI:17203)
notoamide (CHEBI:145690) has functional parent L-proline (CHEBI:17203)
Phe-Ala-Pro (CHEBI:73617) has functional parent L-proline (CHEBI:17203)
Phe-Pro-Pro (CHEBI:73644) has functional parent L-proline (CHEBI:17203)
Phe-Pro-Thr (CHEBI:138789) has functional parent L-proline (CHEBI:17203)
Pro-Arg (CHEBI:73645) has functional parent L-proline (CHEBI:17203)
Pro-Arg-Pro (CHEBI:144903) has functional parent L-proline (CHEBI:17203)
Pro-Cys (CHEBI:157881) has functional parent L-proline (CHEBI:17203)
Pro-Glu-Ile (CHEBI:144613) has functional parent L-proline (CHEBI:17203)
Pro-Hyp (CHEBI:74767) has functional parent L-proline (CHEBI:17203)
Pro-Met (CHEBI:141444) has functional parent L-proline (CHEBI:17203)
Pro-Pro (CHEBI:73646) has functional parent L-proline (CHEBI:17203)
Pro-Pro-Pro (CHEBI:73647) has functional parent L-proline (CHEBI:17203)
Pro-Ser (CHEBI:73648) has functional parent L-proline (CHEBI:17203)
Pro-Thr (CHEBI:141395) has functional parent L-proline (CHEBI:17203)
Pro-Trp-Val-Gly (CHEBI:73650) has functional parent L-proline (CHEBI:17203)
Pro-Val-Gly-Pro (CHEBI:73649) has functional parent L-proline (CHEBI:17203)
Pro-Val-Val-Pro (CHEBI:176850) has functional parent L-proline (CHEBI:17203)
Ser-Asp-Lys-Pro (CHEBI:191177) has functional parent L-proline (CHEBI:17203)
Thr-Pro (CHEBI:73662) has functional parent L-proline (CHEBI:17203)
Thr-Pro-Pro (CHEBI:164196) has functional parent L-proline (CHEBI:17203)
Thr-Pro-Tyr (CHEBI:73661) has functional parent L-proline (CHEBI:17203)
Trp-Pro (CHEBI:141449) has functional parent L-proline (CHEBI:17203)
Tyr-Pro (CHEBI:141456) has functional parent L-proline (CHEBI:17203)
Val-Asn-Pro (CHEBI:73697) has functional parent L-proline (CHEBI:17203)
Val-Pro (CHEBI:73701) has functional parent L-proline (CHEBI:17203)
Val-Pro-Pro (CHEBI:73696) has functional parent L-proline (CHEBI:17203)
royal jelly (CHEBI:78665) has part L-proline (CHEBI:17203)
L-proline-d7 (CHEBI:192088) is a L-proline (CHEBI:17203)
L-prolinium (CHEBI:32864) is conjugate acid of L-proline (CHEBI:17203)
L-prolinate (CHEBI:32862) is conjugate base of L-proline (CHEBI:17203)
D-proline (CHEBI:16313) is enantiomer of L-proline (CHEBI:17203)
L-proline residue (CHEBI:50342) is substituent group from L-proline (CHEBI:17203)
L-prolino group (CHEBI:32866) is substituent group from L-proline (CHEBI:17203)
L-prolyl group (CHEBI:32865) is substituent group from L-proline (CHEBI:17203)
L-proline zwitterion (CHEBI:60039) is tautomer of L-proline (CHEBI:17203)
IUPAC Name
L-proline
INN Source
proline ChemIDplus
Synonyms Sources
(−)-(S)-proline NIST Chemistry WebBook
(−)-2-pyrrolidinecarboxylic acid ChemIDplus
(−)-proline ChemIDplus
(2S)-pyrrolidine-2-carboxylic acid IUPAC
(S)-2-carboxypyrrolidine DrugBank
(S)-2-pyrrolidinecarboxylic acid ChemIDplus
(S)-pyrrolidine-2-carboxylic acid ChEBI
2-Pyrrolidinecarboxylic acid KEGG COMPOUND
L-(−)-proline NIST Chemistry WebBook
L-α-pyrrolidinecarboxylic acid ChemIDplus
L-Prolin ChEBI
L-Proline KEGG COMPOUND
L-pyrrolidine-2-carboxylic acid ChemIDplus
P ChEBI
prolina ChemIDplus
PROLINE PDBeChem
prolinum ChemIDplus
Manual Xrefs Databases
4125 DrugCentral
C00001388 KNApSAcK
C00148 KEGG COMPOUND
D00035 KEGG DRUG
DB00172 DrugBank
HMDB0000162 HMDB
L-proline Wikipedia
PRO PDBeChem
PRO MetaCyc
View more database links
Registry Numbers Types Sources
147-85-3 CAS Registry Number KEGG COMPOUND
147-85-3 CAS Registry Number NIST Chemistry WebBook
147-85-3 CAS Registry Number ChemIDplus
50152 Gmelin Registry Number Gmelin
80810 Beilstein Registry Number Beilstein
80810 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
13 January 2023