CHEBI:17203 - L-proline

Main ChEBI Ontology Automatic Xrefs
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
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
Homo sapiens (NCBI:9606) See: DOI
Homo sapiens (NCBI:9606) Found in blood serum (BTO:0001239). 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 )
Biological Role(s): micronutrient

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 compatible osmolytes (CHEBI:23366)
L-proline (CHEBI:17203) has role micronutrient (CHEBI:27027)
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 L-proline derivative (CHEBI:84186) 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)
Asn-Asn-Pro-Ser (CHEBI:73407) 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)
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-Pro (CHEBI:70744) has functional parent L-proline (CHEBI:17203)
Gly-Pro-Hyp (CHEBI:74135) 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)
Phe-Ala-Pro (CHEBI:73617) has functional parent L-proline (CHEBI:17203)
Phe-Pro-Pro (CHEBI:73644) has functional parent L-proline (CHEBI:17203)
Pro-Arg (CHEBI:73645) has functional parent L-proline (CHEBI:17203)
Pro-Gly (CHEBI:73594) has functional parent L-proline (CHEBI:17203)
Pro-Hyp (CHEBI:74767) 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-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)
Thr-Pro (CHEBI:73662) has functional parent L-proline (CHEBI:17203)
Thr-Pro-Tyr (CHEBI:73661) 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-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
Database Links Databases
C00001388 KNApSAcK
C00148 KEGG COMPOUND
D00035 KEGG DRUG
DB00172 DrugBank
HMDB00162 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 ChemIDplus
147-85-3 CAS Registry Number NIST Chemistry WebBook
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
16 March 2015