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L-proline (CHEBI:17203)

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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:42067, CHEBI:13154, CHEBI:21373, CHEBI:6286, CHEBI:45159, CHEBI:45040, CHEBI:45100, CHEBI:184637
Supplier Information
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Formula Source
C5H9NO2 ChEBI
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 Source
Isolated from Homo sapiens (NCBI:9606) DOI
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): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
micronutrient

compatible osmolytes

metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(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 on the ChEBI Ontology
ChEBI Ontology
Outgoing L-proline (CHEBI:17203) has role compatible osmolytes (CHEBI:23366)
L-proline (CHEBI:17203) has role human metabolite (CHEBI:77746)
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 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,3S)-3,4-dihydroxy-L-proline (CHEBI:27041) has functional parent L-proline (CHEBI:17203)
3-hydroxy-L-proline (CHEBI:20056) has functional parent L-proline (CHEBI:17203)
4-hydroxy-L-proline (CHEBI:18240) has functional parent L-proline (CHEBI:17203)
4-oxo-L-proline (CHEBI:16821) has functional parent L-proline (CHEBI:17203)
5-oxo-L-proline (CHEBI:18183) has functional parent L-proline (CHEBI:17203)
N-(2,4-dinitrophenyl)-L-proline (CHEBI:53086) 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)
zofenopril (CHEBI:78539) has functional parent L-proline (CHEBI:17203)
zofenoprilat (CHEBI:82602) 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 MetaCyc
PRO PDBeChem
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
31 July 2014

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