CHEBI:17203 - L-proline

ChEBI IDCHEBI:17203
ChEBI NameL-proline
Stars
ASCII NameL-proline
DefinitionPyrrolidine 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.
Secondary ChEBI IDsCHEBI:6286, CHEBI:13154, CHEBI:21373, CHEBI:42067, CHEBI:45040, CHEBI:45100, CHEBI:45159, CHEBI:184637
Last Modified13 January 2023
DownloadsMolfile
FormulaC5H9NO2
Net Charge0
Average Mass115.132
Monoisotopic Mass115.06333
SMILESO=C(O)[C@@H]1CCCN1
InChIInChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1
InChIKeyONIBWKKTOPOVIA-BYPYZUCNSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Homo sapiens (ncbitaxon:9606)
- DOI (10.1038/nbt.2488)
blood serum (BTO:0000133) MetaboLights (MTBLS90)
Chlamydomonas reinhardtii (ncbitaxon:3055) - PubMed (25515814)
Saccharomyces cerevisiae (ncbitaxon:4932) - PubMed (24678285) Source: yeast.sf.net
Escherichia coli (ncbitaxon:562) - PubMed (21988831)
Mus musculus (ncbitaxon:10090) - PubMed (19425150) Source: BioModels - MODEL1507180067
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
mouse metabolite  Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
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.
micronutrient  Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions.
Saccharomyces cerevisiae metabolite  Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
Escherichia coli metabolite  Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
Daphnia magna metabolite  A Daphnia metabolite produced by the species Daphnia magna.
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Application:
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.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
(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)
(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)
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)
N,N-dimethyl-prolyl-proline (CHEBI:233685) 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
prolineChemIDplus
Synonyms  Source
L-ProlineKEGG COMPOUND
2-Pyrrolidinecarboxylic acidKEGG COMPOUND
PChEBI
(2S)-pyrrolidine-2-carboxylic acidIUPAC
(S)-pyrrolidine-2-carboxylic acidChEBI
L-ProlinChEBI
Manual XrefsDatabases
C00148KEGG COMPOUND
C00148KEGG COMPOUND
PROPDBeChem
D00035KEGG DRUG
DB00172DrugBank
HMDB0000162HMDB
PROMetaCyc
L-prolineWikipedia
C00001388KNApSAcK
4125DrugCentral
Registry NumbersSources
Gmelin:50152Gmelin
Reaxys:80810Reaxys
CAS:147-85-3KEGG COMPOUND
CAS:147-85-3ChemIDplus
CAS:147-85-3NIST Chemistry WebBook
Citations