L-proline (CHEBI:17203)

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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

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

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Molfile

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2.6178 -1.7552 0.0062 O 0 0 0 0 0 0 0 0 0 0 0 0

1.4896 -1.4533 -0.3525 C 0 0 0 0 0 0 0 0 0 0 0 0

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0.8101 -0.2780 0.1603 C 0 0 1 0 0 0 0 0 0 0 0 0

0.4653 0.6664 -0.9155 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.5551 -0.5700 0.8210 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.3656 0.7273 0.6378 C 0 0 0 0 0 0 0 0 0 0 0 0

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-1.0808 -1.3920 0.3243 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.3804 0.5080 0.2936 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.4368 1.2743 1.5812 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1330 2.4356 0.0600 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.2255 1.8909 -1.2232 H 0 0 0 0 0 0 0 0 0 0 0 0

2 1 2 0 0 0 0

3 2 1 0 0 0 0

4 2 1 0 0 0 0

4 5 1 0 0 0 0

6 4 1 0 0 0 0

7 6 1 0 0 0 0

8 7 1 0 0 0 0

8 5 1 0 0 0 0

3 9 1 0 0 0 0

4 10 1 0 0 0 0

5 11 1 0 0 0 0

6 12 1 0 0 0 0

6 13 1 0 0 0 0

7 14 1 0 0 0 0

7 15 1 0 0 0 0

8 16 1 0 0 0 0

8 17 1 0 0 0 0

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Wikipedia	License
Proline (symbol Pro or P) is an organic acid classed as a proteinogenic amino acid (used in the biosynthesis of proteins), although it does not contain the amino group -NH2 but is rather a secondary amine. The secondary amine nitrogen is in the protonated form (NH2+) under biological conditions, while the carboxyl group is in the deprotonated −COO− form. The "side chain" from the α carbon connects to the nitrogen forming a pyrrolidine loop, classifying it as a aliphatic amino acid. It is non-essential in humans, meaning the body can synthesize it from the non-essential amino acid L-glutamate. It is encoded by all the codons starting with CC (CCU, CCC, CCA, and CCG). Proline is the only proteinogenic amino acid which is a secondary amine, as the nitrogen atom is attached both to the α-carbon and to a chain of three carbons that together form a five-membered ring.
Read full article at Wikipedia

Formula

C5H9NO2

Net Charge

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 base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

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) 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
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	Reaxys Registry Number	Reaxys

Citations

Last Modified

13 January 2023

CHEBI:17203 - L-proline

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