AFCDB: L-Proline (FDB000570)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:37 UTC

Update date

2024-11-29 22:27:22 UTC

Primary ID

FDB000570

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

L-Proline

Description

Proline or L-proline abbreviated Pro or is one of the twenty amino acids used in living organisms as the building blocks of proteins. Proline is sometimes called an imino acid, although the IUPAC definition of an imine requires a carbon-nitrogen double bond. Proline is a non-essential amino acid that is largely synthesized from glutamic acid. While proline biosynthetic pathways exist from eubacteria to eukaryotes, in the most prevalent pathway, proline is cyclized from glutamate. First glutamate is phosphorylated to gamma-glutamyl phosphate by gamma-glutamyl kinase, then second, reduced to gamma-glutamyl semialdehyde by gamma-glutamyl phosphate reductase, then third, cyclized spontaneously to delta(1)-pyrroline-5-carboxylate and fourth, reduced to proline by delta(1)-pyrroline-5-carboxylate reductase. In higher plants and animals, the first two steps are catalysed by a bi-functional delta(1) -pyrroline-5-carboxylate synthase. Alternative pathways of proline formation use the initial steps of the arginine biosynthetic pathway to ornithine, which can be converted to delta(1)-pyrroline-5-carboxylate by ornithine aminotransferase and then reduced to proline or converted directly to proline by ornithine cyclodeaminase (PMID: 25367752). Proline is an essential component of collagen and is important for proper functioning of joints and tendons. It is a potential endogenous excitotoxin/neurotoxin, which causes damage to nerve cells and nerve tissues. Proline, when injected into the brains of rats, non-selectively destroyed pyramidal and granule cells (PMID: 3409032) suggesting that it can act as a neurotoxin. Proline can also be a metabotoxin which is an endogenously produced metabolite that causes adverse health effects at chronically high levels. At least five inborn errors of metabolism, including hyperprolinemia type I, hyperprolinemia type II, iminoglycinuria, prolinemia type II, and pyruvate carboxylase deficiency are associated with chronically high levels of proline (PMID: 18806117). Hyperprolinemia I and II are caused by deficiencies in the enzymatic activities of proline dehydrogenase and Delta-1-pyrroline-5-carboxylate reductase, respectively.

CAS Number

147-85-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	365 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-2.6	ChemAxon
logS	0.5	ALOGPS
pKa (Strongest Acidic)	1.94	ChemAxon
pKa (Strongest Basic)	11.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	28.06 m³·mol⁻¹	ChemAxon
Polarizability	11.5 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C5H9NO2

IUPAC name

(2S)-pyrrolidine-2-carboxylic acid

InChI Identifier

InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1

InChI Key

ONIBWKKTOPOVIA-BYPYZUCNSA-N

Isomeric SMILES

OC(=O)[C@@H]1CCCN1

Average Molecular Weight

115.1305

Monoisotopic Molecular Weight

115.063328537

Classification

Description

Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Proline and derivatives

Alternative Parents

Substituents

Proline or derivatives
Alpha-amino acid
L-alpha-amino acid
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine
Amino acid
Carboxylic acid
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Secondary amine
Organoheterocyclic compound
Azacycle
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Amine
Organopnictogen compound
Organic oxide
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

proteinogenic amino acid (CHEBI:17203 )
L-alpha-amino acid (CHEBI:17203 )
proline (CHEBI:17203 )
glutamine family amino acid (CHEBI:17203 )
Common amino acids (C00148 )

Ontology

Hemodialysis

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Tissue and substructures:

All tissues

Organ and components:

Prostate

Biofluid and excreta:

Subcellular:

Cell and elements:

Extracellular

Role

Indirect biological role:

Environmental role:

Environmental contaminant

Industrial application:

Food and nutrition:

Nutritional supplement

Pharmaceutical industry:

Pharmaceutical

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 52.16%; H 7.88%; N 12.17%; O 27.79%	DFC
Melting Point	Mp 220-222° dec.	DFC
Boiling Point	Not Available
Experimental Water Solubility	162 mg/mL at 25 oC	MERCK INDEX (1996)
Experimental logP	-2.54	HANSCH,C ET AL. (1995)
Experimental pKa	pKa2 10.6 (NH2)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D -60.4 (c, 1 in 5M HCl)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	L-Proline, 2 TMS, GC-MS Spectrum	splash10-0006-0910000000-a9127c0e370afb80259b	Spectrum
GC-MS	L-Proline, 2 TMS, GC-MS Spectrum	splash10-000f-0910000000-3195f21e625520d51316	Spectrum
GC-MS	L-Proline, non-derivatized, GC-MS Spectrum	splash10-0006-0900000000-119af746c347969e8ae7	Spectrum
GC-MS	L-Proline, 2 TMS, GC-MS Spectrum	splash10-006x-8900000000-b31beabb1ed6235e7145	Spectrum
GC-MS	L-Proline, 1 TMS, GC-MS Spectrum	splash10-00di-9100000000-c1c67bc521741ee891cb	Spectrum
GC-MS	L-Proline, 2 TMS, GC-MS Spectrum	splash10-0006-1900000000-84e6fb318323fd0261b1	Spectrum
GC-MS	L-Proline, 1 TMS, GC-MS Spectrum	splash10-00xs-8910000000-74b0c34ca5fd7c85f1d9	Spectrum
GC-MS	L-Proline, non-derivatized, GC-MS Spectrum	splash10-00fu-9000000000-716c3d01b301162863b6	Spectrum
GC-MS	L-Proline, non-derivatized, GC-MS Spectrum	splash10-0006-0900000000-0d7354201ed866c87b13	Spectrum
GC-MS	L-Proline, non-derivatized, GC-MS Spectrum	splash10-0006-0910000000-a9127c0e370afb80259b	Spectrum
GC-MS	L-Proline, non-derivatized, GC-MS Spectrum	splash10-000f-0910000000-3195f21e625520d51316	Spectrum
GC-MS	L-Proline, non-derivatized, GC-MS Spectrum	splash10-0006-0900000000-119af746c347969e8ae7	Spectrum
GC-MS	L-Proline, non-derivatized, GC-MS Spectrum	splash10-001i-1920000000-09006ee4e7a137d8a45a	Spectrum
GC-MS	L-Proline, non-derivatized, GC-MS Spectrum	splash10-006x-8900000000-b31beabb1ed6235e7145	Spectrum
GC-MS	L-Proline, non-derivatized, GC-MS Spectrum	splash10-0006-1900000000-84e6fb318323fd0261b1	Spectrum
GC-MS	L-Proline, non-derivatized, GC-MS Spectrum	splash10-00xs-8910000000-74b0c34ca5fd7c85f1d9	Spectrum
GC-MS	L-Proline, non-derivatized, GC-MS Spectrum	splash10-00di-9100000000-c1c67bc521741ee891cb	Spectrum
Predicted GC-MS	L-Proline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00fu-9000000000-d203e3dfb0701403a75b	Spectrum
Predicted GC-MS	L-Proline, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9000000000-56471980a375d26046ca	Spectrum
Predicted GC-MS	L-Proline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Proline, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Proline, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Proline, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00xr-9600000000-ba51a901e786b1a4663e	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9000000000-f72e2f3812225708fc56	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00di-9000000000-59887da6580f63bcc1c5	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-00fu-9000000000-c69dcaf7cb2d1e9d285e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0930000000-984f9a23ebfe28f95017	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-9000000000-f75575cac28a54aa923d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-9000000000-221cfb8c82f3df76eb51	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0900000000-e5741fd9870218d57caf	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0900000000-6bc9b4e775be37fa18d9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-9000000000-a8eb419b26655a6a1dab	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-9000000000-873ee03b61d1ffcae70f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0900000000-61d583960651669fb9e6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-03di-0900000000-2c23774af5f6a0c217d5	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-03di-0900000000-d89c1e626ef24a79c89f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-03di-1900000000-fc27094f2eb75e65b438	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-014i-1900000000-3221c23504b8847abf8d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-9100000000-8169367f5127c57fae12	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00di-9000000000-f704eb8402fcacfccd18	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-00di-9000000000-ccd74eea36efab2cbab8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-00di-9000000000-9f214692cd39a6581813	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positive	splash10-014i-0900000000-ef038c77922e4c89eeb0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-9400000000-4073ea1df57a60b36d69	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-00di-9000000000-495fdbd2f565bd794632	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-03di-0900000000-e1d0a4b20419dc7bae92	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-6900000000-eba8ceb2a71d2726acd0	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

17203

Phenol-Explorer ID

Not Available

DrugBank ID

DB02853

HMDB ID

HMDB00162

CRC / DFC (Dictionary of Food Compounds) ID

EAFUS ID

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1035851

SuperScent ID

Not Available

Wikipedia ID

Proline

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Name	Gene Name	UniProt ID
Prolyl 4-hydroxylase subunit alpha-2	P4HA2	O15460
Prolyl 4-hydroxylase subunit alpha-1	P4HA1	P13674
Bifunctional glutamate/proline--tRNA ligase	EPRS	P07814
Proline synthase co-transcribed bacterial homolog protein	PROSC	O94903
Pyrroline-5-carboxylate reductase	P5CR2	Q4W8W1
Prolyl 4-hydroxylase subunit alpha-3	P4HA3	Q7Z4N8
Egl nine homolog 1	EGLN1	Q9GZT9
Egl nine homolog 2	EGLN2	Q96KS0
Egl nine homolog 3	EGLN3	Q9H6Z9
Transmembrane prolyl 4-hydroxylase	P4HTM	Q9NXG6
Trans-L-3-hydroxyproline dehydratase	L3HYPDH	Q96EM0
Peptidyl-prolyl cis-trans isomerase F, mitochondrial	PPIF	P30405
Peptidyl-prolyl cis-trans isomerase A	PPIA	P62937
Peptidyl-prolyl cis-trans isomerase B	PPIB	P23284
Peptidyl-prolyl cis-trans isomerase G	PPIG	Q13427
Probable proline--tRNA ligase, mitochondrial	PARS2	Q7L3T8
Peptidyl-prolyl cis-trans isomerase H	PPIH	O43447

Pathways

Name	SMPDB Link	KEGG Link
Arginine and Proline Metabolism	SMP00020	map00330
Transcription/Translation	SMP00019	Not Available
Metabolism and Physiological Effects of Oxalic acid	SMP0124875	Not Available
Metabolism and Physiological Effects of N-Acetylproline	SMP0126660	Not Available
Metabolism and Physiological Effects of Isovalerylglycine	SMP0126748	Not Available
Metabolism and Physiological Effects of 3-Methylhistidine	SMP0126757	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

L-Proline (FDB000570)

Structure for FDB000570 (L-Proline)