ContaminantDB: L-Proline

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (23)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:51:05 UTC

Update Date

2026-05-14 16:31:22 UTC

Accession Number

CHEM003371

Identification

Common Name

L-Proline

Class

Small Molecule

Description

L-Proline 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 synthesized from glutamic acid. It is an essential component of collagen and is important for proper functioning of joints and tendons.

Contaminant Sources

EAFUS Chemicals
FooDB Chemicals
HMDB Contaminants - Feces
HMDB Contaminants - Urine
HPV EPA Chemicals
My Exposome Chemicals
T3DB toxins

Contaminant Type

Amine
Animal Toxin
Dietary Supplement
Drug
Food Toxin
Household Toxin
Metabolite
Micronutrient
Natural Compound
Non-Essential Amino Acid
Nutraceutical
Organic Compound
Supplement

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-(S)-Proline	ChEBI
(-)-2-Pyrrolidinecarboxylic acid	ChEBI
(-)-Proline	ChEBI
(2S)-Pyrrolidine-2-carboxylic acid	ChEBI
(S)-2-Carboxypyrrolidine	ChEBI
(S)-2-Pyrrolidinecarboxylic acid	ChEBI
(S)-Pyrrolidine-2-carboxylic acid	ChEBI
2-Pyrrolidinecarboxylic acid	ChEBI
L-(-)-Proline	ChEBI
L-alpha-Pyrrolidinecarboxylic acid	ChEBI
L-Prolin	ChEBI
L-Pyrrolidine-2-carboxylic acid	ChEBI
P	ChEBI
Prolina	ChEBI
PROLINE	ChEBI
Prolinum	ChEBI
(-)-2-Pyrrolidinecarboxylate	Generator
(2S)-Pyrrolidine-2-carboxylate	Generator
(S)-2-Pyrrolidinecarboxylate	Generator
(S)-Pyrrolidine-2-carboxylate	Generator
2-Pyrrolidinecarboxylate	Generator
L-a-Pyrrolidinecarboxylate	Generator
L-a-Pyrrolidinecarboxylic acid	Generator
L-alpha-Pyrrolidinecarboxylate	Generator
L-Α-pyrrolidinecarboxylate	Generator
L-Α-pyrrolidinecarboxylic acid	Generator
L-Pyrrolidine-2-carboxylate	Generator
(S)-(-)-Proline	HMDB
(S)-(-)-Pyrrolidine-2-carboxylate	HMDB
(S)-(-)-Pyrrolidine-2-carboxylic acid	HMDB
(S)-2-Pyrralidinecarboxylate	HMDB
(S)-2-Pyrralidinecarboxylic acid	HMDB
(S)-Proline	HMDB
L Proline	HMDB

Chemical Formula

C₅H₉NO₂

Average Molecular Mass

115.131 g/mol

Monoisotopic Mass

115.063 g/mol

CAS Registry Number

147-85-3

IUPAC Name

(2S)-pyrrolidine-2-carboxylic acid

Traditional Name

L-proline

SMILES

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

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

Chemical Taxonomy

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Lysosome
Membrane
Mitochondria

Biofluid Locations

Not Available

Tissue Locations

All Tissues
Prostate

Pathways

Name	SMPDB Link	KEGG Link
Arginine and Proline Metabolism	SMP00020	map00330
Transcription/Translation	SMP00019	Not Available
Hyperprolinemia Type I	SMP00361	Not Available
Hyperprolinemia Type II	SMP00360	Not Available
Iminoglycinuria	SMP00193	Not Available
Prolinemia Type II	SMP00208	Not Available
Pyruvate Carboxylase Deficiency	SMP00350	Not Available

Applications

nutraceutical

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	221 dec°C
Boiling Point	Not Available
Solubility	1.62E+005 mg/L (at 25°C)

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0006-0910000000-a9127c0e370afb80259b	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-000f-0910000000-3195f21e625520d51316	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0006-0900000000-119af746c347969e8ae7	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-006x-8900000000-b31beabb1ed6235e7145	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-00di-9100000000-c1c67bc521741ee891cb	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0006-1900000000-84e6fb318323fd0261b1	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-00xs-8910000000-74b0c34ca5fd7c85f1d9	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00fu-9000000000-716c3d01b301162863b6	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-0900000000-0d7354201ed866c87b13	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-0910000000-a9127c0e370afb80259b	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000f-0910000000-3195f21e625520d51316	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-0900000000-119af746c347969e8ae7	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-QQ (Non-derivatized)	splash10-001i-1920000000-09006ee4e7a137d8a45a	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-006x-8900000000-b31beabb1ed6235e7145	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0006-1900000000-84e6fb318323fd0261b1	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00xs-8910000000-74b0c34ca5fd7c85f1d9	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00di-9100000000-c1c67bc521741ee891cb	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fu-9000000000-d203e3dfb0701403a75b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9000000000-56471980a375d26046ca	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00xr-9600000000-ba51a901e786b1a4663e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9000000000-f72e2f3812225708fc56	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00di-9000000000-59887da6580f63bcc1c5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-00fu-9000000000-c69dcaf7cb2d1e9d285e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0930000000-984f9a23ebfe28f95017	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-9000000000-f75575cac28a54aa923d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-9000000000-221cfb8c82f3df76eb51	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0900000000-e5741fd9870218d57caf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0900000000-6bc9b4e775be37fa18d9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-9000000000-a8eb419b26655a6a1dab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00di-9000000000-873ee03b61d1ffcae70f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-0900000000-61d583960651669fb9e6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-03di-0900000000-2c23774af5f6a0c217d5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-03di-0900000000-d89c1e626ef24a79c89f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-03di-1900000000-fc27094f2eb75e65b438	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-014i-1900000000-3221c23504b8847abf8d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-9100000000-8169367f5127c57fae12	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00di-9000000000-f704eb8402fcacfccd18	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-00di-9000000000-ccd74eea36efab2cbab8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-00di-9000000000-9f214692cd39a6581813	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positive	splash10-014i-0900000000-ef038c77922e4c89eeb0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-9400000000-4073ea1df57a60b36d69	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-00di-9000000000-495fdbd2f565bd794632	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-03di-0900000000-e1d0a4b20419dc7bae92	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-6900000000-eba8ceb2a71d2726acd0	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Glycogenic, by L-Proline oxidase in the kidney, it is ring-opened and is oxidized to form L-Glutamic acid. L-Ornithine and L-Glutamic acid are converted to L-Proline via L-Glutamic acid-gamma-semialdehyde. It is contained abundantly in collagen, and is intimately involved in the function of arthrosis and chordae.

Metabolism

Hepatic

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

L-Proline is extremely important for the proper functioning of joints and tendons and also helps maintain and strengthen heart muscles.

Minimum Risk Level

Not Available

Health Effects

Chronically high levels of proline are associated with at least 5 inborn errors of metabolism including: Hyperprolinemia Type I, Hyperprolinemia Type II, Iminoglycinuria, Prolinemia Type II and Pyruvate carboxylase deficiency.

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00172

HMDB ID

HMDB0000162

FooDB ID