Record Information
Version1.0
Creation date2010-04-08 22:04:37 UTC
Update date2020-09-17 15:30:36 UTC
Primary IDFDB000570
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Proline
DescriptionProline 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 Number147-85-3
Structure
Thumb
Synonyms
SynonymSource
(-)-(S)-ProlineChEBI
(-)-2-Pyrrolidinecarboxylic acidChEBI
(-)-ProlineChEBI
(2S)-Pyrrolidine-2-carboxylic acidChEBI
(S)-2-CarboxypyrrolidineChEBI
(S)-2-Pyrrolidinecarboxylic acidChEBI
(S)-Pyrrolidine-2-carboxylic acidChEBI
2-Pyrrolidinecarboxylic acidChEBI
L-(-)-ProlineChEBI
L-alpha-Pyrrolidinecarboxylic acidChEBI
L-ProlinChEBI
L-Pyrrolidine-2-carboxylic acidChEBI
PChEBI
ProlinaChEBI
PROLINEChEBI
ProlinumChEBI
(-)-2-PyrrolidinecarboxylateGenerator
(2S)-Pyrrolidine-2-carboxylateGenerator
(S)-2-PyrrolidinecarboxylateGenerator
(S)-Pyrrolidine-2-carboxylateGenerator
2-PyrrolidinecarboxylateGenerator
L-a-PyrrolidinecarboxylateGenerator
L-a-Pyrrolidinecarboxylic acidGenerator
L-alpha-PyrrolidinecarboxylateGenerator
L-Α-pyrrolidinecarboxylateGenerator
L-Α-pyrrolidinecarboxylic acidGenerator
L-Pyrrolidine-2-carboxylateGenerator
(S)-(-)-ProlineHMDB
(S)-(-)-Pyrrolidine-2-carboxylateHMDB
(S)-(-)-Pyrrolidine-2-carboxylic acidHMDB
(S)-2-PyrralidinecarboxylateHMDB
(S)-2-Pyrralidinecarboxylic acidHMDB
(S)-ProlineHMDB
L ProlineHMDB
(L)-Prolinebiospider
2-Pyrralidinecarboxylic acid, (S)-biospider
2-Pyrrolidinecarboxylic acid, (S)-biospider
FEMA 3319db_source
L-Prolinebiospider
L-α-pyrrolidinecarboxylateGenerator
L-α-pyrrolidinecarboxylic acidGenerator
Proline, 9CI; L-formdb_source
Predicted Properties
PropertyValueSource
Water Solubility365 g/LALOGPS
logP-2.7ALOGPS
logP-2.6ChemAxon
logS0.5ALOGPS
pKa (Strongest Acidic)1.94ChemAxon
pKa (Strongest Basic)11.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity28.06 m³·mol⁻¹ChemAxon
Polarizability11.5 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H9NO2
IUPAC name(2S)-pyrrolidine-2-carboxylic acid
InChI IdentifierInChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1
InChI KeyONIBWKKTOPOVIA-BYPYZUCNSA-N
Isomeric SMILESOC(=O)[C@@H]1CCCN1
Average Molecular Weight115.1305
Monoisotopic Molecular Weight115.063328537
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentProline 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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Environmental role:

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 52.16%; H 7.88%; N 12.17%; O 27.79%DFC
Melting PointMp 220-222° dec.DFC
Boiling PointNot Available
Experimental Water Solubility162 mg/mL at 25 oCMERCK INDEX (1996)
Experimental logP-2.54HANSCH,C ET AL. (1995)
Experimental pKapKa2 10.6 (NH2)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -60.4 (c, 1 in 5M HCl)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSL-Proline, 2 TMS, GC-MS Spectrumsplash10-0006-0910000000-a9127c0e370afb80259bSpectrum
GC-MSL-Proline, 2 TMS, GC-MS Spectrumsplash10-000f-0910000000-3195f21e625520d51316Spectrum
GC-MSL-Proline, non-derivatized, GC-MS Spectrumsplash10-0006-0900000000-119af746c347969e8ae7Spectrum
GC-MSL-Proline, 2 TMS, GC-MS Spectrumsplash10-006x-8900000000-b31beabb1ed6235e7145Spectrum
GC-MSL-Proline, 1 TMS, GC-MS Spectrumsplash10-00di-9100000000-c1c67bc521741ee891cbSpectrum
GC-MSL-Proline, 2 TMS, GC-MS Spectrumsplash10-0006-1900000000-84e6fb318323fd0261b1Spectrum
GC-MSL-Proline, 1 TMS, GC-MS Spectrumsplash10-00xs-8910000000-74b0c34ca5fd7c85f1d9Spectrum
GC-MSL-Proline, non-derivatized, GC-MS Spectrumsplash10-00fu-9000000000-716c3d01b301162863b6Spectrum
GC-MSL-Proline, non-derivatized, GC-MS Spectrumsplash10-0006-0900000000-0d7354201ed866c87b13Spectrum
GC-MSL-Proline, non-derivatized, GC-MS Spectrumsplash10-0006-0910000000-a9127c0e370afb80259bSpectrum
GC-MSL-Proline, non-derivatized, GC-MS Spectrumsplash10-000f-0910000000-3195f21e625520d51316Spectrum
GC-MSL-Proline, non-derivatized, GC-MS Spectrumsplash10-0006-0900000000-119af746c347969e8ae7Spectrum
GC-MSL-Proline, non-derivatized, GC-MS Spectrumsplash10-001i-1920000000-09006ee4e7a137d8a45aSpectrum
GC-MSL-Proline, non-derivatized, GC-MS Spectrumsplash10-006x-8900000000-b31beabb1ed6235e7145Spectrum
GC-MSL-Proline, non-derivatized, GC-MS Spectrumsplash10-0006-1900000000-84e6fb318323fd0261b1Spectrum
GC-MSL-Proline, non-derivatized, GC-MS Spectrumsplash10-00xs-8910000000-74b0c34ca5fd7c85f1d9Spectrum
GC-MSL-Proline, non-derivatized, GC-MS Spectrumsplash10-00di-9100000000-c1c67bc521741ee891cbSpectrum
Predicted GC-MSL-Proline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00fu-9000000000-d203e3dfb0701403a75bSpectrum
Predicted GC-MSL-Proline, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9000000000-56471980a375d26046caSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-2c23774af5f6a0c217d5Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03di-0900000000-d89c1e626ef24a79c89fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-03di-1900000000-fc27094f2eb75e65b438Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-0900000000-e1d0a4b20419dc7bae92Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-2c23774af5f6a0c217d5Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-d89c1e626ef24a79c89fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-1900000000-fc27094f2eb75e65b438Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-e1d0a4b20419dc7bae92Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00xr-9600000000-ba51a901e786b1a4663eSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-f72e2f3812225708fc56Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-59887da6580f63bcc1c5Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-00fu-9000000000-c69dcaf7cb2d1e9d285eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0930000000-984f9a23ebfe28f95017Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-9000000000-f75575cac28a54aa923dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-9000000000-221cfb8c82f3df76eb51Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-e5741fd9870218d57cafSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-6bc9b4e775be37fa18d9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-9000000000-a8eb419b26655a6a1dabSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-9000000000-873ee03b61d1ffcae70fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-61d583960651669fb9e6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-1900000000-3221c23504b8847abf8dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-9100000000-8169367f5127c57fae12Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-9000000000-f704eb8402fcacfccd18Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00di-9000000000-ccd74eea36efab2cbab8Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00di-9000000000-9f214692cd39a6581813Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID128566
ChEMBL IDCHEMBL54922
KEGG Compound IDC00148
Pubchem Compound ID145742
Pubchem Substance IDNot Available
ChEBI ID17203
Phenol-Explorer IDNot Available
DrugBank IDDB02853
HMDB IDHMDB00162
CRC / DFC (Dictionary of Food Compounds) IDBDS30-Y:BDS36-E
EAFUS ID3165
Dr. Duke IDPROLINE
BIGG ID34042
KNApSAcK IDC00001388
HET IDPRO
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1035851
SuperScent IDNot Available
Wikipedia IDProline
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Prolyl 4-hydroxylase subunit alpha-2P4HA2O15460
Prolyl 4-hydroxylase subunit alpha-1P4HA1P13674
Bifunctional glutamate/proline--tRNA ligaseEPRSP07814
Proline synthase co-transcribed bacterial homolog proteinPROSCO94903
Pyrroline-5-carboxylate reductaseP5CR2Q4W8W1
Prolyl 4-hydroxylase subunit alpha-3P4HA3Q7Z4N8
Egl nine homolog 1EGLN1Q9GZT9
Egl nine homolog 2EGLN2Q96KS0
Egl nine homolog 3EGLN3Q9H6Z9
Transmembrane prolyl 4-hydroxylaseP4HTMQ9NXG6
Trans-L-3-hydroxyproline dehydrataseL3HYPDHQ96EM0
Peptidyl-prolyl cis-trans isomerase F, mitochondrialPPIFP30405
Peptidyl-prolyl cis-trans isomerase APPIAP62937
Peptidyl-prolyl cis-trans isomerase BPPIBP23284
Peptidyl-prolyl cis-trans isomerase GPPIGQ13427
Probable proline--tRNA ligase, mitochondrialPARS2Q7L3T8
Peptidyl-prolyl cis-trans isomerase HPPIHO43447
Pathways
NameSMPDB LinkKEGG Link
Arginine and Proline MetabolismSMP00020 map00330
Transcription/TranslationSMP00019 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot 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).