Record Information
Version1.0
Creation date2010-04-08 22:04:37 UTC
Update date2018-05-29 00:29:33 UTC
Primary IDFDB000570
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Proline
DescriptionFlavouring ingredient; dietary supplement Proline (abbreviated as Pro or P) is an alpha-amino acid, one of the twenty DNA-encoded amino acids. Its codons are CCU, CCC, CCA, and CCG. It is not an essential amino acid, which means that the human body can synthesize it. It is unique among the 20 protein-forming amino acids in that the alpha-amino group is secondary. The more common L form has S stereochemistry. L-Proline is found in many foods, some of which are unclassified food or beverage, butterfat, yardlong bean, and mixed nuts.
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0006-0910000000-a9127c0e370afb80259bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-000f-0910000000-3195f21e625520d51316View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0006-0900000000-119af746c347969e8ae7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-006x-8900000000-b31beabb1ed6235e7145View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00di-9100000000-c1c67bc521741ee891cbView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0006-1900000000-84e6fb318323fd0261b1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00xs-8910000000-74b0c34ca5fd7c85f1d9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00fu-9000000000-716c3d01b301162863b6View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-0900000000-0d7354201ed866c87b13View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0910000000-a9127c0e370afb80259bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000f-0910000000-3195f21e625520d51316View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0900000000-119af746c347969e8ae7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-QQ (Non-derivatized)splash10-001i-1920000000-09006ee4e7a137d8a45aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006x-8900000000-b31beabb1ed6235e7145View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-1900000000-84e6fb318323fd0261b1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00xs-8910000000-74b0c34ca5fd7c85f1d9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-9100000000-c1c67bc521741ee891cbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fu-9000000000-d203e3dfb0701403a75bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9000000000-56471980a375d26046caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-2c23774af5f6a0c217d5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03di-0900000000-d89c1e626ef24a79c89fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-03di-1900000000-fc27094f2eb75e65b438View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-0900000000-e1d0a4b20419dc7bae92View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-2c23774af5f6a0c217d5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-d89c1e626ef24a79c89fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-1900000000-fc27094f2eb75e65b438View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-e1d0a4b20419dc7bae92View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00xr-9600000000-ba51a901e786b1a4663eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-f72e2f3812225708fc56View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-59887da6580f63bcc1c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-00fu-9000000000-c69dcaf7cb2d1e9d285eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0930000000-984f9a23ebfe28f95017View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-9000000000-f75575cac28a54aa923dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-9000000000-221cfb8c82f3df76eb51View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-e5741fd9870218d57cafView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-6bc9b4e775be37fa18d9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-9000000000-a8eb419b26655a6a1dabView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-9000000000-873ee03b61d1ffcae70fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-61d583960651669fb9e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-1900000000-3221c23504b8847abf8dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-9100000000-8169367f5127c57fae12View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-9000000000-f704eb8402fcacfccd18View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00di-9000000000-ccd74eea36efab2cbab8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00di-9000000000-9f214692cd39a6581813View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
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).