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Record Information
Version1.0
Creation Date2016-09-30 22:20:22 UTC
Update Date2020-06-04 22:35:59 UTC
BMDB IDBMDB0000162
Secondary Accession Numbers
  • BMDB00162
Metabolite Identification
Common NameL-Proline
DescriptionL-Proline, also known as L-prolin, 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. L-Proline exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Proline exists in all living species, ranging from bacteria to humans. L-Proline is a potentially toxic compound. L-Proline has been found to be associated with several diseases known as rheumatoid arthritis, perillyl alcohol administration for cancer treatment, colorectal cancer, and pregnancy; also l-proline has been linked to the inborn metabolic disorders including iminoglycinuria.
Structure
Thumb
Synonyms
ValueSource
(-)-(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
Chemical FormulaC5H9NO2
Average Molecular Weight115.1305
Monoisotopic Molecular Weight115.063328537
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number147-85-3
SMILESNot Available
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 KeyONIBWKKTOPOVIA-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.
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
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Endoplasmic reticulum
  • Lysosome
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point221 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility162.0 mg/mLNot Available
LogP-2.54HANSCH,C ET AL. (1995)
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
  • Endoplasmic reticulum
  • Lysosome
  • Mitochondria
Biospecimen Locations
  • All Tissues
  • Blood
  • Colostrum
  • Liver
  • Longissimus Thoracis Muscle
  • Mammary Gland
  • Milk
  • Muscle
  • Placenta
  • Prostate Tissue
  • Ruminal Fluid
  • Semen
  • Semimembranosus Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BloodDetected and Quantified45.7 uMNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
    • Jiyuan Li, Everes...
details
BloodDetected and Quantified84-110 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified45-68 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified103 +/- 15 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
BloodDetected and Quantified72-78 uMNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
ColostrumDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected and Quantified352 +/- 67 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Longissimus Thoracis MuscleDetected and Quantified174 +/- 59 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified25 +/- 1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified30 +/- 1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified27 +/- 3 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified82.350 +/- 29.96 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified27 +/- 5 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified11 - 47 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified29531.705 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified29531.705 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified29531.705 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified29531.705 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified28663.126 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified28663.126 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified28663.126 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified27 +/- 2 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified30 +/- 2 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified29 +/- 2 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified30 +/- 1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified19.2 +/- 5.6 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified29.0 +/- 9.5 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected and Quantified55.55 +/- 12.68 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified60.57 +/- 15.15 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MuscleDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified5950 +/- 1890 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • S. F. Graham, T. ...
details
MuscleDetected and Quantified6670 +/- 2850 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • S. F. Graham, T. ...
details
MuscleDetected and Quantified5120 +/- 1460 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • S. F. Graham, T. ...
details
MuscleDetected and Quantified5590 +/- 1450 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • S. F. Graham, T. ...
details
MuscleDetected and Quantified240-365 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified158 +/- 33 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified220 +/- 31 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified173 +/- 29 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified159.6 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified158 +/- 24 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified220.4 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified158 +/- 24 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified173.2 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified154.6 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified240-1275 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified50-174 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified117 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified165 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified141 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified130 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified834 +/- 377 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Ruminal FluidDetected and Quantified154.56 +/- 24.18 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
details
SemenDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
SemenDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Semimembranosus MuscleDetected and Quantified203 +/- 60 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
TestisDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
TestisDetected and Quantified191 +/- 40 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified48.9 uMNot SpecifiedNot Specified
Bovine spongiform encephalopathy negative
details
BloodDetected and Quantified55.3 uMNot SpecifiedNot Specified
Bovine spongiform encephalopathy positive
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Sub/clinical ketosis
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Heat stress
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
All Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
High dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Low dose Mycobacterium avium subsp. paratuberculosis-infected
details
ColostrumDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Commercial Product/bacterial growth on ground beef
details
MuscleDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Commercial Product/bacterial growth on ground beef
details
Ruminal FluidDetected and Quantified173.23 +/- 28.4 uMNot SpecifiedNot SpecifiedRumen acidosis
    • Fozia Saleem, Sou...
details
HMDB IDHMDB0000162
DrugBank IDDB00172
Phenol Explorer Compound IDNot Available
FooDB IDFDB000570
KNApSAcK IDC00001388
Chemspider ID128566
KEGG Compound IDC00148
BioCyc IDPRO
BiGG ID34042
Wikipedia LinkL-proline
METLIN ID29
PubChem Compound145742
PDB IDNot Available
ChEBI ID17203
References
Synthesis ReferenceItoh, Tamio. Synthesis of L-proline from L-glutamine. Bulletin of the Chemical Society of Japan (1963), 36(1), 25-9
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
  2. Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6. [PubMed:25108860 ]
  3. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  4. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
  5. Klein MS, Almstetter MF, Nurnberger N, Sigl G, Gronwald W, Wiedemann S, Dettmer K, Oefner PJ: Correlations between milk and plasma levels of amino and carboxylic acids in dairy cows. J Proteome Res. 2013 Nov 1;12(11):5223-32. doi: 10.1021/pr4006537. Epub 2013 Aug 23. [PubMed:23931703 ]
  6. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  7. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
  8. Fooddata+, The Technical University of Denmark (DTU) [Link]

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Presumably involved in the processing and regular turnover of intracellular proteins. Catalyzes the removal of unsubstituted N-terminal amino acids from various peptides.
Gene Name:
LAP3
Uniprot ID:
P00727
Molecular weight:
56289.0
General function:
Amino acid transport and metabolism
Specific function:
Contributes to the degradation of bradykinin. Catalyzes the removal of a penultimate prolyl residue from the N-termini of peptides, such as Arg-Pro-Pro (By similarity).
Gene Name:
XPNPEP1
Uniprot ID:
Q1JPJ2
Molecular weight:
69790.0
General function:
Involved in iron ion binding
Specific function:
Catalyzes the post-translational formation of 4-hydroxyproline in -Xaa-Pro-Gly- sequences in collagens and other proteins.
Gene Name:
P4HA1
Uniprot ID:
Q1RMU3
Molecular weight:
61010.0
General function:
Involved in iron ion binding
Specific function:
Catalyzes the post-translational formation of 4-hydroxyproline in -Xaa-Pro-Gly- sequences in collagens and other proteins.
Gene Name:
P4HA3
Uniprot ID:
Q75UG4
Molecular weight:
61023.0
Reactions
L-Proline + Oxoglutaric acid + Oxygen → Hydroxyproline + Succinic acid + Carbon dioxidedetails
General function:
Amino acid transport and metabolism
Specific function:
Dehydrogenase that converts trans-4-L-hydroxyproline to delta-1-pyrroline-3-hydroxy-5-carboxylate (Hyp) using ubiquinone-10 as the terminal electron acceptor. Can also use proline as a substrate but with a very much lower efficiency. Does not react with other diastereomers of Hyp: trans-4-D-hydroxyproline and cis-4-L-hydroxyproline. Ubiquininone analogs such as menadione, duroquinone and ubiquinone-1 react more efficiently than oxygen as the terminal electron acceptor during catalysis.
Gene Name:
PRODH2
Uniprot ID:
A6QQ74
Molecular weight:
51262.0
General function:
Involved in proline racemase activity
Specific function:
Catalyzes the dehydration of trans-3-hydroxy-L-proline to Delta(1)-pyrroline-2-carboxylate (Pyr2C).
Gene Name:
L3HYPDH
Uniprot ID:
Q3SX04
Molecular weight:
37957.0
General function:
Amino acid transport and metabolism
Specific function:
Enzyme that catalyzes the last step in proline biosynthesis. Proline is synthesized from either glutamate or ornithine; both are converted to pyrroline-5-carboxylate (P5C), and then to proline via pyrroline-5-carboxylate reductases (PYCRs). PYCRL is exclusively linked to the conversion of ornithine to proline.
Gene Name:
PYCR3
Uniprot ID:
Q58D08
Molecular weight:
32035.0
General function:
Amino acid transport and metabolism
Specific function:
Housekeeping enzyme that catalyzes the last step in proline biosynthesis. In some cell types, such as erythrocytes, its primary function may be the generation of NADP(+). Can utilize both NAD and NADP. Has higher affinity for NADP, but higher catalytic efficiency with NADH (By similarity). Involved in cellular response to oxidative stress (By similarity).
Gene Name:
PYCR2
Uniprot ID:
Q17QJ7
Molecular weight:
33630.0
Reactions
L-Proline + NAD → 1-Pyrroline-5-carboxylic acid + NADHdetails
General function:
Amino acid transport and metabolism
Specific function:
Housekeeping enzyme that catalyzes the last step in proline biosynthesis. Can utilize both NAD and NADP, but has higher affinity for NAD. Involved in the cellular response to oxidative stress.
Gene Name:
PYCR1
Uniprot ID:
Q58DT4
Molecular weight:
33454.0
General function:
Involved in cysteine-type endopeptidase activity
Specific function:
Exhibits carboxy-monopeptidase as well as carboxy-dipeptidase activity (By similarity). Capable of producing kinin potentiating peptides (By similarity).
Gene Name:
CTSZ
Uniprot ID:
P05689
Molecular weight:
33886.0
General function:
Not Available
Specific function:
Converts proline to delta-1-pyrroline-5-carboxylate.
Gene Name:
PRODH
Uniprot ID:
Q148G5
Molecular weight:
67080.0
Reactions
1-Pyrroline-5-carboxylic acid → L-Prolinedetails