| Record Information |
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:08:00 -0700 |
| HMDB ID |
HMDB00162 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
| Common Name |
L-Proline |
| 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. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- (-)-(S)-Proline
- (-)-2-Pyrrolidinecarboxylate
- (-)-2-Pyrrolidinecarboxylic acid
- (-)-Proline
- (S)-(-)-Proline
- (S)-(-)-Pyrrolidine-2-carboxylate
- (S)-(-)-Pyrrolidine-2-carboxylic acid
- (S)-2-Carboxypyrrolidine
- (S)-2-Pyrralidinecarboxylate
- (S)-2-Pyrralidinecarboxylic acid
- (S)-2-Pyrrolidinecarboxylate
- (S)-2-Pyrrolidinecarboxylic acid
- (S)-Proline
- 2-Pyrrolidinecarboxylate
- 2-Pyrrolidinecarboxylic acid
- Proline
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| Chemical Formula |
C5H9NO2 |
| Average Molecular Weight |
115.1305 |
| Monoisotopic Molecular Weight |
115.063328537 |
| IUPAC Name |
(2S)-pyrrolidine-2-carboxylic acid |
| Traditional IUPAC Name |
L-proline |
| CAS Registry Number |
147-85-3 |
| 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 |
| Kingdom |
Organic Compounds |
| Super Class |
Amino Acids, Peptides, and Analogues |
| Class |
Amino Acids and Derivatives |
| Sub Class |
Alpha Amino Acids and Derivatives |
| Other Descriptors |
- Aliphatic Heteromonocyclic Compounds
- Common amino acids(KEGG)
- amino acid zwitterion(ChEBI)
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| Substituents |
- Carboxylic Acid
- Pyrrolidine
- Pyrrolidine Carboxylic Acid
- Secondary Aliphatic Amine (Dialkylamine)
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| Direct Parent |
Alpha Amino Acids and Derivatives |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Component of Arginine and proline metabolism
|
| Application |
Not Available |
| Cellular locations |
- Cytoplasm
- Extracellular
- Mitochondria
- Lysosome
- Endoplasmic reticulum
|
| Physical Properties |
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
221 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
162.0 mg/mL |
Not Available |
| LogP |
-2.54 |
HANSCH,C ET AL. (1995) |
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| Predicted Properties |
|
| Spectra |
|
| Gas-MS Spectrum |
| 1H NMR Spectrum |
| 13C NMR Spectrum |
| MS/MS Spectrum Quattro_QQQ 10 |
| MS/MS Spectrum Quattro_QQQ 25 |
| MS/MS Spectrum Quattro_QQQ 40 |
| MS/MS Spectrum EI-B (HITACHI M-80) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20 |
| MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30 |
| [1H,1H] 2D NMR Spectrum |
| [1H,13C] 2D NMR Spectrum |
|
| Biological Properties |
| Cellular Locations |
- Cytoplasm
- Extracellular
- Mitochondria
- Lysosome
- Endoplasmic reticulum
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| Biofluid Locations |
- Blood
- Cerebrospinal Fluid (CSF)
- Saliva
- Urine
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| Tissue Location |
|
| Pathways |
| Name |
SMPDB Link |
KEGG Link |
| Transcription/Translation |
SMP00019
|
Not Available
|
| Arginine and Proline Metabolism |
SMP00020
|
map00330
|
|
| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
198.3 +/- 64.8 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
168.0 (108.0-228.0) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
177.5 +/- 38.6 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
198.0 +/- 63.0 uM |
Children (1-13 year old) |
Male |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
239.0 +/- 70.0 uM |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
168.0 +/- 49.0 uM |
Adult (>18 years old) |
Female |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
230.0 +/- 75.0 uM |
Newborn (0-30 days old) |
Not Specified |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
4.0 (0 - 8.0) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
1.9 +/- 1.0 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Saliva |
Detected and Quantified |
|
>10 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.86 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
<6.08-34.76 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
3.06 /- 1.87 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
2.171 (0.0658-4.276) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
1.1 (0.1-2.5) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
by LC-MS/MS (Biocrates kit)
|
| Urine |
Detected and Quantified |
|
1.0 (0.5-2.0) umol/mmol creatinine |
Newborn (0-30 days old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
4.14 +/- 2.85 umol/mmol creatinine |
Infant (0-1 year old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.5 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|
| Blood |
Detected and Quantified |
|
159.9 +/- 86.3 uM |
Adult (>18 years old) |
Not Specified |
Heart Transplant |
Not Available |
| Blood |
Detected and Quantified |
|
201.0 +/- 149.5 uM |
Adult (>18 years old) |
Both |
Hemodialysis |
Conventional: for 4 h, 3 times/week
|
| Blood |
Detected and Quantified |
|
227.2 +/- 108.4 uM |
Adult (>18 years old) |
Both |
Hemodialysis |
Nocturnal: for 8 h during the night, 6 times/week
|
| Blood |
Detected and Quantified |
|
263.00 (110.00-417.00) uM |
Adult (>18 years old) |
Both |
Glutathione synthetase deficiency |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.68 +/- 0.35 uM |
Adult (>18 years old) |
Both |
Alzheimer's disease |
Not Available |
| Urine |
Detected and Quantified |
|
0.0068 - 0.0549 umol/mmol creatinine |
Adult (>18 years old) |
Both |
ADPKD |
Not Available |
| Urine |
Detected and Quantified |
|
29.6 (19.7-39.47) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Iminoglycinuria |
Not Available |
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| Associated Disorders and Diseases |
| Disease References |
| Hemodialysis |
- Raj DS, Ouwendyk M, Francoeur R, Pierratos A: Plasma amino acid profile on nocturnal hemodialysis. Blood Purif. 2000;18(2):97-102.
Pubmed: 10838467
|
| Alzheimer's disease |
- Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10.
Pubmed: 17031479
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| Glutathione synthetase deficiency |
- http://www.metagene.de/program/d.prg?mp=GLUTATHIONE%20SYNTHETASE%20DEFICIENCY
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| Iminoglycinuria |
- http://www.metagene.de/program/d.prg?mp=IMINOGLYCINURIA
|
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| Associated OMIM IDs |
- 104300
(Alzheimer's disease)
- 266130
(Glutathione synthetase deficiency)
- 242600
(Iminoglycinuria)
|
| External Links |
| DrugBank ID |
DB00172  |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB000570 |
| KNApSAcK ID |
C00001388  |
| Chemspider ID |
128566  |
| KEGG Compound ID |
C00148  |
| BioCyc ID |
PRO  |
| BiGG ID |
34042  |
| Wikipedia Link |
L-Proline  |
| NuGOwiki Link |
HMDB00162  |
| Metagene Link |
HMDB00162  |
| METLIN ID |
29  |
| PubChem Compound |
145742  |
| PDB ID |
PRO  |
| ChEBI ID |
17203  |
| References |
| Synthesis Reference |
Itoh, 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) |
Download (PDF)
|
| General References |
- Deng C, Shang C, Hu Y, Zhang X: Rapid diagnosis of phenylketonuria and other aminoacidemias by quantitative analysis of amino acids in neonatal blood spots by gas chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Jul 25;775(1):115-20.
Pubmed: 12101068
- Azizi M, Junot C, Ezan E, Menard J: Angiotensin I-converting enzyme and metabolism of the haematological peptide N-acetyl-seryl-aspartyl-lysyl-proline. Clin Exp Pharmacol Physiol. 2001 Dec;28(12):1066-9.
Pubmed: 11903317
- Roesel RA, Blankenship PR, Mobley EB, Coryell ME: Increased excretion of histidyl-L-proline diketopiperazine by infants receiving Pregestimil and Nutramigen formulas. Clin Chem. 1986 May;32(5):865-7.
Pubmed: 3698278
- Chambers ST, Kunin CM: Osmoprotective activity for Escherichia coli in mammalian renal inner medulla and urine. Correlation of glycine and proline betaines and sorbitol with response to osmotic loads. J Clin Invest. 1987 Nov;80(5):1255-60.
Pubmed: 3316273
- Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6.
Pubmed: 12297216
- Azizi M, Ezan E, Reny JL, Wdzieczak-Bakala J, Gerineau V, Menard J: Renal and metabolic clearance of N-acetyl-seryl-aspartyl-lysyl-proline (AcSDKP) during angiotensin-converting enzyme inhibition in humans. Hypertension. 1999 Mar;33(3):879-86.
Pubmed: 10082503
- Hart W, van den Hamer CJ, van der Sluys Veer J: The use of hydroxy-DL-proline-2-(14)C in the investigation of hydroxyproline metabolism in normal subjects and in patients with renal insufficiency. Clin Nephrol. 1976 Sep;6(3):379-87.
Pubmed: 991465
- Kanwar YS, Krakower CA, Manaligod JR, Justice P, Wong PW: Biochemical, morphological and hybrid studies in hyperprolinemic mice. Biomedicine. 1975 May;22(3):209-16.
Pubmed: 240452
- Simila S: Hydroxyproline metabolism in type II hyperprolinaemia. Ann Clin Biochem. 1979 Jul;16(4):177-81.
Pubmed: 533224
- Lu SH, Ohshima H, Fu HM, Tian Y, Li FM, Blettner M, Wahrendorf J, Bartsch H: Urinary excretion of N-nitrosamino acids and nitrate by inhabitants of high- and low-risk areas for esophageal cancer in Northern China: endogenous formation of nitrosoproline and its inhibition by vitamin C. Cancer Res. 1986 Mar;46(3):1485-91.
Pubmed: 3943105
- Hausmann D: [Post-traumatic imbalances of plasma amino acids--interference factors or defense mechanisms? A study of protein metabolism in severe craniocerebral trauma] Anasth Intensivther Notfallmed. 1988 Feb;23(1):14-21.
Pubmed: 3364629
- Scriver CR, McInnes RR, Mohyuddin F: Role of epithelial architecture and intracellular metabolism in proline uptake and transtubular reclamation in PRO/re mouse kidney. Proc Natl Acad Sci U S A. 1975 Apr;72(4):1431-5.
Pubmed: 1055415
- Boden G, Rezvani I, Owen OE: Effects of glucagon on plasma amino acids. J Clin Invest. 1984 Mar;73(3):785-93.
Pubmed: 6142902
- Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7.
Pubmed: 12097436
- Feldman JM, Plonk JW, Admiraal J, Sidbury, JB: Plasma amino acids in patients with the carcinoid syndrome. Cancer. 1976 Nov;38(5):2127-31.
Pubmed: 136295
- Humbertclaude V, Rivier F, Roubertie A, Echenne B, Bellet H, Vallat C, Morin D: Is hyperprolinemia type I actually a benign trait? Report of a case with severe neurologic involvement and vigabatrin intolerance. J Child Neurol. 2001 Aug;16(8):622-3.
Pubmed: 11510941
- Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4.
Pubmed: 19212411
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| Enzymes |
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| Name: |
Cytosol aminopeptidase
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| Reactions: |
- Release of N-terminal proline from a peptide ALL_REAC (other) R00135 COFACTOR Manganese [CPD:C00034]
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| Gene Name: |
LAP3 |
| Uniprot ID: |
P28838  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Prolyl 3-hydroxylase 1
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| Reactions: |
- procollagen L-proline + 2-oxoglutarate + O2 = procollagen trans-3-hydroxy-L-proline + succinate + CO2 [RN:R03218]
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| Gene Name: |
LEPRE1 |
| Uniprot ID: |
Q32P28  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Prolyl 3-hydroxylase 2
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| Reactions: |
- procollagen L-proline + 2-oxoglutarate + O2 = procollagen trans-3-hydroxy-L-proline + succinate + CO2 [RN:R03218]
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| Gene Name: |
LEPREL1 |
| Uniprot ID: |
Q8IVL5  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Prolyl 3-hydroxylase 3
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| Reactions: |
- procollagen L-proline + 2-oxoglutarate + O2 = procollagen trans-3-hydroxy-L-proline + succinate + CO2 [RN:R03218]
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| Gene Name: |
LEPREL2 |
| Uniprot ID: |
Q8IVL6  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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