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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-08-12 20:18:30 UTC
Update Date2020-02-26 21:24:35 UTC
HMDB IDHMDB0003411
Secondary Accession Numbers
  • HMDB03411
Metabolite Identification
Common NameD-Proline
DescriptionD-Proline, also known as D-prolin or DPR, 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. D-Proline is a drug. D-Proline is a very strong basic compound (based on its pKa). D-Proline exists in all living species, ranging from bacteria to humans. D-proline can be converted into 1-pyrroline-2-carboxylic acid; which is mediated by the enzyme D-amino-acid oxidase. In humans, D-proline is involved in the metabolic disorder called prolinemia type II. D-Proline is a potentially toxic compound. The D-enantiomer of proline.
Structure
Data?1582752275
Synonyms
ValueSource
(2R)-Pyrrolidine-2-carboxylic acidChEBI
(R)-2-CarboxypyrrolidineChEBI
(R)-Pyrrolidine-2-carboxylic acidChEBI
D-ProlinChEBI
DPRChEBI
(2R)-Pyrrolidine-2-carboxylateGenerator
(R)-Pyrrolidine-2-carboxylateGenerator
R)-2-CarboxypyrrolidineHMDB
R-ProlineHMDB
ProlineHMDB
Chemical FormulaC5H9NO2
Average Molecular Weight115.1305
Monoisotopic Molecular Weight115.063328537
IUPAC Name(2R)-pyrrolidine-2-carboxylic acid
Traditional NameD-proline
CAS Registry Number344-25-2
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-/m1/s1
InChI KeyONIBWKKTOPOVIA-SCSAIBSYSA-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
  • D-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
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point221 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Polarizability11.39 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fu-9000000000-d203e3dfb0701403a75bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9000000000-56471980a375d26046caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-6900000000-eba8ceb2a71d2726acd0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9200000000-c52871a4097a833a301aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9000000000-50a811fa0506a025048aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3900000000-ba371efbf747c7eed1a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03k9-9600000000-f8a0815fbf4d1b2713afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-133753f87329f1da7d39Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Lysosome
  • Peroxisome
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
Associated Disorders and Diseases
Disease References
Autosomal dominant polycystic kidney disease
  1. Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]
Associated OMIM IDs
  • 601313 (Autosomal dominant polycystic kidney disease)
DrugBank IDDB02853
Phenol Explorer Compound IDNot Available
FooDB IDFDB023166
KNApSAcK IDNot Available
Chemspider ID8640
KEGG Compound IDC00763
BioCyc IDD-PROLINE
BiGG ID35916
Wikipedia LinkD-proline
METLIN IDNot Available
PubChem Compound8988
PDB IDNot Available
ChEBI ID16313
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Goan SR, Junghahn I, Wissler M, Becker M, Aumann J, Just U, Martiny-Baron G, Fichtner I, Henschler R: Donor stromal cells from human blood engraft in NOD/SCID mice. Blood. 2000 Dec 1;96(12):3971-8. [PubMed:11090086 ]
  2. Rhaleb NE, Peng H, Harding P, Tayeh M, LaPointe MC, Carretero OA: Effect of N-acetyl-seryl-aspartyl-lysyl-proline on DNA and collagen synthesis in rat cardiac fibroblasts. Hypertension. 2001 Mar;37(3):827-32. [PubMed:11244003 ]
  3. Clayton PT, Eaton S, Aynsley-Green A, Edginton M, Hussain K, Krywawych S, Datta V, Malingre HE, Berger R, van den Berg IE: Hyperinsulinism in short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency reveals the importance of beta-oxidation in insulin secretion. J Clin Invest. 2001 Aug;108(3):457-65. [PubMed:11489939 ]
  4. 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 ]
  5. Watkins NA, Smethurst PA, Allen D, Smith GA, Ouwehand WH: Platelet alphaIIbbeta3 recombinant autoantibodies from the B-cell repertoire of a post-transfusion purpura patient. Br J Haematol. 2002 Mar;116(3):677-85. [PubMed:11849233 ]
  6. Lalko CC, Deppe E, Ulatowski D, Lutgen A, Hart AP, Patton EA, Lunn DP, Suresh M, Darien BJ: Equine platelet CD62P (P-selectin) expression: a phenotypic and morphologic study. Vet Immunol Immunopathol. 2003 Jan 30;91(2):119-34. [PubMed:12543548 ]
  7. Ozyurt H, Totan A, Sahin S, Kilinc C, Sogut S, Akyol O: Maternal serum and amniotic fluid hydroxyproline levels in neural tube defects. Fetal Diagn Ther. 2003 Sep-Oct;18(5):321-3. [PubMed:12913341 ]
  8. Schwan WR, Wetzel KJ, Gomez TS, Stiles MA, Beitlich BD, Grunwald S: Low-proline environments impair growth, proline transport and in vivo survival of Staphylococcus aureus strain-specific putP mutants. Microbiology. 2004 Apr;150(Pt 4):1055-61. [PubMed:15073314 ]
  9. Bonafe M, Salvioli S, Barbi C, Trapassi C, Tocco F, Storci G, Invidia L, Vannini I, Rossi M, Marzi E, Mishto M, Capri M, Olivieri F, Antonicelli R, Memo M, Uberti D, Nacmias B, Sorbi S, Monti D, Franceschi C: The different apoptotic potential of the p53 codon 72 alleles increases with age and modulates in vivo ischaemia-induced cell death. Cell Death Differ. 2004 Sep;11(9):962-73. [PubMed:15131588 ]
  10. Sarkar A, Caamano S, Fernandez JM: The elasticity of individual titin PEVK exons measured by single molecule atomic force microscopy. J Biol Chem. 2005 Feb 25;280(8):6261-4. Epub 2005 Jan 4. [PubMed:15632200 ]
  11. Babraj JA, Cuthbertson DJ, Smith K, Langberg H, Miller B, Krogsgaard MR, Kjaer M, Rennie MJ: Collagen synthesis in human musculoskeletal tissues and skin. Am J Physiol Endocrinol Metab. 2005 Nov;289(5):E864-9. Epub 2005 Jun 21. [PubMed:15972270 ]
  12. Vitari AC, Deak M, Morrice NA, Alessi DR: The WNK1 and WNK4 protein kinases that are mutated in Gordon's hypertension syndrome phosphorylate and activate SPAK and OSR1 protein kinases. Biochem J. 2005 Oct 1;391(Pt 1):17-24. [PubMed:16083423 ]
  13. Metzner L, Kottra G, Neubert K, Daniel H, Brandsch M: Serotonin, L-tryptophan, and tryptamine are effective inhibitors of the amino acid transport system PAT1. FASEB J. 2005 Sep;19(11):1468-73. [PubMed:16126914 ]
  14. Nagata Y, Higashi M, Ishii Y, Sano H, Tanigawa M, Nagata K, Noguchi K, Urade M: The presence of high concentrations of free D-amino acids in human saliva. Life Sci. 2006 Mar 6;78(15):1677-81. Epub 2006 Feb 9. [PubMed:16480744 ]
  15. Broer S: The SLC6 orphans are forming a family of amino acid transporters. Neurochem Int. 2006 May-Jun;48(6-7):559-67. Epub 2006 Mar 15. [PubMed:16540203 ]
  16. Meyer W, Poehling HM, Neurand K: Intraepidermal distribution of free amino acids in porcine skin. J Dermatol Sci. 1991 Sep;2(5):383-92. [PubMed:1742249 ]
  17. Corfield AP, Clamp JR, Casey AD, Paraskeva C: Characterization of a sialic-acid-rich mucus glycoprotein secreted by a premalignant human colorectal adenoma cell line. Int J Cancer. 1990 Dec 15;46(6):1059-65. [PubMed:2249893 ]
  18. Wolf GC, Hilton CW, Prasad C, Miller JM Jr, Thorneycroft IH: The neuropeptide histidyl proline diketopiperazine throughout human pregnancy: an inverse correlation with amniotic fluid prolactin. Am J Obstet Gynecol. 1990 Mar;162(3):740-5. [PubMed:2316580 ]
  19. Prasad C: Cyclo(His-Pro): its distribution, origin and function in the human. Neurosci Biobehav Rev. 1988 Spring;12(1):19-22. [PubMed:3287238 ]
  20. 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 ]
  21. 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 ]
  22. Linkosalo E, Markkanen H, Syrjanen S: Effects of a lacto-ovo-vegetarian diet on the free amino acid composition of wax-stimulated whole human saliva. J Nutr. 1985 May;115(5):588-92. [PubMed:3998860 ]
  23. Kubilus J, MacDonald MJ, Baden HP: Epidermal proteins of cultured human and bovine keratinocytes. Biochim Biophys Acta. 1979 Jun 19;578(2):484-92. [PubMed:486533 ]
  24. Manicourt D, Brauman H, Orloff S: Synovial fluid beta 2 microglobulin and hydroxyproline fractions in rheumatoid arthritis and nonautoimmune arthropathies. Ann Rheum Dis. 1980 Jun;39(3):207-16. [PubMed:6158297 ]
  25. Miller DR, Mankin HJ, Shoji H, D'Ambrosia RD: Identification of fibronectin in preparations of osteoarthritic human cartilage. Connect Tissue Res. 1984;12(3-4):267-75. [PubMed:6478826 ]
  26. Bogovski PA, Rooma MA, Kann JM: Studies on the excretion of endogenously formed N-nitrosoproline. I. Percutaneous excretion of N-nitrosoproline in humans. IARC Sci Publ. 1984;(57):199-204. [PubMed:6533008 ]
  27. Maurer G, Schreier E, Delaborde S, Nufer R, Shukla AP: Fate and disposition of bromocriptine in animals and man. II: Absorption, elimination and metabolism. Eur J Drug Metab Pharmacokinet. 1983;8(1):51-62. [PubMed:6861794 ]
  28. Levison PR, Tomalin G: The kinetics of hydrolysis of some extended N-aminoacyl-L-arginine methyl esters by human plasma kallikrein. Evidence for subsites S2 and S3. Biochem J. 1982 Apr 1;203(1):149-53. [PubMed:6921035 ]
  29. Canalis E, Raisz LG: Effect of fibroblast growth factor on cultured fetal rat calvaria. Metabolism. 1980 Feb;29(2):108-14. [PubMed:6986532 ]
  30. Whiteley J, Francis MJ, Walton RJ, Smith R: Serum proline imino-peptidase activity in normal adult subjects and in patients with Paget's disease of bone. Clin Chim Acta. 1976 Sep 6;71(2):157-63. [PubMed:822968 ]
  31. Nakamura M, Zhang ZQ, Shan L, Hisa T, Sasaki M, Tsukino R, Yokoi T, Kaname A, Kakudo K: Allelic variants of human calcitonin receptor in the Japanese population. Hum Genet. 1997 Jan;99(1):38-41. [PubMed:9003491 ]
  32. Nagata Y, Masui R, Akino T: The presence of free D-serine, D-alanine and D-proline in human plasma. Experientia. 1992 Oct 15;48(10):986-8. [PubMed:1426150 ]

Enzymes

General function:
Involved in D-amino-acid oxidase activity
Specific function:
Regulates the level of the neuromodulator D-serine in the brain. Has high activity towards D-DOPA and contributes to dopamine synthesis. Could act as a detoxifying agent which removes D-amino acids accumulated during aging. Acts on a variety of D-amino acids with a preference for those having small hydrophobic side chains followed by those bearing polar, aromatic, and basic groups. Does not act on acidic amino acids.
Gene Name:
DAO
Uniprot ID:
P14920
Molecular weight:
39473.75
Reactions
D-Proline + Oxygen → 1-Pyrroline-2-carboxylic acid + Hydrogen peroxidedetails
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). May be required to degrade trans-3-hydroxy-L-proline from the diet and originating from the degradation of proteins such as collagen-IV that contain it.
Gene Name:
L3HYPDH
Uniprot ID:
Q96EM0
Molecular weight:
38137.395