L-Proline
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Basic Info
| Common Name | L-Proline(F05369) |
| 2D Structure | |
| 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. |
| FRCD ID | F05369 |
| CAS Number | 147-85-3 |
| PubChem CID | 145742 |
| Formula | C5H9NO2 |
| IUPAC Name | (2S)-pyrrolidine-2-carboxylic acid |
| InChI Key | ONIBWKKTOPOVIA-BYPYZUCNSA-N |
| InChI | InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1 |
| Canonical SMILES | C1CC(NC1)C(=O)O |
| Isomeric SMILES | C1C[C@H](NC1)C(=O)O |
| Wikipedia | L-Proline |
| Synonyms |
L-(-)-Proline
(2S)-pyrrolidine-2-carboxylic acid
L-proline
147-85-3
proline
(S)-Pyrrolidine-2-carboxylic acid
2-pyrrolidinecarboxylic acid
(-)-Proline
(-)-(S)-Proline
Prolinum
|
| Classifies |
Animal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Amino acids and derivatives - Alpha amino acids and derivatives |
| Direct Parent | Proline and derivatives |
| Alternative Parents | |
| Molecular Framework | Aliphatic heteromonocyclic compounds |
| 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 |
| Description | This compound belongs to the class of organic compounds known as proline and derivatives. These 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 115.132 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 1 |
| Complexity | 103 |
| Monoisotopic Mass | 115.063 |
| Exact Mass | 115.063 |
| XLogP | -2.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 8 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9245 |
| Human Intestinal Absorption | HIA+ | 0.9755 |
| Caco-2 Permeability | Caco2- | 0.6216 |
| P-glycoprotein Substrate | Non-substrate | 0.5641 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9938 |
| Non-inhibitor | 0.9819 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8047 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.5109 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8458 |
| CYP450 2D6 Substrate | Non-substrate | 0.7439 |
| CYP450 3A4 Substrate | Non-substrate | 0.7563 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9045 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9627 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9595 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9656 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9920 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9918 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9555 |
| Non-inhibitor | 0.9506 | |
| AMES Toxicity | Non AMES toxic | 0.8927 |
| Carcinogens | Non-carcinogens | 0.9574 |
| Fish Toxicity | Low FHMT | 0.8303 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.9404 |
| Honey Bee Toxicity | Low HBT | 0.6679 |
| Biodegradation | Ready biodegradable | 0.9077 |
| Acute Oral Toxicity | III | 0.4632 |
| Carcinogenicity (Three-class) | Non-required | 0.7020 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | 0.0855 | LogS |
| Caco-2 Permeability | 0.8778 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.0201 | LD50, mol/kg |
| Fish Toxicity | 3.3375 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.7973 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Sequenced ascorbate-proline-glutathione seed treatment elevates cadmium tolerance in cucumber transplants. | Ecotoxicol Environ Saf | 2018 Jun 15 | 29471279 |
| Varying the ratio of Lys:Met while maintaining the ratios of Thr:Phe, Lys:Thr,Lys:His, and Lys:Val alters mammary cellular metabolites, mammalian target ofrapamycin signaling, and gene transcription. | J Dairy Sci | 2018 Feb | 29248224 |
| Assessing effects of inhaled antibiotics in adults with non-cystic fibrosisbronchiectasis--experiences from recent clinical trials. | Expert Rev Respir Med | 2018 Aug 3:1-14 | 30025482 |
| Evaluation of Metronidazole With and Without Enterococcus Faecium SF68 in ShelterDogs With Diarrhea. | Top Companion Anim Med | 2017 Sep | 29291770 |
| Effects of macro- and micronutrients on exercise-induced hepcidin response inhighly trained endurance athletes. | Appl Physiol Nutr Metab | 2017 Oct | 28605609 |
| Enzymatic characterization of a novel Xaa-Pro aminopeptidase XpmA fromAspergillus oryzae expressed in Escherichia coli. | J Biosci Bioeng | 2017 Nov | 28698148 |
| [Simultaneous determination of 6 kinds of food additives in drink by HPLC-MS/MS]. | Wei Sheng Yan Jiu | 2017 Nov | 29903209 |
| Crystallographic structure of recombinant Lactococcus lactis prolidase to supportproposed structure-function relationships. | Biochim Biophys Acta | 2017 May | 28179139 |
| Intestinal transcriptome modulation by functional diets in rainbow trout: Ahigh-throughput sequencing appraisal to highlight GALT immunomodulation. | Fish Shellfish Immunol | 2017 May | 28300682 |
| Purification and Identification of Antioxidant Peptides from Protein Hydrolysate of Scalloped Hammerhead (Sphyrna lewini) Cartilage. | Mar Drugs | 2017 Mar 1 | 28257057 |
| Daily Intake of Magnesium and its Relation to Urinary Excretion in Korean HealthyAdults Consuming Self-Selected Diets. | Biol Trace Elem Res | 2017 Mar | 27543063 |
| Ileal endogenous losses in pigs feeding a protein-free diet or diets withdifferent contents of casein or crystalline amino acids. | Arch Anim Nutr | 2017 Jun | 28429994 |
| A combination of scGOS/lcFOS with Bifidobacterium breve M-16V protects sucklingrats from rotavirus gastroenteritis. | Eur J Nutr | 2017 Jun | 27112962 |
| The Effect of Postexercise Carbohydrate and Protein Ingestion on Bone Metabolism. | Med Sci Sports Exerc | 2017 Jun | 28121797 |
| Maternal age modulates the effects of early-pregnancy L-proline supplementationon the birth-weight of piglets. | Anim Reprod Sci | 2017 Jun | 28385397 |
| Genotypic-dependent effects of N fertilizer, glutathione, silicon, zinc, andselenium on proteomic profiles, amino acid contents, and quality of ricegenotypes with contrasting grain Cd accumulation. | Funct Integr Genomics | 2017 Jul | 27999965 |
| Molecularly Imprinted Polymer Chemosensor for Selective Determination of an N-Nitroso-l-proline Food Toxin. | Chemistry | 2017 Feb 3 | 28060413 |
| Effect of dietary fiber levels on performance, gizzard development, intestinalmorphology, and nutrient utilization in meat ducks from 1 to 21 days of age. | Poult Sci | 2017 Dec 1 | 29053831 |
| Blood Hematological and Biochemical Constituents, Antioxidant Enzymes, Immunityand Lymphoid Organs of Broiler Chicks Supplemented with Propolis, Bee Pollen and Mannan Oligosaccharides Continuously or Intermittently. | Poult Sci | 2017 Dec 1 | 29053876 |
| Response of broiler chickens fed wheat-based diets to xylanase supplementation. | Poult Sci | 2017 Aug 1 | 28431146 |
Targets
- General Function:
- Procollagen-proline 4-dioxygenase activity
- Specific Function:
- Catalyzes the post-translational formation of 4-hydroxyproline in -Xaa-Pro-Gly- sequences in collagens and other proteins.
- Gene Name:
- P4HA2
- Uniprot ID:
- O15460
- Molecular Weight:
- 60901.42 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Neurotransmitter:sodium symporter activity
- Specific Function:
- Mediates the uptake of a broad range of neutral and cationic amino acids (with the exception of proline) in a Na(+)/Cl(-)-dependent manner.
- Gene Name:
- SLC6A14
- Uniprot ID:
- Q9UN76
- Molecular Weight:
- 72152.145 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Neurotransmitter:sodium symporter activity
- Specific Function:
- Terminates the action of proline by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name:
- SLC6A7
- Uniprot ID:
- Q99884
- Molecular Weight:
- 70909.935 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Trans-l-3-hydroxyproline dehydratase 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 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Virion binding
- Specific Function:
- PPIases accelerate the folding of proteins. It catalyzes the cis-trans isomerization of proline imidic peptide bonds in oligopeptides.
- Gene Name:
- PPIA
- Uniprot ID:
- P62937
- Molecular Weight:
- 18012.42 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Unfolded protein binding
- Specific Function:
- PPIases accelerate the folding of proteins. It catalyzes the cis-trans isomerization of proline imidic peptide bonds in oligopeptides.
- Gene Name:
- PPIB
- Uniprot ID:
- P23284
- Molecular Weight:
- 23742.405 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Proline dehydrogenase activity
- Specific Function:
- Converts proline to delta-1-pyrroline-5-carboxylate.
- Gene Name:
- PRODH
- Uniprot ID:
- O43272
- Molecular Weight:
- 68001.405 Da
References
- Huang TC, Huang YW, Hung HJ, Ho CT, Wu ML: Delta1-pyrroline-5-carboxylic acid formed by proline dehydrogenase from the Bacillus subtilis ssp. natto expressed in Escherichia coli as a precursor for 2-acetyl-1-pyrroline. J Agric Food Chem. 2007 Jun 27;55(13):5097-102. Epub 2007 May 31. [17536821 ]
- General Function:
- Pyrroline-5-carboxylate reductase activity
- 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:
- P32322
- Molecular Weight:
- 33360.27 Da
References
- Huang TC, Huang YW, Hung HJ, Ho CT, Wu ML: Delta1-pyrroline-5-carboxylic acid formed by proline dehydrogenase from the Bacillus subtilis ssp. natto expressed in Escherichia coli as a precursor for 2-acetyl-1-pyrroline. J Agric Food Chem. 2007 Jun 27;55(13):5097-102. Epub 2007 May 31. [17536821 ]
- General Function:
- Pyrroline-5-carboxylate reductase activity
- 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 (PubMed:2722838, PubMed:6894153). Involved in cellular response to oxidative stress (PubMed:25865492).
- Gene Name:
- PYCR2
- Uniprot ID:
- Q96C36
- Molecular Weight:
- 33636.815 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Rna stem-loop binding
- Specific Function:
- Catalyzes the attachment of the cognate amino acid to the corresponding tRNA in a two-step reaction: the amino acid is first activated by ATP to form a covalent intermediate with AMP and is then transferred to the acceptor end of the cognate tRNA. Component of the GAIT (gamma interferon-activated inhibitor of translation) complex which mediates interferon-gamma-induced transcript-selective translation inhibition in inflammation processes. Upon interferon-gamma activation and subsequent phosphorylation dissociates from the multisynthetase complex and assembles into the GAIT complex which binds to stem loop-containing GAIT elements in the 3'-UTR of diverse inflammatory mRNAs (such as ceruplasmin) and suppresses their translation.
- Gene Name:
- EPRS
- Uniprot ID:
- P07814
- Molecular Weight:
- 170589.705 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Peptidyl-prolyl cis-trans isomerase activity
- Specific Function:
- PPIases accelerate the folding of proteins. It catalyzes the cis-trans isomerization of proline imidic peptide bonds in oligopeptides.
- Gene Name:
- PPIC
- Uniprot ID:
- P45877
- Molecular Weight:
- 22763.165 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Poly(a) rna binding
- Specific Function:
- PPIases accelerate the folding of proteins. It catalyzes the cis-trans isomerization of proline imidic peptide bonds in oligopeptides. May be implicated in the folding, transport, and assembly of proteins. May play an important role in the regulation of pre-mRNA splicing.
- Gene Name:
- PPIG
- Uniprot ID:
- Q13427
- Molecular Weight:
- 88616.535 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Ribonucleoprotein complex binding
- Specific Function:
- PPIases accelerate the folding of proteins. It catalyzes the cis-trans isomerization of proline imidic peptide bonds in oligopeptides. Participates in pre-mRNA splicing. May play a role in the assembly of the U4/U5/U6 tri-snRNP complex, one of the building blocks of the spliceosome. May act as a chaperone.
- Gene Name:
- PPIH
- Uniprot ID:
- O43447
- Molecular Weight:
- 19208.04 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Protein complex binding
- Specific Function:
- Basement membrane-associated chondroitin sulfate proteoglycan (CSPG). Has prolyl 3-hydroxylase activity catalyzing the post-translational formation of 3-hydroxyproline in -Xaa-Pro-Gly- sequences in collagens, especially types IV and V. May be involved in the secretory pathway of cells. Has growth suppressive activity in fibroblasts.
- Gene Name:
- P3H1
- Uniprot ID:
- Q32P28
- Molecular Weight:
- 83393.195 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Procollagen-proline 3-dioxygenase activity
- Specific Function:
- Shows prolyl 3-hydroxylase activity catalyzing the post-translational formation of 3-hydroxyproline in -Xaa-Pro-Gly-sequences in collagens, especially types II, IV and V.
- Gene Name:
- P3H2
- Uniprot ID:
- Q8IVL5
- Molecular Weight:
- 80983.685 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Procollagen-proline 3-dioxygenase activity
- Specific Function:
- Has prolyl 3-hydroxylase activity catalyzing the post-translational formation of 3-hydroxyproline in -Xaa-Pro-Gly-sequences in collagens, especially types IV and V.
- Gene Name:
- P3H3
- Uniprot ID:
- Q8IVL6
- Molecular Weight:
- 81835.705 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Procollagen-proline 4-dioxygenase activity
- 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:
- P13674
- Molecular Weight:
- 61048.775 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- L-proline transmembrane transporter activity
- Specific Function:
- Neutral amino acid/proton symporter. Has a pH-dependent electrogenic transport activity for small amino acids such as glycine, alanine and proline. Besides small apolar L-amino acids, it also recognize their D-enantiomers and selected amino acid derivatives such as gamma-aminobutyric acid (By similarity).
- Gene Name:
- SLC36A1
- Uniprot ID:
- Q7Z2H8
- Molecular Weight:
- 53075.045 Da
References
- Thondorf I, Voigt V, Schafer S, Gebauer S, Zebisch K, Laug L, Brandsch M: Three-dimensional quantitative structure-activity relationship analyses of substrates of the human proton-coupled amino acid transporter 1 (hPAT1). Bioorg Med Chem. 2011 Nov 1;19(21):6409-18. doi: 10.1016/j.bmc.2011.08.058. Epub 2011 Sep 5. [21955456 ]
- General Function:
- Peptidyl-prolyl cis-trans isomerase activity
- Specific Function:
- PPIases accelerate the folding of proteins. It catalyzes the cis-trans isomerization of proline imidic peptide bonds in oligopeptides. Involved in regulation of the mitochondrial permeability transition pore (mPTP). It is proposed that its association with the mPTP is masking a binding site for inhibiting inorganic phosphate (Pi) and promotes the open probability of the mPTP leading to apoptosis or necrosis; the requirement of the PPIase activity for this function is debated. In cooperation with mitochondrial TP53 is involved in activating oxidative stress-induced necrosis. Involved in modulation of mitochondrial membrane F(1)F(0) ATP synthase activity and regulation of mitochondrial matrix adenine nucleotide levels. Has anti-apoptotic activity independently of mPTP and in cooperation with BCL2 inhibits cytochrome c-dependent apoptosis.
- Gene Name:
- PPIF
- Uniprot ID:
- P30405
- Molecular Weight:
- 22040.09 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]