L-PROLINE
Relevant Data
Food Additives Approved by WHO:
Flavouring Substances Approved by European Union:
General Information
| Mainterm | L-PROLINE |
| Doc Type | ASP |
| CAS Reg.No.(or other ID) | 147-85-3 |
| Regnum |
172.320 |
From www.fda.gov
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 145742 |
| IUPAC Name | (2S)-pyrrolidine-2-carboxylic acid |
| InChI | 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 |
| Canonical SMILES | C1CC(NC1)C(=O)O |
| Molecular Formula | C5H9NO2 |
| Wikipedia | L-Proline |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 115.132 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 1 |
| Complexity | 103.0 |
| CACTVS Substructure Key Fingerprint | A A A D c c B i M A A A A A A A A A A A A A A A A A A A A W A A A A A A A A A A A A A A A A A A A A A A H g A Q C A A A C C j B g A Q A C A L A A g A I A A C Q C A A A A A A A A A A A A I G I A A A C A B I A g C A E Q A A E E A C Q A A C Y E Q A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 49.3 |
| Monoisotopic Mass | 115.063 |
| Exact Mass | 115.063 |
| Compound Is Canonicalized | True |
| 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 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| 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 |
From admetSAR
ADMET Predicted Profile --- Regression
| 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 |
From admetSAR
Toxicity Profile
| Route of Exposure | None |
|---|---|
| Mechanism of Toxicity | Glycogenic, by L-Proline oxidase in the kidney, it is ring-opened and is oxidized to form L-Glutamic acid. L-Ornithine and L-Glutamic acid are converted to L-Proline via L-Glutamic acid-gamma-semialdehyde. It is contained abundantly in collagen, and is intimately involved in the function of arthrosis and chordae. |
| Metabolism | Hepatic |
| Toxicity Values | None |
| Lethal Dose | None |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
| Minimum Risk Level | None |
| Health Effects | Chronically high levels of proline are associated with at least 5 inborn errors of metabolism including: Hyperprolinemia Type I, Hyperprolinemia Type II, Iminoglycinuria, Prolinemia Type II and Pyruvate carboxylase deficiency. |
| Treatment | None |
| Reference |
|
From T3DB
Taxonomic Classification
| 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. |
From ClassyFire
Targets
- 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
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
- 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
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
- 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
- White TA, Tanner JJ: Cloning, purification and crystallization of Thermus thermophilus proline dehydrogenase. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2005 Aug 1;61(Pt 8):737-9. Epub 2005 Jul 8. [16511143 ]
- 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
- Meng Z, Lou Z, Liu Z, Hui D, Bartlam M, Rao Z: Purification, characterization, and crystallization of human pyrroline-5-carboxylate reductase. Protein Expr Purif. 2006 Sep;49(1):83-7. Epub 2006 Mar 20. [16600630 ]
- 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
- Murahama M, Yoshida T, Hayashi F, Ichino T, Sanada Y, Wada K: Purification and characterization of Delta(1)-pyrroline-5-carboxylate reductase isoenzymes, indicating differential distribution in spinach (Spinacia oleracea L.) leaves. Plant Cell Physiol. 2001 Jul;42(7):742-50. [11479381 ]
- General Function:
- Pyrroline-5-carboxylate reductase activity
- Gene Name:
- PYCRL
- Uniprot ID:
- Q53H96
- Molecular Weight:
- 28663.025 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
- 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
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
- 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
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
- 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
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
- 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
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
- 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
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
- 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
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
- 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
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
- 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
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
- 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
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
- 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
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
- 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
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
- 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
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
- 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
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
- 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 ]
From T3DB