Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C11H12N2O2 |
Molecular Weight | 204.2252 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O
InChI
InChIKey=QIVBCDIJIAJPQS-VIFPVBQESA-N
InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1
Molecular Formula | C11H12N2O2 |
Molecular Weight | 204.2252 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.drugbank.ca/drugs/DB00150Curator's Comment: description was created based on several sources, including
https://www.drugs.com/tryptophan.html
Sources: https://www.drugbank.ca/drugs/DB00150
Curator's Comment: description was created based on several sources, including
https://www.drugs.com/tryptophan.html
Tryptophan is alpha-aminoacid that is used in the biosynthesis of proteins. It is essential aminoacid in humans, meaning the body cannot synthesize and it must be obtained from the diet. Tryptophan is a precursor of serotonin, and as such is sold over the counter in many countries as a dietary supplement for use as an antidepressant, anxiolytic and sleep aid, however application of tryptophan in these indications is not approved by FDA.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1704290
Curator's Comment: Tryptophan is utilized by the brain where it is converted to neuromediator serotonin.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16992614
Curator's Comment: The isolation of tryptophan was first reported by Frederick Hopkins in 1901 through hydrolysis of casein
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: map04726 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2271952 |
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Target ID: map00380 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2271952 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | OPTIMAX Approved UseOptimax capsules are used only in combination with other anti-depressants when these anti-depressants have been used alone in a patient for a period of time but have not been sufficiently effective. Launch Date1.40460478E12 |
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Primary | OPTIMAX Approved UseOptimax 500 ing capsules contain L-tryptophan winch is found naturally in animal and plant proteins. L-tryptophan is considered an essential amino acid because our bodies can't make it. It is important for the development and functioning of many organs in the body. After absorbing L-tryptophan from food, our bodies convert it to 5-HTP (5-liydroxytryptophan) and then to serotonin which reduces feelings of anxiety and depression. Launch Date1.40460478E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
717 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6210561/ |
100 mg/kg single, oral dose: 100 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
TRYPTOPHAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2538 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6210561/ |
100 mg/kg single, oral dose: 100 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
TRYPTOPHAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6210561/ |
100 mg/kg single, oral dose: 100 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
TRYPTOPHAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
10 g single, intravenous Highest studied dose |
healthy, 18-40 years |
|
1800 mg 1 times / day multiple, oral (mean) Dose: 1800 mg, 1 times / day Route: oral Route: multiple Dose: 1800 mg, 1 times / day Sources: |
healthy, 52 years n = 7 Health Status: healthy Age Group: 52 years Sex: F Population Size: 7 Sources: |
Disc. AE: Eosinophilia myalgia syndrome... AEs leading to discontinuation/dose reduction: Eosinophilia myalgia syndrome (7 patients) Sources: |
1.5 g 2 times / day multiple, oral (median) Dose: 1.5 g, 2 times / day Route: oral Route: multiple Dose: 1.5 g, 2 times / day Sources: |
unhealthy, adult |
Disc. AE: Eosinophilia myalgia syndrome... AEs leading to discontinuation/dose reduction: Eosinophilia myalgia syndrome Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Eosinophilia myalgia syndrome | 7 patients Disc. AE |
1800 mg 1 times / day multiple, oral (mean) Dose: 1800 mg, 1 times / day Route: oral Route: multiple Dose: 1800 mg, 1 times / day Sources: |
healthy, 52 years n = 7 Health Status: healthy Age Group: 52 years Sex: F Population Size: 7 Sources: |
Eosinophilia myalgia syndrome | Disc. AE | 1.5 g 2 times / day multiple, oral (median) Dose: 1.5 g, 2 times / day Route: oral Route: multiple Dose: 1.5 g, 2 times / day Sources: |
unhealthy, adult |
PubMed
Title | Date | PubMed |
---|---|---|
Depressive symptoms in hypothyroid disorder with some observations on biochemical correlates. | 2001 |
|
Mechanisms of biosynthesis of protein-derived redox cofactors. | 2001 |
|
Reduced brain serotonin activity disrupts prepulse inhibition of the acoustic startle reflex. Effects of 5,7-dihydroxytryptamine and p-chlorophenylalanine. | 2001 Apr |
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Influence of solvents and leucine configuration at position 5 on tryptophan fluorescence in cyclic enkephalin analogues. | 2001 Apr 5 |
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IL-4 and IL-13 regulate the induction of indoleamine 2,3-dioxygenase activity and the control of Toxoplasma gondii replication in human fibroblasts activated with IFN-gamma. | 2001 Feb |
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Anti-microbial activity and cell binding are controlled by sequence determinants in the anti-microbial peptide PR-39. | 2001 Feb |
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Contribution of tryptophan residues to the CD spectrum of the extracellular domain of human tissue factor: application in folding studies and prediction of secondary structure. | 2001 Feb |
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A comparison of kinetic and regulatory properties of the tetrameric and dimeric forms of wild-type and Thr427-->Pro mutant human phenylalanine hydroxylase: contribution of the flexible hinge region Asp425-Gln429 to the tetramerization and cooperative substrate binding. | 2001 Feb |
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Pumping capacity of bacterial reaction centers and backpressure regulation of energy transduction. | 2001 Feb |
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Mutagenesis of key residues identifies the connection subdomain of HIV-1 reverse transcriptase as the site of inhibition by heme. | 2001 Feb |
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The mood-lowering effect of tryptophan depletion: possible explanation for discrepant findings. | 2001 Feb |
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Interaction of L-tryptophan with alpha-cyclodextrin: studies with calorimetry and proton nuclear magnetic resonance spectroscopy. | 2001 Feb |
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Increased antibacterial activity of 15-residue murine lactoferricin derivatives. | 2001 Feb |
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Interaction of pleurocidin and its analogs with phospholipid membrane and their antibacterial activity. | 2001 Feb |
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Mechanism of porcine pancreatic alpha-amylase. Inhibition of amylose and maltopentaose hydrolysis by alpha-, beta- and gamma-cyclodextrins. | 2001 Feb |
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Active site characterization of the single endo-polygalacturonase produced by Fusarium moniliforme NCIM 1276. | 2001 Feb |
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Effect of hypothyroidism on pathways for iodothyronine and tryptophan uptake into rat adipocytes. | 2001 Feb |
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Excessive activation of serotonin (5-HT) 1B receptors disrupts the formation of sensory maps in monoamine oxidase a and 5-ht transporter knock-out mice. | 2001 Feb 1 |
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Hypochlorous acid damages erythrocyte membrane proteins and alters lipid bilayer structure and fluidity. | 2001 Feb 15 |
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Tryptophan glycoconjugate as a novel marker of renal function. | 2001 Feb 15 |
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Trp 346 and Leu 352 residues in protective antigen are required for the expression of anthrax lethal toxin activity. | 2001 Feb 16 |
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Probing the kinetics of formation of the bacteriophage MS2 translational operator complex: identification of a protein conformer unable to bind RNA. | 2001 Feb 2 |
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Extracellular amino acid profiles in the paraventricular nucleus of the rat hypothalamus are influenced by diet composition. | 2001 Feb 23 |
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N-methyltryptophan oxidase from Escherichia coli: reaction kinetics with N-methyl amino acid and carbinolamine substrates. | 2001 Feb 6 |
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Characterization of the FAD-containing N-methyltryptophan oxidase from Escherichia coli. | 2001 Feb 6 |
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Phosphorescence and optically detected magnetic resonance of HIV-1 nucleocapsid protein complexes with stem-loop sequences of the genomic Psi-recognition element. | 2001 Feb 6 |
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Orientations of Tyr 21 and Tyr 24 in the capsid of filamentous virus Ff determined by polarized Raman spectroscopy. | 2001 Feb 6 |
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Kynurenine aminotransferase I activity in human placenta. | 2001 Feb-Mar |
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Acute tryptophan depletion in schizophrenia. | 2001 Jan |
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Autofluorescence characteristics of immortalized and carcinogen-transformed human bronchial epithelial cells. | 2001 Jan |
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Regional changes in kynurenic acid, quinolinic acid, and glial fibrillary acidic protein concentrations in the fetal sheep brain after experimentally induced placental insufficiency. | 2001 Jan |
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Near-infrared reflectance spectroscopy enables the fast and accurate prediction of the essential amino acid contents in soy, rapeseed meal, sunflower meal, peas, fishmeal, meat meal products, and poultry meal. | 2001 Jan |
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Tryptophan fluorescence of yeast actin resolved via conserved mutations. | 2001 Jan |
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Monoamine compounds in cerebrospinal fluid of healthy subjects punctured without preceding strict bed rest: a pilot study. | 2001 Jan |
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No association between tryptophan hydroxylase gene polymorphism and Alzheimer's disease. | 2001 Jan |
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The unique tryptophan residue of the vitamin D receptor is critical for ligand binding and transcriptional activation. | 2001 Jan |
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Structure and organization of bacteriophage Pf3 probed by Raman and ultraviolet resonance Raman spectroscopy. | 2001 Jan 16 |
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Chalcone derivatives antagonize interactions between the human oncoprotein MDM2 and p53. | 2001 Jan 16 |
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Amino acid phosphoramidate monoesters of 3'-azido-3'-deoxythymidine: relationship between antiviral potency and intracellular metabolism. | 2001 Jan 18 |
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Molecular mechanism of stop codon recognition by eRF1: a wobble hypothesis for peptide anticodons. | 2001 Jan 19 |
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Hydrogen bonds with pi-acceptors in proteins: frequencies and role in stabilizing local 3D structures. | 2001 Jan 19 |
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A differential scanning calorimetric and 31P NMR spectroscopic study of the effect of transmembrane alpha-helical peptides on the lamellar-reversed hexagonal phase transition of phosphatidylethanolamine model membranes. | 2001 Jan 23 |
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Crystal structures of pristine and oxidatively processed lignin peroxidase expressed in Escherichia coli and of the W171F variant that eliminates the redox active tryptophan 171. Implications for the reaction mechanism. | 2001 Jan 26 |
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Molecular engineering of myoglobin: the improvement of oxidation activity by replacing Phe-43 with tryptophan. | 2001 Jan 30 |
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Distributions of intramolecular distances in the reduced and denatured states of bovine pancreatic ribonuclease A. Folding initiation structures in the C-terminal portions of the reduced protein. | 2001 Jan 9 |
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Local and long-range interactions in the thermal unfolding transition of bovine pancreatic ribonuclease A. | 2001 Jan 9 |
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Improvement of encapsulation efficiency of water-in-oil-in-water emulsion with hypertonic inner aqueous phase. | 2001 Jan-Feb |
|
A nonsense mutation in the NDUFS4 gene encoding the 18 kDa (AQDQ) subunit of complex I abolishes assembly and activity of the complex in a patient with Leigh-like syndrome. | 2001 Mar 1 |
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Spectral and metal-binding properties of three single-point tryptophan mutants of the human transferrin N-lobe. | 2001 Mar 1 |
|
Src homology 3 domain-dependent interaction of Nck-2 with insulin receptor substrate-1. | 2001 Mar 1 |
Patents
Sample Use Guides
As a dietary supplement, tryptophan is administered orally with tryptophan-reach food (turkey, eggs, beans) or as dietary supplements in the form of tablets.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2271952
Tryptophan hydroxylase activity was assayed in a low-speed supernatant fraction of cerebral cortex or midbrain from a single rat. The enzyme preparation contained 2 mM dithiothreitol and had been subjected to gel filtration to remove small molecules. The assay was carried out in the presence of 200 uM L-tryptophan and 50 gM DL-6-methyl-5,6,7,8-tetrahydropterin.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:03:31 UTC 2023
by
admin
on
Fri Dec 15 16:03:31 UTC 2023
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Record UNII |
8DUH1N11BX
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Record Status |
Validated (UNII)
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Record Version |
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26602-3
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N06AX02
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9325-2
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FDA ORPHAN DRUG |
796220
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44414-1
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25994-5
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DSLD |
199 (Number of products:65)
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CFR |
21 CFR 172.320
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24457-4
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13817-2
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74767-5
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Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE |
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RADIOLIGAND->TARGET |
Used to monitor tryptophan uptake and metabolism
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METABOLIC ENZYME -> INDUCER |
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Related Record | Type | Details | ||
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METABOLITE TOXIC -> PARENT |
Metabolised to indole by gut lactobacilli then to indoxyl sulfate in the liver by cypE1 and a sulfation enzyme.
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
Formed from tryptophanase from gut bacteria.
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
Metabolized from indole in the liver.
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE ACTIVE -> PARENT |
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
EP
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IMPURITY -> PARENT |
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
EP
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IMPURITY -> PARENT |
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
EP
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IMPURITY -> PARENT |
EP
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IMPURITY -> PARENT |
EP
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IMPURITY -> PARENT |
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
EP
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IMPURITY -> PARENT |
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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