U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C11H12N2O2
Molecular Weight 204.2252
Optical Activity ( - )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRYPTOPHAN

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

HIDE SMILES / InChI

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

Description
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

Curator's Comment: Tryptophan is utilized by the brain where it is converted to neuromediator serotonin.

Originator

Curator's Comment: The isolation of tryptophan was first reported by Frederick Hopkins in 1901 through hydrolysis of casein

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
OPTIMAX

Approved Use

Optimax 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 Date

1.40460478E12
Primary
OPTIMAX

Approved Use

Optimax 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 Date

1.40460478E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
717 μM
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

AUC

ValueDoseCo-administeredAnalytePopulation
2538 μM × h
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

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
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

Doses

DosePopulationAdverse events​
10 g single, intravenous
Highest studied dose
Dose: 10 g
Route: intravenous
Route: single
Dose: 10 g
Sources:
healthy, 18-40 years
Health Status: healthy
Age Group: 18-40 years
Sex: M
Sources:
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
Health Status: unhealthy
Age Group: adult
Sources:
Disc. AE: Eosinophilia myalgia syndrome...
AEs leading to
discontinuation/dose reduction:
Eosinophilia myalgia syndrome
Sources:
AEs

AEs

AESignificanceDosePopulation
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
Health Status: unhealthy
Age Group: adult
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
L-amino acid sensing by the extracellular Ca2+-sensing receptor.
2000 Apr 25
Depressive symptoms in hypothyroid disorder with some observations on biochemical correlates.
2001
Reduced brain serotonin activity disrupts prepulse inhibition of the acoustic startle reflex. Effects of 5,7-dihydroxytryptamine and p-chlorophenylalanine.
2001 Apr
Peripheral interleukin-6 administration increases extracellular concentrations of serotonin and the evoked release of serotonin in the rat striatum.
2001 Apr
Influence of solvents and leucine configuration at position 5 on tryptophan fluorescence in cyclic enkephalin analogues.
2001 Apr 5
Anti-microbial activity and cell binding are controlled by sequence determinants in the anti-microbial peptide PR-39.
2001 Feb
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
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
Pumping capacity of bacterial reaction centers and backpressure regulation of energy transduction.
2001 Feb
Increased antibacterial activity of 15-residue murine lactoferricin derivatives.
2001 Feb
Interaction of pleurocidin and its analogs with phospholipid membrane and their antibacterial activity.
2001 Feb
Active site characterization of the single endo-polygalacturonase produced by Fusarium moniliforme NCIM 1276.
2001 Feb
Tryptophan- and dileucine-based endocytosis signals in the neonatal Fc receptor.
2001 Feb 16
Extracellular amino acid profiles in the paraventricular nucleus of the rat hypothalamus are influenced by diet composition.
2001 Feb 23
Characterization of the FAD-containing N-methyltryptophan oxidase from Escherichia coli.
2001 Feb 6
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
Structural stabilization of [2Fe-2S] ferredoxin from Halobacterium salinarum.
2001 Feb 6
Orientations of Tyr 21 and Tyr 24 in the capsid of filamentous virus Ff determined by polarized Raman spectroscopy.
2001 Feb 6
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
No association between tryptophan hydroxylase gene polymorphism and Alzheimer's disease.
2001 Jan
The unique tryptophan residue of the vitamin D receptor is critical for ligand binding and transcriptional activation.
2001 Jan
Quantifying nutrient production by the microbial symbionts in an aphid.
2001 Jan
Physical exercise and normobaric hypoxia: independent modulators of peripheral cholecystokinin metabolism in man.
2001 Jan
Hypothesized treatment for migraines using low doses of tryptophan, niacin, calcium, caffeine, and acetylsalicylic acid.
2001 Jan
Thermally induced conformational changes in horseradish peroxidase.
2001 Jan
An in vivo study of ovine placental transport of essential amino acids.
2001 Jan
Membrane fusion by an RGD-containing sequence from the core protein VP3 of hepatitis A virus and the RGA-analogue: implications for viral infection.
2001 Jan
Metal-catalyzed oxidation of human growth hormone: modulation by solvent-induced changes of protein conformation.
2001 Jan
Endogenous neurotoxins from tryptophan.
2001 Jan
Ligand binding to integrin alpha(v)beta(3) requires tyrosine 178 in the alpha(v) subunit.
2001 Jan 1
Analysis of the subsite specificity of rat insulysin using fluorogenic peptide substrates.
2001 Jan 12
Structure and organization of bacteriophage Pf3 probed by Raman and ultraviolet resonance Raman spectroscopy.
2001 Jan 16
Chalcone derivatives antagonize interactions between the human oncoprotein MDM2 and p53.
2001 Jan 16
Hydrogen bonds with pi-acceptors in proteins: frequencies and role in stabilizing local 3D structures.
2001 Jan 19
Oxidation of human lens recombinant alphaA-crystallin and cysteine-deficient mutants.
2001 Jan 26
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
Molecular engineering of myoglobin: the improvement of oxidation activity by replacing Phe-43 with tryptophan.
2001 Jan 30
The role of histidine 632 in catalysis by human topoisomerase I.
2001 Jan 5
Low pH-induced conformational changes in vesicular stomatitis virus glycoprotein involve dramatic structure reorganization.
2001 Jan 5
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
Local and long-range interactions in the thermal unfolding transition of bovine pancreatic ribonuclease A.
2001 Jan 9
Spectral and metal-binding properties of three single-point tryptophan mutants of the human transferrin N-lobe.
2001 Mar 1
Identification of the human mitochondrial oxodicarboxylate carrier. Bacterial expression, reconstitution, functional characterization, tissue distribution, and chromosomal location.
2001 Mar 16
Phage display-selected sequences of the heavy-chain CDR3 loop of the anti-digoxin antibody 26-10 define a high affinity binding site for position 16-substituted analogs of digoxin.
2001 Mar 16
Importance of barrier shape in enzyme-catalyzed reactions. Vibrationally assisted hydrogen tunneling in tryptophan tryptophylquinone-dependent amine dehydrogenases.
2001 Mar 2
C-mannosylation and O-fucosylation of the thrombospondin type 1 module.
2001 Mar 2
The molecular mechanism for the genetic disorder familial defective apolipoprotein B100.
2001 Mar 23
Crystallographic evidence for substrate-assisted catalysis in a bacterial beta-hexosaminidase.
2001 Mar 30
The human VPAC1 receptor: three-dimensional model and mutagenesis of the N-terminal domain.
2001 Mar 30
Prostaglandin endoperoxide H synthase-1: the functions of cyclooxygenase active site residues in the binding, positioning, and oxygenation of arachidonic acid.
2001 Mar 30
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
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 Wed Jul 05 23:31:29 UTC 2023
Edited
by admin
on Wed Jul 05 23:31:29 UTC 2023
Record UNII
8DUH1N11BX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRYPTOPHAN
EP   HSDB   II   INCI   INN   MART.   MI   USAN   USP   VANDF  
INN   INCI   USAN  
Official Name English
TRYPTOPHAN [HSDB]
Common Name English
L-TRYPTOPHAN [VANDF]
Common Name English
NSC-13119
Code English
TRYPTOPHAN [INCI]
Common Name English
TRYPTOPHAN [EP MONOGRAPH]
Common Name English
TRYTOPHAN-
Common Name English
TRYPTOPHAN [II]
Common Name English
TRYPTOPHAN [VANDF]
Common Name English
N-ACETYLTRYPTOPHAN IMPURITY A [EP IMPURITY]
Common Name English
TRYPTOPHAN [MART.]
Common Name English
L-TRYPTOPHAN [USP-RS]
Common Name English
Tryptophan [WHO-DD]
Common Name English
tryptophan [INN]
Common Name English
TRYPTOPHAN, L-
WHO-DD  
Systematic Name English
L-TRYPTOPHAN [FCC]
Common Name English
L-TRYPTOPHAN
FCC   USP-RS   VANDF  
Systematic Name English
TRYPTOPHAN ((-),L,S)
Common Name English
1H-INDOLE-3-PROPANOIC ACID, .ALPHA.-AMINO-, (S)-
Systematic Name English
(-)-TRYPTOPHAN
Common Name English
TRYPTOPHAN [USAN]
Common Name English
L-TRYPTOPHAN [JAN]
Common Name English
TRYPTOPHAN [USP MONOGRAPH]
Common Name English
L-.ALPHA.-AMINO-3-INDOLEPROPIONIC ACID
Common Name English
TRYPTOPHAN [MI]
Common Name English
Classification Tree Code System Code
LOINC 25546-3
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
LOINC 34384-8
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
LOINC 3072-6
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LOINC 3071-8
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LOINC 17752-7
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LOINC 53159-0
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LOINC 28608-8
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LOINC 20659-9
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LOINC 15130-8
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LOINC 26602-3
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NCI_THESAURUS C68442
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LOINC 56993-9
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LOINC 3070-0
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LOINC 15145-6
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WHO-ATC N06AX02
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LOINC 9325-2
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FDA ORPHAN DRUG 796220
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LOINC 44414-1
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LOINC 27334-2
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LOINC 32275-0
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LOINC 13418-9
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LOINC 27135-3
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LOINC 3068-4
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LOINC 25139-7
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LOINC 3069-2
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LOINC 25994-5
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DSLD 199 (Number of products:65)
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
CFR 21 CFR 172.320
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
LOINC 24457-4
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
DSLD 2783 (Number of products:447)
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
LOINC 13817-2
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
WHO-VATC QN06AX02
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
LOINC 74767-5
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
Code System Code Type Description
CAS
73-22-3
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY
CHEBI
29954
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY
EVMPD
SUB15631MIG
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY
CHEBI
57912
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY
FDA UNII
8DUH1N11BX
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY
RXCUI
10898
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
200-795-6
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY
INN
6173
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY
ChEMBL
CHEMBL54976
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY
CHEBI
16828
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY
NCI_THESAURUS
C29603
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY
DAILYMED
8DUH1N11BX
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY
HSDB
4142
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY
NSC
13119
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY
DRUG BANK
DB00150
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY
CHEBI
57719
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY
RS_ITEM_NUM
1700501
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY
EPA CompTox
DTXSID5021419
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY
MESH
D014364
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY
DRUG CENTRAL
2780
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY
WIKIPEDIA
TRYPTOPHAN
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY
MERCK INDEX
M11247
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY Merck Index
SMS_ID
100000091926
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY
CHEBI
27897
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY
PUBCHEM
6305
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY
EVMPD
SUB12377MIG
Created by admin on Wed Jul 05 23:31:30 UTC 2023 , Edited by admin on Wed Jul 05 23:31:30 UTC 2023
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> INDUCER
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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
Formed from tryptophanase from gut bacteria.
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Metabolized from indole in the liver.
METABOLITE -> PARENT
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