Record Information
Version1.0
Creation date2010-04-08 22:05:18 UTC
Update date2018-05-29 00:34:33 UTC
Primary IDFDB002250
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Tryptophan
DescriptionConstituent of many plants. Enzymatic hydrolysis production of most plant and animal proteins. Dietary supplement, nutrient Tryptophan is one of the 20 standard amino acids, as well as an essential amino acid in the human diet. Only the L-stereoisomer of tryptophan is used in structural or enzyme proteins, but the D-stereoisomer is occasionally found in naturally produced peptides (for example, the marine venom peptide contryphan).
CAS Number73-22-3
Structure
Thumb
Synonyms
SynonymSource
(2S)-2-Amino-3-(1H-indol-3-yl)propanoic acidChEBI
(S)-alpha-Amino-1H-indole-3-propanoic acidChEBI
(S)-alpha-Amino-beta-(3-indolyl)-propionic acidChEBI
(S)-TryptophanChEBI
L-(-)-TryptophanChEBI
L-beta-3-IndolylalanineChEBI
TrpChEBI
TryptophanChEBI
WChEBI
(2S)-2-Amino-3-(1H-indol-3-yl)propanoateGenerator
(S)-a-Amino-1H-indole-3-propanoateGenerator
(S)-a-Amino-1H-indole-3-propanoic acidGenerator
(S)-alpha-Amino-1H-indole-3-propanoateGenerator
(S)-Α-amino-1H-indole-3-propanoateGenerator
(S)-Α-amino-1H-indole-3-propanoic acidGenerator
(S)-a-Amino-b-(3-indolyl)-propionateGenerator
(S)-a-Amino-b-(3-indolyl)-propionic acidGenerator
(S)-alpha-Amino-beta-(3-indolyl)-propionateGenerator
(S)-Α-amino-β-(3-indolyl)-propionateGenerator
(S)-Α-amino-β-(3-indolyl)-propionic acidGenerator
L-b-3-IndolylalanineGenerator
L-Β-3-indolylalanineGenerator
(-)-TryptophanHMDB
(L)-TryptophanHMDB
(S)-1H-Indole-3-alanineHMDB
(S)-2-Amino-3-(3-indolyl)propionic acidHMDB
(S)-a-Amino-b-indolepropionateHMDB
(S)-a-Amino-b-indolepropionic acidHMDB
(S)-a-Aminoindole-3-propionateHMDB
(S)-a-Aminoindole-3-propionic acidHMDB
(S)-alpha-Amino-beta-indolepropionateHMDB
(S)-alpha-Amino-beta-indolepropionic acidHMDB
(S)-alpha-Aminoindole-3-propionateHMDB
(S)-alpha-Aminoindole-3-propionic acidHMDB
1-beta-3-IndolylalanineHMDB
1beta-3-IndolylalanineHMDB
1H-Indole-3-alanineHMDB
2-Amino-3-indolylpropanoateHMDB
2-Amino-3-indolylpropanoic acidHMDB
3-(1H-indol-3-yl)-L-AlanineHMDB
3-indol-3-YlalanineHMDB
Alpha'-amino-3-indolepropionic acidHMDB
alpha-Aminoindole-3-propionic acidHMDB
ArdeytropinHMDB
H-TRP-OHHMDB
Indole-3-alanineHMDB
KalmaHMDB
L-alpha-Amino-3-indolepropionic acidHMDB
L-alpha-Aminoindole-3-propionic acidHMDB
L-TryptofanHMDB
L-TryptophaneHMDB
Lopac-T-0254HMDB
LyphanHMDB
OptimaxHMDB
PacitronHMDB
SedanoctHMDB
TriptofanoHMDB
TrofanHMDB
TryptacinHMDB
TryptanHMDB
TryptophaneHMDB
TryptophanumHMDB
ArdeydormHMDB
L TryptophanHMDB
L-Tryptophan-ratiopharmHMDB
Merck brand OF tryptophanHMDB
Niddapharm brand OF tryptophanHMDB
ICN brand OF tryptophanHMDB
LevotryptophanHMDB
PMS TryptophanHMDB
PMS-TryptophanHMDB
Ratiopharm brand OF tryptophanHMDB
Esparma brand OF tryptophanHMDB
Ratio-tryptophanHMDB
L Tryptophan ratiopharmHMDB
NaturruheHMDB
Tryptophan metabolism alterationsHMDB
Ardeypharm brand OF tryptophanHMDB
Kalma brand OF tryptophanHMDB
Pharmascience brand OF tryptophanHMDB
Upsher-smith brand OF tryptophanHMDB
Ratio tryptophanHMDB
(S)-(-)-Tryptophanbiospider
(S)-α-Amino-1H-indole-3-propanoic acidbiospider
(S)-2-Amino-3-(1H-indol-3-yl)propanoic acidbiospider
(S)-a-amino-b-(3-Indolyl)-propionateGenerator
(S)-a-amino-b-(3-Indolyl)-propionic acidGenerator
(S)-alpha-amino-beta-(3-Indolyl)-propionateGenerator
(S)-Tryptophan 1H-Indole-3-alanine, (S)-biospider
(S)-α-amino-1H-indole-3-propanoateGenerator
(S)-α-amino-1H-indole-3-propanoic acidGenerator
(S)-α-amino-β-(3-indolyl)-propionateGenerator
(S)-α-amino-β-(3-indolyl)-propionic acidGenerator
1H-Indole-3-alanine, (S)-biospider
1H-Indole-3-propanoic acid, α-amino-, (S)-biospider
1H-Indole-3-propanoic acid, alpha-amino-, (S)-biospider
2-amino-3-IndolylpropanoateHMDB
2-amino-3-Indolylpropanoic acidHMDB
alpha-Amino-3-indolepropionic acid, L-biospider
L-(-)-Tryptophanebiospider
L-α-Amino-3-indolepropionic acidbiospider
L-α-Aminoindole-3-propionic acidbiospider
L-β-3-Indolylalaninebiospider
L-a-Aminoindole-3-propionic acidbiospider
L-Alanine, 3-(1H-indol-3-yl)-biospider
L-Tryptophan (9CI)biospider
L-β-3-indolylalanineGenerator
Lopac-t-0254HMDB
Tryptophan, 9CI, 8CI, USAN; L-formdb_source
Tryptophan, L- (8CI)biospider
Predicted Properties
PropertyValueSource
Water Solubility1.36 g/LALOGPS
logP-1.1ALOGPS
logP-1.1ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)2.54ChemAxon
pKa (Strongest Basic)9.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area79.11 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.2 m³·mol⁻¹ChemAxon
Polarizability21.05 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC11H12N2O2
IUPAC name(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
InChI IdentifierInChI=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
InChI KeyQIVBCDIJIAJPQS-VIFPVBQESA-N
Isomeric SMILESN[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O
Average Molecular Weight204.2252
Monoisotopic Molecular Weight204.089877638
Classification
Description belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct ParentIndolyl carboxylic acids and derivatives
Alternative Parents
Substituents
  • Indolyl carboxylic acid derivative
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • 3-alkylindole
  • Indole
  • Aralkylamine
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Amine
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 64.69%; H 5.92%; N 13.72%; O 15.67%DFC
Melting PointMp ca. 282° dec.DFC
Boiling PointNot Available
Experimental Water Solubility13.4 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-1.06HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]21D -5.7 (5M HCl)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0udi-0190000000-feaec8547634dddcad8cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0udi-0390000000-45a6c4fd79081597d44aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0udi-0290000000-34f7274f31a4cb321a0bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0fk9-9270000000-9761607cbe821f87f172View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-001i-0900000000-3faeed7ad32e1755c03cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0udi-0290000000-9c57a732e337fade3cb6View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-0900000000-d054a214c1717940989fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-0290000000-9860799c854e5c9ac1c7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0190000000-feaec8547634dddcad8cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0390000000-45a6c4fd79081597d44aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0290000000-34f7274f31a4cb321a0bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-QQ (Non-derivatized)splash10-0udi-3729000000-86129db57aaf1a245f93View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fk9-9270000000-9761607cbe821f87f172View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-0900000000-3faeed7ad32e1755c03cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-0290000000-9c57a732e337fade3cb6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0560-4900000000-fa932bc4cffed0ca66b7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00e9-9560000000-6829a8b2a2096883999fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0910000000-db5439a5499b19881720View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014m-0900000000-cc4a579a29d19a1c0d44View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00kf-3900000000-a931a9df4c855603d06eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0290000000-5fa576241f151a3a01a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0900000000-417ea0b6e4e18e5fbde1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-38f5ce97d594f3e3f12dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-783ffff22f31096f238fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0290000000-3ced9d310dda312f8582View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0900000000-a050919a36b995d34553View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-1ddec73daead0ffadce4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-a8c9c60f075a675f6629View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0290602010-c09c931538bff74ac400View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0900000000-0fed327c2a56f556e04cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0090000000-98ec1c2c012e58eab924View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0090000000-fc77784da5d9b288d751View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0290601010-d6f94902c0cf639cb7bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0900000000-27633a4f7ecfac45c730View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0090000000-ee6cb8392b2e8d644bc1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0090000000-d81c86eceee1c9824b02View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0190000000-0e8b883dc8ab06c89d77View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0uxu-2940000000-cb35b9680612e19d8b3aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-2900000000-7cc592351cc616b1d75fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014i-1900000000-987615a0add5eb2c3169View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014i-1900000000-f150d9d1e19c72d337a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0a4r-0690000000-ea2d79df0b56be85abddView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID6066
ChEMBL IDCHEMBL54976
KEGG Compound IDC00078
Pubchem Compound ID6305
Pubchem Substance IDNot Available
ChEBI ID16828
Phenol-Explorer IDNot Available
DrugBank IDDB00150
HMDB IDHMDB00929
CRC / DFC (Dictionary of Food Compounds) IDCHP14-U:CHP19-Z
EAFUS ID3777
Dr. Duke IDL-TRYPTOPHAN|TRYPTOPHAN
BIGG ID33772
KNApSAcK IDC00001396
HET IDTRP
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDTryptophan
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
anti anxiety52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti dementia52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti depressant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti dyskineticDUKE
anti hypertensive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti insomniac52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti manicDUKE
anti menopausal52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti migraine52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti Parkinsonian48407 A drug used in the treatment of Parkinson's disease.DUKE
anti phenylketonuric52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti prostaglandin49020 A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.DUKE
anti psychotic35476 Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect.DUKE
anti rheumatic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti scoliotic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
carcinogenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
essentialDUKE
hypnoticDUKE
hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
hypotensiveDUKE
insulinase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
insulinotonicDUKE
monoamine precursorDUKE
prolactinogenicDUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
serotoninergic48278 DUKE
tumor promoter50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
Enzymes
NameGene NameUniProt ID
Aromatic-L-amino-acid decarboxylaseDDCP20711
Tryptophan 5-hydroxylase 1TPH1P17752
Tryptophan 5-hydroxylase 2TPH2Q8IWU9
Tryptophan--tRNA ligase, cytoplasmicWARSP23381
Tryptophan--tRNA ligase, mitochondrialWARS2Q9UGM6
Pathways
NameSMPDB LinkKEGG Link
Transcription/TranslationSMP00019 Not Available
Tryptophan MetabolismSMP00063 map00380
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).