AFCDB: L-Tryptophan (FDB002250)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:18 UTC

Update date

2024-11-29 22:27:53 UTC

Primary ID

FDB002250

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

L-Tryptophan

Description

L-Tryptophan, also known as Trp or W, 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. L-Tryptophan is a very strong basic compound (based on its pKa). L-Tryptophan exists in all living species, ranging from bacteria to humans. Within humans, L-tryptophan participates in a number of enzymatic reactions. In particular, L-tryptophan can be converted into n'-formylkynurenine through the action of the enzyme tryptophan 2,3-dioxygenase. In addition, L-tryptophan and tetrahydrobiopterin can be converted into 5-hydroxy-L-tryptophan and 4a-hydroxytetrahydrobiopterin through its interaction with the enzyme tryptophan 5-hydroxylase 1. The L-enantiomer of tryptophan. In humans, L-tryptophan is involved in tryptophan metabolism. Outside of the human body, L-Tryptophan is found, on average, in the highest concentration within a few different foods, such as caseins, steller sea lions, and evening primroses and in a lower concentration in thunnus, kefirs, and garden onions. L-Tryptophan has also been detected, but not quantified in, several different foods, such as thistles, gelatins, garden onion (var.), alpine sweetvetchs, and remoulades. This could make L-tryptophan a potential biomarker for the consumption of these foods.

CAS Number

73-22-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.36 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-1.1	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	2.54	ChemAxon
pKa (Strongest Basic)	9.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.11 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	56.2 m³·mol⁻¹	ChemAxon
Polarizability	21.05 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C11H12N2O2

IUPAC name

(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid

InChI Identifier

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

InChI Key

QIVBCDIJIAJPQS-VIFPVBQESA-N

Isomeric SMILES

N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O

Average Molecular Weight

204.2252

Monoisotopic Molecular Weight

204.089877638

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

proteinogenic amino acid (CHEBI:16828 )
L-alpha-amino acid (CHEBI:16828 )
tryptophan (CHEBI:16828 )
erythrose 4-phosphate/phosphoenolpyruvate family amino acid (CHEBI:16828 )
Common amino acids (C00078 )

Ontology

Ingestion

Source:

Food

Synthetic:

Personal care product

Biological:

Animal

Plant:

Biological location:

Subcellular:

Organ and components:

Prostate

Cell and elements:

Extracellular

Cell:

Biofluid and excreta:

Role

Indirect biological role:

Industrial application:

Food and nutrition:

Nutritional supplement

Pharmaceutical industry:

Whole grain cereal products

Nuts and legumes:

Nuts

Legumes:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 64.69%; H 5.92%; N 13.72%; O 15.67%	DFC
Melting Point	Mp ca. 282° dec.	DFC
Boiling Point	Not Available
Experimental Water Solubility	13.4 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	-1.06	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]21D -5.7 (5M HCl)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	L-Tryptophan, 3 TMS, GC-MS Spectrum	splash10-0udi-0190000000-feaec8547634dddcad8c	Spectrum
GC-MS	L-Tryptophan, 3 TMS, GC-MS Spectrum	splash10-0udi-0390000000-45a6c4fd79081597d44a	Spectrum
GC-MS	L-Tryptophan, non-derivatized, GC-MS Spectrum	splash10-0udi-0290000000-34f7274f31a4cb321a0b	Spectrum
GC-MS	L-Tryptophan, 3 TMS, GC-MS Spectrum	splash10-0fk9-9270000000-9761607cbe821f87f172	Spectrum
GC-MS	L-Tryptophan, 1 TMS, GC-MS Spectrum	splash10-001i-0900000000-3faeed7ad32e1755c03c	Spectrum
GC-MS	L-Tryptophan, 3 TMS, GC-MS Spectrum	splash10-0udi-0290000000-9c57a732e337fade3cb6	Spectrum
GC-MS	L-Tryptophan, non-derivatized, GC-MS Spectrum	splash10-001i-0900000000-d054a214c1717940989f	Spectrum
GC-MS	L-Tryptophan, non-derivatized, GC-MS Spectrum	splash10-0udi-0290000000-9860799c854e5c9ac1c7	Spectrum
GC-MS	L-Tryptophan, non-derivatized, GC-MS Spectrum	splash10-0udi-0190000000-feaec8547634dddcad8c	Spectrum
GC-MS	L-Tryptophan, non-derivatized, GC-MS Spectrum	splash10-0udi-0390000000-45a6c4fd79081597d44a	Spectrum
GC-MS	L-Tryptophan, non-derivatized, GC-MS Spectrum	splash10-0udi-0290000000-34f7274f31a4cb321a0b	Spectrum
GC-MS	L-Tryptophan, non-derivatized, GC-MS Spectrum	splash10-0udi-3729000000-86129db57aaf1a245f93	Spectrum
GC-MS	L-Tryptophan, non-derivatized, GC-MS Spectrum	splash10-0fk9-9270000000-9761607cbe821f87f172	Spectrum
GC-MS	L-Tryptophan, non-derivatized, GC-MS Spectrum	splash10-001i-0900000000-3faeed7ad32e1755c03c	Spectrum
GC-MS	L-Tryptophan, non-derivatized, GC-MS Spectrum	splash10-0udi-0290000000-9c57a732e337fade3cb6	Spectrum
Predicted GC-MS	L-Tryptophan, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0560-4900000000-fa932bc4cffed0ca66b7	Spectrum
Predicted GC-MS	L-Tryptophan, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00e9-9560000000-6829a8b2a2096883999f	Spectrum
Predicted GC-MS	L-Tryptophan, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Tryptophan, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Tryptophan, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Tryptophan, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Tryptophan, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Tryptophan, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0290602010-c09c931538bff74ac400	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0900000000-0fed327c2a56f556e04c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0090000000-98ec1c2c012e58eab924	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00di-0090000000-fc77784da5d9b288d751	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0290601010-d6f94902c0cf639cb7bc	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0900000000-27633a4f7ecfac45c730	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0udi-0090000000-ee6cb8392b2e8d644bc1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0090000000-d81c86eceee1c9824b02	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0190000000-0e8b883dc8ab06c89d77	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0uxu-2940000000-cb35b9680612e19d8b3a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-014i-2900000000-7cc592351cc616b1d75f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-014i-1900000000-987615a0add5eb2c3169	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-014i-1900000000-f150d9d1e19c72d337a8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0uxr-2960000000-f4c878f3abb1609bb5c5	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0090000000-c73c9b49139319c80b18	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0gb9-0930000000-da94834297fcc5b3d3c5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0900000000-94061fd1f6b08445cdf3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0900000000-e78172f4f27df232466e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0900000000-93406e2cdb79770abc7d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0190000000-0e8b883dc8ab06c89d77	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0uxu-2940000000-cb35b9680612e19d8b3a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-2900000000-5187dac98dbd6834d6ba	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-1900000000-987615a0add5eb2c3169	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-1900000000-174bb4d4390c75ae9a09	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0900000000-0fed327c2a56f556e04c	2017-09-14	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16828

Phenol-Explorer ID

Not Available

DrugBank ID

DB00150

HMDB ID

HMDB00929

CRC / DFC (Dictionary of Food Compounds) ID

CHP14-U:CHP19-Z

EAFUS ID

3777

Dr. Duke ID

L-TRYPTOPHAN|TRYPTOPHAN

BIGG ID

33772

KNApSAcK ID

C00001396

HET ID

TRP

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Tryptophan

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
analgesic	35480	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 anxiety	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti dementia	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti depressant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti dyskinetic			DUKE
anti hypertensive	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti insomniac	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti manic			DUKE
anti menopausal	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti migraine	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
antioxidant	22586	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 Parkinsonian	48407	A drug used in the treatment of Parkinson's disease.	DUKE
anti phenylketonuric	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti prostaglandin	49020	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 psychotic	35476	Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect.	DUKE
anti rheumatic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti scoliotic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
carcinogenic	50903	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
essential			DUKE
hypnotic			DUKE
hypoglycemic	35526	A drug which lowers the blood glucose level.	DUKE
hypotensive			DUKE
insulinase inhibitor	23924	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
insulinotonic			DUKE
monoamine precursor			DUKE
prolactinogenic			DUKE
sedative	35717	A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.	DUKE
serotoninergic	48278		DUKE
tumor promoter	50903	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

Name	Gene Name	UniProt ID
Aromatic-L-amino-acid decarboxylase	DDC	P20711
Tryptophan 5-hydroxylase 1	TPH1	P17752
Tryptophan 5-hydroxylase 2	TPH2	Q8IWU9
Tryptophan--tRNA ligase, cytoplasmic	WARS	P23381
Tryptophan--tRNA ligase, mitochondrial	WARS2	Q9UGM6

Pathways

Name	SMPDB Link	KEGG Link
Transcription/Translation	SMP00019	Not Available
Tryptophan Metabolism	SMP00063	map00380
Metabolism and Physiological Effects of Indole Acetic Acid	SMP0123235	Not Available
Metabolism and Physiological Effects of Indoxyl Sulfate	SMP0123237	Not Available
Metabolism and Physiological Effects of Indoxyl glucuronide	SMP0123239	Not Available
Metabolism and Physiological Effects of Quinolinic Acid	SMP0123249	Not Available
Metabolism and Physiological Effects of Kynurenic Acid	SMP0123300	Not Available
Metabolism and Physiological Effects of Indoxyl glucoside (indican)	SMP0124742	Not Available
Metabolism and Physiological Effects of Kynurenine	SMP0125524	Not Available
Metabolism and Physiological Effects of N-Acetyltryptophan	SMP0126721	Not Available
Metabolism and Physiological Effects of Indolelactic Acid	SMP0126749	Not Available
Metabolism and Physiological Effects of Indolelacetyl glutamine	SMP0126755	Not Available
Metabolism and Physiological Effects of 2-Aminobenzoic acid	SMP0126869	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not 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).

L-Tryptophan (FDB002250)

Structure for FDB002250 (L-Tryptophan)