Showing Compound (±)-Tryptophan (FDB002251)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:18 UTC

Update date

2020-02-24 19:10:28 UTC

Primary ID

FDB002251

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(±)-Tryptophan

Description

(±)-Tryptophan, also known as HTRP or triptofano, 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 (±)-Tryptophan is found, on average, in the highest concentration within a few different foods, such as red bell peppers (Capsicum annuum), casein, and dried milk and in a lower concentration in sausage, crisp bread, and common mushrooms (Agaricus bisporus) (±)-Tryptophan has also been detected, but not quantified in, several different foods, such as gadiformes (Gadiformes), prickly pears (Opuntia), lard, other candy, and chocolate spread. This could make (±)-tryptophan a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (±)-Tryptophan.

CAS Number

54-12-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Show entries

Search:

Synonym	Source
(+-)-Tryptophan	HMDB
(+/-)-2-amino-3-(3-indolyl)propionic acid	HMDB
(+/-)-2-Amino-3-(3-indolyl)propionic acid	biospider
(+/-)-alpha-amino-3-indolepropionic acid	HMDB
(+/-)-alpha-Amino-3-indolepropionic acid	biospider
2-Amino-3-(1H-indol-3-yl)propanoate	Generator
2-Amino-3-(1H-indol-3-yl)propanoic acid	ChEBI
a-Amino-b-(3-indolyl)-propionate	Generator
a-Amino-b-(3-indolyl)-propionic acid	Generator
a-Amino-b-3-indolepropionate	Generator

Showing 1 to 10 of 35 entries

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	21.19 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

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)

InChI Key

QIVBCDIJIAJPQS-UHFFFAOYSA-N

Isomeric SMILES

NC(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
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

alpha-amino acid (CHEBI:27897 )
aromatic amino acid (CHEBI:27897 )
aminoalkylindole (CHEBI:27897 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Cucurbitaceae

Biological location:

Biofluid and excreta:

Urine

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Search:

Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	-1.05	HANSCH,C ET AL. (1995)
Experimental pKa	7.38
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 64.69%; H 5.92%; N 13.72%; O 15.67%	DFC
Melting Point	Mp 293°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-001i-2900000000-c6c45a933a953618aa8c	2014-09-20	View Spectrum
GC-MS	(±)-Tryptophan, 2 TMS, GC-MS Spectrum	splash10-00lr-1940000000-7d24b93f0df6ee59c1cf	Spectrum
GC-MS	(±)-Tryptophan, 2 TMS, GC-MS Spectrum	splash10-0udi-0290000000-1a8228e2b523be1ae691	Spectrum
GC-MS	(±)-Tryptophan, non-derivatized, GC-MS Spectrum	splash10-0udi-0390000000-bf55780347500228fa0a	Spectrum
GC-MS	(±)-Tryptophan, non-derivatized, GC-MS Spectrum	splash10-0fsi-0930000000-a768dbcdd61c5ddfc7ff	Spectrum
Predicted GC-MS	(±)-Tryptophan, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-057i-5900000000-19287f7752709aae95d9	Spectrum
Predicted GC-MS	(±)-Tryptophan, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00e9-9560000000-6829a8b2a2096883999f	Spectrum
Predicted GC-MS	(±)-Tryptophan, non-derivatized, 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 , negative	splash10-0udi-0290000000-177c39ffff7351ae58e7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-014i-0920000000-31f2bf06783a35cb177e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0zfr-0890000000-70571859405f22f7726d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0uxr-1960000000-4794df4619ca53da8a26	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0zfr-0790000000-71f96432b70be90e3e76	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0900000000-678ef44eecd71f98f4bc	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-014i-1910000000-3b90b4510b3064cd8257	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udi-0090000000-30198ffd85182eef6dbb	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udi-0190000000-2319c76338ccc72cea91	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udi-0690000000-2d67e3b24d52541620df	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udi-0390000000-32f53d15608910742122	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0gb9-1940000000-4d8b6d43d6dc47a0a53c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udi-0090000000-672eea5be46683e01aa3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0900000000-b167000b756e70598ebb	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udi-0290000000-f83d06a826ee6963c139	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udi-0190000000-af6a41a358461c4944d5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-014i-1930000000-fe537846c01a00076d1b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0uxr-1980000000-bc34bf853c58cd38c9ce	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udi-0290000000-fff893c43aa27aebf582	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0920000000-825129a9df3095f19bd0	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a59-0900000000-142753592a64d1b21225	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0900000000-4f3eacbba35070501781	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-3490000000-de7027f417d1320c2b85	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9830000000-415cd821aca8befd3e58	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00xr-9600000000-8e10a14ed0f3f1b8fb23	2015-05-27	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, 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, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 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