Milk Composition Database: Showing metabocard for Leucyl-Tryptophan (BMDB0062247)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2018-07-17 17:22:33 UTC

Update Date

2020-04-22 15:51:44 UTC

MCDB ID

BMDB0062247

Secondary Accession Numbers

BMDB62247

Metabolite Identification

Common Name

Leucyl-Tryptophan

Description

Leucyl-tryptophan, also known as L-W dipeptide or leu-TRP, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Leucyl-tryptophan is possibly soluble (in water) and a very strong basic compound (based on its pKa).

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
L-Leucyl-L-tryptophan	HMDB
L-W Dipeptide	HMDB
Leu-TRP	HMDB
Leucine tryptophan dipeptide	HMDB
Leucine-tryptophan dipeptide	HMDB
Leucyltryptophan	HMDB
LW Dipeptide	HMDB
2-[(2-Amino-1-hydroxy-4-methylpentylidene)amino]-3-(1H-indol-3-yl)propanoate	HMDB

Chemical Formula

C₁₇H₂₃N₃O₃

Average Molecular Weight

317.3828

Monoisotopic Molecular Weight

317.173941617

IUPAC Name

2-[(2-amino-1-hydroxy-4-methylpentylidene)amino]-3-(1H-indol-3-yl)propanoic acid

Traditional Name

2-[(2-amino-1-hydroxy-4-methylpentylidene)amino]-3-(1H-indol-3-yl)propanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)CC(N)C(O)=NC(CC1=CNC2=CC=CC=C12)C(O)=O

InChI Identifier

InChI=1S/C17H23N3O3/c1-10(2)7-13(18)16(21)20-15(17(22)23)8-11-9-19-14-6-4-3-5-12(11)14/h3-6,9-10,13,15,19H,7-8,18H2,1-2H3,(H,20,21)(H,22,23)

InChI Key

BQVUABVGYYSDCJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Leucine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid amide
Indolyl carboxylic acid derivative
Alpha-amino acid or derivatives
3-alkylindole
Indole or derivatives
Indole
N-acyl-amine
Substituted pyrrole
Fatty amide
Benzenoid
Fatty acyl
Heteroaromatic compound
Pyrrole
Secondary carboxylic acid amide
Carboxamide group
Amino acid or derivatives
Amino acid
Carboxylic acid
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Primary amine
Amine
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Carbonyl group
Primary aliphatic amine
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.32	ALOGPS
logP	0.25	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.67	ChemAxon
pKa (Strongest Basic)	9.61	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	111.7 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	87.7 m³·mol⁻¹	ChemAxon
Polarizability	33.8 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001c-9430000000-111ee24fc21d1a2cc3fe	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-059f-5913000000-655faaa87fc44cd9f5d3	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gbi-4439000000-8ae5f2cb6f62cf7dcdeb	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05n0-9521000000-74d7ff0d11213429bb74	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0api-9400000000-c840db0800144172a6fc	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0259000000-d95cbcd5571f7c3c9ffc	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0g70-2962000000-09d7db38a5e898f3828e	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0mvi-7930000000-bdaa022359948f990775	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0079000000-86dbe7fcdf4762e171e6	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-5980000000-f6c0e18400cdcb28f00e	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-066u-2900000000-1546bff373e866583581	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ap0-0594000000-1fe104ecc7fb2d93e5ec	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ap0-4972000000-302b5774c5d8dc99eeb2	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9300000000-10aa344c996bc16c51c2	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected but not Quantified	Not Applicable	PMID: 28306241	details
Detected but not Quantified	Not Applicable	PMID: 28965405	details
Detected but not Quantified	Not Applicable	PMID: 29291809	details

External Links

HMDB ID

HMDB0028940

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB098213

KNApSAcK ID

Not Available

Chemspider ID

291664

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

329275

PDB ID

Not Available

ChEBI ID

174310

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
Tang C, Zhang K, Zhan T, Zhao Q, Zhang J: Metabolic Characterization of Dairy Cows Treated with Gossypol by Blood Biochemistry and Body Fluid Untargeted Metabolome Analyses. J Agric Food Chem. 2017 Oct 25;65(42):9369-9378. doi: 10.1021/acs.jafc.7b03544. Epub 2017 Oct 17. [PubMed:28965405 ]
Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]

Showing metabocard for Leucyl-Tryptophan (BMDB0062247)

Structure for BMDB0062247 (Leucyl-Tryptophan)