ChemFOnt: Showing chemical card for Tryptophylhydroxyproline (CFc000010337)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:57:45 UTC

Chemfont ID

CFc000010337

Molecule Identification

Common Name

Tryptophylhydroxyproline

Definition

Tryptophylhydroxyproline is a dipeptide composed of tryptophan and hydroxyproline. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Tryptophan hydroxyproline dipeptide	HMDB
L-Tryptophyl-L-hydroxyproline	HMDB
TRP-HPro	HMDB
Tryptophan-hydroxyproline dipeptide	HMDB
W-HP Dipeptide	HMDB
WHP Dipeptide	HMDB
TRP-Hyp	HMDB
L-TRP-L-Hyp	HMDB
Tryptophyl-hydroxyproline	HMDB
(2S,4R)-1-[(2S)-2-Amino-3-(1H-indol-3-yl)propanoyl]-4-hydroxypyrrolidine-2-carboxylate	HMDB
Tryptophylhydroxyproline	HMDB

Chemical Formula

C₁₆H₁₉N₃O₄

Average Molecular Weight

317.345

Monoisotopic Molecular Weight

317.137556104

IUPAC Name

(2S,4R)-1-[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]-4-hydroxypyrrolidine-2-carboxylic acid

Traditional Name

(2S,4R)-1-[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]-4-hydroxypyrrolidine-2-carboxylic acid

CAS Registry Number

844640-75-1

SMILES

N[C@@H](CC1=CNC2=CC=CC=C12)C(=O)N1C[C@H](O)C[C@H]1C(O)=O

InChI Identifier

InChI=1S/C16H19N3O4/c17-12(5-9-7-18-13-4-2-1-3-11(9)13)15(21)19-8-10(20)6-14(19)16(22)23/h1-4,7,10,12,14,18,20H,5-6,8,17H2,(H,22,23)/t10-,12+,14+/m1/s1

InChI Key

XMEUQXQNFRSXLF-OSMZGAPFSA-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
Proline or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Triptan
Alpha-amino acid or derivatives
3-alkylindole
Indole
Indole or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Aralkylamine
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Tertiary carboxylic acid amide
Pyrrolidine
Pyrrole
Secondary alcohol
Amino acid or derivatives
Carboxamide group
Amino acid
Azacycle
Organoheterocyclic compound
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Hydrocarbon derivative
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Alcohol
Organonitrogen compound
Carbonyl group
Organooxygen compound
Amine
Primary amine
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0029084)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	5.22 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-2.5	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.6	ChemAxon
pKa (Strongest Basic)	7.95	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	119.65 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	82.51 m³·mol⁻¹	ChemAxon
Polarizability	31.88 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0029084

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112089

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

140079196

PDB ID

Not Available

ChEBI ID

189878

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Tryptophylhydroxyproline (CFc000010337)

MOL for CFc000010337 (Tryptophylhydroxyproline)

3D MOL for CFc000010337 (Tryptophylhydroxyproline)

3D SDF for CFc000010337 (Tryptophylhydroxyproline)

3D-SDF for CFc000010337 (Tryptophylhydroxyproline)

PDB for CFc000010337 (Tryptophylhydroxyproline)

3D PDB for CFc000010337 (Tryptophylhydroxyproline)

SMILES for CFc000010337 (Tryptophylhydroxyproline)

INCHI for CFc000010337 (Tryptophylhydroxyproline)

Structure for CFc000010337 (Tryptophylhydroxyproline)

3D Structure for CFc000010337 (Tryptophylhydroxyproline)