ChemFOnt: Showing chemical card for APGPR Enterostatin (CFc000002654)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:35 UTC

Chemfont ID

CFc000002654

Molecule Identification

Common Name

APGPR Enterostatin

Definition

Enterostatin APGPR (Ala-Pro-Gly-Pro-Arg) is a pentapeptide released from procolipase during fat digestion. In addition to the pancreas, enterostatin-immunoreactive cells are also present in the antrum and proximal small intestine. Enterostatin selectively reduces fat intake, decreases insulin secretion, and also increases energy expenditure by activating brown adipose tissue during high-fat feeding. Enterostatins are pentapeptides derived from the NH2-terminus of procolipase after tryptic cleavage and belong to the family of gut-brain peptides. Enterostatin is generated by the action of trypsin on procolipase in the intestinal lumen. Its structure is highly conserved in evolution, with an amino acid sequence of XPXPR. Three enterostatin sequences, Val-Pro-Asp-Pro-Arg (VPDPR), Val-Pro-Gly-Pro-Arg (VPGPR), and Ala-Pro-Gly-Pro-Arg (APGPR), have been studied extensively and shown to be almost equally effective in their ability to decrease dietary fat preference. Enterostatins are selective inhibitors of appetite, particularly of fat intake. Hyperenterostatinemia in obesity is probably secondary to enterostatin resistance; therefore, the regulatory system is producing more enterostatin to counteract the resistance. This is very similar to hyperinsulinemia and hyperleptinemia in obesity. The diminution in the meal-induced secretion of enterostatin in obesity suggests a delay in the appearance of satiety, leading to increased caloric intake. In rats enterostatin decreases body weight by decreasing fat-calorie intake and increasing the sympathetic firing rate of the nerves in interscapular brown adipose tissue. Enterostatin levels are elevated in the plasma of obese women, and enterostatin secretion is diminished after satiety. Oral administration of enterostatin, however, has no effect on food intake, energy expenditure, or body weight in subjects with a preference for a high-fat diet experiencing a negative energy and fat balance, and the physiology of enterostatin in humans remains to be defined. (PMID: 10084574 , 9526102 , 8886249 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Ala-pro-gly-pro-arg	MeSH
APGPR	MeSH
Procolipase activation peptide	MeSH
Alanyl-prolyl-glycyl-prolyl-arginine	MeSH
H-Ala-pro-gly-pro-arg-OH	HMDB
L-Alanyl-L-prolylglycyl-L-prolyl-L-arginine	HMDB
N2-[1-[N-(1-L-Alanyl-L-prolyl)glycyl]-L-prolyl] L-arginine	HMDB
(2S)-2-({[(2S)-1-[2-({[(2S)-1-[(2S)-2-aminopropanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)acetyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-5-carbamimidamidopentanoate	Generator, HMDB

Chemical Formula

C₂₁H₃₆N₈O₆

Average Molecular Weight

496.5605

Monoisotopic Molecular Weight

496.275780924

IUPAC Name

(2S)-2-{[(2S)-1-(2-{[(2S)-1-[(2S)-2-aminopropanoyl]pyrrolidin-2-yl]formamido}acetyl)pyrrolidin-2-yl]formamido}-5-[(diaminomethylidene)amino]pentanoic acid

Traditional Name

enterostatin

CAS Registry Number

117830-79-2

SMILES

C[C@H](N)C(=O)N1CCC[C@H]1C(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCN=C(N)N)C(O)=O

InChI Identifier

InChI=1S/C21H36N8O6/c1-12(22)19(33)29-10-4-6-14(29)17(31)26-11-16(30)28-9-3-7-15(28)18(32)27-13(20(34)35)5-2-8-25-21(23)24/h12-15H,2-11,22H2,1H3,(H,26,31)(H,27,32)(H,34,35)(H4,23,24,25)/t12-,13-,14-,15-/m0/s1

InChI Key

ITZMJCSORYKOSI-AJNGGQMLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-).

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoyl derivatives

Direct Parent

Benzoyl derivatives

Alternative Parents

Substituents

Benzoyl
Benzaldehyde
Aryl-aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aldehyde
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzaldehydes (CHEBI:17169 )
an aryl aldehyde (BENZALDEHYDE )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 10084574)

Source

Endogenous

Endogenous (HMDB: HMDB0006117)

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	0.73 g/L	ALOGPS
logP	-3	ALOGPS
logP	-5.4	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.49	ChemAxon
pKa (Strongest Basic)	11.25	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	226.54 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	123.7 m³·mol⁻¹	ChemAxon
Polarizability	50.75 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0006117

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023831

KNApSAcK ID

Not Available

Chemspider ID

2340236

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3082883

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Bowyer R C; Jehanli A M; Patel G; Hermon-Taylor J Development of enzyme-linked immunosorbent assay for free human pro-colipase activation peptide (APGPR). Clinica chimica acta; international journal of clinical chemistry (1991), 200(2-3), 137-52.

Showing chemical card for APGPR Enterostatin (CFc000002654)

MOL for CFc000002654 (APGPR Enterostatin)

3D MOL for CFc000002654 (APGPR Enterostatin)

3D SDF for CFc000002654 (APGPR Enterostatin)

3D-SDF for CFc000002654 (APGPR Enterostatin)

PDB for CFc000002654 (APGPR Enterostatin)

3D PDB for CFc000002654 (APGPR Enterostatin)

SMILES for CFc000002654 (APGPR Enterostatin)

INCHI for CFc000002654 (APGPR Enterostatin)

Structure for CFc000002654 (APGPR Enterostatin)

3D Structure for CFc000002654 (APGPR Enterostatin)