ContaminantDB: VPGPR Enterostatin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 05:52:35 UTC

Update Date

2016-11-09 01:21:20 UTC

Accession Number

CHEM035549

Identification

Common Name

VPGPR Enterostatin

Class

Small Molecule

Description

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-[1-[N-(1-L-Valyl-L-prolyl)glycyl]-L-prolyl]-L-arginine	HMDB
L-Valyl-L-prolylglycyl-L-prolyl-L-arginine	HMDB
(2S)-2-({[(2S)-1-[2-({[(2S)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)acetyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-5-carbamimidamidopentanoate	Generator, HMDB

Chemical Formula

C₂₃H₄₀N₈O₆

Average Molecular Mass

524.614 g/mol

Monoisotopic Mass

524.307 g/mol

CAS Registry Number

144964-56-7

IUPAC Name

(2S)-2-{[(2S)-1-(2-{[(2S)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]formamido}acetyl)pyrrolidin-2-yl]formamido}-5-[(diaminomethylidene)amino]pentanoic acid

Traditional Name

(2S)-2-{[(2S)-1-(2-{[(2S)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]formamido}acetyl)pyrrolidin-2-yl]formamido}-5-[(diaminomethylidene)amino]pentanoic acid

SMILES

CC(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/C23H40N8O6/c1-13(2)18(24)21(35)31-11-5-7-15(31)19(33)28-12-17(32)30-10-4-8-16(30)20(34)29-14(22(36)37)6-3-9-27-23(25)26/h13-16,18H,3-12,24H2,1-2H3,(H,28,33)(H,29,34)(H,36,37)(H4,25,26,27)/t14-,15-,16-,18-/m0/s1

InChI Key

QVZKZDOWTVQTPL-OVWQWFNUSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Valine or derivatives
Proline or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Alpha-amino acid or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine-2-carboxamide
Branched fatty acid
Heterocyclic fatty acid
Fatty acyl
Fatty acid
Pyrrolidine
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Guanidine
Amino acid
Secondary carboxylic acid amide
Carboximidamide
Organoheterocyclic compound
Propargyl-type 1,3-dipolar organic compound
Azacycle
Organic 1,3-dipolar compound
Carboxylic acid
Monocarboxylic acid or derivatives
Primary amine
Primary aliphatic amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Amine
Organonitrogen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.39 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-4.5	ChemAxon
logS	-3.1	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	12	ChemAxon
Refractivity	132.7 m³·mol⁻¹	ChemAxon
Polarizability	54.6 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fi0-9331300000-d2a1d2e5ebbba667634a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9321020000-48a69e256a3399d3c208	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-6864490000-90c6f290f6c618dbd5e8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00fr-9531000000-e07d244d22eecaeb5ac3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9310000000-a6c8363faab096a3f22c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1000920000-8fcb3a8178d7cf59bea6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-053r-8434910000-b6478147066844a932f4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0abc-9310000000-c9f3617f8f1896db08eb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-1000490000-fbd0aec065f15bfea07d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05fr-1101930000-078c1f95830b442c54b2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9421100000-d3f11d79314fc69b26cb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0001190000-15f8ae07ad55b89cc515	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05di-4332490000-ef2cb92d58eb9a213b53	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-6490000000-ea74bb27e91e11b6dcbf	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0003577

FooDB ID

FDB023200

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

8090424

ChEBI ID

Not Available

PubChem Compound ID

9914775

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Prasad C, Imamura M, Debata C, Svec F, Sumar N, Hermon-Taylor J: Hyperenterostatinemia in premenopausal obese women. J Clin Endocrinol Metab. 1999 Mar;84(3):937-41.

2. Ashmarin IP, Karazeeva EP, Lyapina LA, Samonina GE: The simplest proline-containing peptides PG, GP, PGP, and GPGG: regulatory activity and possible sources of biosynthesis. Biochemistry (Mosc). 1998 Feb;63(2):119-24.

3. Rytter E, Erlanson-Albertsson C, Lindahl L, Lundquist I, Viberg U, Akesson B, Oste R: Changes in plasma insulin, enterostatin, and lipoprotein levels during an energy-restricted dietary regimen including a new oat-based liquid food. Ann Nutr Metab. 1996;40(4):212-20.

VPGPR Enterostatin (CHEM035549)

Structure for CHEM035549: VPGPR Enterostatin