Bovine Metabolome Database: Showing metabocard for Val-Pro-Pro (BMDB0062578)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2018-07-17 17:51:18 UTC

Update Date

2020-03-13 17:37:00 UTC

BMDB ID

BMDB0062578

Secondary Accession Numbers

BMDB62578

Metabolite Identification

Common Name

Val-Pro-Pro

Description

Val-pro-pro, also known as VPP or L-val-L-pro-L-pro, 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. Val-pro-pro 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-Val-L-pro-L-pro	ChEBI
V-p-p	ChEBI
VPP	ChEBI
Valine-proline-proline	MeSH
Valyl-prolyl-proline	MeSH
VPP Peptide	MeSH

Chemical Formula

C₁₅H₂₅N₃O₄

Average Molecular Weight

311.382

Monoisotopic Molecular Weight

311.184506297

IUPAC Name

(2S)-1-[(2S)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carboxylic acid

Traditional Name

(2S)-1-[(2S)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H25N3O4/c1-9(2)12(16)14(20)17-7-3-5-10(17)13(19)18-8-4-6-11(18)15(21)22/h9-12H,3-8,16H2,1-2H3,(H,21,22)/t10-,11-,12-/m0/s1

InChI Key

DOFAQXCYFQKSHT-SRVKXCTJSA-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 or derivatives
N-acyl-alpha-amino acid
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
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine-2-carboxamide
Tertiary carboxylic acid amide
Pyrrolidine
Carboxamide group
Amino acid or derivatives
Amino acid
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Carboxylic acid
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

tripeptide (CHEBI:73696 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

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	0.03	ALOGPS
logP	-2.5	ChemAxon
logS	-0.85	ALOGPS
pKa (Strongest Acidic)	3.44	ChemAxon
pKa (Strongest Basic)	8.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	103.94 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	79.47 m³·mol⁻¹	ChemAxon
Polarizability	32.43 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-4498000000-93076d38f81a1b7bb662	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0600-9210000000-26221da87366c3500c57	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0600-9100000000-cdfe40385fc60c1cb71c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03xr-0098000000-8894f7c772623d1e0202	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02ta-6971000000-551fa020422bbb50bf38	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02mj-9710000000-c9d8b26a5b808c822bc2	View in MoNA

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Milk

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 26686724	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB098402

KNApSAcK ID

Not Available

Chemspider ID

7993950

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9818200

PDB ID

Not Available

ChEBI ID

73696

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10. [PubMed:26686724 ]

Showing metabocard for Val-Pro-Pro (BMDB0062578)

Structure for BMDB0062578 (Val-Pro-Pro)