Showing metabocard for Val-Pro-Pro (BMDB0062578)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-07-17 17:51:18 UTC
Update Date2020-03-13 17:37:00 UTC
MCDB ID BMDB0062578
Secondary Accession Numbers
  • BMDB62578
Metabolite Identification
Common NameVal-Pro-Pro
DescriptionVal-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
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
L-Val-L-pro-L-proChEBI
V-p-pChEBI
VPPChEBI
Valine-proline-prolineMeSH
Valyl-prolyl-prolineMeSH
VPP PeptideMeSH
Chemical FormulaC15H25N3O4
Average Molecular Weight311.382
Monoisotopic Molecular Weight311.184506297
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 NumberNot 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 KeyDOFAQXCYFQKSHT-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.03ALOGPS
logP-2.5ChemAxon
logS-0.85ALOGPS
pKa (Strongest Acidic)3.44ChemAxon
pKa (Strongest Basic)8.21ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area103.94 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity79.47 m³·mol⁻¹ChemAxon
Polarizability32.43 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-4498000000-93076d38f81a1b7bb6622019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0600-9210000000-26221da87366c3500c572019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0600-9100000000-cdfe40385fc60c1cb71c2019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-0098000000-8894f7c772623d1e02022019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02ta-6971000000-551fa020422bbb50bf382019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02mj-9710000000-c9d8b26a5b808c822bc22019-02-23View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB098402
KNApSAcK IDNot Available
Chemspider ID7993950
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9818200
PDB IDNot Available
ChEBI ID73696
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]