Valyl-Valine

Common Name

Valyl-Valine Description

Valyl-Valine is a dipeptied compoosed of two valine residues. 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. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite. Structure

Synonyms

Value Source L-Valyl-L-valineHMDB V-V DipeptideHMDB Val-valHMDB Valine valine dipeptideHMDB Valine-valine dipeptideHMDB ValylvalineHMDB VV DipeptideHMDB

Chemical Formlia

C₁₀H₂₀N₂O₃ Average Molecliar Weight

216.2774 Monoisotopic Molecliar Weight

216.147392516 IUPAC Name

2-(2-amino-3-methylbutanamido)-3-methylbutanoic acid Traditional Name

val-val CAS Registry Number

Not Available SMILES

InChI Identifier

InChI Key

KRNYOVHEKOBTEF-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Carboxylic acids and derivatives Direct Parent

Dipeptides Alternative Parents

Valine and derivatives

N-acyl-alpha amino acids

Alpha amino acid amides

Methyl-branched fatty acids

N-acyl amines

Secondary carboxylic acid amides

Amino acids

Monocarboxylic acids and derivatives

Carboxylic acids

Organopnictogen compounds

Organic oxides

Monoalkylamines

Hydrocarbon derivatives

Carbonyl compounds

Substituents

Alpha-dipeptide

N-acyl-alpha-amino acid

Valine or derivatives

N-acyl-alpha amino acid or derivatives

Alpha-amino acid amide

Alpha-amino acid or derivatives

Branched fatty acid

Methyl-branched fatty acid

N-acyl-amine

Fatty amide

Fatty acid

Fatty acyl

Amino acid or derivatives

Secondary carboxylic acid amide

Carboxamide group

Amino acid

Carboxylic acid

Monocarboxylic acid or derivatives

Organic nitrogen compound

Organonitrogen compound

Primary aliphatic amine

Organooxygen compound

Primary amine

Hydrocarbon derivative

Carbonyl group

Organic oxide

Organopnictogen compound

Amine

Organic oxygen compound

Aliphatic acyclic compound

Molecliar Framework

Aliphatic acyclic compounds External Descriptors

Not Available Ontology Status

Expected but not Quantified Origin

Endogenous

Biofunction

Not Available Application

Not Available Cellliar locations

Not Available Physical Properties State

Solid Experimental Properties

Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogP-1.61Extrapolated

Predicted Properties

Property Value Source Water Solubility22.3 mg/mLALOGPS logP-1.4ALOGPS logP-1.6ChemAxon logS-0.99ALOGPS pKa (Strongest Acidic)4.01ChemAxon pKa (Strongest Basic)8.51ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count3ChemAxon Polar Surface Area92.42 ŲChemAxon Rotatable Bond Count5ChemAxon Refractivity55.79 m³·mol^-1ChemAxon Polarizability23.24 ųChemAxon Number of Rings0ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Not Available Biological Properties Cellliar Locations

Not Available Biofluid Locations

Not Available Tissue Location

Not Available Pathways

Not Available Normal Concentrations Not Available Abnormal Concentrations

Not Available Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

Not Available DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

Not Available Phenol Explorer Metabolite ID

Not Available FoodDB ID

Not Available 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 NuGOwiki Link

HMDB29140 Metagene Link

HMDB29140 METLIN ID

Not Available PubChem Compound

Not Available PDB ID

Not Available ChEBI ID

Not Available

Product: YM-58483

References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References

1. Nath M, Pokharia S, Eng G, Song X, Kumar A: New triorganotin (IV) derivatives of dipeptides as models for metal-protein interactions: synthesis, structural characterization and biological studies. Spectrochim Acta A Mol Biomol Spectrosc. 2006 Jan;63(1):66-75. Epub 2005 Jun 9. [PubMed:15950528 ]
2. Takahashi N, Sato T: Preferential utilization of dipeptides by Porphyromonas gingivalis. J Dent Res. 2001 May;80(5):1425-9. [PubMed:11437213 ]
3. Yang S, Jia C, Zhu H, Han S: CYP1A1 Ile462Val polymorphism and cervical cancer: evidence from a meta-analysis. Tumour Biol. 2012 Dec;33(6):2265-72. doi: 10.1007/s13277-012-0488-y. Epub 2012 Sep 5. [PubMed:22948778 ]
4. Marco-Pallares J, Nager W, Kramer UM, Cunillera T, Camara E, Cucurell D, Schule R, Schols L, Rodriguez-Fornells A, Munte TF: Neurophysiological markers of novelty processing are modulated by COMT and DRD4 genotypes. Neuroimage. 2010 Nov 15;53(3):962-9. doi: 10.1016/j.neuroimage.2010.02.012. Epub 2010 Feb 12. [PubMed:20156565 ]
5. Kawashiro K, Ishizaki H, Sugiyama S, Hayashi H: Esterification of N-benzyloxycarbonyldipeptides in ethanol-water with immobilized papain. Biotechnol Bioeng. 1993 Jul;42(3):309-14. [PubMed:18613014 ]
6. Qian QJ, Yang L, Wang YF, Zhang HB, Guan LL, Chen Y, Ji N, Liu L, Faraone SV: Gene-gene interaction between COMT and MAOA potentially predicts the intelligence of attention-deficit hyperactivity disorder boys in China. Behav Genet. 2010 May;40(3):357-65. doi: 10.1007/s10519-009-9314-8. Epub 2009 Nov 26. [PubMed:19941049 ]
7. Pakhomova SA, Korovaitseva GI, Monchakovskaia MIu, Vilianov VB, Frolova LP, Kasparov SV, Kolesnichenko EV, Golimbet VE: [Molecular-genetic study of early-onset schizophrenia]. Zh Nevrol Psikhiatr Im S S Korsakova. 2010;110(2):66-9. [PubMed:20436453 ]
8. Kulikova MA, Maluchenko NV, Timofeeva MA, Shlepzova VA, Schegolkova JV, Sysoeva OV, Ivanitsky AM, Tonevitsky AG: Effect of functional catechol-O-methyltransferase Val158Met polymorphism on physical aggression. Bull Exp Biol Med. 2008 Jan;145(1):62-4. [PubMed:19024004 ]
9. Rowe JB, Hughes L, Williams-Gray CH, Bishop S, Fallon S, Barker RA, Owen AM: The val158met COMT polymorphisms effect on atrophy in healthy aging and Parkinsons disease. Neurobiol Aging. 2010 Jun;31(6):1064-8. doi: 10.1016/j.neurobiolaging.2008.07.009. Epub 2008 Aug 27. [PubMed:18755526 ]
10. Kogiso M, Okada Y, Yase K, Shimizu T: Metal-complexed nanofiber formation in water from dicarboxylic valylvaline bolaamphiphiles. J Colloid Interface Sci. 2004 May 15;273(2):394-9. [PubMed:15082373 ]
11. Golimbet VE, Brusov OS, Factor MI, Zlobina GP, Lezheiko TV, Lavrushina OM, Petrova EA, Savina MA, Skvortsova VI: [Interaction effect of serotonin transporter gene and brain-derived neurotrophic factor on the platelet serotonin content in stroke patients]. Zh Nevrol Psikhiatr Im S S Korsakova. 2010;110(4 Suppl 2):42-5. [PubMed:20738025 ]
12. Nieder M, Hager L: Conversion of alpha-amino acids and peptides to nitriles and aldehydes by bromoperoxidase. Arch Biochem Biophys. 1985 Jul;240(1):121-7. [PubMed:4015093 ]
13. Whalley HC, Baig BJ, Hall J, Job DE, McIntosh AM, Cunningham-Owens DG, Johnstone EC, Lawrie SM: Effects of the BDNF val66met polymorphism on prefrontal brain function in a population at high genetic risk of schizophrenia. Am J Med Genet B Neuropsychiatr Genet. 2010 Dec 5;153B(8):1474-82. doi: 10.1002/ajmg.b.31128. Epub 2010 Oct 18. [PubMed:20957650 ]
14. Kibitov AO, Voskoboeva EIu, Brodianskii VM, Chuprova NA, Smirnova EV: [Association study of the Val158Met polymorphism of the catechol-O-methyltransferase gene and alcoholism and heroin dependence: the role of a family history]. Zh Nevrol Psikhiatr Im S S Korsakova. 2010;110(4):84-8. [PubMed:20517217 ]
15. Golimbet VE, Panteleeva GP, Bologov PV, Korovaitseva GI, Abramova LI: [Molecular-genetic approach to the clinical and nosologic differentiation of schizoaffective disorder]. Zh Nevrol Psikhiatr Im S S Korsakova. 2010;110(10):48-52. [PubMed:21183914 ]
16. Kogiso M, Okada Y, Hanada T, Yase K, Shimizu T: Self-assembled peptide fibers from valylvaline bola-amphiphiles by a parallel beta-sheet network. Biochim Biophys Acta. 2000 Jul 26;1475(3):346-52. [PubMed:10913835 ]

PMID: 10821800

Common Name

Valyl-Valine Description

Valyl-Valine is a dipeptied compoosed of two valine residues. 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. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite. Structure

Synonyms

Value Source L-Valyl-L-valineHMDB V-V DipeptideHMDB Val-valHMDB Valine valine dipeptideHMDB Valine-valine dipeptideHMDB ValylvalineHMDB VV DipeptideHMDB

Chemical Formlia

C₁₀H₂₀N₂O₃ Average Molecliar Weight

216.2774 Monoisotopic Molecliar Weight

216.147392516 IUPAC Name

2-(2-amino-3-methylbutanamido)-3-methylbutanoic acid Traditional Name

val-val CAS Registry Number

Not Available SMILES

InChI Identifier

InChI Key

KRNYOVHEKOBTEF-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Carboxylic acids and derivatives Direct Parent

Dipeptides Alternative Parents

Valine and derivatives

N-acyl-alpha amino acids

Alpha amino acid amides

Methyl-branched fatty acids

N-acyl amines

Secondary carboxylic acid amides

Amino acids

Monocarboxylic acids and derivatives

Carboxylic acids

Organopnictogen compounds

Organic oxides

Monoalkylamines

Hydrocarbon derivatives

Carbonyl compounds

Substituents

Alpha-dipeptide

N-acyl-alpha-amino acid

Valine or derivatives

N-acyl-alpha amino acid or derivatives

Alpha-amino acid amide

Alpha-amino acid or derivatives

Branched fatty acid

Methyl-branched fatty acid

N-acyl-amine

Fatty amide

Fatty acid

Fatty acyl

Amino acid or derivatives

Secondary carboxylic acid amide

Carboxamide group

Amino acid

Carboxylic acid

Monocarboxylic acid or derivatives

Organic nitrogen compound

Organonitrogen compound

Primary aliphatic amine

Organooxygen compound

Primary amine

Hydrocarbon derivative

Carbonyl group

Organic oxide

Organopnictogen compound

Amine

Organic oxygen compound

Aliphatic acyclic compound

Molecliar Framework

Aliphatic acyclic compounds External Descriptors

Not Available Ontology Status

Expected but not Quantified Origin

Endogenous

Biofunction

Not Available Application

Not Available Cellliar locations

Not Available Physical Properties State

Solid Experimental Properties

Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogP-1.61Extrapolated

Predicted Properties

Property Value Source Water Solubility22.3 mg/mLALOGPS logP-1.4ALOGPS logP-1.6ChemAxon logS-0.99ALOGPS pKa (Strongest Acidic)4.01ChemAxon pKa (Strongest Basic)8.51ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count3ChemAxon Polar Surface Area92.42 ŲChemAxon Rotatable Bond Count5ChemAxon Refractivity55.79 m³·mol^-1ChemAxon Polarizability23.24 ųChemAxon Number of Rings0ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Not Available Biological Properties Cellliar Locations

Not Available Biofluid Locations

Not Available Tissue Location

Not Available Pathways

Not Available Normal Concentrations Not Available Abnormal Concentrations

Not Available Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

Not Available DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

Not Available Phenol Explorer Metabolite ID

Not Available FoodDB ID

Not Available 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 NuGOwiki Link

HMDB29140 Metagene Link

HMDB29140 METLIN ID

Not Available PubChem Compound

Not Available PDB ID

Not Available ChEBI ID

Not Available

Product: YM-58483

References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References

1. Nath M, Pokharia S, Eng G, Song X, Kumar A: New triorganotin (IV) derivatives of dipeptides as models for metal-protein interactions: synthesis, structural characterization and biological studies. Spectrochim Acta A Mol Biomol Spectrosc. 2006 Jan;63(1):66-75. Epub 2005 Jun 9. [PubMed:15950528 ]
2. Takahashi N, Sato T: Preferential utilization of dipeptides by Porphyromonas gingivalis. J Dent Res. 2001 May;80(5):1425-9. [PubMed:11437213 ]
3. Yang S, Jia C, Zhu H, Han S: CYP1A1 Ile462Val polymorphism and cervical cancer: evidence from a meta-analysis. Tumour Biol. 2012 Dec;33(6):2265-72. doi: 10.1007/s13277-012-0488-y. Epub 2012 Sep 5. [PubMed:22948778 ]
4. Marco-Pallares J, Nager W, Kramer UM, Cunillera T, Camara E, Cucurell D, Schule R, Schols L, Rodriguez-Fornells A, Munte TF: Neurophysiological markers of novelty processing are modulated by COMT and DRD4 genotypes. Neuroimage. 2010 Nov 15;53(3):962-9. doi: 10.1016/j.neuroimage.2010.02.012. Epub 2010 Feb 12. [PubMed:20156565 ]
5. Kawashiro K, Ishizaki H, Sugiyama S, Hayashi H: Esterification of N-benzyloxycarbonyldipeptides in ethanol-water with immobilized papain. Biotechnol Bioeng. 1993 Jul;42(3):309-14. [PubMed:18613014 ]
6. Qian QJ, Yang L, Wang YF, Zhang HB, Guan LL, Chen Y, Ji N, Liu L, Faraone SV: Gene-gene interaction between COMT and MAOA potentially predicts the intelligence of attention-deficit hyperactivity disorder boys in China. Behav Genet. 2010 May;40(3):357-65. doi: 10.1007/s10519-009-9314-8. Epub 2009 Nov 26. [PubMed:19941049 ]
7. Pakhomova SA, Korovaitseva GI, Monchakovskaia MIu, Vilianov VB, Frolova LP, Kasparov SV, Kolesnichenko EV, Golimbet VE: [Molecular-genetic study of early-onset schizophrenia]. Zh Nevrol Psikhiatr Im S S Korsakova. 2010;110(2):66-9. [PubMed:20436453 ]
8. Kulikova MA, Maluchenko NV, Timofeeva MA, Shlepzova VA, Schegolkova JV, Sysoeva OV, Ivanitsky AM, Tonevitsky AG: Effect of functional catechol-O-methyltransferase Val158Met polymorphism on physical aggression. Bull Exp Biol Med. 2008 Jan;145(1):62-4. [PubMed:19024004 ]
9. Rowe JB, Hughes L, Williams-Gray CH, Bishop S, Fallon S, Barker RA, Owen AM: The val158met COMT polymorphisms effect on atrophy in healthy aging and Parkinsons disease. Neurobiol Aging. 2010 Jun;31(6):1064-8. doi: 10.1016/j.neurobiolaging.2008.07.009. Epub 2008 Aug 27. [PubMed:18755526 ]
10. Kogiso M, Okada Y, Yase K, Shimizu T: Metal-complexed nanofiber formation in water from dicarboxylic valylvaline bolaamphiphiles. J Colloid Interface Sci. 2004 May 15;273(2):394-9. [PubMed:15082373 ]
11. Golimbet VE, Brusov OS, Factor MI, Zlobina GP, Lezheiko TV, Lavrushina OM, Petrova EA, Savina MA, Skvortsova VI: [Interaction effect of serotonin transporter gene and brain-derived neurotrophic factor on the platelet serotonin content in stroke patients]. Zh Nevrol Psikhiatr Im S S Korsakova. 2010;110(4 Suppl 2):42-5. [PubMed:20738025 ]
12. Nieder M, Hager L: Conversion of alpha-amino acids and peptides to nitriles and aldehydes by bromoperoxidase. Arch Biochem Biophys. 1985 Jul;240(1):121-7. [PubMed:4015093 ]
13. Whalley HC, Baig BJ, Hall J, Job DE, McIntosh AM, Cunningham-Owens DG, Johnstone EC, Lawrie SM: Effects of the BDNF val66met polymorphism on prefrontal brain function in a population at high genetic risk of schizophrenia. Am J Med Genet B Neuropsychiatr Genet. 2010 Dec 5;153B(8):1474-82. doi: 10.1002/ajmg.b.31128. Epub 2010 Oct 18. [PubMed:20957650 ]
14. Kibitov AO, Voskoboeva EIu, Brodianskii VM, Chuprova NA, Smirnova EV: [Association study of the Val158Met polymorphism of the catechol-O-methyltransferase gene and alcoholism and heroin dependence: the role of a family history]. Zh Nevrol Psikhiatr Im S S Korsakova. 2010;110(4):84-8. [PubMed:20517217 ]
15. Golimbet VE, Panteleeva GP, Bologov PV, Korovaitseva GI, Abramova LI: [Molecular-genetic approach to the clinical and nosologic differentiation of schizoaffective disorder]. Zh Nevrol Psikhiatr Im S S Korsakova. 2010;110(10):48-52. [PubMed:21183914 ]
16. Kogiso M, Okada Y, Hanada T, Yase K, Shimizu T: Self-assembled peptide fibers from valylvaline bola-amphiphiles by a parallel beta-sheet network. Biochim Biophys Acta. 2000 Jul 26;1475(3):346-52. [PubMed:10913835 ]

PMID: 10821800