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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 21:03:51 UTC
Update Date2022-09-22 18:34:56 UTC
HMDB IDHMDB0029140
Secondary Accession Numbers
  • HMDB29140
Metabolite Identification
Common NameValylvaline
DescriptionValylvaline, also known as H-L-val-L-val-OH or V-V, belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. Valylvaline has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make valylvaline a potential biomarker for the consumption of these foods. Valylvaline is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Valylvaline.
Structure
Data?1582753380
Synonyms
ValueSource
H-L-Val-L-val-OHChEBI
H-Val-val-OHChEBI
L-Val-L-valChEBI
V-VChEBI
L-Valyl-L-valineHMDB
V-V DipeptideHMDB
Val-valHMDB
Valine valine dipeptideHMDB
Valine-valine dipeptideHMDB
VV DipeptideHMDB
Di-valineHMDB
N-L-Valyl-L-valineHMDB
N-ValylvalineHMDB
Valyl-valineHMDB
ValylvalineChEBI
Chemical FormulaC10H20N2O3
Average Molecular Weight216.281
Monoisotopic Molecular Weight216.147392512
IUPAC Name(2S)-2-[(2S)-2-amino-3-methylbutanamido]-3-methylbutanoic acid
Traditional Name(2S)-2-[(2S)-2-amino-3-methylbutanamido]-3-methylbutanoic acid
CAS Registry Number3918-94-3
SMILES
CC(C)[C@H](N)C(=O)N[C@@H](C(C)C)C(O)=O
InChI Identifier
InChI=1S/C10H20N2O3/c1-5(2)7(11)9(13)12-8(6(3)4)10(14)15/h5-8H,11H2,1-4H3,(H,12,13)(H,14,15)/t7-,8-/m0/s1
InChI KeyKRNYOVHEKOBTEF-YUMQZZPRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • N-acyl-alpha-amino acid
  • Valine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Fatty acyl
  • Fatty acid
  • Amino acid or derivatives
  • Amino acid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic oxide
  • Organic oxygen compound
  • Primary aliphatic amine
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Primary amine
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.61Extrapolated
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility22.3 g/LALOGPS
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
Polarizability23.38 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+157.52130932474
DeepCCS[M-H]-155.12530932474
DeepCCS[M-2H]-188.00930932474
DeepCCS[M+Na]+163.48530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ValylvalineCC(C)[C@H](N)C(=O)N[C@@H](C(C)C)C(O)=O2648.5Standard polar33892256
ValylvalineCC(C)[C@H](N)C(=O)N[C@@H](C(C)C)C(O)=O1653.6Standard non polar33892256
ValylvalineCC(C)[C@H](N)C(=O)N[C@@H](C(C)C)C(O)=O1663.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Valylvaline,1TMS,isomer #1CC(C)[C@H](N)C(=O)N[C@H](C(=O)O[Si](C)(C)C)C(C)C1728.1Semi standard non polar33892256
Valylvaline,1TMS,isomer #2CC(C)[C@H](NC(=O)[C@@H](N[Si](C)(C)C)C(C)C)C(=O)O1749.0Semi standard non polar33892256
Valylvaline,1TMS,isomer #3CC(C)[C@H](N)C(=O)N([C@H](C(=O)O)C(C)C)[Si](C)(C)C1699.7Semi standard non polar33892256
Valylvaline,2TMS,isomer #1CC(C)[C@H](N[Si](C)(C)C)C(=O)N[C@H](C(=O)O[Si](C)(C)C)C(C)C1804.6Semi standard non polar33892256
Valylvaline,2TMS,isomer #1CC(C)[C@H](N[Si](C)(C)C)C(=O)N[C@H](C(=O)O[Si](C)(C)C)C(C)C1759.8Standard non polar33892256
Valylvaline,2TMS,isomer #2CC(C)[C@H](N)C(=O)N([C@H](C(=O)O[Si](C)(C)C)C(C)C)[Si](C)(C)C1713.6Semi standard non polar33892256
Valylvaline,2TMS,isomer #2CC(C)[C@H](N)C(=O)N([C@H](C(=O)O[Si](C)(C)C)C(C)C)[Si](C)(C)C1796.1Standard non polar33892256
Valylvaline,2TMS,isomer #3CC(C)[C@H](N[Si](C)(C)C)C(=O)N([C@H](C(=O)O)C(C)C)[Si](C)(C)C1755.4Semi standard non polar33892256
Valylvaline,2TMS,isomer #3CC(C)[C@H](N[Si](C)(C)C)C(=O)N([C@H](C(=O)O)C(C)C)[Si](C)(C)C1770.4Standard non polar33892256
Valylvaline,2TMS,isomer #4CC(C)[C@H](NC(=O)[C@H](C(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O1914.8Semi standard non polar33892256
Valylvaline,2TMS,isomer #4CC(C)[C@H](NC(=O)[C@H](C(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O1795.6Standard non polar33892256
Valylvaline,3TMS,isomer #1CC(C)[C@H](NC(=O)[C@H](C(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C1913.6Semi standard non polar33892256
Valylvaline,3TMS,isomer #1CC(C)[C@H](NC(=O)[C@H](C(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C1887.4Standard non polar33892256
Valylvaline,3TMS,isomer #2CC(C)[C@H](N[Si](C)(C)C)C(=O)N([C@H](C(=O)O[Si](C)(C)C)C(C)C)[Si](C)(C)C1781.6Semi standard non polar33892256
Valylvaline,3TMS,isomer #2CC(C)[C@H](N[Si](C)(C)C)C(=O)N([C@H](C(=O)O[Si](C)(C)C)C(C)C)[Si](C)(C)C1844.9Standard non polar33892256
Valylvaline,3TMS,isomer #3CC(C)[C@@H](C(=O)O)N(C(=O)[C@H](C(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1909.4Semi standard non polar33892256
Valylvaline,3TMS,isomer #3CC(C)[C@@H](C(=O)O)N(C(=O)[C@H](C(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1916.3Standard non polar33892256
Valylvaline,4TMS,isomer #1CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](C(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1983.7Semi standard non polar33892256
Valylvaline,4TMS,isomer #1CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)[C@H](C(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1998.9Standard non polar33892256
Valylvaline,1TBDMS,isomer #1CC(C)[C@H](N)C(=O)N[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)C1955.1Semi standard non polar33892256
Valylvaline,1TBDMS,isomer #2CC(C)[C@H](NC(=O)[C@@H](N[Si](C)(C)C(C)(C)C)C(C)C)C(=O)O1972.3Semi standard non polar33892256
Valylvaline,1TBDMS,isomer #3CC(C)[C@H](N)C(=O)N([C@H](C(=O)O)C(C)C)[Si](C)(C)C(C)(C)C1914.9Semi standard non polar33892256
Valylvaline,2TBDMS,isomer #1CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)C2216.3Semi standard non polar33892256
Valylvaline,2TBDMS,isomer #1CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)C2157.2Standard non polar33892256
Valylvaline,2TBDMS,isomer #2CC(C)[C@H](N)C(=O)N([C@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)C)[Si](C)(C)C(C)(C)C2152.6Semi standard non polar33892256
Valylvaline,2TBDMS,isomer #2CC(C)[C@H](N)C(=O)N([C@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)C)[Si](C)(C)C(C)(C)C2201.3Standard non polar33892256
Valylvaline,2TBDMS,isomer #3CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@H](C(=O)O)C(C)C)[Si](C)(C)C(C)(C)C2204.2Semi standard non polar33892256
Valylvaline,2TBDMS,isomer #3CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@H](C(=O)O)C(C)C)[Si](C)(C)C(C)(C)C2141.8Standard non polar33892256
Valylvaline,2TBDMS,isomer #4CC(C)[C@H](NC(=O)[C@H](C(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2336.7Semi standard non polar33892256
Valylvaline,2TBDMS,isomer #4CC(C)[C@H](NC(=O)[C@H](C(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2166.5Standard non polar33892256
Valylvaline,3TBDMS,isomer #1CC(C)[C@H](NC(=O)[C@H](C(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2568.4Semi standard non polar33892256
Valylvaline,3TBDMS,isomer #1CC(C)[C@H](NC(=O)[C@H](C(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2434.1Standard non polar33892256
Valylvaline,3TBDMS,isomer #2CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)C)[Si](C)(C)C(C)(C)C2434.1Semi standard non polar33892256
Valylvaline,3TBDMS,isomer #2CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N([C@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)C)[Si](C)(C)C(C)(C)C2399.1Standard non polar33892256
Valylvaline,3TBDMS,isomer #3CC(C)[C@@H](C(=O)O)N(C(=O)[C@H](C(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2566.3Semi standard non polar33892256
Valylvaline,3TBDMS,isomer #3CC(C)[C@@H](C(=O)O)N(C(=O)[C@H](C(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2454.1Standard non polar33892256
Valylvaline,4TBDMS,isomer #1CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](C(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2829.1Semi standard non polar33892256
Valylvaline,4TBDMS,isomer #1CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](C(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2698.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Valylvaline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valylvaline 10V, Positive-QTOFsplash10-014i-3490000000-ba3c7b790904d5a2b1262021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valylvaline 20V, Positive-QTOFsplash10-0fk9-9500000000-9a8d3974fc6b9e9f0a652021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valylvaline 40V, Positive-QTOFsplash10-0ab9-9000000000-b990a9717c8bf989a4712021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valylvaline 10V, Negative-QTOFsplash10-014i-0190000000-40b068dba9854168bb962021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valylvaline 20V, Negative-QTOFsplash10-014i-3900000000-4948906383ed6b1d9eab2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valylvaline 40V, Negative-QTOFsplash10-0006-9100000000-4c81a7c8957e89d579922021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB112141
KNApSAcK IDNot Available
Chemspider ID96710
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound107475
PDB IDNot Available
ChEBI ID73704
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot 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, Vil'ianov 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 polymorphism's effect on atrophy in healthy aging and Parkinson's 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 ]
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