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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-06 21:03:48 UTC
Update Date2020-02-26 21:42:59 UTC
HMDB IDHMDB0029127
Secondary Accession Numbers
  • HMDB29127
Metabolite Identification
Common NameValylglycine
DescriptionValylglycine is a dipeptide composed of valine and glycine. It is an incomplete breakdown product of protein digestion or protein catabolism. Dipeptides are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Some dipeptides are known to have physiological or cell-signalling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis.
Structure
Data?1582753379
Synonyms
ValueSource
L-Val-glyChEBI
V-GChEBI
ValylglycineChEBI
VGChEBI
L-ValylglycineHMDB
N-L-ValylglycineHMDB
N-ValylglycineHMDB
V-G dipeptideHMDB
VG dipeptideHMDB
Val-GlyHMDB
Valine glycine dipeptideHMDB
Valine-glycine dipeptideHMDB
Valyl-glycineHMDB
Chemical FormulaC7H14N2O3
Average Molecular Weight174.2
Monoisotopic Molecular Weight174.100442319
IUPAC Name2-[(2S)-2-amino-3-methylbutanamido]acetic acid
Traditional Name[(2S)-2-amino-3-methylbutanamido]acetic acid
CAS Registry Number686-43-1
SMILES
CC(C)[C@H](N)C(=O)NCC(O)=O
InChI Identifier
InChI=1S/C7H14N2O3/c1-4(2)6(8)7(12)9-3-5(10)11/h4,6H,3,8H2,1-2H3,(H,9,12)(H,10,11)/t6-/m0/s1
InChI KeyIOUPEELXVYPCPG-LURJTMIESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Valine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Fatty acyl
  • Fatty amide
  • N-acyl-amine
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Carboxylic acid salt
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Primary aliphatic amine
  • Organic zwitterion
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-3.06Extrapolated
Predicted Properties
PropertyValueSource
Water Solubility26.3 g/LALOGPS
logP-2.5ALOGPS
logP-3.1ChemAxon
logS-0.82ALOGPS
pKa (Strongest Acidic)3.87ChemAxon
pKa (Strongest Basic)8.51ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity42.3 m³·mol⁻¹ChemAxon
Polarizability17.71 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 ]
  2. 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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID5361214
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6993110
PDB IDNot Available
ChEBI ID73699
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gordon-Smith EC, Dacie JV, Blecher TE, French EA, Wiltshirre BG, Lehmann H: Haemoglobin Nottingham, beta FG 5 (98) valgly: a new unstable haemoglobin producing severe haemolysis. Proc R Soc Med. 1973 Jun;66(6):507-8. [PubMed:4781799 ]
  2. Kizer JS, Bateman RC Jr, Miller CR, Humm J, Busby WH Jr, Youngblood WW: Purification and characterization of a peptidyl glycine monooxygenase from porcine pituitary. Endocrinology. 1986 Jun;118(6):2262-7. [PubMed:3698913 ]
  3. D'Alagni M, Pispisa B: Effect of urea on the optical rotatory dispersion of diketopiperazines of L-serine, L-alanine, L-lysine, L-valine, and L-valylglycine. J Biol Chem. 1969 Nov 10;244(21):5843-8. [PubMed:5350939 ]