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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-05-18 14:04:04 UTC
Update Date2020-02-26 21:39:04 UTC
HMDB IDHMDB0013716
Secondary Accession Numbers
  • HMDB13716
Metabolite Identification
Common NameNorvaline
DescriptionNorvaline is a non-proteinogenic branched-chain amino acid. It has previously been reported to be a natural component of an antifungal peptide of Bacillus subtilis. Norvaline and other modified branched chain amino acids have received attention in recent studies, as they appear to be incorporated in some recombinant proteins found in E. coli. Norvaline is an amino acid with the chemical formula C5H11NO2, isomeric with valine. This amino acid is often made synthetically.
Structure
Data?1582753144
Synonyms
ValueSource
(R)-NorvalineChEBI
D-2-Aminovaleric acidChEBI
D-ApeChEBI
D-NorvalineChEBI
D-NvaChEBI
D-2-Aminopentanoic acidKegg
D-2-AminovalerateGenerator
D-2-AminopentanoateGenerator
(.+-.)-norvalineHMDB
(.+/-.)-norvalineHMDB
2-Amino-DL-valeric acidHMDB
2-Aminopentanoic acidsHMDB
2-Aminovaleric acidHMDB
2-Aminovaleric acidsHMDB
alpha -DL-Aminopentanoic acidHMDB
alpha-Aminopentanoic acidHMDB
alpha-Aminovaleric acidHMDB
alpha-DL-Aminopentanoic acidHMDB
DL-2-Aminopentanoic acidHMDB
DL-alpha -Aminovaleric acidHMDB
DL-alpha-Amino-N-valenic acidHMDB
DL-alpha-Aminovaleric acidHMDB
DL-NorvalineHMDB
Norvaline (acd/name 4.0)HMDB
NorvalinesHMDB
Chemical FormulaC5H11NO2
Average Molecular Weight117.1463
Monoisotopic Molecular Weight117.078978601
IUPAC Name(2R)-2-aminopentanoic acid
Traditional NameD-(-)-norvaline
CAS Registry Number760-78-1
SMILES
CCC[C@@H](N)C(O)=O
InChI Identifier
InChI=1S/C5H11NO2/c1-2-3-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m1/s1
InChI KeySNDPXSYFESPGGJ-SCSAIBSYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentD-alpha-amino acids
Alternative Parents
Substituents
  • D-alpha-amino acid
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point303 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility83.9 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility212 g/LALOGPS
logP-2ALOGPS
logP-1.9ChemAxon
logS0.26ALOGPS
pKa (Strongest Acidic)2.71ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity29.62 m³·mol⁻¹ChemAxon
Polarizability12.51 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fu-9000000000-463db7a51bc96eebb0fcSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9400000000-0b48fca984c779b8df56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-9600000000-2f35fd2b5cbb04e2b774Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-37a67ae027626a67be6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-b4ab8ccafd1a67b71b08Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3900000000-13e844a45f41a4d61e38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9600000000-b57d7c5c40031d4c9b27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-554519282162f7a95cd6Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.02 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
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. 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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID388660
KEGG Compound IDC01799
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNorvaline
METLIN IDNot Available
PubChem Compound439575
PDB IDNot Available
ChEBI ID28804
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available