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Record Information
Version1.0
Created at2020-03-18 23:26:07 UTC
Updated at2022-12-13 23:36:22 UTC
CannabisDB IDCDB000136
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameL-Valine
Description
Structure
Thumb
Synonyms
Chemical FormulaC5H11NO2
Average Molecular Weight117.15
Monoisotopic Molecular Weight117.079
IUPAC Name(2S)-2-amino-3-methylbutanoic acid
Traditional NameL-valine
CAS Registry Number72-18-4
SMILES
CC(C)[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m0/s1
InChI KeyKZSNJWFQEVHDMF-BYPYZUCNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as valine and derivatives. Valine and derivatives are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentValine and derivatives
Alternative Parents
Substituents
  • Valine or derivatives
  • Alpha-amino acid
  • L-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
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point295 - 300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility58.5 mg/mLNot Available
logP-2.26HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP-2.3ALOGPS
logP-2ChemAxon
logS0.26ALOGPS
pKa (Strongest Acidic)2.72ChemAxon
pKa (Strongest Basic)9.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity29.49 m³·mol⁻¹ChemAxon
Polarizability12.19 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
MS/MS
NMR
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Propionyl-CoA carboxylase beta chain, mitochondrialPCCB3q21-q22P05166 details
Catechol O-methyltransferaseCOMT22q11.21P21964 details
Branched-chain-amino-acid aminotransferase, cytosolicBCAT112p12.1P54687 details
Branched-chain-amino-acid aminotransferase, mitochondrialBCAT219q13O15382 details
Valine--tRNA ligaseVARS6p21.3P26640 details
Valine--tRNA ligase, mitochondrialVARS26p21.33Q5ST30 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Monocarboxylate transporter 10SLC16A106q21-q22Q8TF71 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Catechol O-methyltransferaseCOMT22q11.21P21964 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.537 mg/g dry wt
    • David S. Wishart,...
details
GabriolaDetected and Quantified0.334 mg/g dry wt
    • David S. Wishart,...
details
Island HoneyDetected and Quantified0.422 mg/g dry wt
    • David S. Wishart,...
details
QuadraDetected and Quantified0.439 mg/g dry wt
    • David S. Wishart,...
details
Sensi StarDetected and Quantified0.198 mg/g dry wt
    • David S. Wishart,...
details
Tangerine DreamDetected and Quantified0.172 mg/g dry wt
    • David S. Wishart,...
details
HMDB IDHMDB0000883
DrugBank IDDB00161
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004905
KNApSAcK IDC00001398
Chemspider ID6050
KEGG Compound IDC00183
BioCyc IDVAL
BiGG ID34167
Wikipedia LinkL-valine
METLIN ID5842
PubChem Compound6287
PDB IDNot Available
ChEBI ID16414
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Dancis J, Hutzler J, Tada K, Wada Y, Morikawa T, Arakawa T: Hypervalinemia. A defect in valine transamination. Pediatrics. 1967 Jun;39(6):813-7. [PubMed:6067402 ]

Enzymes

General function:
Involved in ligase activity
Specific function:
Not Available
Gene Name:
PCCB
Uniprot ID:
P05166
Molecular weight:
58215.13
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
General function:
Involved in catalytic activity
Specific function:
Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine.
Gene Name:
BCAT1
Uniprot ID:
P54687
Molecular weight:
38644.77
General function:
Involved in catalytic activity
Specific function:
Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine. May also function as a transporter of branched chain alpha-keto acids.
Gene Name:
BCAT2
Uniprot ID:
O15382
Molecular weight:
33776.315
General function:
Involved in nucleotide binding
Specific function:
Not Available
Gene Name:
VARS
Uniprot ID:
P26640
Molecular weight:
140474.755
General function:
Involved in nucleotide binding
Specific function:
Not Available
Gene Name:
VARS2
Uniprot ID:
Q5ST30
Molecular weight:
102414.65

Transporters

General function:
Involved in transmembrane transport
Specific function:
Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells
Gene Name:
SLC16A10
Uniprot ID:
Q8TF71
Molecular weight:
55492.1