Showing Compound Card for L-Valine (CDB000136)

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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
DescriptionValine, abbreviated as Val or V, one of 20 proteinogenic amino acids, is a non-polar amino acid with the chemical formula HO2CCH(NH2)CH(CH3)2. Valine is an essential amino acid that humans do not synthesize and must acquire from diet, usually from protein sources. Along with leucine and isoleucine, valine is a branched-chain amino acid (BCAA), an amino acid whose carbon structure is marked by a branch point. These three amino acids are critical to human life and are particularly involved in stress, energy and muscle metabolism. BCAA supplementation as therapy, both oral and intravenous, in human health and disease holds great promise. Despite their structural similarities, the branched amino acids have different metabolic routes, with valine going solely to carbohydrates, leucine solely to fats and isoleucine to both. The different metabolism accounts for different requirements for these essential amino acids in humans: 12 mg/kg, 14 mg/kg and 16 mg/kg of valine, leucine, and isoleucine, respectively. Furthermore, these amino acids have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors. Many types of inborn errors of BCAA metabolism exist and are marked by various abnormalities. The most common form is the maple syrup urine disease, marked by a sweet urinary odor. Other abnormalities are associated with a wide range of symptoms, such as mental retardation, ataxia, hypoglycemia, spinal muscle atrophy, rash, vomiting and excessive muscle movement. Most forms of BCAA metabolism errors are corrected by dietary restriction of BCAA and at least one form is correctable by supplementation with 10 mg of biotin daily. BCAA are decreased in patients with liver disease, such as hepatitis, hepatic coma, cirrhosis, extrahepatic biliary atresia or portacaval shunt; aromatic amino acids (AAA) tyrosine, tryptophan and phenylalanine, as well as methionine are increased in these conditions. Valine has been established as a useful supplemental therapy for an ailing liver. All the BCAA probably compete with AAA for absorption into the brain. Supplemental BCAA with vitamin B6 and zinc help normalize the BCAA:AAA ratio. In sickle-cell disease, the hydrophobic amino acid valine replaces the hydrophilic amino acid glutamic acid in beta-globin, causing it to misfold. The sickle cell hemoglobin is thus prone to aggregation. Hypervalinemia is another example of an inborn error of metabolism involving valine, not the other BCAA. It is caused by a deficiency in the valine transaminase gene (PMID: 6067402 ). As with most amino acids, L-valine is also found in Cannabis plants (PMID: 6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S)-2-Amino-3-methylbutanoic acidChEBI
(S)-ValineChEBI
2-Amino-3-methylbutyric acidChEBI
L-(+)-alpha-Aminoisovaleric acidChEBI
L-alpha-Amino-beta-methylbutyric acidChEBI
L-ValinChEBI
VChEBI
ValChEBI
VALINEChEBI
(2S)-2-Amino-3-methylbutanoateGenerator
2-Amino-3-methylbutyrateGenerator
L-(+)-a-AminoisovalerateGenerator
L-(+)-a-Aminoisovaleric acidGenerator
L-(+)-alpha-AminoisovalerateGenerator
L-(+)-Α-aminoisovalerateGenerator
L-(+)-Α-aminoisovaleric acidGenerator
L-a-Amino-b-methylbutyrateGenerator
L-a-Amino-b-methylbutyric acidGenerator
L-alpha-Amino-beta-methylbutyrateGenerator
L-Α-amino-β-methylbutyrateGenerator
L-Α-amino-β-methylbutyric acidGenerator
(S)-2-Amino-3-methyl-butanoateHMDB
(S)-2-Amino-3-methyl-butanoic acidHMDB
(S)-2-Amino-3-methylbutanoateHMDB
(S)-2-Amino-3-methylbutanoic acidHMDB
(S)-2-Amino-3-methylbutyrateHMDB
(S)-2-Amino-3-methylbutyric acidHMDB
(S)-a-Amino-b-methylbutyrateHMDB
(S)-a-Amino-b-methylbutyric acidHMDB
(S)-alpha-Amino-beta-methylbutyrateHMDB
(S)-alpha-Amino-beta-methylbutyric acidHMDB
2-Amino-3-methylbutanoateHMDB
2-Amino-3-methylbutanoic acidHMDB
L ValineHMDB
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
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-05fr-9000000000-5d10fb7acd70b2f433682018-05-25View Spectrum
GC-MSL-Valine, 2 TMS, GC-MS Spectrumsplash10-0006-0910000000-23bfcf2795f71f458bdaSpectrum
GC-MSL-Valine, 2 TMS, GC-MS Spectrumsplash10-0006-0920000000-7892bb9d4d9afcc23410Spectrum
GC-MSL-Valine, 2 TMS, GC-MS Spectrumsplash10-0006-0910000000-f2491152816b9c5dc7edSpectrum
GC-MSL-Valine, 1 TMS, GC-MS Spectrumsplash10-0znj-1900000000-7c976d7c11a402db399fSpectrum
GC-MSL-Valine, 2 TMS, GC-MS Spectrumsplash10-00dl-8910000000-78e8ee971ad7298c23cdSpectrum
GC-MSL-Valine, 1 TMS, GC-MS Spectrumsplash10-00di-9200000000-805e6724e5181af78c81Spectrum
GC-MSL-Valine, 2 TMS, GC-MS Spectrumsplash10-0006-0910000000-a212771a5ea868139d5aSpectrum
GC-MSL-Valine, non-derivatized, GC-MS Spectrumsplash10-059t-0900000000-7b8e4e98ac9158bf26d9Spectrum
GC-MSL-Valine, non-derivatized, GC-MS Spectrumsplash10-0006-0910000000-9079324093be9a14d47aSpectrum
GC-MSL-Valine, non-derivatized, GC-MS Spectrumsplash10-0006-0910000000-23bfcf2795f71f458bdaSpectrum
GC-MSL-Valine, non-derivatized, GC-MS Spectrumsplash10-0006-0920000000-7892bb9d4d9afcc23410Spectrum
GC-MSL-Valine, non-derivatized, GC-MS Spectrumsplash10-0006-0910000000-f2491152816b9c5dc7edSpectrum
GC-MSL-Valine, non-derivatized, GC-MS Spectrumsplash10-0znj-1900000000-7c976d7c11a402db399fSpectrum
GC-MSL-Valine, non-derivatized, GC-MS Spectrumsplash10-000i-2920000000-1628d46d5520c5f20de8Spectrum
GC-MSL-Valine, non-derivatized, GC-MS Spectrumsplash10-00dl-8910000000-78e8ee971ad7298c23cdSpectrum
GC-MSL-Valine, non-derivatized, GC-MS Spectrumsplash10-00di-9200000000-805e6724e5181af78c81Spectrum
GC-MSL-Valine, non-derivatized, GC-MS Spectrumsplash10-0006-0910000000-a212771a5ea868139d5aSpectrum
Predicted GC-MSL-Valine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-9000000000-602d1e01bc7567493e4cSpectrum
Predicted GC-MSL-Valine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-9500000000-a758682a7aafbd0d553eSpectrum
Predicted GC-MSL-Valine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Valine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Valine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Valine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Valine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-9000000000-67498a3295a1fe788c4b2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9000000000-fb359f44fcf1b83ee14d2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9000000000-8e5f620c04615765a0622012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014r-0900000000-619d80cc41221405e0bd2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-9000000000-17ab53cec2e6b727c3e92012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-9000000000-0dfbcc85d6423af91eda2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014l-4900000000-c50d79ba3a5013bcf29f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0uxr-0900000000-67a7784963ec75cecaa02012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-9000000000-4569516f23d8a712b4342012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-d928cac1226f19b8edc32012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-34059351f2cbd94a8acc2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-a36d8d68a6705027415f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-0900000000-1a5d8f4c1b293de18fed2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-0900000000-b410df2c18dfc8ab71652012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0gi0-6900000000-c87ff036e3a5d15b76702012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-9000000000-561b3b28fa82e0b106582012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-05fr-9000000000-11e7c0a3d5cf8e4dedfe2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4i-9000000000-6a6f8cd9629b0f09469c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0a4i-9000000000-4518f691bbda5739c0f12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positivesplash10-014i-0900000000-a931cfc8207edac337752012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-9000000000-430332b13b8c6368136b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014i-0900000000-ffb286a8ae38a0a3e6d22012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-9500000000-bb54662a5fd1dd142d902016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-1f7d9c10db4226a383c12016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fu-9000000000-f6d7e45bb3f3436e5eb72016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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

Enzyme Details
1. Propionyl-CoA carboxylase beta chain, mitochondrial
General function:
Involved in ligase activity
Specific function:
Not Available
Gene Name:
PCCB
Uniprot ID:
P05166
Molecular weight:
58215.13
Enzyme Details
2. Catechol O-methyltransferase
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
Enzyme Details
3. Branched-chain-amino-acid aminotransferase, cytosolic
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
Enzyme Details
4. Branched-chain-amino-acid aminotransferase, mitochondrial
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
Enzyme Details
5. Valine--tRNA ligase
General function:
Involved in nucleotide binding
Specific function:
Not Available
Gene Name:
VARS
Uniprot ID:
P26640
Molecular weight:
140474.755
Enzyme Details
6. Valine--tRNA ligase, mitochondrial
General function:
Involved in nucleotide binding
Specific function:
Not Available
Gene Name:
VARS2
Uniprot ID:
Q5ST30
Molecular weight:
102414.65

Transporters

Enzyme Details
1. Monocarboxylate transporter 10
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