CHEBI:16414 - L-valine

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ChEBI Name L-valine
ChEBI ID CHEBI:16414
ChEBI ASCII Name L-valine
Definition The L-enantiomer of valine.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:46376, CHEBI:46282, CHEBI:46484, CHEBI:46418, CHEBI:13186, CHEBI:21417, CHEBI:6321
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Valine (symbol Val or V) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH3+ form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO− form under biological conditions), and a side chain isopropyl group, making it a non-polar aliphatic amino acid. Valine is essential in humans, meaning the body cannot synthesize it; it must be obtained from dietary sources which are foods that contain proteins, such as meats, dairy products, soy products, beans and legumes. It is encoded by all codons starting with GU (GUU, GUC, GUA, and GUG).
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Formula C5H11NO2
Net Charge 0
Average Mass 117.14638
Monoisotopic Mass 117.07898
InChI InChI=1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m0/s1
InChIKey KZSNJWFQEVHDMF-BYPYZUCNSA-N
SMILES CC(C)[C@H](N)C(O)=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Chlamydomonas reinhardtii (NCBI:txid3055) See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932) Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
micronutrient
Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
(via valine )
Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
(via valine )
Application(s): nutraceutical
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
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ChEBI Ontology
Outgoing L-valine (CHEBI:16414) has role Escherichia coli metabolite (CHEBI:76971)
L-valine (CHEBI:16414) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
L-valine (CHEBI:16414) has role algal metabolite (CHEBI:84735)
L-valine (CHEBI:16414) has role human metabolite (CHEBI:77746)
L-valine (CHEBI:16414) has role micronutrient (CHEBI:27027)
L-valine (CHEBI:16414) has role mouse metabolite (CHEBI:75771)
L-valine (CHEBI:16414) has role nutraceutical (CHEBI:50733)
L-valine (CHEBI:16414) is a L-α-amino acid (CHEBI:15705)
L-valine (CHEBI:16414) is a proteinogenic amino acid (CHEBI:83813)
L-valine (CHEBI:16414) is a pyruvate family amino acid (CHEBI:26463)
L-valine (CHEBI:16414) is a valine (CHEBI:27266)
L-valine (CHEBI:16414) is conjugate acid of L-valinate (CHEBI:32851)
L-valine (CHEBI:16414) is conjugate base of L-valinium (CHEBI:32852)
L-valine (CHEBI:16414) is enantiomer of D-valine (CHEBI:27477)
L-valine (CHEBI:16414) is tautomer of L-valine zwitterion (CHEBI:57762)
Incoming L-valine derivative (CHEBI:84129) has functional parent L-valine (CHEBI:16414)
Ac-Tyr-Val-Ala-Asp-chloromethylketone (CHEBI:230455) has functional parent L-valine (CHEBI:16414)
Ala-Leu-Val-Ser (CHEBI:73375) has functional parent L-valine (CHEBI:16414)
Ala-Val-Asp-His (CHEBI:73383) has functional parent L-valine (CHEBI:16414)
Ala-Val-Asp-Pro (CHEBI:73384) has functional parent L-valine (CHEBI:16414)
Ala-Val-Asp-Ser (CHEBI:73386) has functional parent L-valine (CHEBI:16414)
Ala-Val-Asp-Tyr (CHEBI:73391) has functional parent L-valine (CHEBI:16414)
Ala-Val-Pro-Pro (CHEBI:73392) has functional parent L-valine (CHEBI:16414)
Asp-Leu-Phe-Val (CHEBI:73431) has functional parent L-valine (CHEBI:16414)
Asp-Phe-Val-Tyr (CHEBI:73293) has functional parent L-valine (CHEBI:16414)
Asp-Phe-Val-Val (CHEBI:73438) has functional parent L-valine (CHEBI:16414)
Asp-Trp-Trp-Val (CHEBI:73440) has functional parent L-valine (CHEBI:16414)
Asp-Val-Gly-Pro (CHEBI:73441) has functional parent L-valine (CHEBI:16414)
Asp-Val-Pro-Pro (CHEBI:73443) has functional parent L-valine (CHEBI:16414)
Asp-Val-Val-Val (CHEBI:73444) has functional parent L-valine (CHEBI:16414)
cryptomaldamide (CHEBI:156424) has functional parent L-valine (CHEBI:16414)
dolastatin 10 (CHEBI:67357) has functional parent L-valine (CHEBI:16414)
Gln-Val (CHEBI:141433) has functional parent L-valine (CHEBI:16414)
Glu-Ile-Val (CHEBI:73499) has functional parent L-valine (CHEBI:16414)
Glu-Phe-Val (CHEBI:73501) has functional parent L-valine (CHEBI:16414)
Glu-Val-Thr-Leu-Tyr peptide residue (CHEBI:85622) has functional parent L-valine (CHEBI:16414)
Glu-Val-Val (CHEBI:73502) has functional parent L-valine (CHEBI:16414)
Ile-Leu-Val-Tyr (CHEBI:73519) has functional parent L-valine (CHEBI:16414)
Leu-Val (CHEBI:73579) has functional parent L-valine (CHEBI:16414)
Leu-Val-Asp (CHEBI:73576) has functional parent L-valine (CHEBI:16414)
Leu-Val-Gly (CHEBI:73577) has functional parent L-valine (CHEBI:16414)
Leu-Val-Ser (CHEBI:73578) has functional parent L-valine (CHEBI:16414)
Lys-Val (CHEBI:73607) has functional parent L-valine (CHEBI:16414)
Met-Val (CHEBI:73616) has functional parent L-valine (CHEBI:16414)
Phe-Val (CHEBI:73638) has functional parent L-valine (CHEBI:16414)
Phe-Val-Asp (CHEBI:73639) has functional parent L-valine (CHEBI:16414)
Pro-Trp-Val-Gly (CHEBI:73650) has functional parent L-valine (CHEBI:16414)
Pro-Val-Gly-Pro (CHEBI:73649) has functional parent L-valine (CHEBI:16414)
Pro-Val-Val-Pro (CHEBI:176850) has functional parent L-valine (CHEBI:16414)
pyroglutamylvaline (CHEBI:132991) has functional parent L-valine (CHEBI:16414)
soblidotin (CHEBI:32135) has functional parent L-valine (CHEBI:16414)
Trp-Trp-Val (CHEBI:144555) has functional parent L-valine (CHEBI:16414)
Val-Arg (CHEBI:73711) has functional parent L-valine (CHEBI:16414)
Val-Asn (CHEBI:73698) has functional parent L-valine (CHEBI:16414)
Val-Asn-Pro (CHEBI:73697) has functional parent L-valine (CHEBI:16414)
Val-FMDP (CHEBI:74509) has functional parent L-valine (CHEBI:16414)
Val-Gly (CHEBI:73699) has functional parent L-valine (CHEBI:16414)
Val-His (CHEBI:73700) has functional parent L-valine (CHEBI:16414)
Val-Pro (CHEBI:73701) has functional parent L-valine (CHEBI:16414)
Val-Pro-Pro (CHEBI:73696) has functional parent L-valine (CHEBI:16414)
Val-Tyr (CHEBI:73703) has functional parent L-valine (CHEBI:16414)
Val-Val (CHEBI:73704) has functional parent L-valine (CHEBI:16414)
ficellomycin (CHEBI:156531) has part L-valine (CHEBI:16414)
L-valine-d8 (CHEBI:192086) is a L-valine (CHEBI:16414)
L-valinium (CHEBI:32852) is conjugate acid of L-valine (CHEBI:16414)
L-valinate (CHEBI:32851) is conjugate base of L-valine (CHEBI:16414)
D-valine (CHEBI:27477) is enantiomer of L-valine (CHEBI:16414)
L-valine residue (CHEBI:30015) is substituent group from L-valine (CHEBI:16414)
L-valino group (CHEBI:32854) is substituent group from L-valine (CHEBI:16414)
L-valyl group (CHEBI:32853) is substituent group from L-valine (CHEBI:16414)
L-valine zwitterion (CHEBI:57762) is tautomer of L-valine (CHEBI:16414)
IUPAC Name
L-valine
Synonyms Sources
(2S)-2-amino-3-methylbutanoic acid IUPAC
(S)-valine ChemIDplus
2-Amino-3-methylbutyric acid KEGG COMPOUND
L-(+)-alpha-Aminoisovaleric acid HMDB
L-alpha-Amino-beta-methylbutyric acid HMDB
L-Valin ChEBI
L-Valine KEGG COMPOUND
V ChEBI
Val ChEBI
VALINE PDBeChem
Manual Xrefs Databases
4128 DrugCentral
C00001398 KNApSAcK
C00183 KEGG COMPOUND
D00039 KEGG DRUG
DB00161 DrugBank
HMDB0000883 HMDB
L-valine Wikipedia
VAL MetaCyc
VAL PDBeChem
View more database links
Registry Numbers Types Sources
1721136 Reaxys Registry Number Reaxys
2827 Gmelin Registry Number Gmelin
72-18-4 CAS Registry Number KEGG COMPOUND
72-18-4 CAS Registry Number ChemIDplus
72-18-4 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations
Last Modified
11 April 2024