CHEBI:38655 - (S)-2-methylbutyric acid

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ChEBI Name (S)-2-methylbutyric acid ChEBI ID CHEBI:38655 ChEBI ASCII Name (S)-2-methylbutyric acid Definition The (S)-enantiomer of 2-methylbutanoic acid. Stars This entity has been manually annotated by the ChEBI Team. Supplier Information ChemicalBook:CB5289161, ChemicalBook:CB82415020, eMolecules:491376, ZINC000000391203 Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Formula C5H10O2 Net Charge 0 Average Mass 102.13170 Monoisotopic Mass 102.06808 InChI InChI=1S/C5H10O2/c1-3-4(2)5(6)7/h4H,3H2,1-2H3,(H,6,7)/t4-/m0/s1 InChIKey WLAMNBDJUVNPJU-BYPYZUCNSA-N SMILES CC[C@H](C)C(O)=O Roles Classification Chemical Role(s): Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid ) Biological Role(s): bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria. (via 2-methylbutyric acid ) human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). (via 2-methylbutyric acid ) View more via ChEBI Ontology ChEBI Ontology Outgoing (S)-2-methylbutyric acid (CHEBI:38655) is a 2-methylbutyric acid (CHEBI:37070) (S)-2-methylbutyric acid (CHEBI:38655) is conjugate acid of (S)-2-methylbutanoate (CHEBI:145932) (S)-2-methylbutyric acid (CHEBI:38655) is enantiomer of (R)-2-methylbutyric acid (CHEBI:45525) Incoming (S)-2-methylbutanoyl-CoA (CHEBI:90222) has functional parent (S)-2-methylbutyric acid (CHEBI:38655) egonol-2ʼʼʼ-methyl butanoate (CHEBI:69550) has functional parent (S)-2-methylbutyric acid (CHEBI:38655) lovastatin (CHEBI:40303) has functional parent (S)-2-methylbutyric acid (CHEBI:38655) mevinolinic acid (CHEBI:82985) has functional parent (S)-2-methylbutyric acid (CHEBI:38655) pescaprein XXI (CHEBI:67851) has functional parent (S)-2-methylbutyric acid (CHEBI:38655) pescaprein XXII (CHEBI:67852) has functional parent (S)-2-methylbutyric acid (CHEBI:38655) pescaprein XXIII (CHEBI:67853) has functional parent (S)-2-methylbutyric acid (CHEBI:38655) pescaprein XXIV (CHEBI:67854) has functional parent (S)-2-methylbutyric acid (CHEBI:38655) pescaprein XXIX (CHEBI:67859) has functional parent (S)-2-methylbutyric acid (CHEBI:38655) pescaprein XXVII (CHEBI:67857) has functional parent (S)-2-methylbutyric acid (CHEBI:38655) pescaprein XXVIII (CHEBI:67858) has functional parent (S)-2-methylbutyric acid (CHEBI:38655) pescaprein XXX (CHEBI:67860) has functional parent (S)-2-methylbutyric acid (CHEBI:38655) pravastatin (CHEBI:63618) has functional parent (S)-2-methylbutyric acid (CHEBI:38655) pravastatin lactone (CHEBI:145933) has functional parent (S)-2-methylbutyric acid (CHEBI:38655) (S)-2-methylbutanoate (CHEBI:145932) is conjugate base of (S)-2-methylbutyric acid (CHEBI:38655) (R)-2-methylbutyric acid (CHEBI:45525) is enantiomer of (S)-2-methylbutyric acid (CHEBI:38655) IUPAC Name (2S)-2-methylbutanoic acid Synonyms Sources (S)-2-methylbutanoic acid NIST Chemistry WebBook (S)-α-methylbutanoic acid ChEBI Registry Numbers Types Sources 1720485 Beilstein Registry Number Beilstein 1730-91-2 CAS Registry Number ChemIDplus 1730-91-2 CAS Registry Number NIST Chemistry WebBook 3648078 Beilstein Registry Number Beilstein 532948 Gmelin Registry Number Gmelin Citation Hafner EW, Holley BW, Holdom KS, Lee SE, Wax RG, Beck D, McArthur HA, Wernau WC (1991) Branched-chain fatty acid requirement for avermectin production by a mutant of Streptomyces avermitilis lacking branched-chain 2-oxo acid dehydrogenase activity. The Journal of antibiotics 44, 349-356 [PubMed:2026560] [show Abstract] The eight natural avermectins produced by Streptomyces avermitilis have the carbon skeleton of either isobutyric or S-2-methylbutyric acid incorporated into their structures. A mutant of S. avermitilis has been isolated that contains no functional branched-chain 2-oxo acid dehydrogenase activity. The mutant, in contrast to its parent, is unable to grow with isoleucine, valine and leucine as carbon sources. In medium lacking both S(+)-2-methylbutyric and isobutyric acid, the mutant is also incapable of making the natural avermectins, while supplementation with either one of these compounds restores production of the corresponding four natural avermectins. These facts indicate that in S. avermitilis the branched-chain 2-oxo acid dehydrogenase enzyme functions not only to catabolize the cellular branched-chain amino acids in order to meet energy and growth requirements but also to provide the small branched-chain organic acid precursor molecules necessary for avermectin biosynthesis. Supplementation of the mutant strain with R(-)-2-methylbutyric acid yields novel isomeric avermectins unseen in the (unsupplemented) wild-type strain. It was also concluded that acetate and propionate production by branched-chain 2-oxo acid degradation is not absolutely essential for avermectin production. Last Modified 05 November 2015