2-Hydroxy-3-methylvalerate (YMDB01571)

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Identification

YMDB ID

YMDB01571

Name

2-Hydroxy-3-methylvalerate

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

2-Hydroxy-3-methylpentanoic acid or 2-hydroxy-3-methylvaleric acid (HMVA) is an organic acid generated by L-isoleucine metabolism. It is derived from the reduction of 2-Keto-3-methylvaleric acid (KMVA), possibly through the action of a lactate dehydrogenase. There are 4 stereoisomers of HMVA (2S,3S-HMVA, 2R,3R-HMVA, 2S,3R-HMVA and 2R,3S-HMVA), of which the 2S,3S and 2S,3R derivatives are generally separable. [PMID: 1429566]

Structure

MOL SDF PDB SMILES InChI

Synonyms

(2R,3R)-2-Hydroxy-3-methyl-pentanoate
(2R,3R)-2-Hydroxy-3-methyl-pentanoic acid
(2R,3R)-2-Hydroxy-3-methylpentanoate
(2R,3R)-2-Hydroxy-3-methylpentanoic acid
2-Hydroxy-3-methyl-pentanoate
2-Hydroxy-3-methyl-valerate
2-Hydroxy-3-methyl-valeric acid
2-Hydroxy-3-methylpentanoate
2-Hydroxy-3-methylvalerate
2-Hydroxy-3-methylvaleric acid
a-Hydroxy-b-methylvalerate
a-Hydroxy-b-methylvaleric acid
alpha-Hydroxy-beta-methylvalerate
alpha-Hydroxy-beta-methylvaleric acid
HMVA
2-Hydroxy-3-methyl-pentanoic acid

CAS number

488-15-3

Weight

Average: 132.1577
Monoisotopic: 132.07864425

InChI Key

RILPIWOPNGRASR-RFZPGFLSSA-N

InChI

InChI=1S/C6H12O3/c1-3-4(2)5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)/t4-,5-/m1/s1

IUPAC Name

(2R,3R)-2-hydroxy-3-methylpentanoic acid

Traditional IUPAC Name

2-hydroxy-3-methyl-valerate

Chemical Formula

C₆H₁₂O₃

SMILES

CC[C@@H](C)[C@@H](O)C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Hydroxy fatty acids

Alternative Parents

Substituents

Branched fatty acid
Methyl-branched fatty acid
Hydroxy fatty acid
Alpha-hydroxy acid
Hydroxy acid
Monosaccharide
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Hydroxy fatty acids (LMFA01050380 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	149 g/L	ALOGPS
logP	0.74	ALOGPS
logP	0.86	ChemAxon
logS	0.05	ALOGPS
pKa (Strongest Acidic)	4.25	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	32.44 m³·mol⁻¹	ChemAxon
Polarizability	13.77 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
1615 ± 81 µM	YEB media with 0.5 mM glucose	aerobic	Brewer's yeast	Experimentally Determined Not Available
Conversion Details Here

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9000000000-ed210d81f7dd591ba305	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-070i-9430000000-6a69d25573a59e501509	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-ee593b4e36128495adaa	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-dbb7417a40039e144182	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0019-9500000000-af6ad46fd2217e11644c	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-015i-6900000000-a4c1daf19028c3b5134f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-9100000000-869a6d71fe88a292f540	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-b1a7373d307d666ee4d4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001r-6900000000-f3e353eb7493baf38742	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01q0-9500000000-7d4a297dfcfc8042262c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-befdfe1bd9ab81fcab68	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-066r-9200000000-aa3018de5b1cc18a62c9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-066s-9000000000-335c8d3f561c609e78a3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-3aa61810dec2a5384f29	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-6a76fa84654b3400f5b4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2900000000-a2221076b3b27d49107e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9200000000-02760c89b2616afc5434	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	89228
HMDB ID	HMDB00317
Pubchem Compound ID	10796774
Kegg ID	Not Available
ChemSpider ID	8972081
FOODB ID	FDB021944
Wikipedia ID	Not Available
BioCyc ID	Not Available

Structure for #<Compound:0xadd6ba34>