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Identification
YMDB IDYMDB00413
Name(R,R)-butane-2,3-diol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description(2R,3R)-2,3-Butanediol, also known as (R,R)-2,3-butylene glycol or (2R,3R)-butane-2,3-diol, belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions (2R,3R)-2,3-Butanediol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
  • (R,R)-(-)-butane-2,3-diol
  • (R,R)-2,3-Butanediol
  • (R,R)-2,3-Butylene glycol
  • (R,R)-Butane-2,3-diol
  • [R,R]-2,3-butanediol
  • 2,3-Butanediol
  • (-)-(2R,3R)-Butanediol
  • (-)-2,3-Butanediol
  • (2R,3R)-(-)-2,3-Butanediol
  • (2R,3R)-Butane-2,3-diol
  • L-(-)-2,3-Butanediol
  • Levo-2,3-butanediol
CAS number24347-58-8
WeightAverage: 90.121
Monoisotopic: 90.068079564
InChI KeyOWBTYPJTUOEWEK-QWWZWVQMSA-N
InChIInChI=1S/C4H10O2/c1-3(5)4(2)6/h3-6H,1-2H3/t3-,4-/m1/s1
IUPAC Name(2R,3R)-butane-2,3-diol
Traditional IUPAC Name(R,R)-butane-2,3-diol
Chemical FormulaC4H10O2
SMILESC[C@@H](O)[C@@H](C)O
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct Parent1,2-diols
Alternative Parents
Substituents
  • Secondary alcohol
  • 1,2-diol
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility603 g/LALOGPS
logP-0.59ALOGPS
logP-0.38ChemAxon
logS0.83ALOGPS
pKa (Strongest Acidic)14.22ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity23.39 m³·mol⁻¹ChemAxon
Polarizability9.82 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Butanoate metabolismec00650 Map00650
SMPDB ReactionsNot Available
KEGG Reactions
NAD + (R,R)-butane-2,3-diolNADH + hydron + (R)-Acetoin
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9000000000-cc27e53ef044f7cb15a5JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01b9-9520000000-fa7488838e20f2dd123bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-373d8ab05d8ca30b9936JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9000000000-c995422d63c292e20b8fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-5639537d59074e5a4a6cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-aa5e86f920a11ea2d749JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-cef0995334342db934baJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-c4f65aef56394c6d3a25JSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Gonzalez, E., Fernandez, M. R., Larroy, C., Sola, L., Pericas, M. A., Pares, X., Biosca, J. A. (2000). "Characterization of a (2R,3R)-2,3-butanediol dehydrogenase as the Saccharomyces cerevisiae YAL060W gene product. Disruption and induction of the gene." J Biol Chem 275:35876-35885.10938079
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16982
HMDB IDHMDB0033007
Pubchem Compound ID225936
Kegg IDC03044
ChemSpider ID196452
FOODB IDFDB010997
Wikipedia2,3-Butanediol
BioCyc IDBUTANEDIOL

Enzymes

General function:
Involved in zinc ion binding
Specific function:
Catalyzes the irreversible reduction of 2,3-butanediol to (S)-acetoin in the presence of NADH
Gene Name:
BDH1
Uniprot ID:
P39714
Molecular weight:
41537.69922
Reactions
(R)-acetoin + NAD(+) → diacetyl + NADH.