(R,R)-butane-2,3-diol (YMDB00413)

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, belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions. Based on a literature review very few articles have been published on (2R,3R)-2,3-Butanediol.
Structure
Thumb
MOLSDFPDBSMILESInChI
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-diol ↔ NADH + 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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-2e058d12c0f9880bd53dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-77a30103f1d168eecd21JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-4c2f1d8ca7aa89a88c6cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-09fc38b483234e7b66aaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-9000000000-79fde7f9417c0129ac4cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-452a5f79625d3401d495JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
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

Protein Details
1. Diacetyl reductase [(R)-acetoin forming]
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.