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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:53:12 UTC
Update Date2022-03-07 02:53:33 UTC
HMDB IDHMDB0033007
Secondary Accession Numbers
  • HMDB33007
Metabolite Identification
Common Name(2R,3R)-2,3-Butanediol
Description(2R,3R)-2,3-Butanediol is found in cocoa and cocoa products. (2R,3R)-2,3-Butanediol is isolated from cocoa butter and roots of Ruta graveolens (rue).2,3-Butanediol is one of the constitutional isomers of butanediol. The 2R,3R stereoisomer of 2,3-butanediol is produced by a variety of microorganisms, in a process known as butanediol fermentation. It is found in cocoa butter and in the roots of Ruta graveolens. (Wikipedia).
Structure
Data?1563862338
Synonyms
ValueSource
(R,R)-(-)-Butane-2,3-diolChEBI
(R,R)-2,3-ButanediolChEBI
(R,R)-2,3-Butylene glycolChEBI
(-)-(2R,3R)-ButanediolHMDB
(-)-2,3-ButanediolHMDB
(2R,3R)-(-)-2,3-ButanediolHMDB
(2R,3R)-Butane-2,3-diolHMDB
L-(-)-2,3-ButanediolHMDB
levo-2,3-ButanediolHMDB
Chemical FormulaC4H10O2
Average Molecular Weight90.121
Monoisotopic Molecular Weight90.068079564
IUPAC Name(2R,3R)-butane-2,3-diol
Traditional Name(R,R)-butane-2,3-diol
CAS Registry Number24347-58-8
SMILES
C[C@@H](O)[C@@H](C)O
InChI Identifier
InChI=1S/C4H10O2/c1-3(5)4(2)6/h3-6H,1-2H3/t3-,4-/m1/s1
InChI KeyOWBTYPJTUOEWEK-QWWZWVQMSA-N
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
Ontology
Not AvailableNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point19.7 °CNot Available
Boiling Point77.00 to 78.00 °C. @ 10.00 mm HgThe Good Scents Company Information System
Water Solubility759300 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.88Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+117.95431661259
DarkChem[M-H]-114.71131661259
DeepCCS[M+H]+125.39430932474
DeepCCS[M-H]-122.84830932474
DeepCCS[M-2H]-158.87730932474
DeepCCS[M+Na]+133.6930932474
AllCCS[M+H]+126.332859911
AllCCS[M+H-H2O]+122.032859911
AllCCS[M+NH4]+130.432859911
AllCCS[M+Na]+131.632859911
AllCCS[M-H]-127.332859911
AllCCS[M+Na-2H]-132.032859911
AllCCS[M+HCOO]-137.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(2R,3R)-2,3-ButanediolC[C@@H](O)[C@@H](C)O1549.7Standard polar33892256
(2R,3R)-2,3-ButanediolC[C@@H](O)[C@@H](C)O760.1Standard non polar33892256
(2R,3R)-2,3-ButanediolC[C@@H](O)[C@@H](C)O753.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(2R,3R)-2,3-Butanediol,1TMS,isomer #1C[C@@H](O)[C@@H](C)O[Si](C)(C)C901.5Semi standard non polar33892256
(2R,3R)-2,3-Butanediol,2TMS,isomer #1C[C@@H](O[Si](C)(C)C)[C@@H](C)O[Si](C)(C)C1028.0Semi standard non polar33892256
(2R,3R)-2,3-Butanediol,1TBDMS,isomer #1C[C@@H](O)[C@@H](C)O[Si](C)(C)C(C)(C)C1123.9Semi standard non polar33892256
(2R,3R)-2,3-Butanediol,2TBDMS,isomer #1C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)O[Si](C)(C)C(C)(C)C1483.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (2R,3R)-2,3-Butanediol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9000000000-cc27e53ef044f7cb15a52016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (2R,3R)-2,3-Butanediol GC-MS (2 TMS) - 70eV, Positivesplash10-01b9-9520000000-fa7488838e20f2dd123b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (2R,3R)-2,3-Butanediol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (2R,3R)-2,3-Butanediol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R,3R)-2,3-Butanediol 10V, Positive-QTOFsplash10-0006-9000000000-373d8ab05d8ca30b99362016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R,3R)-2,3-Butanediol 20V, Positive-QTOFsplash10-006x-9000000000-c995422d63c292e20b8f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R,3R)-2,3-Butanediol 40V, Positive-QTOFsplash10-0a4i-9000000000-5639537d59074e5a4a6c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R,3R)-2,3-Butanediol 10V, Negative-QTOFsplash10-000i-9000000000-aa5e86f920a11ea2d7492016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R,3R)-2,3-Butanediol 20V, Negative-QTOFsplash10-000i-9000000000-cef0995334342db934ba2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R,3R)-2,3-Butanediol 40V, Negative-QTOFsplash10-00di-9000000000-c4f65aef56394c6d3a252016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R,3R)-2,3-Butanediol 10V, Positive-QTOFsplash10-0a4i-9000000000-2e058d12c0f9880bd53d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R,3R)-2,3-Butanediol 20V, Positive-QTOFsplash10-0a4i-9000000000-77a30103f1d168eecd212021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R,3R)-2,3-Butanediol 40V, Positive-QTOFsplash10-0002-9000000000-4c2f1d8ca7aa89a88c6c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R,3R)-2,3-Butanediol 10V, Negative-QTOFsplash10-000i-9000000000-09fc38b483234e7b66aa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R,3R)-2,3-Butanediol 20V, Negative-QTOFsplash10-000f-9000000000-79fde7f9417c0129ac4c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (2R,3R)-2,3-Butanediol 40V, Negative-QTOFsplash10-0006-9000000000-452a5f79625d3401d4952021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB010997
KNApSAcK IDNot Available
Chemspider ID196452
KEGG Compound IDC03044
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound225936
PDB IDNot Available
ChEBI ID16982
Food Biomarker OntologyNot Available
VMH IDBTD_RR
MarkerDB IDNot Available
Good Scents IDrw1138431
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in acid-amino acid ligase activity
Specific function:
Accepts ubiquitin from the E1 complex and catalyzes its covalent attachment to other proteins. In vitro catalyzes 'Lys-48'-linked polyubiquitination. Mediates the selective degradation of short-lived and abnormal proteins. Functions in the E6/E6-AP-induced ubiquitination of p53/TP53. Mediates ubiquitination of PEX5 and autoubiquitination of STUB1 and TRAF6. Involved in the signal-induced conjugation and subsequent degradation of NFKBIA, FBXW2-mediated GCM1 ubiquitination and degradation, MDM2-dependent degradation of p53/TP53 and the activation of MAVS in the mitochondria by DDX58/RIG-I in response to viral infection. Essential for viral activation of IRF3.
Gene Name:
UBE2D2
Uniprot ID:
P62837
Molecular weight:
16735.06
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]