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(S)-Propane-1,2-diol (M2MDB001511)

Record Information
Version2.0
Creation Date2012-07-30 14:54:38 -0600
Update Date2015-09-13 12:56:14 -0600
Secondary Accession Numbers
  • ECMDB21102
Identification
Name:(S)-Propane-1,2-diol
DescriptionPropylene glycol, also called 1,2-propanediol or propane-1,2-diol, is an organic compound, specifically, a diol or double alcohol. It is a colorless, nearly odorless, clear, viscous liquid, hygroscopic and miscible with water, acetone, and chloroform. Propylene glycol contains an asymmetrical carbon atom, so it exists in two stereoisomers. (Wikipedia) The L or S isomer of propane-1,2-diol can be produced in E. coli by methylglyoxal degradation and anaerobic L-lactaldehyde degradation, where in both processes it is a waste product removed from the cell. (EcoCyc)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (2S)-propane-1,2-diol
  • (S)-1,2-propanediol
  • (S)-Propane-1,2-diol
  • (S)-propylene glycol
  • 1,2-Dihydroxypropane
  • 1,2-Propane-diol
  • 1,2-Propanediol
  • L-1,2-Propanediol
  • Propane-1,2-diol
  • Propanediol
  • Propylene glycol
  • S-(+)-Propylene glycol
  • S-1,2-PROPANEDIOL
Chemical Formula:C3H8O2
Weight:Average: 76.0944
Monoisotopic: 76.0524295
InChI Key:DNIAPMSPPWPWGF-VKHMYHEASA-N
InChI:InChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3/t3-/m0/s1
CAS number:4254-15-3
IUPAC Name:(2S)-propane-1,2-diol
Traditional IUPAC Name:(S)-1,2-propanediol
SMILES:C[C@H](O)CO
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
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:-59 °C (-74 oF)
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility952 g/LALOGPS
logP-1.1ALOGPS
logP-0.79ChemAxon
logS1.1ALOGPS
pKa (Strongest Acidic)14.47ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity18.97 m³·mol⁻¹ChemAxon
Polarizability8.01 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Hydrogen ion + Lactaldehyde + NADH <> (S)-Propane-1,2-diol + NAD
(S)-Propane-1,2-diol + NAD > Lactaldehyde + NADH
(R)-Propane-1,2-diol + (S)-Propane-1,2-diol + NAD <> D-Lactaldehyde + (S)-Lactaldehyde + NADH + Hydrogen ion
SMPDB Pathways:
Propanoate metabolismPW000940 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-055g-9000000000-27df50480b6cca9d0e9bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0kp0-9520000000-ffe4848ba88742d1a4d6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-0a1a58ae50ca7bfbc92fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9000000000-4f58eaf424aa13185ca2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-d0e5def95a7a7879dc71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-5bf5d9d3c7cf604af9a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-9000000000-ea5b27ac0cc585591f63View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-ecc48f7be3304c6cc1e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-9000000000-ea4d9d80ebf7615e6811View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-a77309b9b0e17e94870dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-7bb23415e61ec73a459cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-9000000000-5dba4634f494296e1347View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9000000000-2174cc6a153316ad8c52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-a1a685f935041163641bView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID29002
HMDB IDHMDB06213
Pubchem Compound ID439846
Kegg IDC02917
ChemSpider ID388890
Wikipedia(S)-propane-1,2-diol
BioCyc IDPROPANE-1-2-DIOL
EcoCyc IDPROPANE-1-2-DIOL
Ligand ExpoPGQ

Enzymes

Protein Details
1. Lactaldehyde reductase
General function:
Involved in oxidoreductase activity
Specific function:
(R)-propane-1,2-diol + NAD(+) = (R)- lactaldehyde + NADH
Gene Name:
fucO
Uniprot ID:
P0A9S1
Molecular weight:
40644
Reactions
(R)-propane-1,2-diol + NAD(+) = (R)-lactaldehyde + NADH.
(S)-propane-1,2-diol + NAD(+) = (S)-lactaldehyde + NADH.

Transporters

Protein Details
1. Outer membrane protein N
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
Protein Details
2. Outer membrane pore protein E
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
Protein Details
3. Outer membrane protein F
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
Protein Details
4. Outer membrane protein C
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368