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Showing metabocard for Propylene glycol (HMDB0001881)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
enzymes (3) Show 3 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-02-24 13:28:50 UTC
Update Date2023-02-21 17:15:55 UTC
HMDB IDHMDB0001881
Secondary Accession Numbers
  • HMDB01881
Metabolite Identification
Common NamePropylene glycol
DescriptionPropylene glycol (CAS: 57-55-6), also known as 1,2-propanediol, is an organic compound (a diol alcohol), usually a tasteless, odourless, and colourless clear oily liquid that is hygroscopic and miscible with water, acetone, and chloroform. It is manufactured by the hydration of propylene oxide. Propylene glycol is used as a solvent for intravenous, oral, and topical pharmaceutical preparations It is generally considered safe. However, in large doses, it can be toxic, especially if given over a short period of time. Intravenous lorazepam contains the largest amount of propylene glycol of commonly used drugs. In adults with normal liver and kidney function, the terminal half-life of propylene glycol ranges from 1.4 to 3.3 hours. Propylene glycol is metabolized by the liver to form lactate, acetate, and pyruvate. The nonmetabolized drug is excreted in the urine mainly as the glucuronide conjugate, approximately 12 to 45 percent is excreted unchanged in urine. Renal clearance decreases as the dose administered increases (390 ml/minute/173 m2 at a dose of 5 g/day but only 144 ml/minute/173 m2 at a dose of 21 g/day). These data suggest that renal clearance declines at higher propylene glycol doses because of the saturation of proximal tubular secretion of the drug. As an acceptable level of propylene glycol has not been defined, the clinical implication of a propylene glycol level is unclear. The World Health Organization (WHO) recommends a maximum consumption of 25 mg/kg/day (1.8 g/day for a 75 kg male) of propylene glycol when used as a food additive, but this limit does not address its use as a drug solvent. No maximum dose is recommended in the literature for intravenous therapy with propylene glycol. Intoxication occurs at much higher doses than the WHO dose limit and is exclusive to pharmacologic exposure. Propylene glycol toxicity includes the development of serum hyperosmolality, lactic acidosis, and kidney failure. It has been suggested that proximal tubular necrosis is the cause of acute kidney injury from propylene glycol. Along these lines, proximal tubular cell injury occurs in cultured human cells exposed to propylene glycol. Acute tubular necrosis was described with propylene glycol toxicity in a case of concomitant administration of intravenous lorazepam and trimethoprim sulfamethoxazole. Propylene glycol induced intoxication can also mimic sepsis or systemic inflammatory response syndrome (SIRS). Patients suspected of having sepsis with negative cultures should be evaluated for propylene glycol toxicity if they have been exposed to high dose lorazepam or other medications containing this solvent (PMID:17555487 ).
Structure
Data?1676999755
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001881 (Propylene glycol)


  Mrv1652303262021352D          

  5  4  0  0  1  0            999 V2000
    1.0717    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.2061    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3572   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3571    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
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3D MOL for HMDB0001881 (Propylene glycol)

HMDB0001881
     RDKit          3D
Propylene glycol
 13 12  0  0  0  0  0  0  0  0999 V2000
   -1.2269   -0.6357    0.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2244    0.2874   -0.3231 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6695    1.5986   -0.3299 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1186    0.2585    0.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6563   -1.0125    0.4540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9054   -0.1497    1.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7262   -1.4821    0.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8792   -1.0293   -0.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0232   -0.0241   -1.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9320    1.9246   -1.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0363    0.6604    1.4205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7872    0.9290   -0.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9884   -1.3249   -0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  6
  3 10  1  0
  4 11  1  0
  4 12  1  0
  5 13  1  0
M  END
Download

3D SDF for HMDB0001881 (Propylene glycol)


  Mrv1652303262021352D          

  5  4  0  0  1  0            999 V2000
    1.0717    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.2061    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3572   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3571    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001881

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H](O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3/t3-/m1/s1

> <INCHI_KEY>
DNIAPMSPPWPWGF-GSVOUGTGSA-N

> <FORMULA>
C3H8O2

> <MOLECULAR_WEIGHT>
76.0944

> <EXACT_MASS>
76.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
8.010010240094317

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-propane-1,2-diol

> <ALOGPS_LOGP>
-1.10

> <JCHEM_LOGP>
-0.7921040560000001

> <ALOGPS_LOGS>
1.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.996044021064442

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.470762978766011

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8584492517004216

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
18.9724

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.52e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
R-1,2-propanediol

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0001881 (Propylene glycol)

HMDB0001881
     RDKit          3D
Propylene glycol
 13 12  0  0  0  0  0  0  0  0999 V2000
   -1.2269   -0.6357    0.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2244    0.2874   -0.3231 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6695    1.5986   -0.3299 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1186    0.2585    0.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6563   -1.0125    0.4540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9054   -0.1497    1.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7262   -1.4821    0.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8792   -1.0293   -0.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0232   -0.0241   -1.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9320    1.9246   -1.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0363    0.6604    1.4205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7872    0.9290   -0.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9884   -1.3249   -0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  6
  3 10  1  0
  4 11  1  0
  4 12  1  0
  5 13  1  0
M  END
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PDB for HMDB0001881 (Propylene glycol)

HEADER    PROTEIN                                 26-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAR-20         0                                  
HETATM    1  C   UNK     0       2.001   1.155   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.667   0.385   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.667  -1.155   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.667   1.155   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.001   0.385   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0001881 (Propylene glycol)

COMPND    HMDB0001881
HETATM    1  C1  UNL     1      -1.227  -0.636   0.288  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.224   0.287  -0.323  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.669   1.599  -0.330  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.119   0.258   0.390  1.00  0.00           C  
HETATM    5  O2  UNL     1       1.656  -1.013   0.454  1.00  0.00           O  
HETATM    6  H1  UNL     1      -1.905  -0.150   1.012  1.00  0.00           H  
HETATM    7  H2  UNL     1      -0.726  -1.482   0.827  1.00  0.00           H  
HETATM    8  H3  UNL     1      -1.879  -1.029  -0.537  1.00  0.00           H  
HETATM    9  H4  UNL     1      -0.023  -0.024  -1.369  1.00  0.00           H  
HETATM   10  H5  UNL     1      -0.932   1.925  -1.229  1.00  0.00           H  
HETATM   11  H6  UNL     1       1.036   0.660   1.421  1.00  0.00           H  
HETATM   12  H7  UNL     1       1.787   0.929  -0.201  1.00  0.00           H  
HETATM   13  H8  UNL     1       1.988  -1.325  -0.404  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    4    9
CONECT    3   10
CONECT    4    5   11   12
CONECT    5   13
END
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SMILES for HMDB0001881 (Propylene glycol)

C[C@@H](O)CO
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INCHI for HMDB0001881 (Propylene glycol)

InChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3/t3-/m1/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(R)-1,2-PropanediolChEBI
R-1,2-PROPANEDIOLChEBI
(R)-Propylene glycolChEBI, KEGG
(-)-1,2-PropanediolHMDB
(-)-Propylene glycolHMDB
(2R)-1,2-PropanediolHMDB
(2R)-Propane-1,2-diolHMDB
(R)-(-)-1,2-PropanediolHMDB
(R)-2-Hydroxy-1-propanolHMDB
1,2-(RS)-PropanediolHMDB
1,2-DihydroxypropaneHMDB
1,2-PropanediolHMDB
1,2-Propylene glycolHMDB
1-Deoxy-sn-glycerolHMDB
2,3-PropanediolHMDB
2-HydroxypropanolHMDB
D-(-)-PropanediolHMDB
Isopropylene glycolHMDB
Methylethyl glycolHMDB
Methylethylene glycolHMDB
Monopropylene glycolHMDB
Propylene glycolHMDB
R-(-)-1,2-PropanediolHMDB
R-(-)-Propylene glycolHMDB
alpha-Propylene glycolHMDB
α-Propylene glycolHMDB
Chemical FormulaC3H8O2
Average Molecular Weight76.0944
Monoisotopic Molecular Weight76.0524295
IUPAC Name(2R)-propane-1,2-diol
Traditional NameR-1,2-propanediol
CAS Registry Number4254-14-2
SMILES
C[C@@H](O)CO
InChI Identifier
InChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3/t3-/m1/s1
InChI KeyDNIAPMSPPWPWGF-GSVOUGTGSA-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
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Health effectOrganoleptic effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial application
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-60 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 20 °CNot Available
LogP-0.92HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+119.19430932474
DeepCCS[M-H]-116.75830932474
DeepCCS[M-2H]-152.93130932474
DeepCCS[M+Na]+127.62830932474
AllCCS[M+H]+123.032859911
AllCCS[M+H-H2O]+118.632859911
AllCCS[M+NH4]+127.232859911
AllCCS[M+Na]+128.432859911
AllCCS[M-H]-131.232859911
AllCCS[M+Na-2H]-136.832859911
AllCCS[M+HCOO]-143.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Propylene glycolC[C@@H](O)CO1505.0Standard polar33892256
Propylene glycolC[C@@H](O)CO711.0Standard non polar33892256
Propylene glycolC[C@@H](O)CO735.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Propylene glycol,1TMS,isomer #1C[C@H](CO)O[Si](C)(C)C848.9Semi standard non polar33892256
Propylene glycol,1TMS,isomer #2C[C@@H](O)CO[Si](C)(C)C857.7Semi standard non polar33892256
Propylene glycol,2TMS,isomer #1C[C@H](CO[Si](C)(C)C)O[Si](C)(C)C999.7Semi standard non polar33892256
Propylene glycol,1TBDMS,isomer #1C[C@H](CO)O[Si](C)(C)C(C)(C)C1082.8Semi standard non polar33892256
Propylene glycol,1TBDMS,isomer #2C[C@@H](O)CO[Si](C)(C)C(C)(C)C1081.2Semi standard non polar33892256
Propylene glycol,2TBDMS,isomer #1C[C@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1427.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Propylene glycol GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014j-0900000000-d90655d5a614c4ddf9982020-03-26HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Propylene glycol GC-MS (2 TMS)splash10-014i-1900000000-ab4a1ff05d12757111702020-03-26HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Propylene glycol EI-B (Non-derivatized)splash10-0002-9000000000-a18bede40461dace657b2020-03-26HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Propylene glycol EI-B (Non-derivatized)splash10-0002-9000000000-6d2345a66e2cf8d2d3792020-03-26HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Propylene glycol GC-EI-TOF (Non-derivatized)splash10-014j-0900000000-d90655d5a614c4ddf9982020-03-26HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Propylene glycol GC-MS (Non-derivatized)splash10-014i-1900000000-ab4a1ff05d12757111702020-03-26HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Propylene glycol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-9000000000-cbc512db1a4c5510015e2020-03-26Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Propylene glycol Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0a7i-9000000000-6c96c59f8ba2e0e5353e2020-03-26HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propylene glycol Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-005d-9000000000-ae07e4049d24341335ec2020-03-26HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propylene glycol Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-00aj-9000000000-f455f8f0f79f9970711a2020-03-26HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propylene glycol EI-B (HITACHI RMU-7M) , Positive-QTOFsplash10-0002-9000000000-c5bf57086deb14e124952020-03-26HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propylene glycol EI-B (HITACHI M-80B) , Positive-QTOFsplash10-0002-9000000000-6d2345a66e2cf8d2d3792020-03-26HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propylene glycol 10V, Positive-QTOFsplash10-004i-9000000000-0a1a58ae50ca7bfbc92f2015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propylene glycol 20V, Positive-QTOFsplash10-0a6r-9000000000-4f58eaf424aa13185ca22015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propylene glycol 40V, Positive-QTOFsplash10-052f-9000000000-d0e5def95a7a7879dc712015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propylene glycol 10V, Negative-QTOFsplash10-004i-9000000000-5bf5d9d3c7cf604af9a32015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propylene glycol 20V, Negative-QTOFsplash10-056r-9000000000-ea5b27ac0cc585591f632015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propylene glycol 40V, Negative-QTOFsplash10-0a4i-9000000000-ecc48f7be3304c6cc1e02015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propylene glycol 10V, Negative-QTOFsplash10-0a6r-9000000000-ea4d9d80ebf7615e68112021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propylene glycol 20V, Negative-QTOFsplash10-0a4i-9000000000-a77309b9b0e17e94870d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propylene glycol 40V, Negative-QTOFsplash10-0006-9000000000-7bb23415e61ec73a459c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propylene glycol 10V, Positive-QTOFsplash10-0a4l-9000000000-5dba4634f494296e13472021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propylene glycol 20V, Positive-QTOFsplash10-0a4l-9000000000-2174cc6a153316ad8c522021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propylene glycol 40V, Positive-QTOFsplash10-0006-9000000000-a1a685f935041163641b2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2020-03-26Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 500 MHz, H2O, experimental)2020-03-26Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Breath
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Sweat
  • Urine
Tissue Locations
  • Epidermis
  • Intestine
  • Neuron
  • Platelet
  • Skeletal Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified22.3 +/- 3.3 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0-5.0 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified2.0 (0.0-5.0) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified33 +/- 50 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.63 +/- 0.4 (0 - 1.0) uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not AvailableNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected and Quantified3 (<1-50) uMAdult (>18 years old)Male
Normal		 details
SalivaDetected and Quantified20 (<1-178) uMAdult (>18 years old)Male
Normal		 details
SalivaDetected and Quantified17 (<1-84) uMAdult (>18 years old)Male
Normal		 details
SalivaDetected and Quantified8 (<1-46) uMAdult (>18 years old)Female
Normal		 details
SalivaDetected and Quantified1-121 uMAdult (>18 years old)Male
normal		 details
SalivaDetected and Quantified1-140 uMAdult (>18 years old)Male
normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected and Quantified26.76 +/- 21.09 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
 details
SalivaDetected and Quantified>10 uMAdult (>18 years old)BothNormal details
SweatDetected and Quantified< 10 uMAdult (60 years old)Male
Normal		 details
SweatDetected and Quantified< 10 uMAdult (40 years old)Male
Normal		 details
UrineDetected and Quantified20.586 +/- 22.556 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected and Quantified6.7 (1.4-44.3) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified7.0 (2.9) uMAdult (>18 years old)FemaleDown syndrome pregnancy details
BloodDetected and Quantified6.6 (1.9) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified36.3 +/- 19.9 uMAdult (>18 years old)BothHeart Transplant details
BloodDetected and Quantified9.66 +/- 4.10 uMAdult (>18 years old)Female
Pregnancy with fetuses with trisomy 18		 details
BloodDetected and Quantified7.94 +/- 3.69 uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified9.9 (4.9) uMAdult (>18 years old)FemaleEarly preeclampsia details
BloodDetected and Quantified8.0 (3.4) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified8.84 (2.78) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified8.25 (2.09) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified11.1 (5.0) uMAdult (>18 years old)FemaleLate-onset preeclampsia details
BloodDetected and Quantified11.8 (4.9) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified15.0 (5.0-35.4) uMAdult (>18 years old)Both
Cirrhosis		 details
BreathDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothAsthma details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected and Quantified2.0 (0.0-31.0) umol/mmol creatinineNot SpecifiedBothLung cancer details
UrineDetected and Quantified150.63 +/- 491.323 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Cirrhosis
  1. Casazza JP, Frietas J, Stambuk D, Morgan MY, Veech RL: The measurement of 1,2-propanediol, D, L-2,3-butanediol and meso-2,3-butanediol in controls and alcoholic cirrhotics. Alcohol Alcohol Suppl. 1987;1:607-9. [PubMed:3426740 ]
Early preeclampsia
  1. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ]
Pregnancy
  1. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ]
  2. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: First-trimester metabolomic detection of late-onset preeclampsia. Am J Obstet Gynecol. 2013 Jan;208(1):58.e1-7. doi: 10.1016/j.ajog.2012.11.003. Epub 2012 Nov 13. [PubMed:23159745 ]
  3. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomic analysis for first-trimester Down syndrome prediction. Am J Obstet Gynecol. 2013 May;208(5):371.e1-8. doi: 10.1016/j.ajog.2012.12.035. Epub 2013 Jan 8. [PubMed:23313728 ]
  4. Bahado-Singh RO, Akolekar R, Chelliah A, Mandal R, Dong E, Kruger M, Wishart DS, Nicolaides K: Metabolomic analysis for first-trimester trisomy 18 detection. Am J Obstet Gynecol. 2013 Jul;209(1):65.e1-9. doi: 10.1016/j.ajog.2013.03.028. Epub 2013 Mar 25. [PubMed:23535240 ]
  5. Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Late-onset preeclampsia
  1. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: First-trimester metabolomic detection of late-onset preeclampsia. Am J Obstet Gynecol. 2013 Jan;208(1):58.e1-7. doi: 10.1016/j.ajog.2012.11.003. Epub 2012 Nov 13. [PubMed:23159745 ]
Asthma
  1. van de Kant KD, van Berkel JJ, Jobsis Q, Lima Passos V, Klaassen EM, van der Sande L, van Schayck OC, de Jongste JC, van Schooten FJ, Derks E, Dompeling E, Dallinga JW: Exhaled breath profiling in diagnosing wheezy preschool children. Eur Respir J. 2013 Jan;41(1):183-8. doi: 10.1183/09031936.00122411. [PubMed:23277518 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Lung Cancer
  1. Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2009 Jan;37(Database issue):D603-10. doi: 10.1093/nar/gkn810. Epub 2008 Oct 25. [PubMed:18953024 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDDB02159
Phenol Explorer Compound IDNot Available
FooDB IDFDB008274
KNApSAcK IDC00007410
Chemspider ID228188
KEGG Compound IDC02912
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPropylene_glycol
METLIN IDNot Available
PubChem Compound259994
PDB IDNot Available
ChEBI ID28972
Food Biomarker OntologyNot Available
VMH ID12PPD_R
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceTuck, Michael William Marshall. Preparation of propylene glycol by hydrogenation of glycerol. PCT Int. Appl. (2008), 20pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [PubMed:12097436 ]
  2. Brucks R, Nanavaty M, Jung D, Siegel F: The effect of ultrasound on the in vitro penetration of ibuprofen through human epidermis. Pharm Res. 1989 Aug;6(8):697-701. [PubMed:2813262 ]
  3. Claverie F, Giordano-Labadie F, Bazex J: [Contact eczema induced by propylene glycol. Concentration and vehicle adapted for for patch tests]. Ann Dermatol Venereol. 1997;124(4):315-7. [PubMed:9739936 ]
  4. Li N, Liu Z, Jia X, Cui W, Wang W, Zhang X, Han C, Chen J, Wang M: [Study on the toxicological effect of chloropropanols on rats]. Wei Sheng Yan Jiu. 2003 Jul;32(4):349-52. [PubMed:14535099 ]
  5. Maltaris T, Dimmler A, Muller A, Binder H, Hoffmann I, Kohl J, Siebzehnrubl E, Beckmann MW, Dittrich R: The use of an open-freezing system with self-seeding for cryopreservation of mouse ovarian tissue. Reprod Domest Anim. 2005 Jun;40(3):250-4. [PubMed:15943700 ]
  6. Li GL, van der Geest R, Chanet L, van Zanten E, Danhof M, Bouwstra JA: In vitro iontophoresis of R-apomorphine across human stratum corneum. Structure-transport relationship of penetration enhancement. J Control Release. 2002 Nov 7;84(1-2):49-57. [PubMed:12399167 ]
  7. Fare JC, Guesnon P, Helouis JJ, Normand S, Andre JL, Duvaldestin P: [Intramuscular premedication with diazepam in a fat emulsion]. Cah Anesthesiol. 1984 May-Jun;32(4):303-6. [PubMed:6529665 ]
  8. Reichard GA Jr, Skutches CL, Hoeldtke RD, Owen OE: Acetone metabolism in humans during diabetic ketoacidosis. Diabetes. 1986 Jun;35(6):668-74. [PubMed:3086164 ]
  9. Casazza JP, Frietas J, Stambuk D, Morgan MY, Veech RL: The measurement of 1,2-propanediol, D, L-2,3-butanediol and meso-2,3-butanediol in controls and alcoholic cirrhotics. Alcohol Alcohol Suppl. 1987;1:607-9. [PubMed:3426740 ]
  10. Vaddi HK, Ho PC, Chan YW, Chan SY: Oxide terpenes as human skin penetration enhancers of haloperidol from ethanol and propylene glycol and their modes of action on stratum corneum. Biol Pharm Bull. 2003 Feb;26(2):220-8. [PubMed:12576684 ]
  11. Fernandez C, Marti-Mestres G, Ramos J, Maillols H: LC analysis of benzophenone-3: II application to determination of 'in vitro' and 'in vivo' skin penetration from solvents, coarse and submicron emulsions. J Pharm Biomed Anal. 2000 Dec;24(1):155-65. [PubMed:11108549 ]
  12. Vaddi HK, Ho PC, Chan SY: Terpenes in propylene glycol as skin-penetration enhancers: permeation and partition of haloperidol, Fourier transform infrared spectroscopy, and differential scanning calorimetry. J Pharm Sci. 2002 Jul;91(7):1639-51. [PubMed:12115825 ]
  13. Gancevici GG: Role of complement inhibition in topical therapy of muco-cutaneous herpes simplex virus infections. Roum Arch Microbiol Immunol. 1993 Oct-Dec;52(4):293-303. [PubMed:7827366 ]
  14. Liu JH, Gao D, He LQ, Moey LK, Hua K, Liu ZB: The phase diagram for the ternary system propylene glycol-sodium chloride-water and their application to platelet cryopreservation. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2003 Feb;11(1):92-5. [PubMed:12667299 ]
  15. Rajasenan RS, Riley RJ, Leeder JS: Expression and inducibility of antigens in severe combined immunodeficient mice recognized by human anti-P450 antibodies. Toxicol Appl Pharmacol. 1995 Nov;135(1):89-99. [PubMed:7482543 ]
  16. Decherchi P, Lammari-Barreault N, Cochard P, Carin M, Rega P, Pio J, Pellissier JF, Ladaique P, Novakovitch G, Gauthier P: CNS axonal regeneration with peripheral nerve grafts cryopreserved by vitrification: cytological and functional aspects. Cryobiology. 1997 May;34(3):214-39. [PubMed:9160994 ]
  17. Trottet L, Owen H, Holme P, Heylings J, Collin IP, Breen AP, Siyad MN, Nandra RS, Davis AF: Are all aciclovir cream formulations bioequivalent? Int J Pharm. 2005 Nov 4;304(1-2):63-71. Epub 2005 Sep 1. [PubMed:16139970 ]
  18. Miller DL, Wildnauer RH: Thermoanalytical probes for the analysis of physical properties of stratum corneum. J Invest Dermatol. 1977 Sep;69(3):287-9. [PubMed:894064 ]
  19. Zar T, Graeber C, Perazella MA: Recognition, treatment, and prevention of propylene glycol toxicity. Semin Dial. 2007 May-Jun;20(3):217-9. [PubMed:17555487 ]

Enzymes

Enzyme Details
1. Aldose reductase
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name:
AKR1B1
Uniprot ID:
P15121
Molecular weight:
35853.125
Reactions
Propylene glycol + NADP → Lactaldehyde + NADPH + Hydrogen Iondetails
Enzyme Details
2. Coagulation factor XIII A chain
General function:
Involved in protein-glutamine gamma-glutamyltransferase activity
Specific function:
Factor XIII is activated by thrombin and calcium ion to a transglutaminase that catalyzes the formation of gamma-glutamyl-epsilon-lysine cross-links between fibrin chains, thus stabilizing the fibrin clot. Also cross-link alpha-2-plasmin inhibitor, or fibronectin, to the alpha chains of fibrin.
Gene Name:
F13A1
Uniprot ID:
P00488
Molecular weight:
83267.785
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 ]
Enzyme Details
3. Aldo-keto reductase family 1 member B10
General function:
Not Available
Specific function:
Acts as all-trans-retinaldehyde reductase. Can efficiently reduce aliphatic and aromatic aldehydes, and is less active on hexoses (in vitro). May be responsible for detoxification of reactive aldehydes in the digested food before the nutrients are passed on to other organs.
Gene Name:
AKR1B10
Uniprot ID:
O60218
Molecular weight:
Not Available
Reactions
Propylene glycol + NADP → Lactaldehyde + NADPH + Hydrogen Iondetails