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Showing metabocard for Acrolein (HMDB0041822)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-13 11:41:02 UTC
Update Date2023-02-21 17:28:58 UTC
HMDB IDHMDB0041822
Secondary Accession Numbers
  • HMDB41822
Metabolite Identification
Common NameAcrolein
DescriptionAcrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colourless liquid with a piercing, disagreeable, acrid smell. The smell of burnt fat (i.e. when cooking oil is heated to its smoke point) is caused by glycerol in the burning fat breaking down into acrolein. It is produced industrially from propylene and mainly used as a biocide and a building block to other chemical compounds, such as the amino acid methionine. Acrolein is used as an etherification agent in the preparation of modified food starches. Acrolein is an herbicide and algicide used in water treatment. It is produced by microorganisms, e.g. Clostridium perfringens. Acrolein is a relatively electrophilic compound and a reactive one, hence its high toxicity. It is a good Michael acceptor, hence its useful reaction with thiols. It forms acetals readily, a prominent one being the spirocycle derived from pentaerythritol, diallylidene pentaerythritol. Acrolein participates in many Diels-Alder reactions, even with itself. Via Diels-Alder reactions, it is a precursor to some commercial fragrances, including lyral, norbornene-2-carboxaldehyde, and myrac aldehyde. Acrolein is toxic and is a strong irritant for the skin, eyes, and nasal passages. The main metabolic pathway for acrolein is the alkylation of glutathione. The WHO suggests a 'tolerable oral acrolein intake' of 7.5 µg/day per kilogram of body weight. Although acrolein occurs in French fries, the levels are only a few micrograms per kilogram. Acrolein has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID:22626821 ).
Structure
Data?1677000538
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0041822 (Acrolein)


  Mrv1652308132018532D          

  4  3  0  0  0  0            999 V2000
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
M  END
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3D MOL for HMDB0041822 (Acrolein)

HMDB0041822
     RDKit          3D
Acrolein
  8  7  0  0  0  0  0  0  0  0999 V2000
    1.2077    0.0652    0.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0005   -0.4024    0.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2115    0.1452   -0.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1175    1.1290   -1.0354 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0912   -0.3481    0.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2708    0.9233   -0.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0780   -1.2401    0.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1622   -0.2722   -0.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  1  5  1  0
  1  6  1  0
  2  7  1  0
  3  8  1  0
M  END
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3D SDF for HMDB0041822 (Acrolein)


  Mrv1652308132018532D          

  4  3  0  0  0  0            999 V2000
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041822

> <DATABASE_NAME>
hmdb

> <SMILES>
C=CC=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H4O/c1-2-3-4/h2-3H,1H2

> <INCHI_KEY>
HGINCPLSRVDWNT-UHFFFAOYSA-N

> <FORMULA>
C3H4O

> <MOLECULAR_WEIGHT>
56.0633

> <EXACT_MASS>
56.02621475

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
5.579617832379615

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
prop-2-enal

> <ALOGPS_LOGP>
0.18

> <JCHEM_LOGP>
0.37433104033333325

> <ALOGPS_LOGS>
0.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.306968103107292

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
16.366

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acrolein

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0041822 (Acrolein)

HMDB0041822
     RDKit          3D
Acrolein
  8  7  0  0  0  0  0  0  0  0999 V2000
    1.2077    0.0652    0.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0005   -0.4024    0.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2115    0.1452   -0.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1175    1.1290   -1.0354 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0912   -0.3481    0.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2708    0.9233   -0.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0780   -1.2401    0.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1622   -0.2722   -0.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  1  5  1  0
  1  6  1  0
  2  7  1  0
  3  8  1  0
M  END
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PDB for HMDB0041822 (Acrolein)

HEADER    PROTEIN                                 13-AUG-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-AUG-20         0                                  
HETATM    1  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3                                                            
MASTER        0    0    0    0    0    0    0    0    4    0    6    0
END
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3D PDB for HMDB0041822 (Acrolein)

COMPND    HMDB0041822
HETATM    1  C1  UNL     1       1.208   0.065   0.079  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.000  -0.402   0.326  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.211   0.145  -0.249  1.00  0.00           C  
HETATM    4  O1  UNL     1      -1.118   1.129  -1.035  1.00  0.00           O  
HETATM    5  H1  UNL     1       2.091  -0.348   0.509  1.00  0.00           H  
HETATM    6  H2  UNL     1       1.271   0.923  -0.609  1.00  0.00           H  
HETATM    7  H3  UNL     1      -0.078  -1.240   0.995  1.00  0.00           H  
HETATM    8  H4  UNL     1      -2.162  -0.272  -0.015  1.00  0.00           H  
CONECT    1    2    2    5    6
CONECT    2    3    7
CONECT    3    4    4    8
END
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SMILES for HMDB0041822 (Acrolein)

C=CC=O
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INCHI for HMDB0041822 (Acrolein)

InChI=1S/C3H4O/c1-2-3-4/h2-3H,1H2
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View in JSmolView Stereo Labels
Synonyms
ValueSource
AcrylaldehydeChEBI
Acrylic aldehydeChEBI
PropenalChEBI
2-Propen-1-oneHMDB
2-PropenalHMDB, MeSH
2-PropenaldehydeHMDB
AcquiniteHMDB
AcraldehydeHMDB, MeSH
AcroleinaHMDB
Aldehyde, acrylicHMDB, MeSH
Aldehyde, allylHMDB, MeSH
Aldehyde, ethyleneHMDB, MeSH
Allyl aldehydeHMDB, MeSH
AqualinHMDB, MeSH
AqualineHMDB
BiocideHMDB
CH2=chchoHMDB
CroleanHMDB
Ethylene aldehydeHMDB, MeSH
MagnacideHMDB
Magnacide HHMDB
Magnacide H and bHMDB
PapiteHMDB
Prop-2-en-1-alHMDB
Prop-2-enalHMDB
PropenaldehydeHMDB
Propylene aldehydeHMDB
SlimicideHMDB
trans-Acrolein formylethyleneHMDB
2 PropenalMeSH, HMDB
Chemical FormulaC3H4O
Average Molecular Weight56.0633
Monoisotopic Molecular Weight56.02621475
IUPAC Nameprop-2-enal
Traditional Nameacrolein
CAS Registry Number107-02-8
SMILES
C=CC=O
InChI Identifier
InChI=1S/C3H4O/c1-2-3-4/h2-3H,1H2
InChI KeyHGINCPLSRVDWNT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as enals. These are an alpha,beta-unsaturated aldehyde of general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentEnals
Alternative Parents
Substituents
  • Enal
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Aldehyde
  • 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
Biological roleIndustrial applicationEnvironmental role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-87.7 °CNot Available
Boiling Point52.00 to 53.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility212 mg/mL at 25 °CNot Available
LogP-0.01Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility107 g/LALOGPS
logP0.18ALOGPS
logP0.37ChemAxon
logS0.28ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity16.37 m³·mol⁻¹ChemAxon
Polarizability5.58 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+118.71730932474
DeepCCS[M-H]-116.75530932474
DeepCCS[M-2H]-152.47730932474
DeepCCS[M+Na]+126.88930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AcroleinC=CC=O790.9Standard polar33892256
AcroleinC=CC=O448.5Standard non polar33892256
AcroleinC=CC=O477.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Acrolein EI-B (Non-derivatized)splash10-0a4i-9000000000-f6aba25388da7855f3eb2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acrolein EI-B (Non-derivatized)splash10-004i-9000000000-a667e77a9d666459b4112017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acrolein EI-B (Non-derivatized)splash10-0a4i-9000000000-f6aba25388da7855f3eb2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acrolein EI-B (Non-derivatized)splash10-004i-9000000000-a667e77a9d666459b4112018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acrolein GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-9000000000-4a086c1c9c7836b7b3072016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acrolein GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-056r-9000000000-34c0891db414206d2b402014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrolein 10V, Positive-QTOFsplash10-0a4i-9000000000-cf50f66835baacbc5db42015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrolein 20V, Positive-QTOFsplash10-0a4i-9000000000-abefe6f7a672744326c12015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrolein 40V, Positive-QTOFsplash10-0a6r-9000000000-32a4911454ef635f19ed2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrolein 10V, Negative-QTOFsplash10-0a4i-9000000000-4740fe3b45257adba96a2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrolein 20V, Negative-QTOFsplash10-0a4i-9000000000-e578c9fb2097eb472d122015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrolein 40V, Negative-QTOFsplash10-0a4i-9000000000-c28d7e42ec75bd010f502015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrolein 10V, Positive-QTOFsplash10-0a4i-9000000000-af8a08e40e7604e1b1052021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrolein 20V, Positive-QTOFsplash10-0a4i-9000000000-a0d6dd919aed0acdb7152021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrolein 40V, Positive-QTOFsplash10-000i-9000000000-f12145ad941c7b169c502021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrolein 10V, Negative-QTOFsplash10-0a4i-9000000000-23a60e5f52ca732e0f562021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrolein 20V, Negative-QTOFsplash10-0a4i-9000000000-23a60e5f52ca732e0f562021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrolein 40V, Negative-QTOFsplash10-0a4i-9000000000-23a60e5f52ca732e0f562021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-18Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
 details
BloodDetected and Quantified30.32 +/- 8.92 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Both
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified180.15 uMAdult (>18 years old)Bothuremia details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)		 details
Associated Disorders and Diseases
Disease References
Uremia
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008307
KNApSAcK IDC00052796
Chemspider ID7559
KEGG Compound IDC01471
BioCyc IDACROLEIN
BiGG IDNot Available
Wikipedia LinkAcrolein
METLIN IDNot Available
PubChem Compound7847
PDB IDNot Available
ChEBI ID15368
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029851
Good Scents IDrw1216121
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]