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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
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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

$$$$
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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
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
Environmental roleIndustrial applicationBiological 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
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
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)Not Available
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 ]