Showing metabocard for acrolein (MMDBc0033138)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:36:16 UTC
Update Date2024-04-30 20:01:02 UTC
Metabolite IDMMDBc0033138
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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fd12c3a83d8>


  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 #<Metabolite:0x00007fd12c3a83d8>

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 #<Metabolite:0x00007fd12c3a83d8>


  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>
MMDBc0033138

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x00007fd12c3a83d8>

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 #<Metabolite:0x00007fd12c3a83d8>

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 #<Metabolite:0x00007fd12c3a83d8>

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 #<Metabolite:0x00007fd12c3a83d8>

C=CC=O
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INCHI for #<Metabolite:0x00007fd12c3a83d8>

InChI=1S/C3H4O/c1-2-3-4/h2-3H,1H2
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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
Molecular FormulaC3H4O
Average Mass56.0633
Monoisotopic Mass56.02621475
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