Showing metabocard for 3-Methyl-2-butenal (MMDBc0051700)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-05-16 20:31:42 UTC
Update Date2024-09-29 11:10:41 UTC
Metabolite IDMMDBc0051700
Metabolite Identification
Common Name3-Methyl-2-butenal
Description3-Methyl-2-butenal, also known as senecialdehyde or 3,3-dimethylacrolein, belongs to the class of organic compounds known as enals. These are alpha,beta-unsaturated aldehydes of the 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. 3-methyl-2-butenal has been detected, but not quantified, in several different foods, such as common oregano, beechnuts, oval-leaf huckleberries, tea leaf willows, and red rice. This could make 3-methyl-2-butenal a potential biomarker for the consumption of these foods. 3-Methyl-2-butenal is a derivative of acrolein that is an alpha, beta-unsaturated carbonyl metabolite. It can be formed endogenously during lipid peroxidation or after oxidative stress, and is considered to play an important role in human carcinogenesis. The endogenously formed acroleins are a constant source of DNA damage, can lead to mutation, and can also induce tumours in humans (PMID:8319634 ). 3-Methyl-2-butenal, which is an unsaturated aldehyde bearing substitution at the alkene terminus, is a poor inactivator of the enzymes protein tyrosine phosphatases (PTPs). The inactivation of PTPs can yield profound biological consequences arising from the disruption of cellular signalling pathways (PMID:17655273 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f91fe070c00>


  Mrv1652309042000342D          

  6  5  0  0  0  0            999 V2000
   -2.6560    1.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3705    1.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6560    2.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9415    1.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2271    1.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5126    1.0714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f91fe070c00>

HMDB0012157
     RDKit          3D
3-Methyl-2-butenal
 14 13  0  0  0  0  0  0  0  0999 V2000
    0.1365   -0.9655    1.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3079   -0.0245   -0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6136    0.0332   -0.8034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6559    0.7566   -0.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9902    0.7925    0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2027    0.0147    1.0388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1056   -0.4079    1.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6713   -1.7199    0.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0697   -1.5809    1.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9015    1.1247   -0.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3981   -0.5629   -0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4515   -0.3476   -1.8503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4845    1.4278   -1.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7686    1.4597   -0.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  2  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  3 10  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
  5 14  1  0
M  END
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3D SDF for #<Metabolite:0x00007f91fe070c00>


  Mrv1652309042000342D          

  6  5  0  0  0  0            999 V2000
   -2.6560    1.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3705    1.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6560    2.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9415    1.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2271    1.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5126    1.0714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0051700

> <DATABASE_NAME>
MIME

> <SMILES>
CC(C)=CC=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O/c1-5(2)3-4-6/h3-4H,1-2H3

> <INCHI_KEY>
SEPQTYODOKLVSB-UHFFFAOYSA-N

> <FORMULA>
C5H8O

> <MOLECULAR_WEIGHT>
84.1164

> <EXACT_MASS>
84.057514878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
9.509065212790638

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methylbut-2-enal

> <ALOGPS_LOGP>
0.97

> <JCHEM_LOGP>
1.0043273066666667

> <ALOGPS_LOGS>
-0.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9135992021592005

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
26.3215

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.36e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
prenal

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for #<Metabolite:0x00007f91fe070c00>

HMDB0012157
     RDKit          3D
3-Methyl-2-butenal
 14 13  0  0  0  0  0  0  0  0999 V2000
    0.1365   -0.9655    1.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3079   -0.0245   -0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6136    0.0332   -0.8034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6559    0.7566   -0.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9902    0.7925    0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2027    0.0147    1.0388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1056   -0.4079    1.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6713   -1.7199    0.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0697   -1.5809    1.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9015    1.1247   -0.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3981   -0.5629   -0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4515   -0.3476   -1.8503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4845    1.4278   -1.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7686    1.4597   -0.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  2  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  3 10  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
  5 14  1  0
M  END
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PDB for #<Metabolite:0x00007f91fe070c00>

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -4.958   2.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.292   2.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.958   4.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.624   2.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.291   2.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.957   2.000   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for #<Metabolite:0x00007f91fe070c00>

COMPND    HMDB0012157
HETATM    1  C1  UNL     1       0.136  -0.965   1.006  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.308  -0.024  -0.117  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.614   0.033  -0.803  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.656   0.757  -0.521  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.990   0.793   0.077  1.00  0.00           C  
HETATM    6  O1  UNL     1      -2.203   0.015   1.039  1.00  0.00           O  
HETATM    7  H1  UNL     1      -0.106  -0.408   1.954  1.00  0.00           H  
HETATM    8  H2  UNL     1      -0.671  -1.720   0.804  1.00  0.00           H  
HETATM    9  H3  UNL     1       1.070  -1.581   1.154  1.00  0.00           H  
HETATM   10  H4  UNL     1       1.901   1.125  -0.830  1.00  0.00           H  
HETATM   11  H5  UNL     1       2.398  -0.563  -0.277  1.00  0.00           H  
HETATM   12  H6  UNL     1       1.452  -0.348  -1.850  1.00  0.00           H  
HETATM   13  H7  UNL     1      -0.484   1.428  -1.345  1.00  0.00           H  
HETATM   14  H8  UNL     1      -2.769   1.460  -0.290  1.00  0.00           H  
CONECT    1    2    7    8    9
CONECT    2    3    4    4
CONECT    3   10   11   12
CONECT    4    5   13
CONECT    5    6    6   14
END
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SMILES for #<Metabolite:0x00007f91fe070c00>

CC(C)=CC=O
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INCHI for #<Metabolite:0x00007f91fe070c00>

InChI=1S/C5H8O/c1-5(2)3-4-6/h3-4H,1-2H3
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Synonyms
ValueSource
3,3-Dimethyl-acrylaldehydeChEBI
3,3-DimethylacroleinChEBI
3-MethylcrotonaldehydeChEBI
beta,beta-DimethylacroleinChEBI
beta-MethylcrotonaldehydeChEBI
PrenalChEBI
SenecialdehydeChEBI
SenecioaldehydeChEBI
b,b-DimethylacroleinGenerator
Β,β-dimethylacroleinGenerator
b-MethylcrotonaldehydeGenerator
Β-methylcrotonaldehydeGenerator
3-Methylbut-2-enalHMDB
beta,beta-Dimethylacrylic aldehydeHMDB
2-Methyl-2-buten-4-alHMDB
3,3-DimethylacrylaldehydeHMDB
3-Methyl-2-buten-1-alHMDB
3-Methyl-2-butenalHMDB
3-Methyl-2-butenaldehydeHMDB
β,β-Dimethylacrylic aldehydeHMDB
Molecular FormulaC5H8O
Average Mass84.1164
Monoisotopic Mass84.057514878
IUPAC Name3-methylbut-2-enal
Traditional Nameprenal
CAS Registry NumberNot Available
SMILES
CC(C)=CC=O
InChI Identifier
InChI=1S/C5H8O/c1-5(2)3-4-6/h3-4H,1-2H3
InChI KeySEPQTYODOKLVSB-UHFFFAOYSA-N