Showing metabocard for Heptenal (MMDBc0033648)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:57:23 UTC
Update Date2024-10-06 20:31:56 UTC
Metabolite IDMMDBc0033648
Metabolite Identification
Common NameHeptenal
Description(2E)-2-Heptenal, also known as 3-butylacrolein or 2-trans-heptenal, belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. (2E)-2-Heptenal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, (2E)-2-heptenal is considered to be a fatty aldehyde lipid molecule. Uremic toxins such as 2-Heptenal are actively transported into the kidneys via organic ion transporters (especially OAT3). (2E)-2-Heptenal is an almond, and fatty tasting compound. (2E)-2-Heptenal is found, on average, in the highest concentration within safflowers. (2E)-2-Heptenal has also been detected, but not quantified, in several different foods, such as roselles, common grapes, cucumbers, garden tomato, and evergreen blackberries. (2E)-2-Heptenal is a potentially toxic compound. Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. As a uremic toxin, this compound can cause uremic syndrome. Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f91ccdef548>


  Mrv1652303202019012D          

  8  7  0  0  0  0            999 V2000
   -1.6205    2.4455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9061    2.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1916    2.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5229    2.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2373    2.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9518    2.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6663    2.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3808    2.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f91ccdef548>

HMDB0033827
     RDKit          3D
(2E)-2-Heptenal
 20 19  0  0  0  0  0  0  0  0999 V2000
   -2.4745    0.6616   -0.5242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7015    0.0446    0.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8789   -1.1415    0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1391   -0.8127   -0.8708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1114    0.2134   -0.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4171   -0.0477   -0.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3975    0.9198    0.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1162    2.0911    0.4052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8176    1.1687   -1.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0803   -0.0768   -1.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2232    1.3626   -0.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0732    0.7978    1.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4485   -0.3333    1.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4891   -1.9815   -0.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3317   -1.4930    1.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3230   -0.4368   -1.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6983   -1.7439   -1.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8186    1.2101   -0.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7027   -1.0439   -0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4405    0.6415    0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  6 19  1  0
  7 20  1  0
M  END
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3D SDF for #<Metabolite:0x00007f91ccdef548>


  Mrv1652303202019012D          

  8  7  0  0  0  0            999 V2000
   -1.6205    2.4455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9061    2.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1916    2.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5229    2.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2373    2.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9518    2.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6663    2.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3808    2.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033648

> <DATABASE_NAME>
MIME

> <SMILES>
CCCC\C=C\C=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H12O/c1-2-3-4-5-6-7-8/h5-7H,2-4H2,1H3/b6-5+

> <INCHI_KEY>
NDFKTBCGKNOHPJ-AATRIKPKSA-N

> <FORMULA>
C7H12O

> <MOLECULAR_WEIGHT>
112.1696

> <EXACT_MASS>
112.088815006

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
13.585285157409732

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-hept-2-enal

> <ALOGPS_LOGP>
2.30

> <JCHEM_LOGP>
2.09467203

> <ALOGPS_LOGS>
-1.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.203719992137635

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
35.842499999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-heptenal, (2E)-

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for #<Metabolite:0x00007f91ccdef548>

HMDB0033827
     RDKit          3D
(2E)-2-Heptenal
 20 19  0  0  0  0  0  0  0  0999 V2000
   -2.4745    0.6616   -0.5242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7015    0.0446    0.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8789   -1.1415    0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1391   -0.8127   -0.8708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1114    0.2134   -0.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4171   -0.0477   -0.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3975    0.9198    0.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1162    2.0911    0.4052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8176    1.1687   -1.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0803   -0.0768   -1.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2232    1.3626   -0.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0732    0.7978    1.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4485   -0.3333    1.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4891   -1.9815   -0.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3317   -1.4930    1.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3230   -0.4368   -1.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6983   -1.7439   -1.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8186    1.2101   -0.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7027   -1.0439   -0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4405    0.6415    0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  6 19  1  0
  7 20  1  0
M  END
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PDB for #<Metabolite:0x00007f91ccdef548>

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  O   UNK     0      -3.025   4.565   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.691   5.335   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.358   4.565   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.976   5.335   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310   4.565   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.643   5.335   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.977   4.565   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.311   5.335   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for #<Metabolite:0x00007f91ccdef548>

COMPND    HMDB0033827
HETATM    1  C1  UNL     1      -2.475   0.662  -0.524  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.701   0.045   0.595  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.879  -1.141   0.177  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.139  -0.813  -0.871  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.111   0.213  -0.428  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.417  -0.048  -0.376  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.398   0.920   0.048  1.00  0.00           C  
HETATM    8  O1  UNL     1       3.116   2.091   0.405  1.00  0.00           O  
HETATM    9  H1  UNL     1      -1.818   1.169  -1.246  1.00  0.00           H  
HETATM   10  H2  UNL     1      -3.080  -0.077  -1.095  1.00  0.00           H  
HETATM   11  H3  UNL     1      -3.223   1.363  -0.071  1.00  0.00           H  
HETATM   12  H4  UNL     1      -1.073   0.798   1.064  1.00  0.00           H  
HETATM   13  H5  UNL     1      -2.449  -0.333   1.342  1.00  0.00           H  
HETATM   14  H6  UNL     1      -1.489  -1.981  -0.185  1.00  0.00           H  
HETATM   15  H7  UNL     1      -0.332  -1.493   1.078  1.00  0.00           H  
HETATM   16  H8  UNL     1      -0.323  -0.437  -1.806  1.00  0.00           H  
HETATM   17  H9  UNL     1       0.698  -1.744  -1.097  1.00  0.00           H  
HETATM   18  H10 UNL     1       0.819   1.210  -0.130  1.00  0.00           H  
HETATM   19  H11 UNL     1       2.703  -1.044  -0.676  1.00  0.00           H  
HETATM   20  H12 UNL     1       4.441   0.642   0.066  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3   12   13
CONECT    3    4   14   15
CONECT    4    5   16   17
CONECT    5    6    6   18
CONECT    6    7   19
CONECT    7    8    8   20
END
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SMILES for #<Metabolite:0x00007f91ccdef548>

CCCC\C=C\C=O
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INCHI for #<Metabolite:0x00007f91ccdef548>

InChI=1S/C7H12O/c1-2-3-4-5-6-7-8/h5-7H,2-4H2,1H3/b6-5+
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Synonyms
ValueSource
(2E)-HeptenalChEBI
(e)-2-Hepten-1-alChEBI
2-trans-HeptenalChEBI
3-ButylacroleinChEBI
beta-ButylacroleinChEBI
Hept-(e)-2-enalChEBI
Hept-2(e)-enalChEBI
Hept-trans-2-enalChEBI
N-Hept-trans-2-enalChEBI
trans-2-Hepten-1-alChEBI
trans-2-HeptenalChEBI
b-ButylacroleinGenerator
Β-butylacroleinGenerator
(e)-2-HeptenalChEMBL, HMDB
2-Hept-enalHMDB
alpha-HeptenalHMDB
ButylacroleinHMDB
FEMA 3165HMDB
2-Heptenal, (e)-isomerMeSH, HMDB
2-HeptenalMeSH
Molecular FormulaC7H12O
Average Mass112.1696
Monoisotopic Mass112.088815006
IUPAC Name(2E)-hept-2-enal
Traditional Name2-heptenal, (2E)-
CAS Registry Number29381-66-6
SMILES
CCCC\C=C\C=O
InChI Identifier
InChI=1S/C7H12O/c1-2-3-4-5-6-7-8/h5-7H,2-4H2,1H3/b6-5+
InChI KeyNDFKTBCGKNOHPJ-AATRIKPKSA-N