Hmdb loader

Showing metabocard for (2E)-2-Heptenal (HMDB0033827)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Show more...Show more...Show more...Show more...
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 18:36:06 UTC
Update Date2023-02-21 17:23:39 UTC
HMDB IDHMDB0033827
Secondary Accession Numbers
  • HMDB33827
Metabolite Identification
Common Name(2E)-2-Heptenal
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
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0033827 ((2E)-2-Heptenal)

  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
Download

3D MOL for HMDB0033827 ((2E)-2-Heptenal)

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
Download

3D SDF for HMDB0033827 ((2E)-2-Heptenal)

  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>
HMDB0033827

> <DATABASE_NAME>
hmdb

> <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

$$$$
Download

3D-SDF for HMDB0033827 ((2E)-2-Heptenal)

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
Download

PDB for HMDB0033827 ((2E)-2-Heptenal)

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
Download

3D PDB for HMDB0033827 ((2E)-2-Heptenal)

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
Download

SMILES for HMDB0033827 ((2E)-2-Heptenal)

CCCC\C=C\C=O
Download

INCHI for HMDB0033827 ((2E)-2-Heptenal)

InChI=1S/C7H12O/c1-2-3-4-5-6-7-8/h5-7H,2-4H2,1H3/b6-5+
Download
View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC7H12O
Average Molecular Weight112.1696
Monoisotopic Molecular Weight112.088815006
IUPAC Name(2E)-hept-2-enal
Traditional Name2-heptenal, (2E)-
CAS Registry Number2463-63-0
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
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentMedium-chain aldehydes
Alternative Parents
Substituents
  • Medium-chain aldehyde
  • Enal
  • Alpha,beta-unsaturated aldehyde
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Health effectOrganoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point90.00 to 91.00 °C. @ 50.00 mm HgThe Good Scents Company Information System
Water Solubility0The Good Scents Company Information System
LogP2.300 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.16 +/- 0.05 uMAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.49 +/- 0.15 uMAdult (>18 years old)Bothuremia 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 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008060
KNApSAcK IDC00034755
Chemspider ID4446437
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283316
PDB IDNot Available
ChEBI ID143912
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029828
Good Scents IDrw1028241
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 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .