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Showing metabocard for Hexenal (HMDB0253154)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 11:21:47 UTC
Update Date2021-09-26 23:06:11 UTC
HMDB IDHMDB0253154
Secondary Accession NumbersNone
Metabolite Identification
Common NameHexenal
Description2-Hexenal, also known as 2-hexenaldehyde or 3-propyl-acrolein, 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. 2-Hexenal is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Hexenal is a sweet, almond, and apple tasting compound. Outside of the human body, 2-Hexenal has been detected, but not quantified in, several different foods, such as sweet cherries, asparagus, blackcurrants, black elderberries, and cucumbers. This could make 2-hexenal a potential biomarker for the consumption of these foods. 2-Hexenal is a potentially toxic compound. Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. 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. Increased levels of uremic toxins can stimulate the production of reactive oxygen species. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. This compound has been identified in human blood as reported by (PMID: 31557052 ). Hexenal is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Hexenal is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0253154 (Hexenal)


  Mrv0541 02241218292D          

  7  6  0  0  0  0            999 V2000
   -4.1545    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4400    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7255    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0111    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2966    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5821    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1324    3.7125    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  3  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
M  END
Download

3D MOL for HMDB0253154 (Hexenal)

HMDB0253154
     RDKit          3D
Hexenal
 17 16  0  0  0  0  0  0  0  0999 V2000
   -2.7245    0.2107    0.3191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2636   -0.0952    0.6386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4227   -0.0810   -0.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9746   -0.3863   -0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9648    0.4853   -0.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3227    0.2066   -0.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6724   -0.8501    0.5026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2384   -0.7636    0.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7825    0.8735   -0.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1678    0.7878    1.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8707    0.7395    1.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1496   -1.0371    1.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7583   -0.8077   -1.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5096    0.9336   -1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1493   -1.3310    0.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7139    1.4114   -0.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0899    0.9333   -0.2692 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  2  3
  5  6  1  0
  6  7  2  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
M  END
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3D SDF for HMDB0253154 (Hexenal)


  Mrv0541 02241218292D          

  7  6  0  0  0  0            999 V2000
   -4.1545    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4400    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7255    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0111    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2966    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5821    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1324    3.7125    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  3  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253154

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCC=CC=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O/c1-2-3-4-5-6-7/h4-6H,2-3H2,1H3

> <INCHI_KEY>
MBDOYVRWFFCFHM-UHFFFAOYSA-N

> <FORMULA>
C6H10O

> <MOLECULAR_WEIGHT>
98.143

> <EXACT_MASS>
98.073164942

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
11.57239313659726

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
hex-2-enal

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
1.650103365

> <ALOGPS_LOGS>
-1.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.201821978414376

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
31.241499999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hexenal

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0253154 (Hexenal)

HMDB0253154
     RDKit          3D
Hexenal
 17 16  0  0  0  0  0  0  0  0999 V2000
   -2.7245    0.2107    0.3191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2636   -0.0952    0.6386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4227   -0.0810   -0.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9746   -0.3863   -0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9648    0.4853   -0.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3227    0.2066   -0.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6724   -0.8501    0.5026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2384   -0.7636    0.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7825    0.8735   -0.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1678    0.7878    1.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8707    0.7395    1.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1496   -1.0371    1.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7583   -0.8077   -1.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5096    0.9336   -1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1493   -1.3310    0.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7139    1.4114   -0.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0899    0.9333   -0.2692 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  2  3
  5  6  1  0
  6  7  2  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
M  END
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PDB for HMDB0253154 (Hexenal)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -7.755   6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -6.421   7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.088   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.754   7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.420   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.087   7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.247   6.930   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                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0253154 (Hexenal)

COMPND    HMDB0253154
HETATM    1  C1  UNL     1      -2.724   0.211   0.319  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.264  -0.095   0.639  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.423  -0.081  -0.614  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.975  -0.386  -0.212  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.965   0.485  -0.445  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.323   0.207  -0.064  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.672  -0.850   0.503  1.00  0.00           O  
HETATM    8  H1  UNL     1      -3.238  -0.764   0.179  1.00  0.00           H  
HETATM    9  H2  UNL     1      -2.783   0.873  -0.557  1.00  0.00           H  
HETATM   10  H3  UNL     1      -3.168   0.788   1.170  1.00  0.00           H  
HETATM   11  H4  UNL     1      -0.871   0.740   1.281  1.00  0.00           H  
HETATM   12  H5  UNL     1      -1.150  -1.037   1.176  1.00  0.00           H  
HETATM   13  H6  UNL     1      -0.758  -0.808  -1.372  1.00  0.00           H  
HETATM   14  H7  UNL     1      -0.510   0.934  -1.069  1.00  0.00           H  
HETATM   15  H8  UNL     1       1.149  -1.331   0.269  1.00  0.00           H  
HETATM   16  H9  UNL     1       1.714   1.411  -0.932  1.00  0.00           H  
HETATM   17  H10 UNL     1       4.090   0.933  -0.269  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3   11   12
CONECT    3    4   13   14
CONECT    4    5    5   15
CONECT    5    6   16
CONECT    6    7    7   17
END
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SMILES for HMDB0253154 (Hexenal)

CCCC=CC=O
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INCHI for HMDB0253154 (Hexenal)

InChI=1S/C6H10O/c1-2-3-4-5-6-7/h4-6H,2-3H2,1H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-HexenaldehydeChEBI
3-Propyl-acroleinChEBI
alpha,beta-HexylenaldehydeChEBI
Alpha.beta-hexylenaldehydChEBI
beta-PropylacroleinChEBI
Hexen-2-alChEBI
Hexen-2-en-1-alChEBI
Hexylenic aldehydeChEBI
Leaf aldehydeChEBI
a,b-HexylenaldehydeGenerator
Α,β-hexylenaldehydeGenerator
b-PropylacroleinGenerator
Β-propylacroleinGenerator
2-Hexen-1-alHMDB
3-Propyl acroleinHMDB
3-PropylacroleinHMDB
beta-Propyl acroleinHMDB
FEMA 2560HMDB
Hex-2-en-1-alHMDB
Hex-2-enalHMDB
HexenalHMDB
EvipanMeSH
HexobarbitalMeSH
Hexobarbital, sodiumMeSH
HexobarbitoneMeSH
Sodium hexobarbitalMeSH
Chemical FormulaC6H10O
Average Molecular Weight98.143
Monoisotopic Molecular Weight98.073164942
IUPAC Namehex-2-enal
Traditional Namehexenal
CAS Registry NumberNot Available
SMILES
CCCC=CC=O
InChI Identifier
InChI=1S/C6H10O/c1-2-3-4-5-6-7/h4-6H,2-3H2,1H3
InChI KeyMBDOYVRWFFCFHM-UHFFFAOYSA-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
Process
Industrial process
Role
Industrial applicationEnvironmental role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP1.8ALOGPS
logP1.65ChemAxon
logS-1.5ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.24 m³·mol⁻¹ChemAxon
Polarizability11.57 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+129.35330932474
DeepCCS[M-H]-126.84930932474
DeepCCS[M-2H]-163.00130932474
DeepCCS[M+Na]+137.40830932474
AllCCS[M+H]+124.532859911
AllCCS[M+H-H2O]+120.132859911
AllCCS[M+NH4]+128.632859911
AllCCS[M+Na]+129.832859911
AllCCS[M-H]-129.032859911
AllCCS[M+Na-2H]-132.832859911
AllCCS[M+HCOO]-137.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
HexenalCCCC=CC=O1177.3Standard polar33892256
HexenalCCCC=CC=O821.4Standard non polar33892256
HexenalCCCC=CC=O839.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Hexenal GC-MS (Non-derivatized) - 70eV, Positivesplash10-05r0-9000000000-f80d6978daedea323aa62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexenal GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexenal 10V, Positive-QTOFsplash10-0002-9000000000-db77fc4d5edd7bdc39072015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexenal 20V, Positive-QTOFsplash10-000t-9000000000-8c4cc267531a0c711b322015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexenal 40V, Positive-QTOFsplash10-0a4l-9000000000-1018f15c3b2d6e22c2262015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexenal 10V, Negative-QTOFsplash10-0002-9000000000-9232ec723afab464ccc22015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexenal 20V, Negative-QTOFsplash10-0002-9000000000-a839e50ee7ad7503877e2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexenal 40V, Negative-QTOFsplash10-0006-9000000000-4a1d88a16ebce778de702015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexenal 10V, Positive-QTOFsplash10-0540-9000000000-6923af674dd1206069572021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexenal 20V, Positive-QTOFsplash10-052r-9000000000-3ea4a5ca74032209afaf2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexenal 40V, Positive-QTOFsplash10-0573-9000000000-b0552bcc819f05df9c042021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexenal 10V, Negative-QTOFsplash10-0002-9000000000-649f52184fb4997b20fb2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexenal 20V, Negative-QTOFsplash10-004i-9000000000-3e77d5cdc17bcd3c255e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexenal 40V, Negative-QTOFsplash10-0n2d-9000000000-022c1508f6a2751bcc392021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008081
KNApSAcK IDC00035480
Chemspider ID4444608
KEGG Compound IDC08497
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCis-3-Hexenal
METLIN IDNot Available
PubChem Compound5281168
PDB IDNot Available
ChEBI ID19591
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]