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Showing NP-Card for hexenal (NP0270729)

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Record Information
Version2.0
Created at2022-09-08 16:46:32 UTC
Updated at2022-09-08 16:46:33 UTC
NP-MRD IDNP0270729
Secondary Accession NumbersNone
Natural Product 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. hexenal is found in Aethus indicus, Ageratum conyzoides, Arctium lappa, Aristolochia debilis, Basella alba, Capillipedium parviflorum, Capparis spinosa, Clinopodium serpyllifolium, Echinophora tenuifolia, Euploea sylvester, Farfugium japonicum, Gonioctena viminalis, Medicago sativa, Origanum sipyleum, Peristeria elata, Pimenta racemosa, Quercus agrifolia, Riptortus pedestris, Robinia pseudoacacia, Salvia sclarea and Tripleurospermum maritimum. hexenal was first documented in 2010 (PMID: 20936263). Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease (PMID: 26475511).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0270729 (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 NP0270729 (hexenal)

     RDKit          3D

 17 16  0  0  0  0  0  0  0  0999 V2000
   -2.2772   -0.0959   -0.4527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2917   -0.2680    0.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0594    0.6177    0.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6205    0.2724   -0.7965 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8745   -0.1450   -0.9101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7693   -0.3227    0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9381   -0.7193    0.0244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2845    0.2321   -0.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9216    0.6649   -1.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4552   -1.0877   -0.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9675   -1.3269    0.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8099    0.0614    1.6061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4294    1.6785    0.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5556    0.5554    1.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0276    0.3715   -1.7228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2600   -0.3690   -1.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4509   -0.1193    1.2098 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  0
  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
Download

3D SDF for NP0270729 (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>
NP0270729

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
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3D-SDF for NP0270729 (hexenal)

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PDB for NP0270729 (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 NP0270729 (hexenal)
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SMILES for NP0270729 (hexenal)
CCCC=CC=O
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INCHI for NP0270729 (hexenal)
InChI=1S/C6H10O/c1-2-3-4-5-6-7/h4-6H,2-3H2,1H3
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View in JSmol
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 Mass98.1430 Da
Monoisotopic Mass98.07316 Da
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aethus indicusLOTUS Database
Ageratum conyzoidesLOTUS Database
Arctium lappaLOTUS Database
Aristolochia debilisLOTUS Database
Basella albaLOTUS Database
Capillipedium parviflorumLOTUS Database
Capparis spinosaLOTUS Database
Clinopodium serpyllifoliumLOTUS Database
Echinophora tenuifoliaLOTUS Database
Euploea sylvesterLOTUS Database
Farfugium japonicumLOTUS Database
Gonioctena viminalisLOTUS Database
Medicago sativaLOTUS Database
Origanum sipyleumLOTUS Database
Peristeria elataLOTUS Database
Pimenta racemosaLOTUS Database
Quercus agrifoliaLOTUS Database
Riptortus pedestrisLOTUS Database
Robinia pseudoacaciaLOTUS Database
Salvia sclareaLOTUS Database
Tripleurospermum maritimumLOTUS Database
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
HMDB IDHMDB0031496  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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  
Good Scents IDNot Available
References
General References
  1. Neng NR, Nogueira JM: Determination of short-chain carbonyl compounds in drinking water matrices by bar adsorptive micro-extraction (BAmuE) with in situ derivatization. Anal Bioanal Chem. 2010 Dec;398(7-8):3155-63. doi: 10.1007/s00216-010-4256-9.  Epub 2010 Oct 9. [PubMed:20936263  ] 
  2. Nikaido Y, Yamada J, Migita K, Shiba Y, Furukawa T, Nakashima T, Ueno S: cis-3-Hexenol and trans-2-hexenal mixture prevents development of PTSD-like phenotype in rats. Behav Brain Res. 2016 Jan 15;297:251-8. doi: 10.1016/j.bbr.2015.10.023. Epub 2015  Oct 22. [PubMed:26475511  ] 
  3. LOTUS database [Link]