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Showing metabocard for 2-Hexenal (HMDB0031496)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:43:40 UTC
Update Date2022-03-07 02:53:00 UTC
HMDB IDHMDB0031496
Secondary Accession Numbers
  • HMDB31496
Metabolite Identification
Common Name2-Hexenal
Description2-Hexenal (CAS: 505-57-7), also known as 2-hexenaldehyde or 3-propylacrolein, belongs to the class of organic compounds known as medium-chain aldehydes. These are aldehydes with a chain length containing between 6 and 12 carbon atoms. Thus, 2-hexenal is considered to be a fatty aldehyde lipid molecule. Outside of the human body, 2-hexenal is found, on average, in the highest concentration within a few different foods, such as corn, tea, and bilberries. 2-Hexenal has also been detected, but not quantified in, several different foods, such as common wheat, ginkgo nuts, spearmints, sunflowers, and watermelons. This could make 2-hexenal a potential biomarker for the consumption of these foods. (E)-2-Hexenal is found in allspice. It is used in perfumery and flavouring. (E)-2-Hexenal has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031496 (2-Hexenal)

  Mrv1652309272007432D          

  7  6  0  0  0  0            999 V2000
   -3.1584    2.6227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4440    3.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7295    2.6227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0150    3.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3005    2.6227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4138    3.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1283    2.6227    0.0000 C   0  0  0  0  0  0  0  0  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
  1  2  2  0  0  0  0
M  END
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3D MOL for HMDB0031496 (2-Hexenal)

HMDB0031496
     RDKit          3D
2-Hexenal
 17 16  0  0  0  0  0  0  0  0999 V2000
   -2.6333    0.7353   -0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4021   -0.1224   -0.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2612    0.4165    0.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9079   -0.4794    0.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0557   -0.0154   -0.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1891   -0.8905   -0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1786   -2.1211   -0.2631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4880    0.0617    0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4323    1.4789    0.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9410    1.1576   -1.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5759   -1.1731   -0.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0336   -0.0252   -1.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0658    1.4424    0.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5217    0.4877    1.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8633   -1.5376    0.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0705    1.0469   -0.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0898   -0.4626   -0.8955 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
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3D SDF for HMDB0031496 (2-Hexenal)

  Mrv1652309272007432D          

  7  6  0  0  0  0            999 V2000
   -3.1584    2.6227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4440    3.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7295    2.6227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0150    3.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3005    2.6227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4138    3.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1283    2.6227    0.0000 C   0  0  0  0  0  0  0  0  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
  1  2  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031496

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC\C=C\C=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O/c1-2-3-4-5-6-7/h4-6H,2-3H2,1H3/b5-4+

> <INCHI_KEY>
MBDOYVRWFFCFHM-SNAWJCMRSA-N

> <FORMULA>
C6H10O

> <MOLECULAR_WEIGHT>
98.145

> <EXACT_MASS>
98.073164942

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
11.572393136597263

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-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>
(E)-2-hexenal

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0031496 (2-Hexenal)

HMDB0031496
     RDKit          3D
2-Hexenal
 17 16  0  0  0  0  0  0  0  0999 V2000
   -2.6333    0.7353   -0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4021   -0.1224   -0.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2612    0.4165    0.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9079   -0.4794    0.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0557   -0.0154   -0.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1891   -0.8905   -0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1786   -2.1211   -0.2631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4880    0.0617    0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4323    1.4789    0.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9410    1.1576   -1.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5759   -1.1731   -0.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0336   -0.0252   -1.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0658    1.4424    0.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5217    0.4877    1.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8633   -1.5376    0.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0705    1.0469   -0.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0898   -0.4626   -0.8955 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
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PDB for HMDB0031496 (2-Hexenal)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0      -5.896   4.896   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.562   5.666   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.228   4.896   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.895   5.666   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.561   4.896   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.772   5.666   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.106   4.896   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    3    1                                                       
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 HMDB0031496 (2-Hexenal)

COMPND    HMDB0031496
HETATM    1  C1  UNL     1      -2.633   0.735  -0.127  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.402  -0.122  -0.335  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.261   0.417   0.525  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.908  -0.479   0.263  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.056  -0.015  -0.238  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.189  -0.890  -0.491  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.179  -2.121  -0.263  1.00  0.00           O  
HETATM    8  H1  UNL     1      -3.488   0.062   0.175  1.00  0.00           H  
HETATM    9  H2  UNL     1      -2.432   1.479   0.641  1.00  0.00           H  
HETATM   10  H3  UNL     1      -2.941   1.158  -1.109  1.00  0.00           H  
HETATM   11  H4  UNL     1      -1.576  -1.173  -0.054  1.00  0.00           H  
HETATM   12  H5  UNL     1      -1.034  -0.025  -1.395  1.00  0.00           H  
HETATM   13  H6  UNL     1      -0.066   1.442   0.150  1.00  0.00           H  
HETATM   14  H7  UNL     1      -0.522   0.488   1.580  1.00  0.00           H  
HETATM   15  H8  UNL     1       0.863  -1.538   0.472  1.00  0.00           H  
HETATM   16  H9  UNL     1       2.070   1.047  -0.437  1.00  0.00           H  
HETATM   17  H10 UNL     1       4.090  -0.463  -0.895  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 HMDB0031496 (2-Hexenal)

CCC\C=C\C=O
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INCHI for HMDB0031496 (2-Hexenal)

InChI=1S/C6H10O/c1-2-3-4-5-6-7/h4-6H,2-3H2,1H3/b5-4+
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC6H10O
Average Molecular Weight98.145
Monoisotopic Molecular Weight98.073164942
IUPAC Name(2E)-hex-2-enal
Traditional Name(E)-2-hexenal
CAS Registry Number6728-26-3
SMILES
CCC\C=C\C=O
InChI Identifier
InChI=1S/C6H10O/c1-2-3-4-5-6-7/h4-6H,2-3H2,1H3/b5-4+
InChI KeyMBDOYVRWFFCFHM-SNAWJCMRSA-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
Organoleptic effect
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point47.00 °C. @ 17.00 mm HgThe Good Scents Company Information System
Water Solubility5261 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.790 (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
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.23 +/- 0.07 uMAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.63 +/- 0.21 uMAdult (>18 years old)Bothuremia details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection		 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 IDFDB004502
KNApSAcK IDC00000351
Chemspider ID4444608
KEGG Compound IDC08497
BioCyc IDTRANS-2-HEXENAL
BiGG IDNot Available
Wikipedia LinkCis-3-Hexenal
METLIN IDNot Available
PubChem Compound5281168
PDB IDNot Available
ChEBI ID28913
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029832
Good Scents IDrw1013831
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.. .