Showing NP-Card for 2-Hexenal (NP0002780)

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Record Information
Version2.0
Created at2020-11-23 19:40:15 UTC
Updated at2021-08-19 23:59:22 UTC
NP-MRD IDNP0002780
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Hexenal
Provided ByBMRBBMRB logo
Description2-Hexenal, also known as (e)-hex-2-enal or b-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. Thus, 2-hexenal is considered to be a fatty aldehyde. 2-Hexenal is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 2-Hexenal is found in Aethus indicus, Ageratum conyzoides, Aloe arborescens, Aristolochia debilis, Basella alba, Thea sinensis , Capillipedium parviflorum, Capparis spinosa, Citrus limon, Citrus sinensis, Clinopodium serpyllifolium, Dianthus caryophyllus L. , Echinophora tenuifolia, Euploea sylvester, Farfugium japonicum, Gonioctena viminalis, Lonicera japonica, Micromeria maderensis, Nelumbo nucifera, Nepeta racemosa, Origanum sipyleum, Origanum vulgare, Peristeria elata, Petasites albus , Pimenta racemosa, Quercus agrifolia, Riptortus clavatus, Robinia pseudoacacia, Salvia sclarea, Brassica hirta and Thymus longicaulis. 2-Hexenal was first documented in 2011 (PMID: 21548650). Based on a literature review a small amount of articles have been published on 2-Hexenal (PMID: 22177713) (PMID: 22417509).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002780 (2-Hexenal)

     RDKit          2D

 17 16  0  0  0  0  0  0  0  0999 V2000
   -3.1461   -0.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6757    0.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2052    0.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2652    0.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2571   -0.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7275   -0.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2061    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4424    1.2262    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8498   -1.7147    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6165   -0.5406    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3793   -1.4184    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9720    1.5225    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5016    1.8188    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0911   -1.1220    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7438    2.0663    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7785   -1.9021    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7194   -1.3095    0.0000 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  6
  1  9  1  0
  1 10  1  0
  2 11  1  1
  2 12  1  0
  3 13  1  1
  3 14  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
M  END
Download

3D MOL for NP0002780 (2-Hexenal)

NP0002780
     RDKit          3D

 17 16  0  0  0  0  0  0  0  0999 V2000
   -2.7055   -0.2762    0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2937    0.0667    0.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3763    0.1293   -0.6631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9689    0.4720   -0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9950   -0.3318   -0.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3266    0.0300    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5126    1.1084    0.7535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7847   -1.0594   -0.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1749   -0.7195    1.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2900    0.6226   -0.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8488   -0.6087    1.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3287    1.0797    1.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7385    0.8524   -1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3883   -0.8728   -1.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1286    1.3919    0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8443   -1.2540   -0.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1535   -0.6304   -0.0273 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 NP0002780 (2-Hexenal)

     RDKit          2D

 17 16  0  0  0  0  0  0  0  0999 V2000
   -3.1461   -0.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6757    0.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2052    0.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2652    0.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2571   -0.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7275   -0.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2061    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4424    1.2262    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8498   -1.7147    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6165   -0.5406    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3793   -1.4184    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9720    1.5225    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5016    1.8188    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0911   -1.1220    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7438    2.0663    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7785   -1.9021    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7194   -1.3095    0.0000 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  6
  1  9  1  0
  1 10  1  0
  2 11  1  1
  2 12  1  0
  3 13  1  1
  3 14  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
M  END
> <DATABASE_ID>
NP0002780

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0002780 (2-Hexenal)

NP0002780
     RDKit          3D

 17 16  0  0  0  0  0  0  0  0999 V2000
   -2.7055   -0.2762    0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2937    0.0667    0.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3763    0.1293   -0.6631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9689    0.4720   -0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9950   -0.3318   -0.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3266    0.0300    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5126    1.1084    0.7535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7847   -1.0594   -0.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1749   -0.7195    1.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2900    0.6226   -0.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8488   -0.6087    1.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3287    1.0797    1.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7385    0.8524   -1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3883   -0.8728   -1.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1286    1.3919    0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8443   -1.2540   -0.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1535   -0.6304   -0.0273 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

PDB for NP0002780 (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 NP0002780 (2-Hexenal)

COMPND    NP0002780
HETATM    1  C1  UNL     1      -2.705  -0.276   0.188  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.294   0.067   0.552  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.376   0.129  -0.663  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.969   0.472  -0.171  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.995  -0.332  -0.364  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.327   0.030   0.135  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.513   1.108   0.754  1.00  0.00           O  
HETATM    8  H1  UNL     1      -2.785  -1.059  -0.586  1.00  0.00           H  
HETATM    9  H2  UNL     1      -3.175  -0.720   1.114  1.00  0.00           H  
HETATM   10  H3  UNL     1      -3.290   0.623  -0.097  1.00  0.00           H  
HETATM   11  H4  UNL     1      -0.849  -0.609   1.311  1.00  0.00           H  
HETATM   12  H5  UNL     1      -1.329   1.080   1.043  1.00  0.00           H  
HETATM   13  H6  UNL     1      -0.738   0.852  -1.406  1.00  0.00           H  
HETATM   14  H7  UNL     1      -0.388  -0.873  -1.130  1.00  0.00           H  
HETATM   15  H8  UNL     1       1.129   1.392   0.357  1.00  0.00           H  
HETATM   16  H9  UNL     1       1.844  -1.254  -0.891  1.00  0.00           H  
HETATM   17  H10 UNL     1       4.153  -0.630  -0.027  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 NP0002780 (2-Hexenal)

CCC\C=C\C=O
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INCHI for NP0002780 (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 JSmol
Synonyms
Chemical FormulaC6H10O
Average Mass98.1450 Da
Monoisotopic Mass98.07316 Da
IUPAC Name(2E)-hex-2-enal
Traditional Name(E)-2-hexenal
CAS Registry NumberNot Available
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental 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
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 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
Good Scents IDrw1013831
References
General References
  1. Sakamaki K, Ishizaki S, Ohkubo Y, Tateno Y, Fujita A: Identification of the medicinal off-flavor compound formed from ascorbic acid and (E)-hex-2-enal. J Agric Food Chem. 2011 Jun 22;59(12):6667-71. doi: 10.1021/jf200846h. Epub 2011 May 23. [PubMed:21548650 ]
  2. Joo MJ, Merkel C, Auras R, Almenar E: Development and characterization of antimicrobial poly(l-lactic acid) containing trans-2-hexenal trapped in cyclodextrins. Int J Food Microbiol. 2012 Feb 15;153(3):297-305. doi: 10.1016/j.ijfoodmicro.2011.11.015. Epub 2011 Nov 29. [PubMed:22177713 ]
  3. De Lucca AJ, Carter-Wientjes CH, Boue S, Bhatnagar D: Volatile trans-2-hexenal, a soybean aldehyde, inhibits Aspergillus flavus growth and aflatoxin production in corn. J Food Sci. 2011 Aug;76(6):M381-6. doi: 10.1111/j.1750-3841.2011.02250.x. [PubMed:22417509 ]