Showing NP-Card for 2-Dodecenal (NP0046097)

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Record Information
Version2.0
Created at2022-03-17 19:48:20 UTC
Updated at2022-03-17 19:48:20 UTC
NP-MRD IDNP0046097
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Dodecenal
Description2-Dodecenal, also known as eryngial or trans-2-dodecenal, 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-dodecenal is considered to be a fatty aldehyde lipid molecule. A trans-2,3-unsaturated fatty aldehyde that is (E)-dodec-2-ene in which the allylic methyl group has been oxidised to the corresponding aldehyde. 2-Dodecenal is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Dodecenal is a sweet, citrus, and fat tasting compound. Outside of the human body, 2-Dodecenal has been detected, but not quantified in, lemons. 2-Dodecenal is found in Santalum album . 2-Dodecenal was first documented in 1964 (PMID: 14194100). This could make 2-dodecenal a potential biomarker for the consumption of these foods (PMID: 15012807) (PMID: 15161192) (PMID: 15612802) (PMID: 21062639) (PMID: 24139239) (PMID: 26667677).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0046097 (2-Dodecenal)

  Mrv0541 05061305402D          

 13 12  0  0  0  0            999 V2000
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
M  END
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3D MOL for NP0046097 (2-Dodecenal)

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3D SDF for NP0046097 (2-Dodecenal)
  Mrv0541 05061305402D          

 13 12  0  0  0  0            999 V2000
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0046097

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCC\C=C\C=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H22O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h10-12H,2-9H2,1H3/b11-10+

> <INCHI_KEY>
SSNZFFBDIMUILS-ZHACJKMWSA-N

> <FORMULA>
C12H22O

> <MOLECULAR_WEIGHT>
182.3025

> <EXACT_MASS>
182.167065326

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
24.02999220812369

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-dodec-2-enal

> <ALOGPS_LOGP>
5.45

> <JCHEM_LOGP>
4.317515355

> <ALOGPS_LOGS>
-5.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.203792945095838

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
58.847500000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.79e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-dodecenal

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0046097 (2-Dodecenal)
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PDB for NP0046097 (2-Dodecenal)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.266   4.771   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.599   4.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.933   4.771   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      18.933   6.311   0.000  0.00  0.00           O+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    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

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3D PDB for NP0046097 (2-Dodecenal)
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SMILES for NP0046097 (2-Dodecenal)
CCCCCCCCC\C=C\C=O
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INCHI for NP0046097 (2-Dodecenal)
InChI=1S/C12H22O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h10-12H,2-9H2,1H3/b11-10+
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Synonyms
ValueSource
(2E)-DodecenalChEBI
(e)-2-Dodecen-1-alChEBI
(e)-Dodec-2-en-1-alChEBI
EryngialChEBI
trans-2-DodecenalChEBI
trans-Dodec-2-enalChEBI
beta-Octyl acroleinHMDB
FEMA 2402HMDB
Chemical FormulaC12H22O
Average Mass182.3025 Da
Monoisotopic Mass182.16707 Da
IUPAC Name(2E)-dodec-2-enal
Traditional Name2-dodecenal
CAS Registry Number4826-62-4
SMILES
CCCCCCCCC\C=C\C=O
InChI Identifier
InChI=1S/C12H22O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h10-12H,2-9H2,1H3/b11-10+
InChI KeySSNZFFBDIMUILS-ZHACJKMWSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Citrus limonFooDB
Santalum albumPlant
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
logP5.45ALOGPS
logP4.32ChemAxon
logS-5ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity58.85 m³·mol⁻¹ChemAxon
Polarizability24.03 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031020  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003013  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283361  
PDB IDNot Available
ChEBI ID133741  
Good Scents IDNot Available
References
General References
  1. WHEELER JW, MEINWALD J, HURST JJ, EISNER T: TRANS-2-DODECENAL AND 2-METHYL-1, 4-QUINONE PRODUCED BY A MILLIPEDE. Science. 1964 May 1;144(3618):540-1. doi: 10.1126/science.144.3618.540. [PubMed:14194100  ] 
  2. Kubo I, Fujita K, Nihei K, Kubo A: Anti-Salmonella activity of (2E)-alkenals. J Appl Microbiol. 2004;96(4):693-9. doi: 10.1111/j.1365-2672.2003.02175.x. [PubMed:15012807  ] 
  3. Kubo I, Fujita K, Kubo A, Nihei K, Ogura T: Antibacterial activity of coriander volatile compounds against Salmonella choleraesuis. J Agric Food Chem. 2004 Jun 2;52(11):3329-32. doi: 10.1021/jf0354186. [PubMed:15161192  ] 
  4. Choi HS: Aroma evaluation of an aquatic herb, Changpo (Acorus calamus Var. angustatus Bess), by AEDA and SPME. J Agric Food Chem. 2004 Dec 29;52(26):8099-104. doi: 10.1021/jf040239p. [PubMed:15612802  ] 
  5. Paul JH, Seaforth CE, Tikasingh T: Eryngium foetidum L.: a review. Fitoterapia. 2011 Apr;82(3):302-8. doi: 10.1016/j.fitote.2010.11.010. Epub 2010 Nov 6. [PubMed:21062639  ] 
  6. Forbes WM, Gallimore WA, Mansingh A, Reese PB, Robinson RD: Eryngial (trans-2-dodecenal), a bioactive compound from Eryngium foetidum: its identification, chemical isolation, characterization and comparison with ivermectin in vitro. Parasitology. 2014 Feb;141(2):269-78. doi: 10.1017/S003118201300156X. Epub 2013 Oct 21. [PubMed:24139239  ] 
  7. Erdem SA, Nabavi SF, Orhan IE, Daglia M, Izadi M, Nabavi SM: Blessings in disguise: a review of phytochemical composition and antimicrobial activity of plants belonging to the genus Eryngium. Daru. 2015 Dec 14;23:53. doi: 10.1186/s40199-015-0136-3. [PubMed:26667677  ] 
  8. Janssen AM, Scheffer JJ, Baerheim Svendsen A, Aynehchi Y: The essential oil of Ducrosia anethifolia (DC.) Boiss. Chemical composition and antimicrobial activity. Pharm Weekbl Sci. 1984 Aug 24;6(4):157-60. doi: 10.1007/BF01954043. [PubMed:6483572  ]